Methyl 3-amino-4-methylthiophene-2-carboxylate → HCID 54749370, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 2-(7-hydroxy-3,4-dimethyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxamido)acetate. A mixture of ethyl 7-hydroxy-3,4-dimethyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxylate (0.477 g, 1.78 mmol, prepared analogously to Method 3 utilizing commercially available methyl 3-amino-4-methylthiophene-2-carboxylate (Aldrich, Milwaukee, Wis.)) and tert-butyl 2-aminoacetate hydrochloride (0.598 g, 3.57 mmol) in dioxane and DIEA was stirred at 90° C. for 12 hours. The mixture was cooled to room temperature, diluted with CHCl3, washed with water (1×) and brine (1×), dried over MgSO4, and evaporated. Purification by flash chromatography (hexanes to hexanes/EtOAc=1:1) UV gave the title compound as a white solid (27 mg). MS (ESI) m/z: Calculated; 352.4: Observed; 353.1. 1H NMR (300 MHz, CDCl3) δ ppm 10.73 (1H, br. s), 7.36 (1H, s), 4.12 (2H, d, J=5.4 Hz), 3.88 (3H, s), 2.62 (3H, s), 1.50 (9H, s).

Provenance & Evidence