Ammonia → 5-[2-Amino-5-(3-chloro-phenyl)-pyridin-3-yl]-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

5-[2-Amino-5-(3-chloro-phenyl)-pyridin-3-yl]-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid methyl ester (57 mg, 0.11 mmol, 1.0 Eq.) was suspended in 7M NH3 in MeOH (10 mL) and heated to 100° C. in a pressure tube for 3 days. The reaction was allowed to cool to ambient temperature, the solvent was removed in vacuo and the product purified by column chromatography (ISCO Companion™, 12 g column, 0-10% MeOH/DCM). The solvent was removed in vacuo and the compound was partitioned between DCM (10 mL) and water (10 mL). The organic layer was extracted with DCM (2×7 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid (20 mg, 0.08 mmol, 54%); 1H NMR (400 MHz, d-6 DMSO) δ 1.71 (3H, d), 6.04 (1H, q), 6.30 (2H, br s), 7.05 (1H, s), 7.12 (1 h, br s), 7.33-7.36 (2H, m), 7.40-7.48 (3H, m), 7.58-7.63 (2H, m), 7.70-7.72 (1H, br m), 8.35 (1H, d).

Provenance & Evidence