Trimethyl orthoformate → N-((1S,3R,4S)-3-ethyl-4-(6-tosylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-((1S,3S,4R)-3-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylcyclopentyl)cyclopropanesulfonamide (0.160 g, 0.309 mmol), trimethyl orthoformate (3.42 mL, 30.9 mmol) and toluene-4-sulfonic acid hydrate (0.006 g, 0.031 mmol) in MeOH (3.1 mL) was heated at about 65° C. for about 1 h then heated at about 60° C. for about 14 h. The reaction mixture was cooled to ambient temperature and concd under reduced pressure. The residue was dissolved in EtOAc (10 mL) and washed with saturated aqueous NaHCO3 (5 mL), water (5 mL), and brine (5 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered and concd under reduced pressure to give N-((1S,3R,4S)-3-ethyl-4-(6-tosylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide as a yellow solid (0.130 g, 76%): LC/MS (Table 1, Method n) Rt=0.76 min; MS m/z 528 (M+H)+.

Provenance & Evidence