Water → HCID 68869725, compound

Participants

Reaction Steps

To a suspension of sodium hydride (washed with hexane, 30 mg, 1.3 mmol) in N,N-dimethylformamide (2 mL) was added 2-propanethiol (117 μL, 1.3 mmol) at 0° C. After stirring for 30 min, a N,N-dimethylformamide solution of 5-(chloromethyl)-1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazole (Step E) was added and the mixture was stirred at 100° C. for 17.5 h. Water (5 mL) was added and the mixture was extracted with ethyl acetate (15 mL×2) and washed with brine (5 mL). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by pTLC (hexane:ethyl acetate=3:1) to give the title compound (74 mg, 67% over 2 steps) as pale brown oil.

Provenance & Evidence