Hydrochloric Acid → HCID 178428303, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of butyl trans-4-{1-fluoro-1-[5-(3-methyl-5-{[4-(trifluoromethyl)-pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}cyclohexanecarboxylate (80 mg, 0.14 mmol) in methanol (1.5 mL) was added sodium hydroxide (1.0 M in H2O, 0.28 mL, 0.28 mmol) and the reaction was heated to 60° C. overnight. Then, the reaction was cooled to room temperature, acidified to a pH of ˜3 with HCl (1.0 M in water) and diluted with water and ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to afford racemic trans-4-{1-fluoro-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}cyclohexanecarboxylic acid. MS ESI calc'd. for C24H25F4N4O2S [M+H]+ 509. found 509. 1H NMR (500 MHz, DMSO-d6) 12.01 (s, 1H), 10.28 (s, 1H), 8.84 (d, J=4.8, 1H), 8.07 (d, J=3.3, 1H), 8.02 (s, 1H), 7.47 (s, 1H), 7.29 (d, J=4.9, 1H), 7.19 (s, 1H), 2.32 (s, 3H), 2.16-2.01 (m, 1H), 2.00-1.87 (m, 4H), 1.85 (s, 1H), 1.67 (s, 3H), 1.35-1.19 (m, 4H).

Provenance & Evidence