Tag: M.W=200-300

41965-95-1, 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. 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, A new synthetic method of this compound is introduced below.

2-acetyl-10-[(3-chloro-4-methoxybenzyl)amino]-l,2,3,4- tetrahydrobenzo[b][l,6]naphthyridine-8-carbonitrile, H [00206] A mixture of 26 (0.14 mmol), 3-chloro-4-methoxybenzyl amine hydrochloride (0.70 mmol), TEA (0.70 mmol) and Nal (0.007 mmol) in NMP (2 mL) was heated to 130 C and stirred overnight. The mixture was diluted with CH2C12 (10 mL) and washed with H20 (2×10 mL) and brine (10 mL). The organic layers were dried over Na2S04, filtered and evaporated under reduced pressure. Flash Chromatography (AcOEt: MeOH 9: 1) gave the desired product (20%> yield). MS ESI (m/z) 421 (M+H)+; 1H NMR (300 MHz, CDC13) delta 8.34 (s, IH), 7.96 (d, IH, J=8.7 Hz), 7.73 (dd, lH, Ji=1.5, J2=9.0 Hz), 7.31 (d, 1H, J=2.1 Hz), 7.20 (dd, IH, Ji=2.1, J2=8.4 Hz) , 6.93 (d, IH, J=8.1 Hz), 4.70 (s, 2H), 4.64 (d, 2H, J=6.0 Hz), 4.42 (s, IH), 3.91 (s, 3H), 3.82 (t, 2H, J=6.0 Hz), 3.20 (t, 2H, J=6.0 Hz), 2.21 (s, 3H).

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; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; FIORITO, Jole; ARANCIO, Ottavio; WASMUTH, Andrew; WO2015/9930; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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. 2770-11-8

General procedure: A mixture of NaOH solution (2 molL-1, 20mL), 1,4-dioxane (2 mL) and compound 4 (5 mmol) was dissolved and cooled to 0 C in an ice bath. While stirring the mixture, compound 14, 15 or 16 was added slowly. Afterwards, the mixture was stirred for another 5h at room temperature. The mixture was then extracted with ethyl acetate, and the solvent was removed in vacuum. The crude product was purified by column chromatography on silica gel to give compounds 17a-17i, 18a-18i or 19a-19i in yields of 30-73%. All the compounds were list in Table1 and the spectral parameters for 1H NMR, IR and MS were as follows.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2770-11-8.

Reference:
Article; Wen, Fang; Jin, Hong; Tao, Ke; Hou, Taiping; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 244 – 251;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6579-54-0 as follows. 6579-54-0

(a) Step 1 [0256] A solution of 1H-indole-3-carboxaldehyde (0.290 g, 2.00 mmol) in methylene chloride (4 mL) was added with 2,6-dichlorophenylsulfonyl chloride (0.589 g, 2.40 mmol) and diisopropylethylamine (0.310 g, 2.40 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate to terminate the reaction, and then extracted three times with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 1-(2,6-dichlorophenylsulfonyl)-1H-indole-3-carboxaldehyde (0.658 g, 93%).1H NMR (300 MHz, CDCl3) delta 7.32-7.38 (m, 2H), 7.41-7.45 (m, 1H), 7.48-7.51 (m, 2H), 7.63-7.67 (m, 1H), 8.28-8.31 (m, 1H), 8.41 (s, 1H), 10.18 (s, 1H).

According to the analysis of related databases, 6579-54-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The University of Tokyo; Riken; NAGANO Tetsuo; OKABE Takayoshi; KOJIMA Hirotatsu; SAITO Nae; NAKANO Hirofumi; ABE Masanao; TANAKA Akiko; HONMA Teruki; YOKOYAMA Shigeyuki; TSUGANEZAWA Keiko; YUKI Hitomi; EP2565192; (2013); 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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, A new synthetic method of this compound is introduced below., 33863-76-2

To a mixture of 8-(l-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6- carboxamide (350 mg, 1.01 mmol, single enantiomer, [a]D2o: +35 in acetonitrile), cesium carbonate (1288 mg, 3.95 mmol), (9,9-dimethyl-9H-xanthene-4,5- diyl)bis(diphenylphosphine) (147 mg, 0.25 mmol) and l-bromo-3-chloro-5-fluorobenzene (467 mg, 2.23 mmol) in degassed 1,4-dioxane (2ml), was addedtris(dibenzylideneacetone)dipalladium (70 mg, 0.08 mmol). The suspension was heated in a sealed container at 95C for 16 hrs. The reaction mixture was filtered through a short pad of dicalite and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with 0 to 8% isopropanol in DCM. The solvent was evaporated to dryness, the product triturated with diethyl ether – DCM (9: 1), collected by filtration and dried to afford 8-(l-(3-chloro-5-fluorophenylamino)ethyl)-N,N- dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (320 mg; 67%) as a clear yellow solid. Mass Spectrum: M+H+ 474. [a]D20: -138. NMR Spectrum (DMSOd6): 1.52 (d, 3H), 2.75 (bs, 3H), 2.95 (bs, 3H), 3.49-3.63 (m, 4H), 3.70-3.79 (m, 4H), 4.98-5.07 (m, 1H), 5.60 (s, 1H), 6.23 (d, 1H), 6.42 (d, 1H), 6.43 (ddd, 1H), 6.94 (d, 1H), 7.54 (d, 1H), 7.80 (d, 1H).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARLAAM, Bernard, Christophe; DEGORCE, Sebastien, Louis; LAMBERT-VAN DER BREMPT, Christine, Marie, Paul; MORGENTIN, Remy, Robert; PLE, Patrick; WO2011/51704; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

