Cyanogen Bromide → N-((1S,3S,4R)-3-(2-amino-6-tosylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)-4-ethylcyclopentyl)cyclopropane-sulfonamide

Participants

Reaction Steps

To a solution of N-((1S,3S,4R)-3-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylcyclopentyl)cyclopropanesulfonamide (0.200 g, 0.301 mmol, Example #23 Step I) in MeOH (3.0 mL) was added cyanogen bromide (5 M in MeCN, 0.482 mL, 2.41 mmol) dropwise. The reaction was stirred at ambient temperature for about 16 h. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM to give N-((1S,3S,4R)-3-(2-amino-6-tosylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)-4-ethylcyclopentyl)cyclopropane-sulfonamide (0.11 g, 67%) as a brown solid: LC/MS (Table 1, Method a) Rt=2.00 min; MS m/z: 543 (M+H)+.

Provenance & Evidence