Category: 939412-86-9

Adding a certain compound to certain chemical reactions, such as: 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, belongs to Pyrazines 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 939412-86-9, name: (3-Chloropyrazin-2-yl)methanamine hydrochloride

To a solution of 1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxylic acid (6 g, 33 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (6 g, 33 mmol) in 200 mL of DCM was added TEA (9 g, 88 mmol) dropwise. The resulting mixture was stirred at room temperature for 5 mins, and then HATU (12.5 g, 33 mmol) was added to the solution in portions at 0 C. The mixture was stirred at room temperature for 2 hours. Water was added, the DCM layers was separated, and washed with brine, dried over Na2SO4. The solvent was removed and the residue was purified by column chromatography on silica gel (PE/THF = 5/1 v/v%) to afford N-((3-chloropyrazin-2- yl)methyl)-1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxamide (1.5 g, 15 %). MS-ESI (m/z): 306 (M+1) + (Acq Method: 10-80AB_2min_220&254.1cm; Rt: 0.93 min)

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; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/116504; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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., Application In Synthesis of (3-Chloropyrazin-2-yl)methanamine hydrochloride

To a solution of 3-isopropyl-3- (methoxycarbonyl) cyclohexanecarboxylic acid (4.4 g, 19.3 mmol) in THF (100 mL) was added (3-chloropyrazin-2-yl) methanamine hydrochloride (5.2 g, 28.9 mmol) , HATU (11 g, 28.9 mmol) and TEA (11.7 g, 115.8 mmol) . The mixture was stirred at room temperature overnight. The reaction mixture was diluted with EA and water, the organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with PE/THF 5/1 to give methyl 3- ( ( (3-chloropyrazin-2-yl) methyl) carbamoyl) -1-isopropylcyclohexanecarboxylate. 1H NMR (400 MHz, CDCl3) delta ppm: 0.86 (t, J 6.65 Hz, 6 H) , 1.16 -1.32 (m, 2 H) , 1.36 -1.47 (m, 2 H) , 1.69 -1.87 (m, 3 H) , 2.07 -2.16 (m, 1 H) , 2.22 -2.42 (m, 2 H) , 3.69 (s, 3 H) , 4.56 -4.76 (m, 2 H) , 6.79 (s, 1 H) , 8.31 (d, J 2.74 Hz, 1 H) , 8.45 (d, J 2.74 Hz, 1 H) .

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; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ANDRESEN, Brain M.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (111 pag.)WO2016/106624; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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 a solution of (3S,7R,9aS)-3-methyl-4-oxooctahydropyrido[2,l- c][l ,4]oxazine-7-carboxylic acid (55 mg, 0.26 mmol) in anhydrous DCM (1 mL) was added oxalyl dichloride (0.068 mL, 0.77 mmol) in DCM (0.5 mL) at 0C under N2 atmosphere, and followed by 1 drop of DMF. The resulting mixture was stirred at 0C for 2 hrs. The reaction mixture was evaporated, dissolved with DCM (0.5 mL), and added to a solution of (3-chloropyrazin-2-yl)methanamine hydrochloride (56.1 mg, 0.31 mmol), and triethylamine (0.079 mL, 0.57 mmol) in DCM (1 mL), at 0C under N2 atmosphere, and the mixture was stirred for 12 hrs at 15 C.Then the mixture was diluted with DCM (5 mL), and H20 (5 mL). The organic layer was washed with brine (5 mL), dried over Na2S04, evaporated to get the crude product, which was then purified by prep-TLC (PE/THF=1 : 1) to give (3S,7R,9aS)-N-((3-chloropyrazin-2- yl)methyl)-3-methyl-4-oxooctahydropyrido[2, 1 -c] [ 1 ,4]oxazine-7-carboxamide (55 mg, yield: 62.9 %). 1H NMR (400MHz, CDC13) delta = 8.42 (d, J=2.5 Hz, IH), 8.29 (d, J=2.5 Hz, IH), 7.17 (br. s., IH), 4.76 – 4.57 (m, 2H), 4.16 (q, J=6.9 Hz, IH), 3.92 (dd, J=4.1 , 12.2 Hz, IH), 3.74 (dd, J=2.5, 12.0 Hz, IH), 3.37 – 3.25 (m, IH), 2.73 (t, J=12.3 Hz, IH), 2.42 (tt, J=4.0, 1 1.8 Hz, IH), 2.18 – 2.03 (m, 2H), 1.99 – 1.84 (m, IH), 1.79 – 1.68 (m, 2H), 1.44 (d, J=7.0 Hz, 3H).

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

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

Reference of 939412-86-9, The chemical industry reduces the impact on the environment during synthesis 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, I believe this compound will play a more active role in future production and life.

A mixture of (trans)-2-((benzyloxy)carbonyl)-4-oxooctahydro-l H-pyrido [1 ,2-a] pyrazine-7-carboxylic acid (1.3 g, 3.9 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (840 mg, 4.7 mmol), HATU (2.2 g, 5.8 mmol) and TEA (1.6 g, 15.6 mmol) in DMF (20 mL) was stirred at 25 C for overnight. Then the reaction mixture was poured into water and extracted with EA (50 ml*3). The combined organic phase was washed with brine (100 mL), dried over Na2S04, concentrated under vacuum to give the crude residue, which was purified by silica gel column chromatography (PE/THF = 1/3) to give (trans)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4- oxohexahydro-1 H-pyrido [l ,2-a]pyrazine-2(6H)-carboxylate (600 mg, yield 35.3 %). 1H NMR (400MHz, CD3OD) delta= 8.52 (d, J=2.5 Hz, 1H), 8.33 (d, J=2.3 Hz, 1H), 7.40 – 7.29 (m, 5H), 5.15 (br. s., 2H), 4.77 – 4.67 (m, 1H), 4.12 (br. s., 1H), 3.96 – 3.85 (m, 1H), 3.48 (br. s., 2H), 2.71 (t, J=12.5 Hz, 1H), 2.52 – 2.36 (m, 1H), 2.1 1 – 1.97 (m, 2H), 1.90 – 1.71 (m, 2H).

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-Chloropyrazin-2-yl)methanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;; ; 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

Application 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 a solution of l-methyl-4,5,6,7-tetrahydro-lH-indazole-4-carboxylic acid (6 g, 33 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (6 g, 33 mmol) in 200 mL of DCM was added TEA (9 g, 88 mmol) dropwise. The resulting mixture was stirred at room temperature for 5 mins, and then HATU (12.5 g, 33 mmol) was added to the solution in portions at 0 C. The mixture was stirred at room temperature for 2 hours. Water was added, the DCM layers was separated, and washed with brine, dried over Na2S04. The solvent was removed and the residue was purified by column chromatography on silica gel (PE/THF = 5/1 v/v%) to afford N-((3-chloropyrazin-2- yl)methyl)-l-methyl-4,5,6,7-tetrahydro-lH-indazole-4-carboxamide (1.5 g, 15 %). MS-ESI (m/z): 306 (M+l) + (Acq Method: 10-80AB_2min_220&254.1cm; Rt: 0.93 min)

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.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/113942; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature 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.

4- (benzyloxycarbonyl) bicyclo [2.2.1] heptane-1-carboxylic acid (2g, 6.9mmol), HATU (2.89g, 7.6mmol),DIEA (3.56g, 27.6mmol) and (3-chloropyrazin-2-yl) methylamine hydrochloride (1.3g, 7.24mmol)The DMF (20 mL) solution was stirred at room temperature for 6 hours.Pour into water (100 mL) and extract with ethyl acetate (2 ¡Á 30 mL). The organic phase was washed with saturated aqueous NaCl solution.The organic phase was separated, dried over Na 2 SO 4, filtered and evaporated.Purified by column chromatography with ethyl acetate / petroleum ether = 1: 1 ~ 1: 0 to obtain 2g of the desired compound A-1, yield: 70%.

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

Reference:
Patent; Nanjing Gentai Pharmaceutical Co., Ltd.; Chen Rongyao; (65 pag.)CN110964016; (2020); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route 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.

(2R,5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-(hydroxymethyl) morpholine-4-carboxylate (2g, 4.12 mmol) was dissolved in 100 mL CH2Cl2and cooled to 0 C. TEMPO(0.13 g, 0.82 mmol) was added, followed by (diacetoxyiodo)benzene (2.65 g, 8.24 mmol). The ice bath was removed, and the reaction was allowed to warm to room temperature and stirred overnight. The mixture was diluted with 200 mL ethyl acetate and washed with 10% Na2S203, aq. satd. NaHC03, and brine. The organic phase was dried with Na2S04, filtered and concentrated to give (2R,5R)-4-(tert- butoxycarbonyl)-5 -(((tert-butyl diphenylsilyl)oxy)methyl)morpholine-2-carboxylic acid (1.36g, 66%). LCMS: [M-H]+:498.23 Ret. time= 1.33 min, LC-MS method E). Used as such for the next step without any further purification. (2R,5R)-4-(tert-butoxycarbonyl)-5-(((tert- butyldiphenylsilyl)oxy)methyl)morpholine-2-carboxylic acid (1.5g, 3.0 mmol) and (3- chloropyrazin-2-yl)methanamine. HC1 salt (0.54g, 3.0 mmol) were dissolved in DMF 100 mL. To the reaction mixture was added Et3N (0.76g, 6.0 mmol) followed by slow addition of HATU (1.37g, 3.6 mmol) at 0 C. The reaction was stirred at rt for 1 day under a stream of nitrogen and then quenched with sat. NaHC03 (100 mL) and extracted with EtOAc(2xl50 mL). The combined organic layer was washed with water(200 mL) , brine(200mL), dried over anhydrous Na2S04, filtered, and evaporated. The crude residue was subjected to column purification using 20-50%) EtO Ac/Hex. to give (2R,5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy) methyl)-2-(((3-chloropyrazin- 2-yl)methyl)carbamoyl)morpholine-4-carboxylate (0.86g, 46%). LCMS: [M-Boc +H]+:525.25 Ret. time= 2.74 min, LC-MS method E).

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

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

Related Products 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.

To a mixture of (l^S^-S-^ethoxycarbony^^^^-trimethylcyclopentanecarboxylic acid (4.93 g, 23.01 mmol) and TEA (9.62 mL, 69.0 mmol) and HATU (13.12 g, 34.5 mmol) in DCM (100 mL) was stirred at 12 C for 30 min. (3-chloropyrazin-2-yl) methanamine hydrochloride (4.97 g, 27.6 mmol) was added and the mixture was stirred at 12 C for overnight. The reaction was complete detected by LC-MS. The mixture was added DCM (100 mL) and washed and brine. The organic layer was dried over Na2S04, purified with silica gel to give the title compound. XH NMR (400MHz, CDC13): delta 8.46 (d, J=2.3 Hz, 1H), 8.34 (s, 1H), 6.70 (br. s., 1H), 4.81 – 4.66 (m, 2H), 3.69 (s, 3H), 2.74 (t, J=9.2 Hz, 1H), 2.65 (dt, J=6.8, 12.6 Hz, 1H), 2.34 – 2.22 (m, 1H), 1.91 – 1.80 (m, 1H), 1.54 (ddd, 3=4.1, 9.6, 13.7 Hz, 1H), 1.32 (s, 3H), 1.25 (s, 3H), 0.81 (s, 3H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph, A.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; LIU, Shilan; (85 pag.)WO2016/109219; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. SDS of cas: 939412-86-9

Intermediate 11-14. Step 7 : N-((3-chloropyrazin-2-yl)methyl)-9.9-difluoro-6-oxooctahvdro-lH-quinolizine-3- carboxamide To a solution of 9,9-difluoro-6-oxooctahydro-lH-quinolizine-3-carboxylic acid (1.9 g, 8.15 mmol) in THF (40 ml) was added (3-chloropyrazin-2-yl)methanamine hydrochloride (2.2 g, 12.22 mmol), HATU (4.65 g, 12.22 mmol) and TEA (6.81 ml, 48.9 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was treated with EA (200 ml) and water (200 ml), the organic layer was dried over Na2SC>4, filtered and concentrated. The residue was purified by column chromatography on silica gel eluted with PE/DCM/THF = 1/1/1 to give N-((3-chloropyrazin-2-yl)methyl)-9,9-difluoro-6-oxooctahydro-lH-quinolizine-3-carboxamide. lH NMR (400 MHz, CDC13) delta ppm 1.63 – 1.85 (m, 2 H), 1.99 – 2.29 (m, 3 H), 2.32 – 2.81 (m, 5 H), 3.46 – 3.62 (m, 1 H), 4.33 – 4.98 (m, 3 H), 8.15 – 8.24 (m, 1 H), 8.30 – 8.40 (m, 1 H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph, A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; XU, Jiayi; YU, Wensheng; YU, Younong; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (211 pag.)WO2016/109221; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

To a solution of 3-(l -methoxy-2-methyl-l -oxopropan-2-yl)cyclohexanecarboxylic acid (1500 mg, 6.57 mmol) in THF (20 ml) was added HATU (3748 mg, 9.86 mmol), DIEA (3.44 ml, 19.71 mmol) and(3-chloropyrazin-2-yl)methanamine hydrochloride (1538 mg, 8.54 mmol) in one portion. After the addition was completed, the mixture was stirred at 25 C for 12h. The The reaction was quenched by addtion of water. The mixture was extracted with ethyl acetate several times. The combined organics was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residure was purified by column chromagrophy on silica gel (PE/THF=4) to afford methyl 2-(3-(((3-chloropyrazin-2- yl)methyl)carbamoyl)cyclohexyl)-2-methylpropanoate as a light solid. XH NMR (400 MHz, METHANOL-^) delta ppm 1.01 – 1.07 (m, 1 H) 1.12 (s, 6 H) 1.26 (d, J=12.13 Hz, 1 H) 1.32 – 1.38 (m, 2 H) 1.57 – 1.62 (m, 1 H) 1.69 – 1.77 (m, 2 H) 1.86 (br. s., 2 H) 2.30 – 2.36 (m, 1 H) 3.65 (s, 3 H) 4.60 (s, 2 H) 8.31 – 8.34 (m, 1 H) 8.50 – 8.52 (m, 1 H) ppm.

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; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph, A.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; LIU, Shilan; (85 pag.)WO2016/109219; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem