Hydrochloric Acid → 1,4-dihydro-4-[3-[(2-hydroxyethyl)amino]-1H-indazol-5-yl]-2,6-dimethyl-3,5-pyridinedicarbonitrile

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A mixture of crude 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-5-(3,5-dicyano-2,6-dimethyl-1,4-dihydro-pyridin-4-yl)-indazole-1-carboxylic acid tert-butyl ester (165 mg) and HCl (4M solution in THF, 2 mL) was stirred overnight at room temperature. The mixture was partitioned between dilute aqueous sodium hydrogen carbonate solution (0.5%, 40 mL) and EtOAc (40 mL). The organic extract was dried (Na2SO4), concentrated and the residue purified by chromatography on silica gel to give 1,4-dihydro-4-[3-[(2-hydroxyethyl)amino]-1H-indazol-5-yl]-2,6-dimethyl-3,5-pyridinedicarbonitrile (66 mg) (Cpd. No. 118, Table 2).

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