Sodium cyanoborohydride → HCID 12004116、化合物

反応式

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[F:19][C:20]([F:39])([F:38])[C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][C:25]=2[N:31]1[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]1.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N:13]3[CH2:14][CH2:15][N:16]([CH:34]4[CH2:35][CH2:36][N:31]([C:25]5[CH:26]=[CH:27][CH:28]=[C:29]6[C:24]=5[N:23]=[CH:22][C:21]([C:20]([F:39])([F:38])[F:19])=[CH:30]6)[CH2:32][CH2:33]4)[CH2:17][CH2:18]3)[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

参加物

実験手順

A mixture of 6-methoxy-8-piperazinoquinoline (Example A, Step 4; 0.0825 g) and 1-[3-(trifluoromethyl)quinolin-8-yl]piperidin-4-one (0.1 g) in methanol (5 mL) was treated with sodium cyanoborohydride (Step 4, 0.032 g). The resulting mixture was stirred at room temperature for 18 hours and then concentrated on a rotary evaporator. The residue was taken up in CH2C2, washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate to give the desired product, which was converted to its dihydrochloride salt in using 1N HCl/Et2O to yield 0.035 g as a yellow solid; MS (ES) m/z (relative intensity): 522 (M+H)+ (100).