Pyrazines

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

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 50866-30-3 as follows. Recommanded Product: 50866-30-3

To a solution of 6-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (4.4 g) in dimethylformamide (62 mL) was added acetic acid (2.4 mL), 5-methylpyrazine-2-carbaldehyde (2 g) and sodium triacetoxyborohydride (5.27 g). The reaction mixture stirred for 2 h at ambient temperature and was carefully quenched with saturated sodium bicarbonate solution, extracted 3* with methylene chloride, dried with magnesium sulfate, filtered and concentrated. Purification via Biotage MPLC chromatography eluding with 1-4% methanolmethylene chloride/0.5% saturated ammonium hydroxide provided the title compound (3.9 g). 400 MHz 1H NMR (CDCl3) delta 8.52-8.48 (m, 1H), 8.38 (s, 1H), 8.02 (s, 1H), 4.81-4.75 (m, 1H), 4.11-4.01 (m, 3H), 3.79-3.75 (m, 1H), 3.60-3.53 (m, 2H), 3.40-3.32 (m, 1H), 3.10-3.08 (m, 1H), 2.94 (m, 1H), 2.63-2.57 (m, 1H), 2.53 (d, J=7.5 Hz, 1H), 2.37-2.18 (m, 4H), 1.90-1.83 (m, 2H), 1.67-1.60 (m, 1H), 1.54-1.47 (m, 1H), 0.95-0.92 (m, 3H). MS: (M+H m/z 424.2).

According to the analysis of related databases, 50866-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2009/30003; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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.

3-Amino-6-bromo -N- (3,4- difluorobenzyl) pyrazine-2-carboxamide: A mixture of 1.51 g 3-amino-6-bromo-2-carboxylic acid (6.93 mM mole), 30 ml dimethylformamide, 1.23 ml 3,4-difluoro benzylamine (10.4 mmol) and 2.40 ml N, N- diisopropylethylamine (13.8 mmol) in combination and stirred together, the batch and then 2.89 g (7-azo BTA) -N, N, N ‘, N’- tetramethyluronium hexafluorophosphate (7.60 mmol) and stirred for two hours , was added 250 ml of ethyl acetate and 150 ml of water, filtered, the organic phase was washed with 150 ml aqueous sodium bicarbonate wash, 50 ml brine, dried over magnesium sulfate drained, purified by flash column chromatography (0-50 % ethyl acetate; n-hexane), to collect 0.899 g of yellow powder (38%).

The synthetic route of 486424-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN MA INC.; SUNESIS PHARMACEUTICALS, INC.; ARNDT, JOSEPH; CHAN, TIMOTHY; GUCKIAN, KEVIN; KUMARAVEL, GNANASAMBANDAM; LEE, WEN-CHERNG; LIN, EDWARD YIN-SHIANG; SCOTT, DANIEL; SUN, LIHONG; THOMAS, JERMAINE; VAN VLOTEN, KURT; WANG, DEPING; ZHANG, LEI; ERLANSON, DANIEL; (469 pag.)TWI525093; (2016); B;,
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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 5-chloropyrazine-2-carboxylate

Preparation 10 To a solution of methyl 5-chloropyrazine-2-carboxylate (500 mg) in MeOH (5 mL) was added 28% NH3 aqueous solution (5 mL), and the mixture was stirred at ambient temperature. The precipitated solid was collected by filtration and washed with diisopropyl ether to afford 5-chloropyrazine-2-carboxamide (303 mg) as a solid.

The synthetic route of 33332-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; EP2123651; (2009); 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

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. 17890-77-6, name is 3-Amino-6-bromopyrazine-2-carboxamide, A new synthetic method of this compound is introduced below., Computed Properties of C5H5BrN4O

Step 3: Synthesis of Intermediate D’ as described in the general scheme: 2,5-dibromo-3-amidopyrazine A mixture of C’ (200 g, 922 mM), aq. hydrobromic acid 47% (500 mL) and acetic acid (100 mL) is cooled to -10 C. Bromine (47.25 mL, 922 mM) is then added to the reaction mixture over 45 min at -10 C. A solution of sodium nitrite (190 g, 2.765 M) in water (400 mL) is then added over 2h, whilst maintaining the reaction mixture temperature below -5 C. Upon completion of the addition, the reaction mixture is further stirred for 30 min. A solution of sodium thiosulfate (250 g) in water (712 mL) is then added over 30 min forming a suspension. The solid is isolated by filtration, washed with water (400 mL*2) and dried at 50-55 C. under vacuum to afford crude D’. Crude D’ (186 g) is suspended in a solution of 2-butanone (93 mL) and hexane (279 mL) and then stirred at 30 C. for 1 hr. The solid is isolated by filtration, the cake is washed with a 1:3 mixture of 2-butanone (93 mL) and hexane (186 mL) and dried at 50 C. for 3 hrs to afford clean D’.

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; WIGERINCK, Piet Tom Bert Paul; ANDREWS, Martin James Inglis; De WEER, Marc Maurice Germain; SABOURAULT, Nicholas Luc; KLUGE, Stefan Christian; US2011/118269; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 14667-55-1, name is 2,3,5-Trimethylpyrazine, 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. Recommanded Product: 2,3,5-Trimethylpyrazine

General procedure: An equimolecular mixture of 2,3-dimethylpyrazine (0.46 mmol, 50 mg) and 3,5-dichlorosalicylic acid (0.46 mmol, 95.8 mg) was dissolved in 15 mL ethanol at room temperature and stirred for about 30 min, followed by filtrating and slow evaporation. Colorless block-like crystals were obtained within 2 weeks with the total yield of 23.3%. IR (KBr pellet, cm-1): 3456, 3084, 2856, 2423, 1669, 1580, 1441, 1358, 1313, 1225, 1169, 1008, 875, 803, 742, 697, 608, 553. The colorlessblock-like crystal of cocrystal 2 and colorless needle crystals of cocrystal 3 were obtained in the similar way as cocrystal 1, but utilized 2,5-DMP and TMP instead of 2,3-DMP, with the total yield of 30.2% and 25.2%, respectively. IR (KBr pellet, cm-1) for cocrystal 2: 3445, 3079, 2868, 2402, 1669, 1586, 1447, 1363, 1308, 1225, 1175, 1053, 880, 803, 753, 692, 608, 558. IR (KBr pellet, cm-1) for cocrystal 3: 3445, 3073, 2935, 2402, 1669, 1586, 1441, 1391, 1352, 1285, 1241, 1175, 1024, 886, 708, 603, 558.

The synthetic route of 2,3,5-Trimethylpyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Ya-an; Yan, Cui-Min; Chen, Chen; Zhao, Xiao-Qing; Li, Tian; Sun, Bai-Wang; Research on Chemical Intermediates; vol. 45; 11; (2019); p. 5745 – 5760;,
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. 98-97-5, name is Pyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C5H4N2O2

General procedure: A catalytic amount of concentrated H2SO4 wasadded to a solution of carboxylic acids 16(a-j) (1.0 mmol)in 50 mL of methanol, and the mixture was refluxed for 6 h. It was allowed to cool. The saturated solution ofNaHCO3 was added to the reaction mixture, and it wasextracted with EtOAc (2 X 50 mL). The combined organiclayer was dried Na2SO4 and concentrated to obtain puremethyl esters 17(a-j).

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:
Article; Murty; Penthala, Raju; Polepalli, Sowjanya; Jain; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 627 – 643;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 77112-53-9,Some common heterocyclic compound, 77112-53-9, name is Imidazo[1,2-a]pyrazine-2-carboxylic acid, molecular formula is C7H5N3O2, 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.

General procedure: Imidazo[1,2-a]pyrazine-2-carboxylic acid (5) (1.0 equiv.) Mukaiyama?s reagent and 2-chloro-1-methylpyridinium iodide (1.2 equiv.) were suspended in DMF (5.0 mL) under nitrogen atmosphere. Into the reaction mixture, aliphatic/aromatic amines (6a-l) (1.0 equiv.) and 1-methylimidazole (2.0 equiv.) were added. A homogeneous solution was formed after a gentle stirring. The reaction mixture was sealed in a microwave glass reactor and then irradiated by microwave oven at a constant temperature of 80 C with continuous stirring (1 min ramp, 15 min reaction time). After the reaction was completed, the solvent was removed through a rotary evaporator and the resulting residue was extracted by a biphasic system of 45 mL diethyl ether and 45 mL water. After the layer separation, the ether layer was dried by anhydrous sodium sulphate, followed by an evaporation of ether to get compounds 7a-l (Scheme-I).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Imidazo[1,2-a]pyrazine-2-carboxylic acid, its application will become more common.

Reference:
Article; Jyothi, Boggavarapu; Madhavi, Nannapaneni; Asian Journal of Chemistry; vol. 32; 1; (2020); p. 84 – 90;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 56423-63-3, 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. 56423-63-3, name is 2-Bromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Reaction Scheme 6EXAMPLE 30: l-(4-methoxybeDzylV3-methyl-5-(pyrazin-2-ylVlH-pyrazolor3.4- blpyridine To a stirred solution of compound 8 (230 mg, 0.627 mmol) and 2-bromopyrazine 43 (100 mg, 0.63 mmol) in DME (3 mL), ethanol (1 mL) and water (0.2 mL) was added sodium carbonate (135 mg, 1.26 mmol) and was degassed for 10 min followed by the charging Pd(PPh3)4 (7.5 mg, 0.03 equivalent). The resulting reaction mixture was purged with N2 and degassing was submitted for heating at 80C overnight under pressure in a sealed tube. After completion of the reaction the reaction was diluted with ethyl acetate and water. The organic layer was separated and aqueous phase was extracted with ethyl acetate. The combined organic layer was washed with brine and dried over sodium sulphate and evaporated. The crude product was flash chromatographed with 100-200 mesh silica gel eluting the pure compound at 20% ethyl acetate in hexane as off white colored solid of compound 44 in 30 mg. The product 44 was confirmed by 1H NMR (400 MHz, CDC13) delta: 9.18 (s, 1H), 9.17 (s, 1H), 9.10 (d, J=1.58 Hz, 2H), 8.67 (s, 1H), 8.64 (s, 1H), 7.35 (d, 2H), 6.84 (d, 1H), 5.62 (d, 2H), 3.76 (s, 3H), 2.62 (s, 3H).

The synthetic route of 2-Bromopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem