Category: 51419-59-1

Reference of 51419-59-1,Some common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, molecular formula is C8H9ClO2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Sodium hydride (60percent dispersion in mineral oil) (18 mg, 0.45 mmol) was added to a solution of 2-(4-(Piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one (4) (50 mg, 0.15 mmol) in DMF (10 mL), and the mixture was heated at 100 °C. Appropriate sulfonyl chloride (0.22 mmol) in DMF (3 mL) was added slowly to the reaction mixture. The mixture was stirred at 100 °C for 16 h. After cooling, saturated NaHCO3 solution was added. The reaction mixture was extracted with ethyl acetate and the organic phase was washed with brine. The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was washed with ethyl acetate/hexane (1:10) and purified by column chromatography (ethyl acetate) to provide 2-(4-(4-(substituted)-sulfonyl)piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one.

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rhee, Hee-Kyung; Yoo, Ji Hye; Lee, Eunyoung; Kwon, Young Joo; Seo, Hang-Rhan; Lee, Yun-Sil; Choo, Hea-Young Park; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3900 – 3908;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 51419-59-1, These common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: 5-Chloro-2-nitroaniline (173 mg, 1 mmol) was dissolved in DMF (3 mL) and dry sodium hydride (120 mg, 5 mmol) was added.The obtained mixture was stirred for 1 min and the suitable substitutedbenzenesulfonyl chloride 1 (a?g) or phenylethanesulfonylchloride 3 (a?g) (1,5 mmol) was added in several portions. The reaction was quenched after 2?6 h through the addition of a saturated NaHCO3 aqueous solution (5 mL). The mixture was extractedwith EtOAc (3 10 mL) and dried over Na2SO4. After removal ofthe solvent under reduced pressure, the residue was purified byflash chromatography using cyclohexane/AcOEt (80:20) as eluentand crystallized from Et2O.

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ferro, Stefania; Buemi, Maria Rosa; De Luca, Laura; Agharbaoui, Fatima E.; Pannecouque, Christophe; Monforte, Anna-Maria; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3861 – 3870;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 51419-59-1, These common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

1.0 g of 6-amino-1-propyl-2(1H)-quinolinone and 1.2 equivalents of p-methylbenzylsulfonyl chloride were added to 20 ml of DMF, and 3 equivalents of potassium carbonate was added as an acid binding agent. The reaction was maintained at room temperature and stirred for 12-16 hours. After that, ice water was added and the mixture was extracted with ethyl acetate for three times and the organic phase was combined and dried over anhydrous sodium sulfate. The organic phase was concentrated and the crude product was subjected to silica gel column chromatography to give 1.3 g of compound 1022B with a yield of 70percent. (0326) 1HNMR (400 MHz, DMSO-d6): delta 0.95 (t, 3H), 1.62 (m, 2H), 2.27 (s, 3H), 4.18 (t, 2H), 4.42 (s, 2H), 6.60 (d, 1H), 7.12-7.17 (m, 4H), 7.40 (d, 1H), 7.45 (s, 1H), 7.55 (d, 1H), 7.83 (d, 1H) ppm; 13CNMR (100 MHz, DMSO-d6) delta 11.53, 20.99, 21.54, 43.35, 57.34, 116.08, 119.20, 121.17, 122.14, 124.01, 126.89, 129.46, 131.34, 133.02, 135.97, 138.12, 139.45, 161.12 ppm.

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI INSTITUTES FOR BIOLOGICAL SCIENCES, CHINESE ACADEMY OF SCIENCES; ZHU, Jiankang; ZHANG, Yulu; CAO, Minjie; LIU, Xue; WANG, Qiuhua; US2019/84; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, molecular formula is C8H9ClO2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C8H9ClO2S

To a solution of 6-Amino-l-ethyl-4-methyl-4H-3,l-benzoxazin-2-one (0.140 g, 0.678 mmol) in ethyl acetate (5 mL) was added NN-diisopropylethylamine (0.175 g, 1.35 mmol) and p-tolylmethanesulfonyl chloride (0.180 g, 0.882 mmol). The reaction mixture was stirred for 15 min, concentrated and purified by flash chromatography to give the desired product as a pale solid (54 mg, 21 percent). LCMS : 0.92 min; ES+ 375 (M+H+); lH NMR (CHLOROFORM-d, 400MHz): delta (ppm) 7.12-7.20 (m, 4H), 7.09 (d, IH), 6.92 (d,lH), 6.89 (s, IH), 6.65 (s, IH), 5.29 (q, lH), 4.28 (s, 2H), 3.95 (q, 2H), 2.34 (s, 3H), 1.63 (d, 3H), 1.34 (t, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51419-59-1, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SYNGENTA PARTICIPATIONS AG; CUTLER, Sean, R.; LACHIA, Mathilde, Denise; WENDEBORN, Sebastian, Volker; GODFREY, Christopher, Richard Ayles; SABBADIN, Davide; (82 pag.)WO2018/17490; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

51419-59-1, name is p-Tolylmethanesulfonyl chloride, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C8H9ClO2S

A solution of 1-(4-Amino-phenyl)-3-pyridin-4-ylmethyl-urea (80 mg, 0.33 mmol) in DIVIF (3 mL) was added p-Tolyl-methanesulfonyl chloride (94.7 mg, 0.46 mmol) and TEA (168.4 mg, 1.65 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was washed H20 (10 mL) and extracted with EA (50 mL). The combined organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC (5-95; NH4HCO3) to give n- [4-(3 -pyridin-4-ylmethyl-ureido)-phenyl] -c-p-tolyl-methanesulfonamide (35 mg, yield 26percent) as a white solid. ?H NMR (400 IVIHz, DMSO-d6): oe = 9.49 (s, 1H), 8.68 (s, 1H), 8.51-8.49 (m, 2H), 7.37 (d, J 8.8 Hz, 2H), 7.28 (d, J 5.6 Hz, 2H), 7.18-7.13 (m, 4H), 7.08 (d, J= 8.8 Hz, 2H), 6.71 (t, J= 5.6 Hz, 1H), 4.32 (d, J 5.6 Hz, 2H), 4.29 (s, 2H), 2.29 (s, 3H). MS: m/z 410.9 (M+HH).

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 51419-59-1, These common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

No. B1-152: N-(1?-Methyl-2?-oxo-1?,2?-dihydrospiro[cyclobutane-1,3?-indol]-5-yl)-1-(4-methylphenyl)methanesulfonamide (0136) (0137) In a round-bottom flask which had been dried by heating, and under argon, 1-methyl-1,3-dihydro-2H-indol-2-one (1.00 g, 7 mmol) and 1,3-dibromopropane (2.06 g, 10 mmol) were dissolved in abs. N,N-dimethylformamide, and the mixture was stirred at room temperature for 5 min. The reaction solution was then cooled to 0° C., and sodium hydride (0.82 g, 20 mmol, 60percent strength dispersion) was then added a little at a time. The resulting reaction mixture was stirred for about 2 h, methanol (4 ml) was then added and after a further 5 min sat. ammonium chloride solution (15 ml) and water (200 ml) were added. The aqueous phase was extracted intensively with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (360 mg, 29percent of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.52 (d, 1H), 7.27 (m, 1H), 7.09 (m, 1H), 6.77 (d, 1H), 3.20 (s, 3H), 2.67 (m, 2H), 2.33 (m, 4H). 1?-Methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (360 mg, 1.92 mmol) was added to conc. acetic acid (5 ml), and fuming nitric acid (0.21 ml, 5.06 mmol) was then added carefully. The resulting reaction mixture was stirred at room temperature for 2 h and then diluted with ice-water. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methyl-5?-nitrospiro[cyclobutane-1,3?-indol]-2?(1?H)-one (380 mg, 85percent of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 8.38 (d, 1H), 8.26 (dd, 1H), 6.86 (d, 1H), 3.25 (s, 3H), 2.70 (m, 2H), 2.42 (m, 4H). In the next step, 1?-methyl-5-nitrospiro[cyclobutane-1,3?-indol]-2?(1?H)-one (450 mg, 1.55 mmol) and tin(II) chloride dihydrate (1.40 g, 6.20 mmol) were added together to abs. ethanol and stirred under argon at a temperature of 80° C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 5?-amino-1?-methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (230 mg, 66percent of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 6.98 (d, 1H), 6.62 (m, 2H), 3.14 (s, 3H), 2.64 (m, 2H), 2.38-2.20 (m, 4H). Under argon, 5?-amino-1?-methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (150 mg, 0.79 mmol) and (4-methylphenyl)methanesulfonyl chloride (156 mg, 0.76 mmol) were dissolved in abs. acetonitrile (5 ml) in a round-bottom flask which had been dried by heating, pyridine (0.11 ml, 1.38 mmol) and dimethyl sulfoxide (0.03 ml, 0.42 mmol) were then added and the mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated under reduced pressure, water, dil. hydrochloric acid and dichloromethane were added to the residue that remained and the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclobutane-1,3?-indol]-5?-yl)-1-(4-methylphenyl)methanesulfonamide (118 mg, 46percent of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.29 (m, 3H), 7.16 (d, 1H), 6.96 (br. s, 1H, NH), 6.61 (d, 1H), 4.30 (s, 2H), 3.13 (s, 3H), 2.62 (m, 2H), 2.33 (s, 3H), 2.32-2.17 (m, 4H).

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, Jens; BOJACK, GUIDO; HELMKE, HENDRIK; LEHR, STEFAN; MUELLER, THOMAS; WILLMS, LOTHAR; DITTGEN, JAN; SCHMUTZLER, DIRK; BICKERS, UDO; STREK, HARRY; BALTZ, RACHEL; (88 pag.)US2016/237035; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 51419-59-1, name is p-Tolylmethanesulfonyl chloride, A new synthetic method of this compound is introduced below., Product Details of 51419-59-1

Potassium tert-butoxide (93.8 mg, 836 mumol) was added to a solution of 2-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide (110 mg, 380 mumol) in THF (10 ml) in DMF (2 ml) [Comment: please check]. After 10 min., the reaction mixture was cooled by an ice bath and then a solution of (4-methylphenyl)methanesulfonyl chloride (93.7 mg, 458 mumol) in THF (2 ml) was added. After 70 min., EtOAc and 1 N NaOH aqueous solution were added. The organic phase was extracted with EtOAc and then with DCM. The combined organic phases were washed with water, and brine, dried over Na2SO4 and evaporated to dryness. Chromatography (silica gel, 0 to 2percent MeOH in DCM) provided the title compound as a pale yellow solid (0.080 g; 46percent). LCMS: m/z=457 (MH+).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; F. HOFFMANN-LA ROCHE AG; BUSCHMANN, Helmut; WOLKERSTORFER, Andrea; SZOLAR, Oliver; HANDLER, Norbert; CUSACK, Stephen; SMITH, Mark; SO, Sung-Sau; US2014/38990; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 51419-59-1, name is p-Tolylmethanesulfonyl chloride, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 51419-59-1, Recommanded Product: 51419-59-1

General procedure: A two-step one-pot method for preparing an abscisic acid receptor agonist:Add p-methylbenzyl mercaptan to acetonitrileAnd then adding a chlorinating reagent,Point plate monitoring, after the reaction, move into the ice water bath,Add 4 equivalents of an acid binding agent such as pyridine.After the addition, 7-amino-N-propylquinolinone in acetonitrile was slowly added dropwise.The plate is monitored for reaction, after the reaction, pickling, drying,Further, the abscisic acid receptor agonist can be obtained by column chromatography or recrystallization,

At the same time, in my other blogs, there are other synthetic methods of this type of compound, p-Tolylmethanesulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Shaoyang University; Huang Zhiyou; (7 pag.)CN109678797; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 51419-59-1,Some common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, molecular formula is C8H9ClO2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Sodium hydride (60percent dispersion in mineral oil) (18 mg, 0.45 mmol) was added to a solution of 2-(4-(Piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one (4) (50 mg, 0.15 mmol) in DMF (10 mL), and the mixture was heated at 100 °C. Appropriate sulfonyl chloride (0.22 mmol) in DMF (3 mL) was added slowly to the reaction mixture. The mixture was stirred at 100 °C for 16 h. After cooling, saturated NaHCO3 solution was added. The reaction mixture was extracted with ethyl acetate and the organic phase was washed with brine. The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was washed with ethyl acetate/hexane (1:10) and purified by column chromatography (ethyl acetate) to provide 2-(4-(4-(substituted)-sulfonyl)piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one.

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rhee, Hee-Kyung; Yoo, Ji Hye; Lee, Eunyoung; Kwon, Young Joo; Seo, Hang-Rhan; Lee, Yun-Sil; Choo, Hea-Young Park; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3900 – 3908;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 51419-59-1, The chemical industry reduces the impact on the environment during synthesis 51419-59-1, name is p-Tolylmethanesulfonyl chloride, I believe this compound will play a more active role in future production and life.

Ethyl (2E)-3-(2-fluoro-5-nitrophenyl)acrylate (1000 mg, 4.18 mmol) and 1,1?-bi(cyclopropyl)-l-amine (508 mg, 3.80 mmol) were dissolved under argon in abs. N,N-dimethylformamide (10 mE), and then N,N-diisopropylethylamine (1.32 mE, 7.60 mmol) was added. The resulting reaction mixture was stirred at a temperature of 50 C. for a total of 16 h and, afier cooling to room temperature, water and ethyl acetate were added. The aqueous phase was then extracted repeatedly with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), ethyl (2E)-3-{2-[ 1, 1?-bi(cyclopro- pyl)- 1 -ylamino]-5-nitrophenyl}acrylate (570 mg, 43% of theory) was isolated as a colorless solid, ?H-NMR (400 MHz, CDC13 oe, ppm) 8.27 (d, 1H), 8.16 (m, 1H), 7.63 (d, 1H), 7.18 (d, 1H), 6.46 (d, 1H), 5.19 (br. s, 1H, NH), 4.29 (q, 2H), 1.35 (t, 3H), 1.33-1.27 (m, 1H), 0.78 (m, 4H), 0.49 (m, 2H), 0.18 (m, 2H). Ethyl (2E)-3-{2-[i,i?-bi(cyclopro- pyl)- 1 -ylamino]-5-nitrophenyl}acrylate (570 mg, 1.80 mmol) was then dissolved in abs. ethanol (10 mE), and (Ph3P)3RhC1 (167 mg, 0.18 mmol) was added. After stirring at room temperature for 5 mm, hydrogen was introduced into the reaction solution with a constant gas flow via a gas introduction apparatus for about 9 h. The progress of the reaction was monitored by EC-MS. On completion of conversion, the reaction solution was concentrated under reduced pressure. By column chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), it was possible to isolate ethyl 3-{2-[1,1?-bi(cyclopro- pyl)- 1 -ylamino]-5-nitrophenyl}propanoate (200 mg, 35% of theory) as a colorless solid, ?H-NMR (400 MHz, CDC13 oe, ppm) 8.07 (m, 1H), 7.94 (d, 1H), 7.11 (d, 1H), 5.40 (bt 5, 1H, NH), 4.18 (q, 2H), 2.77 (m, 2H), 2.64 (m, 2H), 1.30-1.24 (m, 4H), 0.76 (m, 4H), 0.46 (m, 2H), 0.17 (m, 2H). Ethyl 3-{2-[ 1, 1?-bi(cyclopropyl)- 1 -ylamino]-5-nitrophenyl}propanoate (200 mg, 0.63 mmol) was dissolved in abs. tetrahydroffiran (8 mE) and added dropwise to a suspension, cooled down to 0 C., of sodium hydride (38 mg, 0.94 mmol, 60% suspension in oil) in abs. tetrahydrothran (5 mE) under argon. The resulting reaction mixture was stirred at 0 C. for 1 h, and then water was added cautiously, followed by ethyl acetate afier stirring for 5 mm. The aqueous phase was then extracted repeatedly with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), 1 -[1, 1?-bi(cyclopropyl)- 1 -yl] -6-nitro-3,4-dihydroquinolin-2 (1H)-one (90 mg, 53%) was isolated as a colorless solid, ?H-NMR (400 MHz, CDC13 oe, ppm) 8.16 (m, 1H), 8.04 (m, 1H), 7.53 (d, 1H), 2.93 (m, 2H), 2.78-2.58 (m, 2H), 1.44 (m, 1H), 1.23 (m, 1H), 1.03 (m, 1H), 0.91-0.82 (m, 2H),0.60-0.45 (m, 3H), 0.28 (m, 1H). In the next step, 1-[1,1?- bi(cyclopropyl)-1 -yl] -6-nitro-3,4-dihydroquinolin-2(1H)-one (90 mg, 0.33 mmol) was added together with tin(II) chloride dihydrate (298 mg, 1.32 mmol) to abs. ethanol (5 mE) and the mixture was stirred under argon at a temperature of 80 C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then extracted repeatedly with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By colunm chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), 6-amino-i -[1,1 ?-bi(cyclopropyl)- 1 -yl]-3,4-dihydroquinolin-2(1H)-one (70 mg, 87% of theory) was isolated as a highly viscous foam, ?H-NMR (400 MHz, CDC13 oe, ppm) 7.18 (m, 1H), 6.58 (m, 1H), 6.48 (d, 1H), 2.78 (m, 2H), 2.59 (m, 2H), 1.47 (m, 1H), 1.08 (m, 1H), 0.98 (m, 1H), 0.90-0.81 (m, 2H), 0.60-0.43 (m, 3H),0.28 (m, 1H). 6-Amino-i -[1 ,i?-bi(cyclopropyl)-i -yl]-3,4-di- hydroquinolin-2(1H)-one (70 mg, 0.29 mmol) was dissolved together with (4-methylphenyl)methanesulfonyl chloride (65 mg, 0.32 mmol) in abs. acetonitrile (5 mE) in a baked- out round-bottom flask under argon, then pyridine (0.05 mE, 0.58 mmol) was added and the mixture was stirred at room temperature for 8 h. The reaction mixture was then concentrated under reduced pressure, the remaining residue was admixed with dil. HC1 and dichloromethane, and the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By colunm chromatography purification of the crude product obtained (ethyl acetate/heptane gradient), N-{ 1 -[1,1 ?-bi(cyclopropyl)-i -yl]-2-oxo-i ,2,3,4-tetrahydroquinolin-6-yl}-i -(4-methylphenyl)methanesulfonamide (32 mg, 27% oftheory) was isolated as …

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, p-Tolylmethanesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, JENS; BOJACK, GUIDO; HELMKE, HENDRIK; WILLMS, LOTHAR; LEHR, STEFAN; MUELLER, THOMAS; DITTGEN, JAN; SCHMUTZLER, DIRK; BALTZ, RACHEL; BICKERS, UDO; (119 pag.)US2018/20662; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics