Hydrochloric Acid → HCID 42638914, compound

Participants

Reaction Steps

To a solution of 4-(3-{5-[5-methyl-4-(3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-indol-1-yl}-propyl)-piperazine-1-carboxylic acid tert-butyl ester (91 mg, 0.16 mmol) in formic acid (2 mL) was added 4 M HCl (0.5 mL). The mixture was stirred for 30 min. The mixture was concentrated and the residue was partitioned between CHCl3 (2×) and 1 M NaOH (5 mL). The combined organic layers were dried and concentrated to give a crude product (52 mg). To a solution of this crude material in dichloroethane (3 mL) was added acetic acid (1 drop) and formaldehyde (37% in water; 0.04 mL, 0.60 mmol) followed by Na(OAc)3BH (127 mg, 0.60 mmol). The resulting mixture was stirred for 2 h before neutralizing with satd. aq. NaHCO3 and extracting with 10% isopropanol in CHCl3 (2×10 mL). The combined organic extracts were dried and concentrated, and purified by FCC to afford 32 mg (42%) of the title compound.

Provenance & Evidence