Trifluoroacetic acid → HCID 90461207, compound

Participants

Reaction Steps

A solution of tert-butyl N-[2-([[1-(4-cyanophenyl)-1H-imidazol-5-yl]methyl](methyl)amino)ethyl]carbamate (90 mg, 0.25 mmol, 1.00 equiv) in trifluoroacetic acid (5 mL) and dichloromethane (5 mL) was stirred at room temperature for 3 h. The resulting mixture was concentrated under vacuum and the crude product was purified by Prep-HPLC with the following conditions (waters-1): Column, XBridge Shield RP18 OBD Column, 5 μm, 19×150 mm; mobile phase, Phase A: water with 0.03% NH4OH Phase B: water with 0.05% TFA; Gradient B (20%˜50% 2 min˜100% 11 min); Detector, UV 254 nm to afford 25.4 mg (39%) of 4-(5-(((2-aminoethyl)(methyl)amino)methyl)-1H-imidazol-1-yl)benzonitrile trifluoroacetate as a white solid. 1H-NMR (300 MHz, CD3OD): δ 7.98-7.95 (m, 3H), 7.83-7.80 (m, 2H), 7.15 (s, 1H), 3.60 (s, 2H), 2.76 (t, J=6.3 Hz, 2H), 2.50 (t, J=6.3 Hz, 2H), 2.16 (s, 3H) ppm. LCMS (method S, ESI): RT=1.18 min, m/z=256.3 [M+H]+.

Provenance & Evidence