Cyclopropanesulfonyl chloride → N-(5-(6-(1-cyclopentyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-3-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)cyclopropanesulfonamide

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Reaction Steps

The compound was prepared using the procedures of Example 334 starting from 5-(6-bromo-3H-imidazo[4,5-b]pyridin-3-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-amine (133 mg, 0.33 mmol) and using cyclopropanesulfonyl chloride (20 mg, 0.66 mmol, 2.0 eq.) and 1-cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.115 g, 0.43 mmol, 2.0 eq.) to give the crude residue which was purified by preparative HPLC to give the product in 27.86% yield (34 mg). 1H NMR (400 MHz, DMSO-d6): δ 10.26 (s, 1H), 8.96 (s, 1H), 8.76-8.75 (d, 1H), 8.45-8.42 (t, 2H), 8.06 (s, 1H), 8.00-7.99 (d, 1H), 7.78-7.70 (m, 2H), 7.49-7.43 (m, 2H), 7.31-7.26 (t, 1H), 4.74-4.70 (t, 1H), 2.84 (m, 1H), 2.14-2.08 (m, 2H), 2.00-1.96 (m, 2H), 1.84-1.81 (m, 2H), 1.69-1.65 (m, 2H), 1.09-1.02 (m, 4H); LC-MS (ESI): Calculated mass: 560.18; Observed mass: 561.2 [M+H]+ (rt: 1.70 min).

Provenance & Evidence