Dimethylamine → N,N-dicyclopropyl-4-(5-(dimethylcarbamoyl)-1-ethyl-1H-pyrazol-3-ylamino)-6-ethyl-1-methyl-1,6-dihydro imidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

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Reaction Steps

A mixture of 3-(7-(dicyclopropylcarbamoyl)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-ylamino)-1-ethyl-1H-pyrazole-5-carboxylic acid (example 101, 28 mg, 0.059 mmol), HATU (26.8 mg, 0.071 mmol) and dimethylamine (2M in THF, 59 μL, 0.118 mmol) in DMF (1 mL) was stirred at room temperature for 2 h. Water was added and the reaction mixture was extracted with ethyl acetate 3 times. The combined organic layers were washed twice with 10% lithium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude was purified by preparative HPLC (Phenomenex Luna 5u C18 column, 21.2×250 mm column, retention time 15.317 min, 30-100% gradient aqueous methanol over 20 minutes containing 10 mM ammonium acetate, flow rate 20 ml/min and monitoring at 254 nm). N,N-dicyclopropyl-4-(5-(dimethylcarbamoyl)-1-ethyl-1H-pyrazol-3-ylamino)-6-ethyl-1-methyl-1,6-dihydro imidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (20 mg, 66.9% yield) was obtained as an off-white solid.

Provenance & Evidence