Triethylamine → HCID 21023791, compound

Participants

Reaction Steps

Ethensulfonic acid {2-[4-(4-chloro-3-methoxy-phenyl)-5-pyridin-4-yl-1H-imidazol-2-yl]-2-methyl-propyl}-amide A solution of ethenesulfonyl chloride (J. Marchand-Brynaert et al., Tetrahedron 1966, 52, 5591) (230 mg, 1.8 mmol) in dichloromethane (10 ml) was cooled to −78° C. and treated with a solution of the product of Example 2 and triethylamine (0.4 ml, 3 mmol) in dichloromethane (10 ml). After 1 hour the reaction mixture was warmed to room temperature and the solution washed with saturated sodium hydrogen carbonate solution. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and the solvent evaporated to give the title compound (254 mg, 38%); MS(ES+) m/e 447/449 [M+H]+. Step 2. 2-(4-Methyl-piperazin-1-yl)-ethanesulfonic acid {2-[4-(4-chloro-3-methoxy-phenyl)-5-pyridin-4-yl-1H-imidazol-2-yl]-2-methyl-propyl}-amide A solution of the produce of Step 1 (110 mg, 0.25 mmol) and N-methylpiperazine (50 mg, 0.5 mmol) in dichloromethane (5 ml) was stirred at room temperature for 72 hours. The solvent was evaporated and the residue was purified by silica gel chromatography to give the title compound (98 mg, 72%); MS(ES+) m/e 547/549 [M+H]+. Step 3. 2-(4-Methyl-piperazin-1-yl)-ethanesulfonic acid {2-[4-(4-chloro-3-hydroxy-phenyl)-5-pyridin-4-yl-1H-imidazol-2-yl]-2-methyl-propyl}-amide The title compound was prepared from the product of Step 2 using the method described in Example 3 and the product purified by silica gel chromatography; MS(ES+) m/e 533/535 [M+H]+.

Provenance & Evidence