Sodium cyanoborohydride → 7-Fluoro-8-{4-[4-(6-methoxyquinolin-8-yl)piperazin-1-yl]piperidin-1-yl}Quinoline

HRID 2241983노트

반응식

HRID 2241983 반응식
[F:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[C:29]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[CH:30]=1)[N:27]=[CH:26][CH:25]=[CH:24]2.C([BH3-])#N.[Na+]>CO.[Cl-].[Na+].O>[F:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][CH:15]([N:34]3[CH2:35][CH2:36][N:31]([C:29]4[CH:30]=[C:21]([O:20][CH3:19])[CH:22]=[C:23]5[C:28]=4[N:27]=[CH:26][CH:25]=[CH:24]5)[CH2:32][CH2:33]3)[CH2:14][CH2:13]2)=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 5003444Sodium cyanoborohydride2회HCID 184141776-Methoxy-8-(piperazin-1-YL)quinolineHCID 573365271-(7-Fluoroquinolin-8-YL)piperidin-4-one

생성물 1

HCID 120041147-Fluoro-8-{4-[4-(6-methoxyquinolin-8-yl)piperazin-1-yl]piperidin-1-yl}Quinoline

시약·촉매·용매 2

HCID 887Methanol용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 1-(7-fluoroquinolin-8-yl)piperidin-4-one (Step 3, 0.26 g) and 6-methyoxy-8-(1-piperazinyl)quinoline (Example A, Step 4; 0.26 g) in anhydrous methanol (10 mL) was added sodium cyanoborohydride (0.11 g). The resulting mixture was stirred at room temperature under nitrogen for 18 hours. An additional aliquot of sodium cyanoborohydride (0.11 g) was added and stirring at room temperature was continued for another 24 hours. The resulting 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 purified by flash chromatography on silica gel using hexane/acetone to give the desired product, which was converted to its trihydrochloride salt in CH2Cl2 using 1M HCl/Et2O to provide 0.12 g of a yellow solid; MS (ES) m/z (relative intensity): 472 (M+H)+ (100).

후처리

  1. stirringstirring at room temperature
  2. waitwas continued for another 24 hours
  3. customThe resulting reaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customThe crude product was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-69bde18468104ad09e7d5d25dffb312d
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671056B2

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