Diethylcarbamoyl chloride → HCID 136403439, compound

Participants

Reaction Steps

To a solution of 2-(4-hydroxy-1-methyl-3-(4-(6-(methylcarbamoyl)pyridin-3-yl)phenyl)-1H-pyrazol-5-yl)-5,7-dihydroimidazo[4,5-f]isoindole-6(1H)-carboxylate 1-16 (63 mg, 0.11 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added potassium tert-butoxide (25 mg, 0.22 mmol) and diethylcarbamoyl chloride (21 mg, 0.15 mmol). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. To the residue was added a 30% solution of trifluoroacetic acid in dichloromethane (4 mL). The reaction mixture was stirred at room temperature for 2 hours. Solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to afford the desired 1-methyl-3-(4-(6-(methylcarbamoyl)pyridin-3-yl)phenyl)-5-(1,5,6,7-tetrahydroimidazo[4,5-f]isoindol-2-yl)-1H-pyrazol-4-yl diethylcarbamate T-17 (48 mg, 0.085 mmol).

Provenance & Evidence