Glycine → HCID 24757245, compound

Participants

Reaction Steps

A mixture of 7-hydroxy-2-(4-phenoxy-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (75 mg, 0.19 mmole) and glycine (286 mg, 3.81 mmole) in 0.5 M sodium methoxide/methanol (7.2 ml) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. Water (75 ml) was added and pH was adjusted to 10 with 1N HCl (2 ml). The mixture was extracted with methyl tert-butyl ether (2×30 ml) and dichloromethane (30 ml). The remaining aqueous layer was acidified to pH=3 with 1N HCl (3 ml). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (55 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.45 (br s, 1H), 8.87 (s, 1H), 8.17 (m, 2H), 7.47 (m, 2H), 7.17 (m, 5H), 4.03 (d, J=6.3 Hz, 2H); MS: (+) m/z 421.07 (M+1). (−) m/z 419.87 (M−1).

Provenance & Evidence