Glycine → HCID 24757332, compound

Participants

Reaction Steps

A mixture of 7-hydroxy-2-(2-methoxy-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (120 mg, 0.36 mmole) and glycine (546 mg, 7.27 mmole) in 0.5 M sodium methoxide/methanol (13.8 ml, 6.91 mmole) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (25 ml) and extracted with methyl tert-butyl ether (2×25 ml). The remaining aqueous layer was acidified to pH=3 with 1N HCl (9 ml). The resulting jelly was extracted with dichloromethane and ethyl acetate. The organic layer was combined, washed with brine and dried in vacuo to give the title compound as a yellow solid (94 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.39 (br s, 1H), 8.88 (s, 1H), 8.45 (d, 1H), 7.62 (m, 1H), 7.33 (d, 1H), 7.18 (t, 1H), 4.01 (s, 3H), 4.03 (d, 2H); MS: (+) m/z 360.25 (M+1).

Provenance & Evidence