Triethylamine → (S)-4-(5-bromo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N-(3-(isopropylcarbamoyl)phenyl)-2-methylpiperazine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of triphosgene (15 mg, 0.05 mmol) in THF (1 ml) at 0° C. under N2 was added dropwise a solution of 3-amino-N-isopropylbenzamide (25 mg, 0.14 mmol) and triethylamine (43 μL, 0.3 mmol) in THF (1 ml). The mixture was stirred for 15 min at 0° C. and another 15 min at room temperature. The piperazine from step C (65 mg, 0.14 mmol) in THF (1 ml) was added, and the resulting mixture was stirred at room temperature overnight, then quenched with MeOH and K2CO3 (97 mg, 0.70 mmol) and filtered. The solution was concentrated under vacuum and purified by Prep-HPLC to give (S)-4-(5-bromo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N-(3-(isopropylcarbamoyl)phenyl)-2-methylpiperazine-1-carboxamide (70 mg, 0.11 mmol, 77%). MS (ES+) [M+H]+=641.

Provenance & Evidence