Hydroxyamine hydrochloride → 3-(5-(5-cyclopropylisoxazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To the above crude mixture of (Z)-3-(5-(3-cyclopropyl-1-(methylthio)-3-oxoprop-1-enylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 31 were added hydroxylamine hydrochloride (174 mg, 2.4 mmol) and DMF (2 mL). The resulting mixture was heated at 100° C. for 30 min. The mixture was purified by preparative LC/MS to give 3-(5-(5-cyclopropylisoxazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (D4). 1H NMR (400 MHz, d6-DMSO) δ 9.21 (s, 1H), 9.13 (s, 1H), 8.10 (s, 1H), 7.96 (s, 1H), 7.39 (d, J=2.4 Hz, 1H), 7.29 (dd, J=2.4, 8.4 Hz, 1H), 7.19 (d, J=8.4 Hz, 1H), 5.83 (s, 1H), 3.72 (s, 3H), 2.79 (s, 3H), 2.07 (s, 3H), 2.05 (m, 1H), 1.01 (m, 2H), 0.84 (m, 2H). MS m/z 387.2 (M+1).

Provenance & Evidence