939412-86-9 Archives

29-Sep-2021 News A new synthetic route of 939412-86-9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Chloropyrazin-2-yl)methanamine hydrochloride, its application will become more common.

Electric Literature of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

(e) (2S,5R)-benzyl5-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-(hydroxymethyl)piperidine-1-carboxylate To a solution of (3S,6S)-1-((benzyloxy)carbonyl)-6-(hydroxymethyl)piperidine-3-carboxylic acid (0.78 g, 2.66 mmol) in 20 mL of DMF was added HATU (1.21 g, 3.2 mmol). After stirring for 30 min under N2, (3-Chloro-pyrazin-2-yl) methanamine hydrochloride (0.48 g, 2.66 mol) and Et3N (0.8 g, 7.98 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours under N2. The mixture was partitioned between EA and water. The organic layer was washed with 1 N HCl and water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford (2S,5R)-benzyl 5-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-(hydroxymethyl) piperidine-1-carboxylate (0.7 g, 63.0% yield). 1HNMR (400 MHz, CD3OD): delta=8.50?8.54 (m, 1H), 8.35 (d, J=2.4 Hz, 1H), 7.31?7.41 (m, 5H), 5.16 (s, 2H), 4.63 (s, 2H), 4.34?4.38 (m, 1H), 4.21?4.25 (m, 1H), 3.72?3.77 (m, 1H), 3.63?3.67 (m, 1H), 3.01?3.07 (m, 1H), 2.46?2.54 (m, 1H), 1.80?1.93 (m, 3H), 1.61?1.71 (m, 1H). MS (ESI): M/Z (M+1): 419.1.

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

S-21 News New learning discoveries about 939412-86-9

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (3-Chloropyrazin-2-yl)methanamine hydrochloride, and friends who are interested can also refer to it.

Reference of 939412-86-9, 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. 939412-86-9 name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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.

HATU (15.91 g, 41.8 mmol) was added to a stirred, cooled 0 C mixture of (6R,8aS)-3-oxooctahydroindolizine-6-carboxylic acid (7.3 g, 39.8 mmol), (3- chloropyrazin-2-yl)methanamine hydrochloride (7.89 g, 43.8 mmol) and DIPEA (10.44 ml, 59.8 mmol) in CH2C12 (25 ml) and the mixture was stirred at room temperature for 1 h. and then concentrated. The residue was purified by column chromatography on silica gel (Isco 240 g silica gel), eluting with CH2Cl2/MeOH (50/1) to give (6R,8aS)-N- ((3-chloropyrazin-2-yl)methyl)-3-oxooctahydroindolizine -6-carboxamide (11.15g, 36.1 mmol, 91 % yield) as a white solid. LC-MS: Ret. time 1.09 min; m/z 309.11 (M+H)+; 1HNMR (CDCI3, 500 Hz): 8.38 (1H, d, J = 2 Hz), 8.25 (1H, d, J = 2 Hz), 7.37 (1H, dd, J = 4 and 4.5 Hz), 4.56-4.72 (2H, m,l), 4.29 (1H, dd, J = 13 and 4.5 Hz),3.42-3.47 (m,l), 2.81 (1H, t, J = 13 Hz), 2.35 (2H, t, J = 8 Hz), 2.17-2.23 (1H, m), 2.04 (1H, d, J = 13.5 Hz), 1.94-1.96 (1H, m), 1.74-1.82 (1H, m), 1.55-1.62 (1H, m), 1.16-1.24 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (3-Chloropyrazin-2-yl)methanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

S News Research on new synthetic routes about 939412-86-9

Synthetic Route of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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 trichloromethyl chloroformate (4.19 mmol, 0.505 ml) in ethyl acetate (5 ml) at 0 C was added dropwise 1 ,4-dioxa-8-azaspiro[4.5]decane (6.98 mmol, 0.895 ml) in ethyl acetate (5ml) and N,N- diisopropylethylamine (6.98 mmol, 1.217 ml). After one hour the mixture was concentrated, the residue was dissolved in dichloromethane (25 ml) and 2-aminomethyl-3-chloropyrazine hydrochloride (content 60%; 10.00 mmol, 3 g) and triethylamine (27.9 mmol, 3.89 ml) were added. After stirring for 16 hours at room temperature the reaction mixture was diluted with water, filtered over decalite, washed with water, filtered over a phase separation filter and concentrated in vacuo. The crude product was dissolved in dichloromethane containing 1 % triethylamine and purification by column chromatography (silica gel; dichloromethane containing 1 % triethylamine) gave N-((3-chloropyrazin-2-yl)methyl)-1 ,4-dioxa-8- azaspiro[4.5]decane-8-carboxamide (1.5 g).

Reference:
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

S-21 News The important role of 939412-86-9

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Product Details of 939412-86-9

The solution of 2- (5-chloro-2-isopropoxy-4-methyl-3- (6- (trifluoromethyl) pyridin-3-yl) phenyl) propanoic acid (680 mg, 1.6 mmol) , (3-chloropyrazin-2-yl) methanamine hydrochloride (366 mg, 2.56 mmol) , Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (1.25 g, 2.4 mmol) and N, N-Diisopropylethylamine (413 mg, 3.2 mmol) in DMF (10 mL) was stirred at room temperature for overnight. After completed, the solvent was evaporated in vacuo and the residue was dissolved with ethyl acetate. The mixture was washed with water, brine and dried over Na 2SO 4, filtered and evaporated in vacuo to give the product (850 mg) which was used directly for the next step without further purification. MS (M+H) + 527.1, 529.1.

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIGENE, LTD.; LI, Jing; ZHAO, Haibo; WANG, Zhiwei; (193 pag.)WO2018/103688; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Sep-21 News Application of 939412-86-9

According to the analysis of related databases, 939412-86-9, the application of this compound in the production field has become more and more popular.

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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., name: (3-Chloropyrazin-2-yl)methanamine hydrochloride

(c) (6R,8aS)-N-((3-chloropyrazin-2-yl)methyl)-3-oxo-1-vinylhexahydro-1H-oxazolo[3,4-a]pyridine-6-carboxamide To a solution of (6R,8aS)-3-oxo-1-vinylhexahydro-1H-oxazolo[3,4-a]pyridine-6-carboxylic acid (60 mg, 0.28 mmol) in DCM (5 mL) was added (COCl)2 (54.1 mg, 0.43 mmol) at 0 C. and stirred at 20 C. for 1 h under N2 atmosphere. The mixture was concentrated in vacuo to give the residue, which was dissolved in THF (2 mL) and followed by (3-chloropyrazin-2-yl)methanamine hydrochloride (76.7 mg, 0.43 mmol) and Et3N (86.2 mg, 0.85 mmol). The mixture was stirred at 20 C. for 5 h. TLC (PE: THF=1:1) showed the starting materials was consumed completely. Then the reaction mixture was poured into water (10 mL), extracted with EA (10 mL*2). The organic layer was concentrated in vacuo and purified with pre-TLC to afford (6R,8aS)-N-((3-chloropyrazin-2-yl)methyl)-3-oxo-1-vinylhexahydro-1H-oxazolo[3,4-a]pyridine-6-carboxamide (30 mg, yield 31.4%) as a white solid. 1HNMR (400 MHz, Methanol-d4): delta=8.53 (dd, J=1.0, 2.5 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 6.04-5.88 (m, 1H), 5.50-5.31 (m, 2H), 4.65-4.57 (m, 3H), 3.98-3.89 (m, 1H), 3.83 (ddd, J=3.4, 8.2, 11.8 Hz, 1H), 3.50-3.42 (m, 1H), 2.58-2.42 (m, 1H), 2.10 (dd, J=2.5, 12.8 Hz, 1H), 2.03-1.95 (m, 1H), 1.77-1.63 (m, 2H), 1.53-1.38 (m, 111).

According to the analysis of related databases, 939412-86-9, the application of this compound in the production field has become more and more popular.

S News The important role of 939412-86-9

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 939412-86-9, These common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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.

2- (5-chloro-2-ethoxy-4-methyl-3- (6-methylpyridin-3-yl) phenyl) propanoic acid (2.7 g, 8.09 mmol) , (3-chloropyrazin-2-yl) methanamine hydrochloride (1.4 g, 9.71 mmol) , HOBt (1.32 g, 24.27 mmol) , EDCI (1.86 g, 9.71 mmol) and DIPEA (3.14 g, 24.27 mmol) were dissolved in THF (30 mL) and stirred at room temperature under N 2 for overnight, brine (20 mL) was added and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over Na 2SO 4. The product (3.2 g in 86.1 %yield) was got. MS (ESI) m/e (M+1) +459.

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIGENE, LTD.; LI, Jing; ZHAO, Haibo; WANG, Zhiwei; (193 pag.)WO2018/103688; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

9/24/2021 News Some scientific research about 939412-86-9

The synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Application of 939412-86-9, 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of SM (1.4 g, crude, 7.8 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (1.4 g, 7.8 mmol), HATU (2.7 mg, 7.8 mmol) and TEA (3.2 mg, 31.2 mmol) in DCM (30 mL) was stirred at 25C overnight. The mixture was quenched with H20 (60 mL) and it was extracted with DCM (25 mL X 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was purified by prep- TLC to give 1 (1.3 g, 50 %). LCMS: m/z = 309 [M+H]+.

The synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIAO, Xibin; SUZHOU BAIJIBUGONG PHARMACEUTICAL TECHNOLOGY CO. LTD.; LI, Jia; LU, Zhijian; ZHOU, Yubo; GAO, Anhui; (100 pag.)WO2018/175512; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

14-Sep-21 News Brief introduction of 939412-86-9

The chemical industry reduces the impact on the environment during synthesis (3-Chloropyrazin-2-yl)methanamine hydrochloride. I believe this compound will play a more active role in future production and life.

Reference of 939412-86-9, 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 59 (3-chloropyrazin-2-yl)methanamine hydrochloride 1a (0.9 g, 5.0 mmol) and 32 N,N-dimethyl formamide (0.02 mL) in 25 dichloromethane (20 mL) at room temperature, was added dropwise a solution of 60 benzyl 3-(chlorocarbonyl)azetidine-1-carboxylate (1.3 g, 5.0 mmol) in dichloromethane (5.0 mL) at room temperature. The resulting mixture was stirred at room temperature for 10 min. The reaction mixture was quenched with saturated 33 sodium bicarbonate solution (30 mL) and the organic phase was separated. The aqueous phase was extracted with dichloromethane (30 mL×2). The combined organic phase was washed with saturated brine (30 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was purified by flash column chromatography (20:1 dichloromethane/methanol) to provide 61 benzyl-3-(((3-chloropyrazin-2-yl)methyl)carbamoyl)azetidine-1-carboxylate 2a (1.20 g, 3.7 mmol, yellow oil). Yield: 75%.1H NMR (400 MHz, CDCl3) delta8.43 (d, J=2.4 Hz, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.35-7.27 (m, 5H), 6.91 (bs, 1H), 5.10 (s, 2H), 4.71 (d, J=4.4 Hz, 2H), 4.27-4.19 (m, 4H), 3.40 (dd, J=6.0 & 6.0 Hz, 1H).

Reference:
Patent; GUANGZHOU INNOCARE PHARMA TECH CO., LTD.; KONG, Norman Xianglong; ZHOU, Chao; CHEN, Xiangyang; US2019/177333; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

9/9/21 News Extracurricular laboratory: Synthetic route of 939412-86-9

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.

Related Products of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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 mixture of compound V (49.8 g), DCM (500 mL) and DMF (5 mL) in a 500 mL three-neck flask, oxalyl chloride (38 g, 1.5 eq) was added at 0~10 C. The reaction mixture was warmed to RT. After completion of the reaction, the solvent was removed by concentration. DCM (200 mL) was added to obtain the compound VI solution in DCM. (0099) To a mixture of compound VII (30 g), DCM (240 mL) and TEA (6 eq) in a 1000 mL three-neck flask at 0~10 C, the solution of compound VI in DCM obtained from the above step was added dropwise, the reaction mixture was warmed to RT. After the reaction was completed, water (300 mL) was added to quench the reaction. The organic phase was washed with IN HCI aqueous solution (500 mL), saturated NaHC03 aqueous solution (500 mL) and water (500 mL). The organic phase was concentrated under vacuum. The crude product was recrystallized from IPAc/Heptane to afford compound VIII (61 g, 98% yield, 99.7% chiral purity).

Reference:
Patent; WANG, Peng; LI, Pixu; GU, Xiangyong; GE, Yadong; WANG, Zhong; GAO, Feng; DU, Qiangqiang; (25 pag.)WO2019/90269; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Extended knowledge of 939412-86-9

A stirred solution of trichloromethyl chloroformate (105 mmol, 12.68 mL) in tetrahydrofuran (100 mL) was cooled to 0 C and a solution of azetidine (88 mmol, 5 g) and N,N-diisopropylethylamine (193 mmol, 33.6 mL) in tetrahydrofuran (100 mL) was added slowly in 25 minutes. After stirring at 0 C for one hour the solids were removed by filtration and the filtrate was concentrated at 50 mbar (50C bath temperature). The residue was added to a solution of 2-aminomethyl-3-chloropyrazine hydrochloride (66.7 mmol, 12 g) and triethylamine (200 mmol, 27.9 mL) in dichloromethane (200 mL) and the reaction mixture was stirred for three hours. The solids were removed by filtration and the filtrate was concentrated in vacuo. Purification using column chromatography (silica gel; gradient dichloromethane / methanol 100:0 to 95:5) yielded 9.5 g of N-((3-chloropyrazin-2-yl)methyl)azetidine-1 -carboxamide. H NMR (CDCl3, 400 MHz): delta 2.30 (quintet, J = 9 Hz, 2H), 4.06 (t, J = 9 Hz, 4H), 4.66 (d, JJ = 2 Hz, 1 H), 8.45 (d, J = 2 Hz, 1 H).