Acetonitrile → HCID 6480511, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of a-8 (0.0002 mol), a-9 (0.0002 mol), 2-bromo-ethanol (0.0006 mol) and triethylamine (0.0011 mol) in acetonitrile (10 ml) was stirred at 30° C. for 12 hours. The solvent was evaporated until dryness. The residue was taken up in CH2Cl2. The organic layer was washed with H2O, dried (over MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 85/15/1; 10 μm). Two fractions were collected and the solvent was evaporated, yielding: 0.028 g fraction 1 (12.4%) and 0.05 g fraction 2 (22%). Fraction 1 was crystallized from 2-propanone/diisopropylether. The precipitate was filtered off and dried, yielding 0.015 g of 2-{2-[1-(2-hydroxy-ethyl)-piperidin-4-ylamino]-5,7-dimethyl-benzoimidazol-1-ylmethyl}-6-methyl-pyridin-3-ol (6.6%, melting point: 143° C.). Fraction 2 was crystallized from 2-propanone/diisopropylether. The precipitate was filtered off and dried, yielding 0.03 g of 2-{2-[1-(2-hydroxy-ethyl)-piperidin-4-ylamino]-4,6-dimethyl-benzoimidazol-1-ylmethyl}-6-methyl-pyridin-3-ol (compound 2, 13%, melting point: 177° C.).

Provenance & Evidence