Acetic Acid → 2-[6-(2,2-Dimethylpropyl)-1H-benzimidazol-2-yl]-2,3-dihydro-1H-inden-2-amine

Participants

Reaction Steps

To a solution of Boc-2-aminoindane-2-carboxylic acid (107 mg, 0.386 mmol) in acetonitrile (2.0 mL) and 4-methylmorpholine (0.11 mL, 1.0 mmol) cooled in an ice/brine bath was added isobutylchloroformate (0.050 mL, 0.38 mmol). The mixture was stirred for 30 minutes and then 4-neopentylbenzene-1,2-diamine (Preparation 83, 82 mg, 0.46 mmol) was added. The reaction mixture was allowed to warm to room temperature and stir for 4 hours. The solvent was evaporated and the resulting oil was dissolved in acetic acid (3.0 mL, 50 mmol) and heated at 65° C. for 16 hours. After cooling, the solvent was removed in vacuo and the residue purified by silica gel column chromatography eluting with a 0-100% ethyl acetate/hexanes gradient. The resulting oil was dissolved in methylene chloride (5 mL) and treated with trifluoroacetic acid (0.5 mL, 6 mmol). After stirring for 2 hours, the reaction mixture was concentrated in vacuo and purified by silica gel column chromatography eluting with a 0-100% CMA80/methylene chloride gradient. This provided the title compound (63.7 mg, 52%) as a white solid.

Provenance & Evidence