Sodium hydride → HCID 58504201, compound

Reaction equation

[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.Cl[C:12]1[C:17]2[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:19][O:20][C:16]=2[CH:15]=[N:14][N:13]=1>CN(C)C=O>[C:21]1([C:18]2[C:17]3[C:12]([O:10][CH2:9][CH:6]4[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]4)=[N:13][N:14]=[CH:15][C:16]=3[O:20][N:19]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Procedure

To sodium hydride (95% dispersion in mineral oil, 0.043 g) in N,N-dimethylformamide (6 mL) at 0° C. was added piperidin-4-ylmethanol (0.206 g). After stirring for 30 minutes, the compound prepared in Example 82 was added. The ice bath was removed and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was then diluted with saturated a sodium bicarbonate solution and extracted with dichloromethane. The organics were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (methanol:concentrated aqueous ammonia:dichloromethane=6:1:94) to obtain the title compound (0.20 g) having the following physical data.