Potassium Hydroxide → 1,7-dimethyl-3-(2-methyl-5-(3-(thiazol-2-yl)isoxazol-5-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To the mixture of hydroxylamine hydrochloride (42 mg, 0.6 mmol) and KOH (34 mg, 0.6 mmol) in EtOH (2 mL) was added the crude (Z)-1,7-dimethyl-3-(2-methyl-5-(1-(methylthio)-3-oxo-3-(thiazol-2-yl)prop-1-enyl amino)phenyl)-1,6-naphthyridin-2(1H)-one 32. The resulting mixture was heated at 80° C. for 30 min. Then NaOEt (40.8 mg, 0.6 mmol) was added and the reaction mixture was refluxed for 1 h. The mixture was purified by preparative LC/MS to give 1,7-dimethyl-3-(2-methyl-5-(3-(thiazol-2-yl)isoxazol-5-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (F1). 1H NMR (400 MHz, d6-DMSO) δ 9.50 (s, 1H), 9.13 (s, 1H), 7.95-8.10 (m, 3H), 7.88 (s, 1H), 7.38 (s, 1H), 7.30 (d, J=8.0 Hz, 1H), 7.18 (d, J=8.0 Hz, 1H), 6.94 (s, 1H), 3.65 (s, 1H), 2.72 (s, 3H), 2.03 (s, 3H). MS m/z 430.1 (M+1).

Provenance & Evidence