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

Participants

Reaction Conditions

Reaction Steps

The mixture of (Z)-1,7-dimethyl-3-(2-methyl-5-(1-(methylthio)-3-oxo-3-(thiazol-2-yl)prop-1-enylamino)phenyl)-1,6-naphthyridin-2(1H)-one 32 (462 mg, 1.0 mmol), O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (293 mg, 2.5 mmol) and K2CO3 (415 mg, 3.0 mmol) in 1,4-dioxane (5 mL) in a sealed vial was heated at 150° C. for 30 h. The mixture was purified by preparative LC/MS to give 1,7-dimethyl-3-(2-methyl-5-(5-(thiazol-2-yl)isoxazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (D9). 1H NMR (400 MHz, d6-DMSO) δ 10.73 (s, 1H), 9.19 (s, 1H), 8.11 (s, 1H), 7.93 (s, 1H), 7.87 (d, J=3.2 Hz, 1H), 7.74 (d, J=3.2 Hz, 1H), 7.65 (d, J=2.4 Hz, 1H), 7.61 (s, 1H), 7.53 (dd, J=2.4, 8.0 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 3.72 (s, 3H), 2.78 (s, 3H), 2.10 (s, 3H). MS m/z 430.2 (M+1).

Provenance & Evidence