Dimethyl Sulfoxide → (S)-1-(2-benzyl-4-(8-methoxy-2-(trifluoromethyl)quinolin-5-yl)piperazin-1-yl)-2-(1H-1,2,4-triazol-5-yl)ethanone

HRID 1423184노트

반응식

HRID 1423184 반응식
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:29])([F:28])[F:27])=[N:19]3)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:32][C:33](=O)[CH2:34][C:35]1[NH:39][CH:38]=[N:37][N:36]=1)C.[C-]#N.[Na+].CS(C)=O>CCOC(C)=O>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:29])([F:27])[F:28])=[N:19]3)[CH2:11][CH2:12][N:13]1[C:33](=[O:32])[CH2:34][C:35]1[NH:36][N:37]=[CH:38][N:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 58188941(S)-5-(3-benzylpiperazin-1-yl)-8-methoxy-2-(trifluoromethyl)quinoline2회HCID 178470790HCID 178470790, 화합물

생성물 1

HCID 66828497(S)-1-(2-benzyl-4-(8-methoxy-2-(trifluoromethyl)quinolin-5-yl)piperazin-1-yl)-2-(1H-1,2,4-triazol-5-yl)ethanone수율 0.7%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A solution of (S)-5-(3-benzylpiperazin-1-yl)-8-methoxy-2-(trifluoromethyl)quinoline (Example 65, Compound 153) (100.0 mg, 0.25 mmol), (4H-[1,2,4]triazol-3-yl)-acetic acid ethyl ester (83 mg, 0.50 mmol), sodium cyanide (24 mg, 0.50 mmol), and DMSO (2 mL). The reaction mixture was heated in a heat block at 100 C for 24 h then cooled to room temperature, diluted with EtOAc, and washed with water followed by brine. The organic portion was dried over MgSO4, filtered, evaporated and purified by silica gel flash chromatography to afford product as a colorless solid (0.9 mg, 0.7%). LC/MS (Method B) 3.32 min, [m/z=510.9].

후처리

  1. temperatureThe reaction mixture was heated in a heat block at 100 C for 24 h
  2. washwashed with water
  3. dry with materialThe organic portion was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-ce5c30eb5f964c29b43a7f7b1a5de5d1
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927546B2

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