Sodium borohydride → HCID 70984094, compound

Participants

Reaction Steps

To a solution of 1,4-dioxaspiro[4.5]dec-8-yl[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanone (Ex 1-20) (100 mg, 0.20 mmol) in methanol (5 mL) was added sodium borohydride (22.5 mg, 0.60 mmol). After one hour, water was carefully added and then diluted with ethyl acetate and water. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel (0-100% ethyl acetate gradient with hexanes) afforded 1,4-dioxaspiro[4.5]dec-8-yl[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanol. MS ESI calc'd. for C24H26F3N4O3S [M+H]+ 507. found 507. 1H NMR (500 MHz, DMSO-d6) δ 10.24 (s, 1H), 8.83 (d, J=4.9, 1H), 7.97-7.94 (m, 2H), 7.45 (s, 1H), 7.27 (d, J=4.9, 1H), 7.15 (s, 1H), 6.18 (d, J=5.1, 1H), 4.61 (t, J=5.1, 1H), 3.80 (s, 4H), 2.30 (s, 3H), 1.84-1.72 (m, 1H), 1.71-1.61 (m, 2H), 1.61-1.51 (m, 2H), 1.52-1.28 (m, 4H). rhSyk=++.

Provenance & Evidence