2-(((Tert-butoxy)carbonyl)amino)-2-(4-chlorophenyl)acetic acid → tert-butyl (1-(4-chlorophenyl)-2-((5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)pyridin-3-yl)amino)-2-oxoethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To pyridine (4 mL) in a sealed vessel was added 2-((tert-butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid (67 mg, 0.24 mmol) (see Preparation 303), (5-aminopyridin-3-yl)(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (52 mg, 0.18 mmol) (see Preparation 95) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (105 mg, 0.28 mmol). The reaction was heated at 50° C. for 18 hours and then evaporated in vacuo and purified by column chromatography (gradient of 100:0 to 88:12 DCM:MeOH) to give the title compound in 49% yield, 64 mg. LCMS (basic): Rt=0.81 min; m/z 549 [M+H]+.

Provenance & Evidence