An efficient synthesis and mechanism of formation of 6-acetyl-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid

Identification of (R)-6-(1-(4-Cyano-3-methylphenyl)-5-cyclopentyl-4,5-dihydro-1H-pyrazol-3-yl)-2-methoxynicotinic Acid, a Highly Potent and Selective Nonsteroidal Mineralocorticoid Receptor Antagonist

“…Step 1: Methyl 6-Acetyl-2-methoxynicotinate. To a stirred solution of 6-acetyl-2-hydroxynicotinic acid 45 (2.00 g, 11 mmol) in N,N-dimethylformamide (30 mL) was added cesium carbonate (10.80 g, 33.1 mmol) followed by iodomethane (3.46 g, 24.3 mmol). The resulting mixture was then stirred at room temperature under nitrogen for 16 h. The mixture was filtered and washed with ethyl acetate.…”

Cyanoacetamides and their thio- and selenocarbonyl analogues as promising reagents for fine organic synthesis

“…507 Salt 248 prepared by the reaction of diacetyl dimethyl ketal 249 with methyl formate in the presence of sodium methoxide reacts with the amide 1a to give trimethyl orthopicolinate 250. 508 The use of a,b-ynones as substrates in the reactions with cyanoacetamides has been described. 85,347,463,509 3-Cyano-6methyl-4-phenylpyridine-2(1H)-thione (136b) was obtained on stirring a solution of acetylphenylacetylene (251) with cyanothioacetamide (1b) in ethanol in the presence of morpholine at 25 8C.…”