反応式
[F:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[F:19][C:20]1[CH:21]=[C:22]2[C:27](=[C:28]([N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[CH:29]=1)[N:26]=[CH:25][CH:24]=[CH:23]2.C([BH3-])#N.[Na+].CCCCCC.CC(C)=O>CO.[Cl-].[Na+].O>[F:19][C:20]1[CH:21]=[C:22]2[C:27](=[C:28]([N:30]3[CH2:35][CH2:34][N:33]([CH:15]4[CH2:16][CH2:17][N:12]([C:3]5[C:2]([F:1])=[C:11]6[C:6]([CH:7]=[CH:8][CH:9]=[N:10]6)=[CH:5][CH:4]=5)[CH2:13][CH2:14]4)[CH2:32][CH2:31]3)[CH:29]=1)[N:26]=[CH:25][CH:24]=[CH:23]2参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
To a solution of 1-(8-fluoroquinolin-7-yl)piperidin-4-one (Step 1, 0.25 g) and 6-fluoro-8-(1-piperazinyl)quinoline (Example B, Step 3; 0.25 g) in anhydrous methanol (10 mL) was added sodium cyanoborohydride (0.11 g). The resulting mixture was stirred at room temperature for 18 hours. An additional aliquot of sodium cyanoborohydride (0.10 g) was added and stirring at room temperature was continued for another 24 hours. The reaction mixture was poured into brine and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated on a rotary evaporator. The crude product was isolated by flash chromatography on silica gel using hexane/acetone to give the desired product as a off-white solid, which was converted to its trihydrochloride salt in CH2Cl2/Et2O diethyl ether using 1M HCl/Et2O to provide 0.11 g as a yellow solid; MS (ES) m/z (relative intensity): 460 (M+H)+ (100).
後処理
- stirringstirring at room temperature
- waitwas continued for another 24 hours
- extractionextracted with ethyl acetate
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated on a rotary evaporator
- customThe crude product was isolated by flash chromatography on silica gel
出典と根拠
- ORDレコード
- ord-bd6781dca4b646cf90acd8b5b5392cae
- 出典データセット
- uspto-grants-2010_03
- 特許番号
- US07671056B2
関連ノート
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