Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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 24241-18-7, Recommanded Product: 2-Amino-3,5-dibromopyrazine

Example 137 Step A: Ethanol (10.0 mL) and chloroacetaldehyde (2.6953 g of 50 % by weight solution in water, 17.17 mmol) were added into a pressure tube containing 2-amino-3, 5- dibromopyrazine (2.015 gm, 7.97 mmol). The heterogeneous reaction mixture was stirred at 70C. The reaction mixture assumed a homogenous appearance after heating began, and precipitation started to appear 3 h later. After a total of 22 h of heating, the reaction mixture was cooled to rt. The precipitate was filtered, washed with EtOH (-10 mL), and exposed to high vacuum to afford impure imidazopyrazine 137A as an ash- colored solid (1.699 g). lH NMR: 9.03 (s, 1H), 8.24 (d, J = 0.9, 1H), 7.91 (d, J = 1.2, 1H). (ESI) m/z (M+H) + = 277.79.

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, 2-Amino-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/84959; (2003); A1;,
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These common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, 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: 5,7-Dichloropyrido[3,4-b]pyrazine

Intermediate 5: 1,1-Dimethylethyl (3R)-3-{[(7-chloropyrido[3,4-b]pyrazin-5-yl)amino]methyl}-1-piperidinecarboxylate 5,7-dichloropyrido[3,4-b]pyrazine (1 g, 5.00 mmol) was taken up in N-Methyl-2-pyrrolidone (NMP) (10 ml) and treated with 1,1-dimethylethyl (3R)-3-(aminomethyl)-1-piperidinecarboxylate (1.179 g, 5.50 mmol) (Apollo Scientific Ltd) and diisopropylethylamine (1.310 ml, 7.50 mmol). The reaction was irradiated in a Biotage microwave at 130 C. for 30 min. The reaction was partitioned between EtOAc (100 ml) and water (100 ml). The organic layer was washed with brine (100 ml), dried using a hydrophobic frit and concentrated to give a black solid. This solid was purified on silica (50 g) and eluted with a 10-40% EtOAc/cyclohexane gradient. The appropriate fractions were combined and concentrated to give the title compound as a deep orange solid (1.542 g). LCMS (Method B): Rt=1.28 min, MH+=377.92

The synthetic route of 5,7-Dichloropyrido[3,4-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Atkinson, Stephen John; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander G.; Shipley, Tracy Jane; Wilson, David Matthew; Watson, Robert J.; US2014/5188; (2014); A1;,
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Electric Literature of 6966-01-4, A common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, 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.

0.15 eq. palladium (II) acetate and 0.2 eq. 1,1′-bis(diphenylphosphino)-ferrocene were combined in dimethylformamide under nitrogen and heated to 50 C. for 20 minutes. Het is as defined herein. The reaction was allowed to cool to room temperature and 1.0 eq. of the pyrazine, 1.5 eq. of the boronic acid and 1.15 eq. of triethylamine were added. The reaction was heated to 90 for 12 hours and allowed to cool to room temperature. The DMF was removed by rotary evaporation. The crude reaction mixture was dissolved in chloroform and washed twice with 1N aq. HCl and then twice with saturated aq. NaHCO3 solution. The organic layer was dried over sodium sulfate, filtered and concentrated. Material was purified by silica gel chromatography using 100% chloroform as eluent.

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2004/180905; (2004); A1;,
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Pyrazine | C4H4N2 – PubChem

58139-04-1, name is 2-Iodo-3-methoxypyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 2-Iodo-3-methoxypyrazine

Step 1: To a stirred mixture of sodium iodide (4.89 g, 32.67 mmol) and 2-iodo-3-methoxypyrazine (2.57 g,10.89 mmol) in acetonitrile (30 mL) at rt was added trimethylsilyl chloride (3.55 g, 32.67 mmol). The mixture was heatedat 70 C for 1.5 h. The mixture was cooled to rt and partitioned between a mixture of DCM, MeOH, and aq 2 M HCl. Theorganic layer was separated and the aqueous layer was extracted with additional DCM/MeOH mixture. The combinedorganic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford 3-iodopyrazin-2(1H)-one (1.21 g, 50%) as a brown solid that did not require further purification. 1H NMR (500 MHz, DMSO-d6) delta 12.54(br s, 1H), 7.42 (d, J = 3.7 Hz, 1H), 7.17 (d, J = 3.7 Hz, 1H); LCMS (ESI) m/z 223 (M+H)+.

The synthetic route of 58139-04-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
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Application of 1458-01-1, A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit. Methyl 3,5-diamino-6-phenylpyrazine-2-carboxylate (3a) General Method A using 2 (500 mg, 2.47 mmol) and phenylboronic acid (360 mg, 3.70 mmol) to give 3a (412 mg, 68%) as an off-yellow solid. MP 194-196 C; 1H NMR (500 MHz, DMSO-d6) delta 7.54 (s, 2H), 7.44 (s, 2H), 7.37 (s, 1H), 7.08 (s, 2H), 6.66 (s, 2H), 3.74 (s, 3H); 13C NMR (126 MHz, DMSO-d6) delta 167.3, 156.0, 154.5, 137.6, 130.1, 128.9, 128.5, 128.1, 111.7, 51.4; IR (neat) nu 3435.3, 3319.6, 3160.5, 2948-2852, 1684.9, 1650.1, 1595.2, 1246.1, 708.2, 646.1 cm-1; HRESI-MS m/z (M + H+) Anal for C12H13N4O2+ 245.1033, found 245.1051.

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
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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. 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H8ClF3N4

2,4, 5-TRIFLUOROPHENYLACETIC acid (2-1) (150 g, 0.789 MOL), Meldrum’s acid (125 g, 0.868 mol), and 4- (DIMETHYLAMINO) pyridine (DMAP) (7.7 g, 0063 mol) were charged into a 5 L three-neck flask. N, N-DIMETHYLACETAMIDE (DMAC) (525 mL) was added in one portion at room temperature to dissolve the solids. N, N-DIISOPROPYLETHYLAMINE (282 mL, 1.62 mol) was added in one portion at room temperature while maintaining the temperature below 40 C. Pivaloyl chloride (107 ML, 0.868 mol) was added dropwise over 1 to 2 h while maintaining the temperature between 0 and 5 C. The reaction mixture was aged at 5 C for 1 h. Triazole hydrochloride 1-4 (180 g, 0.789 mol) was added in one portion at 40-50 C. The reaction solution was aged at 70 C for several h. 5% Aqueous sodium hydrogencarbonate solution (625 ML) was then added dropwise at 20-45 C. The batch was seeded and aged at 20-30 C for 1-2 h. Then an additional 525 mL of 5% aqueous sodium hydrogencarbonate solution was added dropwise over 2-3 h. After aging several h at room temperature, the slurry was cooled to 0-5 C and aged 1 h before filtering the solid. The wet cake was displacement-washed with 20% aqueous DMAC (300 mL), followed by an additional two batches of 20% aqueous DMAC (400 mL), and finally water (400 mL). The cake was suction-dried at room temperature. The isolated yield of final product 2-3 was 89%.

The synthetic route of 762240-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2005/3135; (2005); A1;,
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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. 951626-95-2, name is Ethyl 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 951626-95-2

To a solution of cyclopropylmethyl bromide (0.101 g, 0.75 mmol) and ethyl 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (31.4 mg, 0.150 mmol) in acetonitrile (2 mL) was added cesium carbonate (147 mg, 0.45 mmol). The reaction mixture was heated overnight at 70 C. Upon cooling to room temperature, the insolubles were removed by filtration and the solvent evaporated to dryness to afford crude Intermediate 33.

The synthetic route of 951626-95-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2011/251184; (2011); A1;,
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Pyrazine | C4H4N2 – PubChem

Application of 486424-37-7, A common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, molecular formula is C5H4BrN3O2, 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.

Triethyl amine (0.57 ML, 4.13 mmol) was added to a mixture of 3-AMINO-6-BROMO-2- pyrazinecarboxylic acid (0.30 g, 1.38 mmol; described in: Ellingson, R. C.; Henry, R. L. J. Am. Chem. Soc. 1949,2798-2800), 0- (BENZOTRIAZOL-1-YL)-NNN’, N’- tetramethyluroniumtetrafluoroborate (0.486 g, 1.51 mmol) and 1-hydroxybenzotriazole (0.204 g, 1.51 mmol) in N, N-DIMETHYLFORMAMIDE/ACETONITRILE, (1: 1,5 ML). After stirring for 0.5 h at room temperature, 2-(LH-PYRROL-L-YL)-L-ETANAMINE (0.182 g, 1.65 mmol) was added and the resulting mixture was stirred overnight at room temperature. Approximately, 10 ML water was added and a precipitation was formed. The precipitation was filtered and washed with water which gave 0.21 g (50% yield) of a light brown solid: MS (ESP) M/Z 310,312 (M++1). The solid (0.16 g, 0.516 mmol) from previous step was dissolved in tetrahydrofuran/water (5: 1,5 mL) together with [4- [ (4-methyl-l-piperazinyl) sulfonyl] phenyl] boronic acid (0.220 g, 0.77 mmol), sodium carbonate (0.164 g, 1.55 mmol) and Pd (dppf) CL2 (0.013 g, 1.5 nmmol). The resulting mixture was stirred at 70 C overnight (N2-atmosphere). The mixture was evaporated onto silica and purified on silica using toluene/acetonitrile, (1: 2 to 1: 4), as the eluent which afforded a yellow solid which was dried in vacuo at 40 C. The product was dissolved in a methylene chloride/methanol mixture, (9: 1), and hydrochloride acid in diethyl ether (0.28 mL, 1 M) was added. The precipitate was washed with diethyl ether and dried in vacuo to give 69 mg (23% yield) of the title compound : 1H NMR (DMSO-d6) 5 8.94 (s, 1 H), 8.90 (t, J = 6 Hz, 1 H), 8.43 (d, J = 8 Hz, 2 H), 7.82 (d, J = 8 Hz, 2 H), 6.79 (t, J = 2 HZ, 2 H), 6.01 (t, J = 2 HZ, 2 H), 4.12 (t, J = 7 Hz, 2 H), 3.83 (d, J = 12 Hz, 2 H), 3.63 (quart, J = 6 Hz, 2 H), 3.44 (d, J = 12 Hz, 2 H), 3.15 (m, 2 H), 2.73 (m, 5 H) ; 13C NMR (DMSO-d6) 8 165.8, 154.5, 144.8, 140.8, 135.9, 133.3, 127.9, 126.1, 124.6, 120.7, 107.8, 51.5, 47.6, 43.0, 41.8 ; MS (ESP) M/Z 470 (M++1).

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

Reference:
Patent; ASTRAZENECA AB; WO2004/55009; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 63744-22-9

Example 8-1 :Preparation of 6,8-dibromo-3-iodo-imidazo[1 , 2-a]pyrazineTo a stirred solution of intermediate example 1 -1 (8.7 g g, 31 .4 mmol) in DMF (210 mL) was added NiS (7.42 g, 33 mmoi, 1 .05 eq) in one portion at rt. After 18 h stirring at 60 C, the solvent was removed in vaccuo and the residue was taken up in DCM and washed with water and saturated sodium thiosulfate solution. The organic phase was dried over sodium sulphate, filtered and the solvent was evaporated to yield 9.46 g (74.8 %) 6,8-Dibromo-3-iodo-imidazo[1 ,2-a]pyrazine: 1H-NMR (300 MHz, CDCl3): delta = 8.22 (1 H, s), 7.91 (1 H, s) ppm.

Statistics shows that 63744-22-9 is playing an increasingly important role. we look forward to future research findings about 6,8-Dibromoimidazo[1,2-a]pyrazine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80228; (2012); A1;,
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87486-34-8, A common compound: 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 2a-j (10 mmol, 1.0 eq) , 3,5-dibromo-1-methylpyrazin-2(1H)-one (2.95 g, 11 mmol, 1.1 eq) and DIEA (3.3 mL,20 mmol, 2.0 eq) in MeCN (20mL) was stirred at 80 ¡ãC for 5 hours. After cooling to room temperature, thesolvent was removed in vacuo, and the residue was purified using silica gelchromatography to give the title compounds, yield 72-85percent.

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, 3,5-Dibromo-1-methylpyrazin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Jianhong; Du, Jiatian; Huang, Chong; Wang, Tianqi; Huang, Luyi; Yang, Shengyong; Li, Linli; Bioorganic and Medicinal Chemistry Letters; vol. 29; 13; (2019); p. 1609 – 1613;,
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