Month: January 2021

Application of 932-32-1, These common heterocyclic compound, 932-32-1, name is 2-Chloro-N-methylaniline, 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.

6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (200 mg, 1.19 mmol), 2-chloro-N- methylaniline (185 mg, 1.31 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (57 mg, 0.12 mmol) and sodium tert-butoxide (172 mg, 1.79 mmol) were stirred in 1,4-dioxane (5 mL) and N2(g) was bubbled through the mixture for 10 min. Tris(dibenzylideneacetone)dipalladium(0) (54 mg, 0.06 mmol) was added and the dark mixture heated in a sealed tube at 100C for 2 h. The reaction mixture was cooled to room temperature and DCM and water were added. The aqueous phase was extracted with DCM and the combined organics filtered through a hydrophobic frit and then concentrated in vacuo. The residue was dissolved in DCM (5 mL) and passed through a PL-Thiol MP SPE+ column. DCM was passed through the column and the filtrate concentrated in vacuo. The residue was purified by preparative HPLC to give the desired compound. NuMuRhonu delta (ppm)(DMSO-d6): 8.47 (1 H, s, ArH), 8.02 (1 H, s, ArH), 7.59 (1 H, d, ArH), 7.47-7.38 (2 H, m, ArH), 7.39-7.31 (1 H, m, ArH), 6.39 (1 H, s, ArH), 3.66 (3 H, s, CH3), 3.35 (3 H, s , CH3). LCMS (lOcm ESCI Bicarb MeCN) Rt 3.22 (min) m/z 273 (MH+).

Statistics shows that 2-Chloro-N-methylaniline is playing an increasingly important role. we look forward to future research findings about 932-32-1.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; SCHMITT, Benoit Antoine; GENEY, Raphael Jean Joel; DOYLE, Kevin James; PEACH, Joanne; PALMER, Nicholas John; JONES, Graham Peter; HARDY, David; DUFFY, James Edward Stewart; WO2013/117645; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 70558-11-1, These common heterocyclic compound, 70558-11-1, name is 6-Chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine, 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.

Step 4 Production of (6-chloro-2,3-dihydrobenzo[1,4]oxazin-4-yl)-(3,5-dichloro-4-hydroxyphenyl)-methanone 6-Chloro-3,4-dihydro-2H-benzo[1,4]oxazine (168.4 mg) and 3,5-dichloro-4-hydroxybenzoyl chloride (242.7 mg) obtained in Step 1 of Example 3 were dissolved in ethyl acetate (3 mL), and the mixture was heated under reflux overnight. The solvent was evaporated, and the obtained solid was crystallized from methanol to give the title compound (318.4 mg) as white crystals.

Statistics shows that 6-Chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine is playing an increasingly important role. we look forward to future research findings about 70558-11-1.

Reference:
Patent; Japan Tobacco Inc.; US2007/10670; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 210532-25-5, These common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl 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.

To a stirred suspension of TFA salt of 9-(3-amino-propyl)-6,7,8,9-tetrahydro-5H- carbazole-3-carboxylic acid methyl ester (0.2 g, 0.5 mmol), in 2 ml of dry CH2Cl2, NEt3 (0.208 ml, 1.5 mmol) was added at 0 C. After stirring for 5 min, 3,5-difluorobenzene sulfonylchloride (0.106 g, 0.5 mmol), in 1 ml of dry CH2Cl2 was added and the mixture was stirred for 3 hrs. The reaction mixture was diluted with CH2Cl2, washed sequentially with IN HCl (25 ml), H2O (25 ml) and sat. NaHCO3 (25 ml) solution. The organic layer was separated, dried over anhyd.MgSO4, solvents removed in vacuo and the crude was purified by column chromatography, using EtOAc/hexane as eluents, to obtain 0.14g of the product. 1H NMR 500 MHz CDCl3: 8.2, d, J = 1.4, IH, 7.8, dd, J = 1.6, 8.7, IH, 7.3-7.24, m, 2H, 7.15, d, J = 8.7, IH, 7.04-6.97, m, IH, 4.48, t, J = 5.9, IH, 4.1, t, J = 7, 2H, 3.92, s, 3H, 2.98, q, J = 6.6, 2H, 2.73, t, J = 6.2, 2H, 2.66, t, J = 5.9, 2H, 2.05-1.89, m, 4H, 1.88-1.82, m, 2H.

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ITHERX PHARMACEUTICALS, INC.; WO2009/103022; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 873-38-1, name is 2-Bromo-4-chloroaniline, 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 873-38-1, category: chlorides-buliding-blocks

In a 20 mL microwave vial was added 2-bromo-4-chloroaniline (3 g, 14.53 mmol), 4,4,5,5 -tetramethyl-2-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1,3 ,2-dioxaborolane (5.53 g, 21.80 mmol), KOAc (3.66 g, 37.3 mmol), Pd(dppf)C12-CH2C12 adduct (0.32 g,0.44 mmol) and DMSO (9 mL). The resulting suspension was purged with N2, capped and heated at 80 C for 22 h. The reaction was cooled to rt. Water was added to dissolve the salts, then the reaction was filtered. The remaining solid was suspended in DCM and the insoluble solid was filtered. The filtrate was concentrated and then purified by normal phase chromatography to give 4-chloro-2-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl)aniline (3.15 g, 86% yield) as a white solid. MS(ESI) m/z:172.3 (M-C6H,o+H). ?H NMR (400MHz, CDC13) oe 7.54 (d, J2.6 Hz, 1H), 7.13 (dd, J8.8, 2.6 Hz, 1H), 6.52 (d, J8.6 Hz, 1H), 4.72 (br. s., 2H), 1.34 (s, 12H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 39191-07-6, name is 1-(3-Chlorophenyl)-N-methylmethanamine, 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. Recommanded Product: 1-(3-Chlorophenyl)-N-methylmethanamine

General procedure: 2-(omega-Bromoalkyl)-isoindoline-1,3-dione (1 equiv) with N-methylbenzylamine (1 equiv) or its substituted analog in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 16 h. Once the reaction was finished, the solvent was evaporated under vacuum, producing a residue that was further dissolved in 50 mL of 5 M NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane to dichloromethane/methanol 98:2), yielding a yellow oil. The final product was obtained in the form of hydrochloride salt. The following compounds were obtained.

The synthetic route of 1-(3-Chlorophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guzior, Natalia; Bajda, Marek; Rakoczy, Jurand; Brus, Boris; Gobec, Stanislav; Malawska, Barbara; Bioorganic and Medicinal Chemistry; vol. 23; 7; (2015); p. 1629 – 1637;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H3BrClF

To a mixture of 2-bromo-4-chloro-l-fluorobenzene (2 g, 9.55 mmol) and liT-pyrazole (0.618 g, 9.07 mmol) in DMF (20 mL) was added Cs2C03(6.22 g, 19.10 mmol). The reaction mixture was stirred at 90C for 1 hour. LCMS showed the reaction was completed. The reaction was cooled to 25C, diluted with EtOAc (30 mL) and water (30 mL). The aqueoUs layer was extracted with EtOAc (2 x 30 mL). The combined organic phase was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica (0-10% EtOAc/petroleum ether) to give the title compound.

The synthetic route of 1996-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; DEBENHAM, John, S.; ZHU, Cheng; (64 pag.)WO2020/86416; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 61881-19-4, A common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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.

A mixture of 12 (1.35 g, 1.16 mmol), (N-phenyl)-2,2,2-trifluoroacetoimidoyl chloride (482 mg, 2.32 mmol), andK2CO3 (802 mg, 5.80 mmol) in acetone (23.2 mL) was stirred for 1 h at room temperature. The reaction mixture was filtered through Celite, and concentrated. The crude product was purified by gelpermeation chromatography [S-X3, toluene-EtOAc (75:25)] and silica gel column chromatography with hexane-EtOAc (71:29) to give the title product 13 (1.31 g, 85%). [alpha]D -0.7 (c 1.4, CHCl3);1H-NMR (500 MHz, CDCl3) delta7.38-7.08 (m, 23H, Ar), 6.75-6.71 (m, 3H, Ar, NH), 6.32 (br, 1H, H-1GlcN),5.88-5.80 (m, 1H, H2C=CHCH2), 5.31-5.21 (m, 5H, H2C=CHCH2, H-1Fuc, H-2Fuc, H-3Fuc, H-4Fuc),5.14 (dd, 1H, Jtrans = 10.5 Hz, Jgem = 1.4 Hz, H2C=CHCH2), 4.95 (dd, 1H, J4,5 = 10.5 Hz, J5,6 = 6.4 Hz,H-5Fuc), 4.84 (d, 1H, Jgem = 11.9 Hz, PhCH2), 4.73 (d, 1H, Jgem = 11.4 Hz, PhCH2), 4.64-4.49 (m, 7H,PhCH2 5, H-2GlcN, H-1Gal), 4.44 (d, 1H, Jgem = 11.6 Hz, PhCH2), 4.16 (t, 1H, J2,3 = J3,4 = 9.2 Hz,H-3GlcN), 4.10-4.05 (m, 3H, H2C=CHCH2 2, H-4GlcN), 3.87-3.81 (m, 3H, H-4Gal, H-6aGal, H-5GlcN),3.70 (dd, 1H, J5,6b = 7.5 Hz, Jgem = 9.2 Hz, H-6bGal), 3.62-3.56 (m, 3H, H-2Gal, H-6aGlcN, H-6bGlcN),3.46-3.44 (m, 1H, H-5Gal), 3.24 (dd, 1H, J2,3 = 9.7 Hz, J3,4 = 2.7 Hz, H-3Gal), 2.14 (s, 3H, Ac), 2.02 (s, 3H,Ac), 2.00 (s, 3H, Ac), 0.78 (d, 3 H, H-6Fuc); 13C-NMR (125 MHz,CDCl3) delta 170.4, 120.2, 169.5, 161.2, 142.9, 138.7, 138.4, 138.2, 137.5, 134.9, 129.2, 129.0, 128.8, 128.5, 128.4,128.3, 128.2, 128.1, 128.0, 127.8, 127.8, 127.7, 127.6, 127.3, 124.6, 119.3, 116.6, 103.8, 95.9, 92.4, 81.9, 78.5, 77.6,74.9, 74.8, 74.2, 73.7, 73.7, 73.3, 73.2, 72.2, 71.9, 71.7, 71.6, 68.7, 68.1, 68.0, 66.7, 64.8, 54.7, 20.8, 20.8, 20.7, 15.4.HRMS (ESI) m/z: found [M + Na]+ 1351.3539, C65H70Cl3F3N2O18 calcd. for [M + Na]+ 1351.3539.

The synthetic route of 61881-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kobayashi, Daisuke; Ueki, Akiharu; Yamaji, Tomoya; Nagao, Kazuya; Imamura, Akihiro; Ando, Hiromune; Kiso, Makoto; Ishida, Hideharu; Molecules; vol. 21; 5; (2016);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1435-48-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: As a typical experiment, the reaction of the 2-halopyridine (1 mmol), fluorobenzene derivative (2.5 mmol) and PivOK (0.154 g, 1.1 mmol) at 150 C during 16 h in DMA (3 mL) in the presence of PdCl(C3H5)(dppb) (12 mg, 0.02 mmol) (see tables or schemes) under argon affords the arylation product after evaporation of the solvent and filtration on silica gel

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, 2,4-Dichloro-1-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Boyaala, Rabab; Touzani, Rachid; Guerchais, Veronique; Soule, Jean-Francois; Doucet, Henri; Tetrahedron Letters; vol. 58; 33; (2017); p. 3205 – 3208;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 61881-19-4,Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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.

10249] To a solution of 6-(6?-azidohexyl)-2,3,4-tri-O-ben- zyl-a/3-D-galactopyranose 18 (400 mg, 0.70 mmol) in CH2C12 (7 mE) was added cesium carbonate (340 mg, 1.04 mmol). To the mixture was added 2,2,2-trifluoro-N-pheny- lacetimidoyl chloride 24 (216 mg, 1.04 mmol) and the reaction mixture was stirred at r.t. for 3.5 h after which it was filtered over celite and washed with CH2C12. The solvent was removed in vacuo and the crude product was purified by flash column chromatography on silica gel (gradient hexanes/ EtOAc1 0:1 – 1:1) to yield the imidate 19 (490 mg, 94%) as a colorless oil. [a]Dt+60.8 (c0.4, CHC13); R1O.8O (Hexanes/EtOAc 2:1); IR (film) vm,x 3064, 2934, 2865, 2094, 1717, 1598, 1454, 1321, 1207, 1099, 1027, 910, 734, 696cm?; ?H NMR (400 MHz, CDC13) oe 7.45-6.60 (m, 20H),5.56 (s, 1H), 4.90 (d, J11.5 Hz, 1H), 4.75 (s, J1.5 Hz, 2H),4.68 (s, J12.4 Hz, 2H), 4.58 (d, J11.6 Hz, 1H), 4.00 (t,J8.7 Hz, 1H), 3.84 (d, J2.4 Hz, 1H), 3.58-3.39 (m, 4H),3.34 (dt, J9.3, 6.5 Hz, 1H), 3.23 (dt, J9.3, 6.5 Hz, 1H), 3.14(t, J6.9 Hz, 2H), 1.52-1.38 (m, 4H), 1.32-1.16 (m, 4H); ?3CNMR (101 MHz, CDC13) oe 138.6, 138.3, 138.2, 128.8, 128.6,128.5, 128.4, 128.4, 128.3, 128.0, 127.9, 127.8, 127.7, 124.3,119.4,82.3,78.3,77.4,77.2,76.8,75.7,74.9,74.6,73.4,73.2,71.4, 68.7, 51.5, 29.7, 28.9, 26.7, 25.8; HR ESI Calcd forC41H45F3N406 [M+Na]: 769.3183. found: 769.3239.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; UNIVERSITAeTSSPITAL BASEL; Seeberger, Peter H.; Stallforth, Pierre; De Libero, Gennaro; Cavallari, Marco; US2015/238597; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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. Recommanded Product: 2533-69-9

A round-bottom 3 neck flask was charged with 3,4-diaminobenzenesulfonic acid (8.0 g, 42.5 mmol) and anhydrous MeOH (0.85 L). O-Methyl-1,1,1-trichloroacetimidat was added (2.8 mL, 3.74 g, 21.2 mmol). The resultant suspension was stirred for 24 h at ambient conditions. Additional amount of O-methyl-1,1,1-trichloroacetimidat was added (1.4 mL, 1.87 g, 10.5 mmol) after this time, then reaction mixture was stirred for 72 h days at ambient conditions, heated for 3 h at 50 C. and triethylamine (14 mL, 9.4 g, 93.5 mmol) was added. Stirring was continued at this temperature for 18 h. Then reaction mixture was cooled to 30 C., and an intensive flow of dry HCl was passed through the solution until a precipitate formed. The suspension was filtered off at 40 C., precipitate was washed with MeOH (4¡Á150 mL, stirring of suspension for 10-15 min each turn) and with MeOH-HCl 3.5% solution (100 mL, 1 h of stirring). Product 1H,1’H-2,2′-bibenzimidazole-5,5′-disulfonic acid was pale yellow or colorless, weight 3.5 g, yield 42%. It may contain own hydrochloride as a salt. NMR1 H spectrum (Brucker Avance 300 instrument; solvent d6-dimethyl sulfoxide; delta, ppm; J, Hz): 5.27 br.s (-SO3H in exchange with H2O and NH) 7.73 m (2Ha,2Hb), 8.01 br.s (2Hx). NMR 13C{1H} spectrum (Brucker Avance 300 instrument; solvent d6-dimethyl sulfoxide; delta, ppm): 113.00, 115.41, 123.27, 136.44, 137.60, 142.24, 145.34.

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CRYSOPTIX KK; US2010/279122; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics