Benzaldehyde → HCID 87274243, compound

Participants

Reaction Conditions

Reaction Steps

231 mg of the compound of Example 10 and 80 μl of benzaldehyde were dissolved in 9 ml of 1,2-dichloroethane-9 ml of acetic acid, 210 mg of sodium triacetoxyborohydride was added thereto at 0° C., and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 30 minutes. The reaction solution was alkalinized with saturated aqueous NaHCO3 and 1M aqueous NaOH, and extracted with chloroform. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. Then, to the obtained residue, 5 ml of acetic acid, a total of 160 μl of benzaldehyde, and a total of 404 mg of sodium triacetoxyborohydride were added, and the mixture was stirred at 50° C. for 4 hours. The solvent was evaporated under reduced pressure, saturated aqueous NaHCO3 was added to the obtained residue, and insoluble matter was collected by filtration. Chloroform was added thereto to dissolve it, and the solution was mixed with saturated aqueous NaHCO3 and extracted with chloroform. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-EtOAc=4:1) and the obtained compound was dissolved in EtOAc, and then a 0.5 M HCl-EtOAc solution was added thereto, and the thus-produced precipitate was collected by filtration to obtain 64 mg of N-[5-(4-benzylpiperazin-1-yl)-4-(4-chlorothiophen-2-yl)thiazol-2-yl]-2-methoxyisonicotinamide hydrochloride.

Provenance & Evidence