Trifluoroacetic acid → HCID 9920989, compound

Participants

Reaction Steps

Following general procedure 10, to a stirred solution of the amine (16) (200 mg, 1 equiv.) and Et3N (0.21 mL, 1.5 equiv.) in CH2Cl2 (5 mL) was added benzoyl bromide (0.13 mL, 1.1 equiv.). The resultant mixture was stirred at rt for 30 minutes. The mixture was then diluted with EtOAc and washed successively with 10% citric acid, H2O and brine. The organic extract was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution: 10% EtOAc in hexane to 33% 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 N-[(1-cyano-2-pyrrolidinyl)methyl]benzamide (17).

Provenance & Evidence