Trifluoroacetic acid → HCID 178457351, compound

Participants

Reaction Steps

A solution of [cis-4-(isopropyl-methyl-amino)-cyclohexyl]-carbamic acid tert-butyl ester (0.16 g, 0.6 mmol) in CH2Cl2 (3 mL) was cooled to 0° C., charged with trifluoroacetic acid (1 mL), and stirred at RT for 1 h before being concentrated in vacuo. The residue was dissolved in CH2Cl2 and concentrated in vacuo; this was repeated to afford N-isopropyl-N-methyl-cis-cyclohexane-1,4-diamine. A portion (25 mg, 0.15 mmol) of this material was dissolved in DMF (1 mL). The resulting solution was charged with N,N-diethylisopropylamine (0.13 mL, 0.7 mmol), {2-[2-(3-isopropyl-ureido)-5-trifluoromethyl-benzoylamino]-acetic acid (56 mg, 0.16 mmol), and BOP (97 mg, 0.22 mmol) and stirred for 14 h at RT. The reaction was partitioned between water and EtOAc, and organic phase was washed successively with sat. NH4Cl, water, and brine before being dried (Na2SO4), filtered, and concentrated in vacuo. Purification of the residue by reverse phase HPLC afforded the TFA salt of the title compound as a white powder after lyopholization. MS found: (M+H)+=500.3.

Provenance & Evidence