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CAS No. : | 13924-94-2 | MDL No. : | MFCD09753440 |
Formula : | C6H7N3O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | RPEZSZAVQOVHCZ-UHFFFAOYSA-N |
M.W : | 153.14 | Pubchem ID : | 14536427 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12%; 20% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃; | Example 15 5-[3-(4-Fluoro-phenyl)-2-(4-methanesulfonyl-phenyl)-propionylamino]-pyrazine-2-carboxylic acid ethyl ester To a suspension of a mixture of <strong>[54013-06-8]5-amino-pyrazine-2-carboxylic acid ethyl ester</strong> and 5-amino-pyrazine-2-carboxylic acid methyl ester (approximately 2:1) in CH2Cl2 (40 mL) was added DIEA (1.04 mL, 6 mmol) and DMF (5 mL). To the resulting suspension was added 3-(4-fluorophenyl)-2-(4-methanesulfonylphenyl)propionic acid (prepared as described in example 14, 1.5 g, 4.7 mmol), DMAP (0.17 g, 1.4 mmol) and EDC.HCl (1.08 g, 5.6 mmol) followed by additional CH2Cl2 (10 mL) and DMF (6 mL). The resulting solution was stirred at room temperature overnight. The reaction mixture was poured onto 0.01% aqueous HCl and extracted 3 times into CH2Cl2. The combined organic layer was dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (silica, 30%-50% ethyl acetate/hexanes stepwise gradient), followed by re-purification of the mixed fractions by chromatography (50% ethyl acetate/hexanes) afforded the front-running product, 5-[3-(4-fluorophenyl)-2-(4-methanesulfonylphenyl)-propionylamino]-pyrazine-2-carboxylic acid ethyl ester (438 mg, 20%): m.p. 99-100 C., LC/MS-ESI observed [M+H]+ 472; and the back-running product, 5-[3-(4-fluoro-phenyl)-2-(4-methanesulfonylphenyl)propionylamino]-pyrazine-2-carboxylic acid methyl ester (260 mg, 12%): m.p. 106-107 C., LC/MS-ESI observed [M+H]+ 458. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 120 - 125℃; for 22h;Inert atmosphere; | a. Methyl 5-((3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yI)amino)pyrazine-2- carboxylate (93). To a solution of 77 (1.1303 g, 4.02 mmol), 92 (0.5969 g, 3.90 mmol), CsCO3 (3.12 g, 9.58 mmol), rac-B1NAP (0.1868 g, 0.30 mmol) in toluene (4.5 mL) in a 100 mL round-bottomed flask was added Pd2(dba)3 (0.1780 g, 0.19 mmol). The solution was sparged with nitrogen for 5 mm., then a reflux condenser was fitted to the flask, the atmosphere was evacuated and back-filled with nitrogen (three times), and the reaction was heated to reflux with stirring in an oil bath (125- 120 C) for 22h. After cooling the reaction to room temperature, excess cesium carbonate and other solid particulates were filtered and washed with ethyl acetate, and the organic filtrate was concentrated in vacuo to give a crude product that was purified by column chromatography (150 mL Si02, 20% ethyl acetate:hexanes to 25% ethyl acetate: hexanes) to give 93 (0.8727 g, 63%) as a crystalline solid, m.p. 134.9-137.1 C: ?H NMR (400 MHz, CDC13)6 8.81 (d,J= 1.2, 1H), 8.08 (d,J = 1.6, 1H), 7.32 (s, 1H), 7.20 (s, 1H), 7.03 (br s, 1H), 3.95 (s, 3H), 2.22 (s, 3H), 1.68 (s, 4H), 1.28 (s, 6H), 1.24 (s, 6H); ?3C NMR (100.6 MHz, CDC13) 164.8, 154.3, 145.4, 144.1, 143.6, 132.8, 130.7,129.5, 129.3, 122.2, 52.3, 34.9, 34.8, 34.1, 33.9, 31.8, 31.7, 17.6; IR(neat) 3162, 2961, 1712, 1542, 1306, 1271, 1129 cm1 ES-MS (M+Na)+ calcd for C21H27N3O2Na 376.2001, found 376.2006. |
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