Ethyl Acetate → HCID 58081300, compound

Participants

Reaction Steps

To a solution of 1-((1-Methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methyl)-1H-pyrazole-4-carboxylic acid (130 mg, 0.330 mmol, 65%), tert-Butyl 5-(aminomethyl)-4,6-dimethylpyridin-2-ylcarbamate (99 mg, 0.396 mmol) and DIPEA (0.308 ml, 1.764 mmol) in DCM (4 ml) Propanephosphonic anhydride (50% in EA (0.156 ml, 0.529 mmol) was added at rt. The reaction mixture was stirred at it for 1 h. The reaction mixture was quenched with 1 N NaOH and extracted twice with DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude product was purified by flash-chromatography on silica gel (26 g), gradient of DCM/DCM:MeOH 8:2 (40 ml/min.) from 100/0 (5 min.) to 80/20 (20 min.) to 80/20 5 min. to afford tert-Butyl 5-((1-((1,2-dimethyl-1H-indol-5-yl)methyl)-1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate. MS (Method V) [M+H]+=503.4.

Provenance & Evidence