Stannous chloride dihydrate → N-((1S,3S,4R)-3-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylcyclopentyl)cyclopropanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-((1S,3R,4S)-3-ethyl-4-(5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)cyclopentyl)cyclopropanesulfonamide (0.172 g, 0.314 mmol) in EtOH (6 mL) was added tin (II) chloride dihydrate (0.142 g, 0.628 mmol). The reaction mixture was heated at about 75° C. for about 15 h. Tin (II) chloride dihydrate (0.128 g, 0.565 mmol) was added and the reaction mixture was heated at about 70° C. for about 40 min then heated at about 80° C. for about 3 h. The reaction was cooled to ambient temperature and the solvent was removed under reduced pressure. The reaction mixture was diluted with EtOAc (20 mL) and washed with 1N aqueous NaOH (10 mL), water (10 mL) and brine (10 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered and concd under reduced pressure. EtOH (10 mL) was added and the mixture was concd under reduced pressure to give N-((1S,3S,4R)-3-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylcyclopentyl)cyclopropanesulfonamide (0.160 g, 98%) as a yellow oil: LC/MS (Table 1, Method n) Rt=0.75 min; MS m/z 518 (M+H)+.

Provenance & Evidence