Trifluoroacetic acid → methyl (S)-6-(1-(1-(tert-butoxycarbonyl)azetidin-3-yl)-1H-pyrazol-4-yl)-5-(4-fluorophenoxy)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1051654노트

반응식

HRID 1051654 반응식
FC(F)(F)C(O)=O.[C:8]([O:12][C:13]([N:15]1[CH2:18][CH:17]([N:19]2[CH:23]=[C:22]([C:24]3[C:25]([O:39][C:40]4[CH:45]=[CH:44][C:43]([F:46])=[C:42](Cl)[CH:41]=4)=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]([C:34]([O:36][CH3:37])=[O:35])[C@@H:29]([CH3:38])[CH2:28][CH2:27]4)[CH:21]=[N:20]2)[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>ClCCl>[C:8]([O:12][C:13]([N:15]1[CH2:18][CH:17]([N:19]2[CH:23]=[C:22]([C:24]3[C:25]([O:39][C:40]4[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=4)=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]([C:34]([O:36][CH3:37])=[O:35])[C@@H:29]([CH3:38])[CH2:28][CH2:27]4)[CH:21]=[N:20]2)[CH2:16]1)=[O:14])([CH3:9])([CH3:10])[CH3:11]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 118075840HCID 118075840, 화합물

생성물 1

HCID 118075451methyl (S)-6-(1-(1-(tert-butoxycarbonyl)azetidin-3-yl)-1H-pyrazol-4-yl)-5-(4-fluorophenoxy)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate수율 593%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (1.0 mL, 6.49 mmol) was added to a solution of (S)-methyl 6-(1-(1-(tert-butoxycarbonyl)azetidin-3-yl)-1H-pyrazol-4-yl)-5-(3-chloro-4-fluorophenoxy)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.098 g, 0.033 mmol) in dichloromethane (1.0 mL) and the reaction mixture stirred at rt for 2 h. The mixture was then concentrated and the residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated to afford methyl (S)-6-(1-(1-(tert-butoxycarbonyl)azetidin-3-yl)-1H-pyrazol-4-yl)-5-(4-fluorophenoxy)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.105 g, 100%) as an off-white solid. MS (ESI, pos. ion) m/z 437 [M+H]+.

후처리

  1. concentrationThe mixture was then concentrated
  2. customthe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-317edc89f3fd4f2d953d65969a14c2bf
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388161B2

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