Category: 939412-86-9

Electric Literature 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.

(f) (3S,7R,9aS)-N-((3-chloropyrazin-2-yl)methyl)-3-methyl-4-oxooctahydropyrido[2,1-c][1,4]oxazine-7-carboxamide To a solution of (3S,7R,9aS)-3-methyl-4-oxooctahydropyrido[2,1-c][1,4]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 0 C. under N2 atmosphere, and followed by 1 drop of DMF. The resulting mixture was stirred at 0 C. 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 0 C. under N2 atmosphere, and the mixture was stirred for 12 hrs at 15 C. Then the mixture was diluted with DCM (5 mL), and H2O (5 mL). The organic layer was washed with brine (5 mL), dried over Na2SO4, 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 (400 MHz, CDCl3) delta=8.42 (d, J=2.5 Hz, 1H), 8.29 (d, J=2.5 Hz, 1H), 7.17 (br. s., 1H), 4.76-4.57 (m, 2H), 4.16 (q, J=6.9 Hz, 1H), 3.92 (dd, J=4.1, 12.2 Hz, 1H), 3.74 (dd, J=2.5, 12.0 Hz, 1H), 3.37-3.25 (m, 1H), 2.73 (t, J=12.3 Hz, 1H), 2.42 (tt, J=4.0, 11.8 Hz, 1H), 2.18-2.03 (m, 2H), 1.99-1.84 (m, 1H), 1.79-1.68 (m, 2H), 1.44 (d, J=7.0 Hz, 3H).

Statistics shows that (3-Chloropyrazin-2-yl)methanamine hydrochloride is playing an increasingly important role. we look forward to future research findings about 939412-86-9.

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

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. Recommanded Product: 939412-86-9

(e) (trans)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4-oxohexahydro-1H-pyrido[1,2-a]pyrazine-2(6H)-carboxylate A mixture of (trans)-2-((benzyloxy)carbonyl)-4-oxooctahydro-1H-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 is 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 Na2SO4, 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-1H-pyrido[1,2-a]pyrazine-2(6H)-carboxylate (600 mg, yield 35.3%). 1H NMR (400 MHz, 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), 2.11-1.97 (m, 2H), 1.90-1.71 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939412-86-9, its application will become more common.

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

Related Products 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.

To a solution of l-((benzyloxy)carbonyl)-2-cyanopiperidine-4-carboxylic acid (30 mg, 0.104 mmol) in anhydrous DCM (5 mL) was added HATU (43.5 mg, 0.114 mmol), Et3N (31.56 mg, 0.312 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (20.5 mg, 0.114 mmol). The reaction mixture was stirred at 13 C for 12 hrs. The reaction was quenched by the addtion of water (10 mL), then it was extracted with DCM (10 mL x 3), the combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated to afford the crude product ,which was purified on silica gel column chromatograph (PE/THF = 100% ~ 50 %) to give benzyl 4-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-cyanopiperidine- 1 -carboxylate (40 mg, yeild 93%) .1H NMR (400MHz, METHANOL-d4) delta= 8.54 (d, J=2.5 Hz, 1H), 8.35 (d, J=2.5 Hz, 1H), 7.44 – 7.31 (m, 5H), 5.53 (d, J=4.0 Hz, 1H), 5.21 (d, J=2.5 Hz, 2H), 4.64 (s, 2H), 4.25 (d, J=13.1 Hz, 1H), 2.87 – 2.84 (m, 1H), 2.88 – 2.77 (m, 3H), 2.16 (d, J=12.5 Hz, 1H), 2.02 – 1.91 (m, 2H), 1.66 (dq, J=4.8, 12.9 Hz, 1H).

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; 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, 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.

(g) benzyl 4-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-cyanopiperidine-1-carboxylate To a solution of 1-((benzyloxy)carbonyl)-2-cyanopiperidine-4-carboxylic acid (30 mg, 0.104 mmol) in anhydrous DCM (5 mL) was added HATU (43.5 mg, 0.114 mmol), Et3N (31.56 mg, 0.312 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (20.5 mg, 0.114 mmol). The reaction mixture was stirred at 13 C. for 12 hrs. The reaction was quenched by the addition of water (10 mL), then it was extracted with DCM (10 mL*3), the combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated to afford the crude product, which was purified on silica gel column chromatograph (PE/THF=100%?50%) to give benzyl 4-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-2-cyanopiperidine-1-carboxylate (40 mg, yield 93%) NMR (400 MHz, METHANOL-d4) delta=8.54 (d, J=2.5 Hz, 1H), 8.35 (d, J=2.5 Hz, 1H), 7.44-7.31 (m, 5H), 5.53 (d, J=4.0 Hz, 1H), 5.21 (d, J=2.5 Hz, 2H), 4.64 (s, 2H), 4.25 (d, J=13.1 Hz, 1H), 2.87-2.84 (m, 1H), 2.88-2.77 (m, 3H), 2.16 (d, J=12.5 Hz, 1H), 2.02-1.91 (m, 2H), 1.66 (dq, J=4.8, 12.9 Hz, 1H).

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

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

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.

A mixture of (trans)-6-oxooctahydro-l H-quinolizine-3 -carboxylic acid (520 mg, 2.64 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (570 mg, 3.17 mmol), HATU (1.50 g, 3.95 mmol) and TEA (0.79 g, 7.91 mmol) in DCM (13 mL) was stirred at 25 C overnight. The mixture was quenched with H20 (40 mL) and extracted with DCM (15 mL*3).The combined organic layerswere dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product.The crude product was purified by column chromatography on silica gel eluting with PE / THF (0-60%) to give (trans)- N-((3-chloropyrazin-2-yl)methyl)-6-oxooctahydro-l H-quinolizine-3 -carboxamide (0.7 g, 82.35%) as a light yellow solid. 1H NMR (400MHz, CDC13) delta = 8.53 – 8.41 (m, 1H), 8.33 (d, J=2.5 Hz, 1H), 6.96 (br. s., 1H), 5.08 – 4.88 (m, 1H), 4.73 – 4.61 (m, 2H), 3.40 – 3.26 (m, 1H), 2.72 – 2.57 (m, 1H), 2.47 – 2.28 (m, 3H), 2.12 – 2.00 (m, 2H), 1.89 – 1.77 (m, 4H), 1.73 – 1.62 (m, 1H), 1.58 – 1.47 (m, 1H).

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; 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

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, HPLC of Formula: C5H7Cl2N3

N,N-diisopropylethylamine (109 mmol, 18.01 ml) and a solution of benzyl 3-(chlorocarbonyl)azetidine-1- carboxylate (5.53 g) in dichloromethane (32.5 ml) were added to a stirred suspension of 2-aminomethyl-3- chloropyrazine hydrochloride (content 77%; 21.80 mmol, 5.10 g) in dichloromethane (55 ml) at room temperature to give a dark brown solution. After stirring at room temperature for two hours the reaction mixture was quenched with water and filtered over decalite. Layers were separated and to the aqueous layer saturated aqueous sodium hydrogencarbonate solution was added and the layer was extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane / methanol gradient 10/0 to 9/1 ) to give benzyl 3-((3-chloropyrazin-2- yl)methylcarbamoyl)azetidine-1-carboxylate (6.46 g).NMR (CDCl3, 400 MHz): delta 3.37 -3.45 (m, 1 H), 4.16 – 4.30 (m, 4H), 4.71 (d, J = 5 Hz, 2H), 5.10 (s, 2H), 6.92 – 6.97 (m, 1 H), 7.28 – 7.47 (m, 5H), 8.33 (d, J = 2 Hz, 1 H), 8.44 (d, J = 2 Hz, 1 H).

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; 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

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.

A mixture of trans-4-oxooctahydropyrido[2,l-c][l,4]oxazine-7-carboxylic acid (2.2 g, 11.0 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (2.2 g, 3.70 mmol), HATU (6.3 g, 16.6 mmol ) and triethylamine (4.7mL, 33.1 mmol ) in dichloromethane (100 mL) was stirred at room temperature for 4 hours. The reaction mixture was washed with water (150 mL) and extracted with dichloromethane (50 mLx 3) and the combined organic layers were concentrated in vacuo to afford the crude product, which was purified by silica gel column chromatography (THF: PE = 10%~100%) to give trans-N-((3-chloropyrazin-2-yl)methyl)-4-oxooctahydropyrido[2,l- c][l,4]oxazine-7-carboxamide (2.1 g, 58.3% yield).1HNMR (400 MHz, CD3OD): delta =8.54 (d, J=2.4 Hz, 1H), 8.34 (d, J=2.3 Hz, 1H), 4.74 (dt, J=12.9, 1.9 Hz, 1H), 4.60-4.67 (m, 2H), 4.11 (s, 2H), 4.02 (dd, J=11.9, 4.3 Hz, 1H), 3.56-3.65 (m, 2H), 3.43-3.53 (m, 1H), 2.67-2.76 (m, 1H), 2.49 (tt, J=11.8, 3.7 Hz, 1H), 2.05-2.15 (m, 1H), 1.77-1.88 (m, 2H), 1.50 ppm (dd, J=l 1.8, 3.9 Hz, 1H). MS (ESI): M/Z (M+l): 325.1.

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.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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.

A mixture of (cis)-2-((benzyloxy)carbonyl)-4-oxooctahydro-l H-pyrido [1,2- a]pyrazine-7-carboxylic acid (0.7 g, 2.1 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (450 mg, 2.5 mmol), HATU (1.2 g, 3.1 mmol) and TEA (0.85 g, 8.4 mmol) in DMF (10 mL) was stirred at 25 C for overnight. Then the reaction mixture was poured into water, the mixture was extracted with EA (50 mix 3). The combined organic phase was washed with brine (100 mL), dried over Na2S04, concentrated in vacuo, the residue was purified by silica gel column chromatography (PE/THF = 1/3) to give (cis)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4-oxohexahydro-lH- pyrido[l,2-a]pyrazine-2(6H)-carboxylate (440 mg, yield 45.8 %).

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

Electric Literature of 939412-86-9, 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 939412-86-9 as follows.

Step-2: (0932) Preparation N-((3-chloropyrazin-2-yl)methyl)acetamide: (0933) [00353] To a solution of (3-chloropyrazin-2-yl)methanamine hydrochloride (3.5 g, 19.49 mmol) in dichloromethane (100 mL) was added diisopropylethylamine (10.18 mL, 38.99 mmol) followed by acetic anhydride (3.67 mL, 38.9 mmol) at room temperature. Then the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ice water (100 mL), basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (3 x 200 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified by silica gel column chromatography using 3% methanol in dichloromethane to afford the title compound N-((3- chloropyrazin-2-yl)methyl)acetamide (1.66 g, 46% yield) as a brown solid. Calculated (M+H): 186.0; Found (M+H): 186.1.

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.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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.

Example 3: Synthesis of 3-(4-Fluorophenyl)-imidazo[l,5-a]pyrazine-8-carboxylic acid (3);To a suspension of 2-aminomethyl-3-chloropyrazine hydrochloride (900 mg, 5 mmol) in dichloromethane (25 mL) is added 4-fluorobenzoyl chloride (730 lL, 6.1 mmol) followed by DIPEA (2.0 mL, 11 mmol). After 1 day, the mixture is concentrated and diluted with saturated aqueous ammonium chloride and extracted with EtOAc (3 x 40 mL). The combined organic layers are washed with brine (3 x 25 mL), dried over magnesium sulfate, filtered and concentrated. The residue is passed through a pad of silica gel using dichloromethane-heptane (1: 1) to load the sample and then eluting with dichloromethane to afford N-(3-chloro-pyrazin-2-ylmethyl)-4-fluoro-benzamide as an oil which partially solidified.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; WO2011/56440; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem