Methylamine → 2-(7-Chlorothieno[3,2-b]pyridin-2-yl)-N-methyl-1,3-thiazole-4-carboxamide

Participants

Reaction Steps

To a solution of 2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazole-4-carboxylic acid 43a (0.123 g, 0.41 mmole) in CH2Cl2 cooled at 0° C. was added 2.0 M oxalyl chloride in CH2Cl2 (0.520 ml, 1.04 mmole) and DMF (2 drops). The reaction mixture was stirred at room temperature for 1 h, concentrated and dried. The residue was taken into CH2Cl2 (10 ml), and 2.0 M methylamine in CH2Cl2 (0.250 ml, 0.492 mmole) was added. The reaction mixture was stirred at room temperature for 1 h, and then partitioned between H2O (100 ml) and CH2Cl2 (2×100 ml). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 2–8% CH3OH in CH2Cl2 to give yellow solid (0.116 g, 91%). 1H NMR (300 MHz, CDCl3) δ 8.62 (1H, d, J=5.1 Hz), 8.19 (1H, s), 7.96 (1H, s), 7.33 (1H, d, J=5.1 Hz), 3.06 (3H, d, J=4.9 Hz); ESIMS (MH+): 309.95.

Provenance & Evidence