4-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole → HCID 57941447, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.49 mmol) and 4-chloromethyl-2-(4-chlorophenyl)-thiazole (Maybridge plc, Tintagel, Cornwall, UK; 153 mg, 0.63 mmol) in dimethylformamide (5 mL) was heated at 100° C. for 2 days. The solvent was evaporated and ethyl acetate (50 mL) was added. The solution was washed with water (twice) and brine, dried (magnesium sulfate), filtered, evaporated and purified by chromatography, eluting with 2-3% methanol/dichloromethane to give (4S,7R)-2-[2-(4-Chloro-phenyl)-thiazol-4-ylmethyl]-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (89 mg, 44%) as an off-white foam. APCI(+)-MS (M+H) 414.

Provenance & Evidence