Triethylamine → 4,4,4-trifluoro-3-methyl-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)butan-1-one

Participants

Reaction Steps

A mixture of 6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (prepared as described in Example 2 above, 64 mg, 0.17 mmol), 3-(trifluoromethyl)butanoic acid (27 mg, 0.18 mmol), HATU (73 mg, 0.2 mmol) and triethylamine (85 mg, 0.84 mmol) in THF (7 mL) was stirred overnight. The resulting mixture was partitioned between ethyl acetate and water, and the organic layer was washed sequentially with NaHCO3 (sat'd) and brine, then dried and concentrated. The residue was purified by reverse-phase chromatography (CH3CN-water/TFA) to yield 4,4,4-trifluoro-3-methyl-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)butan-1-one (78 mg).

Provenance & Evidence