Glycine → HCID 68426652, compound

Participants

Reaction Steps

A mixture of 2-(4-cyano-phenyl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (111 mg, 0.34 mmole) and glycine (512 mg, 6.82 mmole) in 0.5 M sodium methoxide/methanol (13 ml, 6.48 mmole) was refluxed for 45 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (35 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 suspension was extracted with chloroform/isopropanol (3:1, 35 ml). The organic suspension was concentrated, washed with water and dried in vacuo to give the title compound as a brown solid (52 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.52 (t, 1H), 8.90 (s, 1H), 8.30 (d, 1H, J=8.2 Hz), 8.04 (d, 1H, J=8.2 Hz), 4.00 (d, 2H, J=5.8 Hz); MS: (+) m/z 355.22 (M+1).

Provenance & Evidence