Hydrogen Peroxide → HCID 58557819, compound

Participants

Reaction Steps

To a solution of N-((1S,3S,4R)-3-(3-allyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-ethylcyclopentyl)cyclopropanesulfonamide (0.090 g, 0.16 mmol, prepared using H with Preparation #12, Preparation #Z.1, HATU and DIEA, and Q with Lawesson's reagent and mercury (II) trifluoroacetate) in THF (3 mL) at about 0° C. was added BH3•DMS (2 M in THF, 0.040 mL, 0.079 mmol). After about 2 h, additional BH3•DMS (2 M in THF, 0.040 mL, 0.079 mmol) was added to the reaction mixture. After about 6 h total, a premixed solution of H2O2 (30% aqueous, 0.324 mL, 3.17 mmol) and NaOH (2 N aqueous, 0.793 mL, 1.58 mmol) was added to the reaction mixture. After stirring for about 15 h, EtOAc (20 mL) and water (20 mL) were added to the reaction mixture. The organic layer was separated, washed with brine (20 mL), and concd in vacuo. The crude residue was purified by chromatography on silica gel (12 g) eluting with EtOAc to provide N-((1S,3R,4S)-3-ethyl-4-(3-(3-hydroxypropyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)cyclopentyl)cyclopropanesulfonamide (0.025 g, 37%) as a white solid: LC/MS (Table 1, Method a) Rt=1.70 min; MS m/z: 432 (M+H)+.

Provenance & Evidence