Hydrochloric Acid → HCID 57732691, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4-{[(methyloxy)imino]methyl}phenyl)-1H-indole-7-carboxamide (21.5 mg, 0.046 mmol) in DCM (3.0 mL) and MeOH (3.0 mL) was added drops of HCl in 1,4-dioxane to maintain pH=4 at 0° C. Sodium cyanoborohydride (29 mg, 0.46 mmol) was then added and stirred overnight at room temperature. Additional HCl in 1,4-dioxane was added to maintain pH=4 in addition to sodium cyanoborohydride (45 mg, 0.72 mmol). Reaction mixture then stirred over 48 h. Additional HCl in 1,4-dioxane was added to maintain pH=4 at 0° C. and stirred till room temperature was achieved. Mixture was quenched with H2O. DCM was then added for aqueous work-up and mixture was concentrated. The reside was then take up in DCM and purified on the SCX SPE cartridge to afford 15.2 mg of the title compound (70%).

Provenance & Evidence