Acetic Acid → HCID 123448882, compound

Participants

Reaction Steps

Tert-butyl-{4-[4-(3-{[(2,5-difluorophenyl)sulfonyl](methoxymethyl)amino}-2-fluorophenyl)-2-(piperidin-4-yl)-1,3-thiazol-5-yl]pyridin-2-yl}methylcarbamate (65 mg, 0.09 mmol) was dissolved in MeOH (5 mL) and glacial acetic acid (15 μL, 0.26 mmol). 37% aqueous formaldehyde (6.5 μL, 0.13 mmol) and sodium cyanoborohydride (8.5 mg, 0.17 mmol) were then added to the mixture, that was stirred at r.t. for 1 h. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and 15% aqueous ammonia. The organic phase was dried over Na2SO4 and evaporated to dryness, to give 34 mg of tert-butyl-{4-[4-(3-{[(2,5-difluorophenyl)sulfonyl](methoxymethyl)amino}-2-fluorophenyl)-2-(1-methylpiperidin-4-yl)-1,3-thiazol-5-yl]pyridin-2-yl}methylcarbamate that were employed for the next step without any further purification.

Provenance & Evidence