Sodium Hydroxide → HCID 136349136, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl ((1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentyl)methylcarbamate (0.60 g, 1.1 mmol, prepared using A from (1R,3R)-3-((tert-butoxycarbonylamino)methyl)cyclopentanecarboxylic acid [AFID] and Preparation #9) and DIEA (0.79 mL, 4.5 mmol) in 1,4-dioxane (5 mL) was added SOCl2 (0.166 mL, 2.27 mmol). The reaction mixture was heated at about 80° C. for about 1 h before it was allowed to cool to ambient temperature. Aqueous NaOH (2 N, 4 mL, 8 mmol) was added to the reaction mixture and heated at about 60° C. for about 2 h. The reaction mixture was allowed to cool to ambient temperature before it was concentrated under reduced pressure. To the residue was added HCl (4N in 1,4-dioxane (20 mL). The organic solution was decanted away from the resulting precipitate to afford ((1R,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)methanamine hydrochloride as a yellow solid (0.11 g, 33%): LC/MS (Table 2, Method a) Rt=1.01 min; MS m/z: 257 (M+H)+.

Provenance & Evidence