Sodium Hydroxide → HCID 178435043, compound

Participants

Reaction Steps

A mixture of trans-6-{4-[(5-methyl-2-phenyl-thiazol-4-ylmethyl)-amino]-cyclohexyl}-3H-benzoxazol-2-one of formula 42 (510 mg, 1.12 mmol), 2N NaOH (1 mL), and p-formaldehyde (168 mg, 5.60 mmol) in MeOH (10 mL) was stirred for 3 hours, NaBH(OAc)3 (332 mg, 1,56 mmol) was added, and the mixture was stirred overnight. The reaction was quenched by addition of MeOH. Concentration under reduced pressure followed by purification by flash chromatography (silica gel, 95:5:1 CH2Cl2:MeOH:NH4OH) gave trans-6-{4-[methyl-(5-methyl-2-phenyl-thiazol-4-ylmethyl)-amino]-cyclohexyl}-3H-benzoxazol-2-one (43) (345 mg, 71%), as a white solid: mp 246-248° C.; IR (KBr): 2927, 1773 cm−1: 1H NMR (500 MHz, DMSO-d6) δ 7.88 (dd, J=8, 2 Hz, 1H), 7.44 (m, 5H), 7.15 (s, 1H), 6.98 (m, 1H), 3.75 (s, 2H), 2.53 (m, 1H), 2.48 (m, 1H), 2.48 (s, 3H), 2.24 (s, 3H), 1.86 (m, 4H), 1.47 (m, 4H); CI-MS (methane) (m/z): 434 [M+H]+; HRMS-API (m/z): [M+H]+ calcd for C25H27N3O2S, 434.1902; found, 434.1903; HPLC: method A, 12.46 minutes (99.0%); method B, 14.05 minutes (98.7%); Anal. Calcd for C25H27N3O2S.0.25H2O: C, 68.54; H, 6.33; N, 9.59. Found: C, 68.21; H, 6.07; N, 9.59.

Provenance & Evidence