Trifluoroacetic acid → HCID 89462643, compound

Participants

Reaction Steps

A mixture of methyl 2-(tert-butoxy)-2-(1-(2-(tert-butoxy)-2-oxoethyl)-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate (49 mg, 0.099 mmol) in Dichloromethane (DCM) (2.0 mL) and TFA (0.4 mL, 0.102 mmol) was stirred at ambient temperature for 60 hours (a dark mixture resulted). LCMS indicated cleavage of both t-butyl ester as well as t-butyl ether. The mixture was concentrated and then used crude in the next step. A mixture of the crude residue, 4-fluoroaniline (0.014 mL, 0.150 mmol) and Hünig's base (0.054 mL, 0.306 mmol) in N,N-Dimethylformamide (DMF) (0.5 mL) was treated with HATU (62.0 mg, 0.163 mmol) and then stirred at ambient temperature for 10 minutes. The mixture was diluted with ethyl acetate, washed with water, then brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-70% Ethyl acetate/hexanes) to give the impure amide product as a pale yellow residue (20.5 mg, 42% yield). LC/MS (m/z) ES+=497 (M+1).

Provenance & Evidence