Sodium hydride → ethyl 3-(6-aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionate

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Reaction Steps

Ethyl 3-(6-aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propionate (100 mg; 0.38 mmol) was dissolved in absolute DMF (2 ml). Sodium hydride (50%; 19 mg; 0.38 mmol) was added, and the reaction mixture was stirred at RT for 1 h. Then 1-[4-(2-bromoethyl)piperidin-1-yl]-2,2-diphenylethanone (148 mg; 0.38 mmol) dissolved in absolute DMF (1 ml) was added. The reaction mixture was stirred at RT for 1 h and then concentrated under reduced pressure. The residue was taken up in 1N HCl and washed with dichlormethane (CH2Cl2; 2×). The aqueous phase was made basic with 1N NaOH and extracted with CH2Cl2 (3×). The combined organic phases were dried over Na2SO4. Removal of the solvent under reduced pressure resulted in ethyl 3-(6-aminopyridin-3-yl)-2-{1-[2-(1-diphenylacetylpiperidin-4-yl)ethyl]-1H-imidazol-4-yl}propionate (71 mg; 0.12 mmol).

Provenance & Evidence