Hydrochloric Acid → HCID 178519329, compound

Participants

Reaction Steps

A solution of lithium triethylborohydride (1 M in THF, 0.8 mL) was slowly added at RT to trans-1-[2-(4-hydroxycyclohexylamino)-pyrimidin-4-yl]-1H-indazole-6-carboxylic acid methyl ester (100 mg) in THF (3 mL). The resulting mixture was stirred for 30 min, and AcOH/EtOH (1:1, 2 mL) was added. The reaction mixture was stirred for 30 min, then poured onto aqueous HCl (0.1 M). The resulting mixture was basified to pH 8 with aqueous NaOH and aqueous NaHCO3, then extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by preparative TLC (DCM/MeOH, 95:5) to give of trans-4-[4-(6-hydroxymethyl-indazol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol (22 mg) as a white solid. MS=340 [M+H]+; MP=216.0-217.7° C.

Provenance & Evidence