939412-86-9 Archives - Page 7 of 9

Extracurricular laboratory: Synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride

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.

Application 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

Analyzing the synthesis route of (3-Chloropyrazin-2-yl)methanamine hydrochloride

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 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 solution of (6R,8aS)-l,l-dimethyl-3-oxohexahydro-lH-oxazolo[3,4- a]pyridine-6-carboxylic acid (100 mg,0.468 mmol) in anhydrous DCM (40 mL) was added (COCl)2 (158.9 mg, 0.469mmol) at 0 C, then DMF (one drop) was added and the mixture was stirred at 25 C for 1.5 hrs. The mixture was concentrated in vacuo, which then diluted with DCM (5 mL) was added to a solution of (3-chloropyrazin-2- yl)methanamine hydrochloride (101.32 mg, 0.562 mmol), TEA (94.91 mg, 0.938 mmol) in DCM (10 mL). The mixture was stirred at 25 C for 3 hrs, The mixture was quenched by the addition of water (10 mL) at 0 C , the mixture was then extracted with DCM (50 mL x 3), the combined organic layers were washed with 1M HC1 (10 mL), brine (20mL), dried over sodium sulfate, filtered and concentrated to give (6R,8aS)-N- ((3 -chloropyrazin-2-yl)methyl)- 1 , 1 -dimethyl-3 -oxohexahydro- 1 H-oxazolo [3 ,4- a]pyridine-6-carboxamide (150 mg, 94.19%) as a colorless oil. 1H NMR (400MHz, CHLOROFORM-d) d = 8.46 (d, J=2.5 Hz, IH), 8.34 (d, J=2.5 Hz, IH), 6.94 (br. s., IH), 4.78 – 4.60 (m, 2H), 4.09 (dd, J=4.1, 12.7 Hz, IH), 3.26 (dd, J=3.3, 11.8 Hz, IH), 3.08 (dd, J=11.8, 13.1 Hz, IH), 2.43 (tt, J=4.1, 11.7 Hz, lH), 2.16 (d, J=12.5 Hz, IH), 1.86 – 1.70 (m, 2H), 1.46 (s, 3H), 1.44 – 1.38 (m, IH), 1.35 (s, 3H).

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

Extracurricular laboratory: Synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride

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.

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

(g) N-((3-chloropyrazin-2-yl)methyl)-1-oxooctahydropyrido[1,2-c][1,3]oxazine-7-carboxamide To a solution of 1-oxooctahydropyrido[1,2-c][1,3]oxazine-7-carboxylic acid (3.13 g, 15.7 mmol) in THF (100 mL) was added (3-chloropyrazin-2-yl)methanamine hydrochloride (2.8 g, 15.7 mmol), TEA (4.8 g, 47.2 mmol) and HATU (6 g, 15.7 mmol). The mixture was stirred at room temperature for 2 h. The reaction was complete detected by LCMS. The reaction mixture was treated with DCM and water, the organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with DCM/THF=5/1 to give N-((3-chloropyrazin-2-yl)methyl)-1-oxooctahydropyrido[1,2-c][1,3]oxazine-7-carboxamide (4.7 g, 92%). 1H-NMR (CDCl3, 400 MHz) delta 1.40-1.49 (m, 1H), 1.71-1.92 (m, 3H), 2.04-2.26 (m, 2H), 2.43-2.57 (m, 1H), 2.81-2.97 (m, 1H), 3.31-3.42 (m, 1H), 4.13-4.27 (m, 2H), 4.46-4.56 (m, 1H), 4.64 (d, J=4.70 Hz, 2H), 8.29 (d, J=2.35 Hz, 1H), 8.44 (d, J=2.35 Hz, 1H).

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; 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

Analyzing the synthesis route of (3-Chloropyrazin-2-yl)methanamine hydrochloride

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.

Application 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.

A suspension of 3-(trifluoromethyl)-1 ,2,4-triazolo[4,3-a]piperazine hydrochloride (10.94 mmol, 2.5 g) in a mixture of tetrahydrofuran (50 ml) and N,N-diisopropylethylamine (32.8 mmol, 5.42 ml) was added to trichloromethyl chloroformate (13.12 mmol, 1.583 ml) in tetrahydrofuran (50 ml) at 0 C. After one hour at 0 C the reaction mixture was filtered over decalite and the filter washed with tetrahydrofuran. Then the filtrate was concentrated in vacuo. The residue (4.52 g, crude) was added to 2-aminomethyl-3- chloropyrazine hydrochloride (content 77%; 8.43 mmol, 1.97 g) in a mixture of dichloromethane (50 ml) and triethylamine (25.3 mmol, 3.52 ml) and the reaction mixture was stirred over night at room temperature. Then the reaction mixture was filtered over decalite and the filter washed with dichloromethane. The filtrate was washed with water. The aqueous layer was extracted three times with dichloromethane. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. The crude product was purification by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) to give N-((3-chloropyrazin-2-yl)methyl)-3- (trifluoromethyl)-5,6-dihydro-[1 ,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxamide (2.707g).

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; 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

New learning discoveries about (3-Chloropyrazin-2-yl)methanamine hydrochloride

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.

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.

A new synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride

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.

Related Products 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.

Application of (3-Chloropyrazin-2-yl)methanamine hydrochloride

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

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 2-aminomethyl-3-chloropyrazine hydrochloride (content 80%; 4.44 mmol, 1 g) and N,N- diisopropylethylamine (17.77 mmol, 3.10 ml) in dichloromethane (20 ml) under N2 at 0C was added N- methylpiperazin-4-carbamoyl chloride hydrochloride (4.89 mmol, 0.973 g). After stirring at room temperature for 18 hours water was added and the mixture extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Purification by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) gave N-((3-chloropyrazin-2-yl)methyl)-4-methylpiperazine-1 -carboxamide (513 mg).

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

New downstream synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride

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

(3-Chloropyrazin-2-yl)methanamine hydrochloride (content 77%, 1.634 g, 6.99 mmol) and 1 -methyl-5- oxopyrrolidine-3-carboxylic acid (1.000 g, 6.99 mmol) were suspended in dichloromethane (20 ml) and the reaction mixture was cooled to 0C under an argon atmosphere. N,N-diisopropylethylamine (3.05 ml, 17.48 mmol), 1 -ethyl-3-(3-dimethylaminopropyl) carbodiimide) hydrochloride (1.474 g, 7.69 mmol) and 1-hydroxy- 7-azabenzotriazole (0.476 g, 3.50 mmol) were added and the reaction mixture was stirred at room temperature overnight. Reaction was worked up by evaporting the solvents and a dark brown oil was obtained. This crude product was submitted to column chromatography (silica gel; dichloromethane / methanol 96/4) to yield impure material that was further purified by column chromatography (silica gel; dichloromethane / methanol 99/1 ) to give N-((3-chloropyrazin-2-yl)methyl)-1 -methyl-5-oxopyrrolidine-3- carboxamide (1.24 g).

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

Extended knowledge of (3-Chloropyrazin-2-yl)methanamine hydrochloride

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 2-aminomethyl-3-chloropyrazine hydrochloride (content 76%, 69.4 mmol, 16.43 g), cis-4- hydroxycyclohexanecarboxylic acid (69.4 mmol, 10 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (104 mmol, 19.95 g), 4-dimethylaminopyridine (6.94 mmol, 0.847 g) in dichloromethane (200 ml) was added N,N-diisopropylethylamine (173 mmol, 30.3 ml, 22.41 g) until pH became eight and the reaction mixture was stirred at room temperature for 18 hours. Then it was concentrated in vacuo, ethyl acetate and water were added and the organic layer separated. The water layer was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried (MgSC ) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane with gradient of 0% to 7% methanol). All fractions that contained product were combined and concentrated in vacuo. The residue was dissolved in dichloromethane (400 ml) and washed with 2 M sodium hydroxide (aq) (three times 100 ml), washed with brine, dried (MgSC ) and concentrated in vacuo to give (cis)-N-((3- chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide (15.47 g)

Application of (3-Chloropyrazin-2-yl)methanamine hydrochloride

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, 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.

N,N-Diisopropylethylamine (19.35 mL, 111.09 mmol) was added dropwise in ten minutes to a mixture of (2S)-2-[benzyloxycarbonyl(methyl)amino]propanoic acid (6.59 g, 27.77 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (5.00 g, 27.77 mmol) and HATU (15.84 g, 41.66 mmol) in dichloromethane (250 mL) and the resulting mixture was stirred for three hours at 20 C. The mixture was washed once with aqueous saturated. sodium bicarbonate solution (200 mL) and once with aqueous saturated ammonium chloride solution (200 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash column chromatography on silicagel (0-100% ethyl acetate in heptane) to give benzyl N-[(1S)-2-[(3-chloropyrazin-2-yl)methylamino]-1-methyl-2- oxo-ethyl]-N-methyl-carbamate (9.2 g, 91.3%) as a colorless oil. Data: LC-MS (Method A) Rt: 5.32 min; m/z 363.2 (M+H)+.

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

Reference:
Patent; ACERTA PHARMA B.V.; BARF, Tjeerd; DE ZWART, Edwin; VERKAIK, Saskia; HOOGENBOOM, Niels; DEMONT, Dennis; KAPTEIN, Allard; COVEY, Todd; (180 pag.)WO2019/239374; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem