Sodium hydride → 4-(benzo[d]thiazol-2-ylamino)-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

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To a solution of 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 1J, 21.2 mg, 0.063 mmol) in DMF (626 μL) was added sodium hydride (10.02 mg, 0.251 mmol) in one portion. After 20 min, 2-bromo-1,3-benzothiazole (53.6 mg, 0.251 mmol) was added. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with water and diluted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organics were washed with 10% LiCl, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography using an Isco 4 g column eluting with 0-5% MeOH/CH2Cl2 to yield 4-(benzo[d]thiazol-2-ylamino)-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (6.8 mg, 21.87% yield) as an off-white solid.

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