Trifluoroacetic acid → HCID 11363568, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.015 g of 4-(3′-cyano-biphenyl-4-yl)-4-(5,6-dichloro-1H-benzoimidazol-2-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester 53 (0.026 mmol) in 3 mL of dichloromethane at 0° C. was added 1 mL of trifluoroacetic acid. The mixture was stirred at 0° C. for 2 h then diluted with 10 mL of toluene and concentrated by rotary evaporation. The resulting residue was dissolved in 25 m) of ethyl acetate and washed with 10% aqueous NaHCO3 and saturated brine. The organic extracts were dried over Na2SO4, filtered and concentrated by rotary evaporation to give the crude product which was purified by reverse phase preparative HPLC to give 0.0113 g of the desired product 4′-[4-(5,6-dichloro-1H-benzoimidazol-2-yloxymethyl)-piperidin-4-yl]-biphenyl-3-carbonitrile 54 as a pale foam. 1H NMR (300 MHz, CDCl3/CD3OD): δ 7.85-7.75 (t, 1H), 7.72-7.70 (dt, 1H), 7.57-7.41 (m, 6H), 7.30(s, 2H), 5.19 (s, 2H), 4.31 (s, 2H), 3.33-3.25 (m, 2H), 2.90-2.82 (d, 2H), 2.47-2.34 (m, 2H), MS (ESI): Calcd m/z for C26H22Cl2N4O.H+=477.1. Found m/z=476.7/478.7 [(M+1)+/(M+3)+].

Provenance & Evidence