4-(Chloromethyl)-2-methyl-1,3-thiazole → HCID 57941333, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (4R,7S)-1-benzyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 49; 109 mg, 0.38 mmol), tetrabutylammonium iodide (147 mg, 0.39 mmol) and 4-(chloromethyl)-2-methylthiazole (Maybridge plc, Tintagel, Cornwall, UK; 60 mg, 0.40 mmol) in dimethylformamide (3.9 mL) was heated at 100° C. for 24 h. A second portion of 4-(chloromethyl)-2-methylthiazole (120 mg, 0.81 mmol) was added and the mixture was heated at 110° C. overnight. The solvent was evaporated and dichloromethane (100 mL) was added. The solution was washed with saturated aqueous sodium thiosulfate (150 mL), saturated aqueous sodium hydrogen carbonate (150 mL) and brine (150 mL), dried (sodium sulfate), filtered, evaporated and purified using a Biotage 40S system, eluting with 2% methanol/dichloromethane, to give (4R,7S)-1-benzyl-7,8,8-trimethyl-2-(2-methyl-thiazol-4-ylmethyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (92 mg, 61%) as a reddish-brown semi-solid. APCI(+)-MS (M+H) 394.

Provenance & Evidence