41965-95-1, Adding a certain compound to certain chemical reactions, such as: 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, 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 41965-95-1.

l-(10-((3-chloro-4-methoxybenzyl)amino)-3,4-dihydrobenzo[][l,6]naphthyridin- 2(lH)-yl)ethan-l-one, I [00241] A solution of 30 (1.15 mmol), 3-chloro-4-methoxybenzylamine hydrochloride (3.45 mmol), Nal (0.06 mmol), and triethylamine (3.45 mmol) in NMP (5.0 mL) was heated at 130 C for 6 h. The solvent was evaporated off and the residue was purified by Flash Chromatography (AcOEt: MeOH 8:2) to give I. MS ESI (m/z) 396 (M+H)+; 1H NMR (400 MHz, CDC13) delta 8.05- 8.02 (m, IH), 7.92 (d, IH, J=9.2 Hz), 7.67-7.63 (m, IH), 7.45-7.40 (m, IH), 7.35 (d, IH, J=2.4 Hz), 7.22 (dd, IH, Ji=2.0, J2=8.4 Hz), 6.92 (d, IH, J=8.4 Hz), 4.75 (s, 2H), 4.65 (d, 2H, J=5.2 Hz), 3.90 (s, 4H), 3.81 (t, 2H, J=6.0 Hz), 3.27 (t, 2H, J=6.4 Hz), 2.20 (s, 3H).

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, 3-Chloro-4-methoxybenzylamine Hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; FIORITO, Jole; ARANCIO, Ottavio; WASMUTH, Andrew; WO2015/9930; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

933190-51-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 933190-51-3 name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 2,2-dimethylpyrrolidine (0.248 g, 2.5 mmol) in DMF (8 mL) was added NaH (0.060 g, 60% dispersion in mineral oil, 2.5 mmol) and stirred for 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (0.233 g, 1 mmol) under N2. The mixture was stirred at room temperature for 16 h. Then it was partitioned between 15 mL of saturated NH4Cl solution and 15 mL of ether. The organic layer was washed with water (10 mL¡Á3) and saturated NaCl solution (10 mL¡Á3), dried over NaSO4, concentrated in vacuo, and purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give 6-chloro-8-(2,2-dimethylpyrrolidin-1-yl)imidazo[1,2-b]pyridazine (0.140 g, 22%) as a light brown solid. LC-MS: [M+H]+, 251.1, tR=1.698 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, 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. 1996-29-8

Potassium /-butoxide (3.9 g, 0.33 mmol) was dissolved in DMSO (25 mL). To this solution was added 3 -methyl pyrazole (2.7 g, 0.33 mmol) and the reaction was heated at 50 C for 30 min. l-Bromo-4-chloro-2-fluorobenzene (4.6 g, 0.22 mmol) was then added and the reaction was stirred at 50 C for 16 h. The reaction was cooled to RT and extracted with water and EtOAc, washed with brine, and dried over Na2S04) filtered and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtO Ac/heptane) provided l-(2- bromo-5-chlorophenyl)-3-methyl-lH-pyrazole and l-(2-bromo-5-chloroplienyl)-5-methyl-lH- pyrazole as a 4: 1 mixture that was used in the next step directly,l-(2-biOmo-5-chlorophenyl)-3-methyl-lH-pyrazole/l-(2-bi mo-5-chlorophenyl)-5- methyl-lH-pyrazole mixture (Intermediate 3, step 1) (1 ,00 g, 3.68 mmol) was dissolved in THF (6 mL) then cooled to 0 C, /-Propyl magnesium chloride (2,76 mL, 2.0 M in THF, 5.52 mmol) was added dropwise and the reaction was warmed to RT for 30 min. The reaction was then cooled to -15 C and paraformaldehyde (166 mg, 5.5 mmol) was added. The reaction mixture was allowed to warm to RT and stirred for 1 h. DMF (500 mL) was added and the reaction was stirred for an additional 1 h. The reaction was quenched with HC1 (2 N, 4 mL), diluted with water, extracted with EtOAc, washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtOAc/heptane) provided 4-chloro-2-(3-methyl-pyrazoI-l -yl)-benzaldehyde

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1996-29-8.

