These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Pyrazinecarboxylic anhydride, its application will become more common.
Application of 4744-50-7,Some common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, 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 10 5-(5,7-Dioxo-5,7-dihydro-pyrrolo[3,4-b]pyrazin-6-ylmethyl)-2-(oxalyl-amino)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid; In a 4-ml scintillating vial, a solution of 2-amino-5-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (148 mg, 0.5 mmol) in tetrahydrofuran (1.0 ml) was treated with a solution of pyrazine phthtalic acid anhydride (85 mg, 0.56 mmol) in tetrahydrofuran (1.0 ml) and N,N-dimethylformamide (0.5 ml). The reaction mixture was allowed to stir at room temperature for 1 h. Diisopropylethylamine (220 mul, 0.13 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (121 mg, 0.6 mmol) were then added. The reaction mixture was shaken vigorously for 10 seconds before being stirred at room temperature for 14 h. The volatiles were evaporated in vacuo and the residue purified by silica gel chromatography using a mixture of dichloromethane/ethyl acetate (3:1) as eluant. Pure fractions were collected and the solvent evaporated in vacuo affording 25 mg (12%) of the 2-amino-5-(5,7-dioxo-5,7-dihydro-pyrrolo[3,4-b]pyrazin-6-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as a solid.1H NMR (300 MHz, CDCl3) delta 8.97 (s, 2H), 4.62-4.49 (m, 2H), 4.21-4.04 (m, 2H), 3.94 (dd, J=14, 4, 1H), 2.91 (d, J=17, 1H), 2.63 (dd, J=17, 10, 1H), 1.68 (s, 9H).In a 4 ml scintillating vial a solution of the above 2-amino-5-(5,7-dioxo-5,7-dihydro-pyrrolo[3,4-b]pyrazin-6-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (25 mg, 0.06 mmol) in tetrahydrofuran (3 ml) was treated with midazol-1-yl-oxo-acetic acid tert-butyl ester (0.36 mmol). After stirring for 3 hours at room temperature the reaction solution was concentrated to dryness in vacuo. The residue was purified by silica gel chromatography using a mixture of hexanes/ethyl acetate (3:1) as eluant. Pure fractions were collected and the solvent evaporated in vacuo affording 31 mg (95%) of 2-(tert-butoxyoxalyl-amino)-5-(5,7-dioxo-5,7-dihydro-pyrrolo[3,4-b]pyrazin-6-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as a solid.1H NMR (300 MHz, CDCl3) delta 12.49 (s, 1H), 8.96 (s, 2H), 4.80-4.61 (m, 2H), 4.21-4.04 (m, 2H), 3.96 (dd, J=14, 4, 1H), 3.03 (d, J=16, 1H), 2.70 (dd, J=17, 10, 1H), 1.60 (s, 9H), 1.59 (s, 9H).In a 25 ml round bottom flask the above 2-(tert-butoxyoxalyl-amino)-5-(5,7-dioxo-5,7-dihydro-pyrrolo[3,4-b]pyrazin-6-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester, (31 mg, 0.06 mmol) was dissolved in 20% trifluoroacetic acid in dichloromethane (4 ml). The solution was left open to the atmosphere without stirring for 24 h. A precipitate was filtered off and washed with diethyl ether, affording after drying 22 mg (90%) of the title compound as a solid.1H NMR (300 MHz, DMSO-d6) delta 12.31 (s, 1H), 9.02 (s, 2), 4.81-4.59 (m, 2H), 3.97-3.81 (m partially obscured by water, 3H), 3.08 (d, J=18, 1H), 2.74-2.53 (m partially obscured by DMSO, 1H).HPLC (254.4 nm) Rt=2.97 min, 89%.MS (APCI) [M-H] 432.4
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Pyrazinecarboxylic anhydride, its application will become more common.
Reference:
Patent; Novo Nordisk A/S; US7115624; (2006); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem