Water → HCID 136376963, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-(benzyloxy)-2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (3.45 g, 10.3 mmol) in DMF (100 mL), was added 94% dimethyl chloromalonate (2.79 mL, 20.6 mmol) and the mixture was stirred for 7.5 h at 100° C. The reaction mixture was allowed to cool to 50° C. and then was dropwise added water (100 mL). The resulting precipitate was collected by filtration and then washed with EtOH (20 mL) and diethyl ether (20 mL) to obtain methyl 2-[5-(benzyloxy)-2-methylpyrazolo[1,5-a]pyridin-3-yl]-4-hydroxy-1,3-thiazole-5-carboxylate as a orange solid, which was used in the next step without further purification. 1H-NMR (DMSO-d6, 300 MHz) 2.59 (3H, s), 3.75 (3H, s), 5.27 (2H, s), 6.87 (1H, dd, J=2.6, 7.6 Hz), 7.32-7.51 (3H, m), 7.52-7.64 (2H, m), 7.88 (1H, d, J=2.6 Hz), 8.67 (1H, d, J=7.6 Hz), 11.79 (1H, br s).

Provenance & Evidence