Reference:
Patent; KAROS PHARMACEUTICALS, INC.; DE LOMBAERT, Stephane; GOLDBERG, Daniel R.; BRAMELD, Kenneth; SJOGREN, Eric Brian; SCRIBNER, Andrew; WO2015/35113; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6579-54-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6579-54-0 name is 2,6-Dichlorobenzenesulfonyl chloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a mixture of 2,4-dichloro-5-methylpyrimidine (4.17g, 25.6mmol) and 4-acetamidophenylboronic acid (5.Og, 27.9mmol) in DME (40ml) was added Et3N (8.92ml, 64.0mmol), H2O (4ml), and dichloro[l,r-bis(diphenylphosphino)ferrocenepalladium (2.8 Ig, 3.44mmol, 13%). The mixture was allowed to stir at reflux for 5hrs. After the mixture was cooled down to rt, the crude mixture was directly filtered on silica gel and eluted with EtOAc. The filtrate was concentrated in vacuo. Further purification was conducted by flash chromatography to afford Intermediate 1 (5.94g, 89%) as a white solid. LCMS: m/z 262 (M+H)+.[0246] To a stirred solution of chloropyrimidine (1.05g, 4.0mmol) in 1-butanol (10ml) was added N-Boc-amino-3-aniline (920mg, 4.4mmol) and the mixture was heated in the sealed tube at 18O0C for 1.5hr. The mixture was cooled down to rt and acidified with IN HCl (20ml). The aqueous layer was washed with EtOAc (50ml). The separated aqueous layer was basified with 2N NaOH to pH 8-9 and extracted with EtOAc (50ml*3). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by flash 5 chromatography to afford product Intermediate K (943mg, 71% as a light yellow solid. LCMS: m/z 334 (M+H)+.[02471 To a stirred suspension of aniline (250mg, 0.75mmol) in THF (5ml) was added DIPEA (157ml, 0.90mmol) and 2,6-dichlorobenzenesulfonyl chloride (203 mg, 0.83mmol) and the mixture containing intermediate K was stirred at reflux for 2hrs. After cooling down to rt, the mixture was diluted with EtOAc, washed with H?O, brine, and dried over Na2SO4. After concentrated in vacuo, the residue was purified by flash chromatography to give product 26 (299mg, 73%) as a light pink solid.1H-NMR (400MHz, d6-DMSO): 10.71 (s, IH), 10.16 (s, IH), 9.54 (s, IH), 8.34 (s, IH), 7.75- 7.69 (m, 5H), 7.60 (dd, 2H), 7.51 (dd, IH), 7.31 (dd, IH), 7.09 (t, IH), 6.66 (dd, IH), 2.25 (s, 3H), 2.08 (s, 3H); MS (EI) C25H2ICl2N5O3S: 542.2 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorobenzenesulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; WO2007/89768; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

933190-51-3, The chemical industry reduces the impact on the environment during synthesis 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life.

A mixture of 8-bromo-6-chloroimidazo[l,2-b]pyridazine (2 g, 8.6 mmol) and 5,6- dimethoxypyridin-2-amine (1.39 g, 9.03 mmol) in DMF (72 ml) was cooled to 0 C. To the mixture was added sodium hydride (1.1 g, 27.5 mmol, 60% dispersion in mineral oil). The reaction was stirred for 10 min then warmed to room temperature. After 15 h the reaction was quenched with saturated sodium bicarbonate solution, and then diluted with water and EtOAc. An insoluble solid was filtered off. The filtrate was separated and the aqueous phase was washed with EtOAc. The combined organic extracts were concentrated in vacuo and the residue obtained was crystalized from methanol to give 6-chloro-N-(5,6-dimethoxypyridin -2- yl)imidazo[l,2-b]pyridazin-8-amine (2.4 g, 7.85 mmo 1, 91.2 %) as light brown needles. 1H NMR (300 MHz, CHLOROFORM- ) delta ppm 8.26 (br. s., 1 H) 7.95 (s, 1 H) 7.81 (s, 1 H) 7.55 (s, 1 H) 7.15 (d, J=7.93 Hz, 1 H) 6.58 (d, J=8.31 Hz, 1 H) 4.12 (s, 3 H) 3.89 (s, 3 H); LC/MS: 305.9 [MH]+.

The chemical industry reduces the impact on the environment during synthesis 8-Bromo-6-chloroimidazo[1,2-b]pyridazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., 27139-97-5

The cooling pipe is attached, the container is again after replacing the argon, distilled water (30 ml), 2-bromo-4-chlorotoluene (5. 23g, 20. 5mmol), tetrakistriphenyl phosphinepalladium (0. 462g, 0. 40mmol), potassium carbonate (2. 76g, 20mmol), and toluene (100 ml) is added, which is circulated to 5 hours. After cooling to room temperature, transferring the liquid content scopolia, organic phase and aqueous phase is separated, the water phase is removed, washed with organic phase. By drying the organic phase is sodium sulfate. Thereafter, by filtration to remove sodium sulfate, organic phase is concentrated. The mixture is purified by silica gel column chromatography (developing solvent: Phenylbicyclohexane), and the purpose of the above chemical eq. (118) is obtained (yield 4. 14g, yield 82. 4percent)

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; NIPPON HOSO KYOKAI <NHK>; KANTO CHEM CO INC; FUKAGAWA HIROHIKO; SHIMIZU TAKAHISA; TAKAHASHI JUNPEI; SHINNAI SATONOBU; TSUCHIYA KAZUHIKO; (53 pag.)JP2015/160849; (2015); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics