Trifluoroacetic acid → HCID 22601244, compound

Participants

Reaction Steps

To a stirred solution of the benzyl carbamate intermediate (34) (1.95 g, 1 equiv.) in MeOH (20 mL) was added palladium on carbon (200 mg, 10%). The solution was evacuated, placed under a H2 atmosphere (35 atm) and shaken for 5 h. The suspension was then filtered through celite and washed with MeOH. The filtrate was concentrated under reduced pressure to afford the desired amine. Following general procedure 10, to a stirred solution of this amine (105 mg, 1 equiv.) and Et3N (160 uL, 2 equiv.) in CH2Cl2 (5 mL) was added benzoyl bromide (90 uL, 1.3 equiv.). The resultant mixture was stirred at rt for 10 min. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (50% EtOAc in hexane) to afford the desired coupled product. The N-Boc group of the coupled product was then converted to the cyanamide (N—CN) following general procedure 3 (i.e. successive treatment with TFA and BrCN). The crude material was purified by flash chromatography (gradient elution: 50% EtOAc in hexane to 67% EtOAc in hexane) to afford the desired cyanamide N-(1-cyano-3-pyrrolidinyl)benzamide (36).

Provenance & Evidence