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4-Fluorophenol → 1,1-Dimethylethyl (2S)-4-({4-[({6-[(4-fluorophenyl)oxy]-2-pyridinyl}carbonyl) (methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

HRID 644759
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HRID 644759 반응식
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[N:17]=[C:16]([C:18]([N:20]([CH3:42])[C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@@H:30]([CH3:41])[CH2:29]3)=[CH:23][CH:22]=2)=[O:19])[CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:12]2[N:17]=[C:16]([C:18]([N:20]([CH3:42])[C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[C@@H:30]([CH3:41])[CH2:29]4)=[CH:23][CH:22]=3)=[O:19])[CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 592621881,1-Dimethylethyl (2S)-4-({4-[[(6-chloro-2-pyridinyl)carbonyl](methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

생성물 1

HCID 592621371,1-Dimethylethyl (2S)-4-({4-[({6-[(4-fluorophenyl)oxy]-2-pyridinyl}carbonyl) (methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate수율 46.2%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

반응 조건

온도
190 °C

실험 절차

To sodium hydride (0.0174 g, 60% dispersion in mineral oil, 0.436 mmol) in DMF (4 mL) was added 4-fluorophenol (0.0488 g, 0.436 mmol) and the mixture stirred under an argon atmosphere for 20 minutes. 1,1-Dimethylethyl (2S)-4-({4-[[(6-chloro-2-pyridinyl)carbonyl](methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate (D107) (0.100 g, 0.218 mmol) was added and the reaction mixture was heated in a microwave at 190° C. for 1.5 h. The reaction mixture was concentrated and the residue partitioned between DCM and water. The aqueous layer was further extracted with DCM and the combined organics were dried over Na2SO4 and concentrated to give a yellow oil which was purified by column chromatography to give the title compound as a colourless oil (0.0539 g). MS (ES): MH+ 535.4.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between DCM and water
  3. extractionThe aqueous layer was further extracted with DCM
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated
  6. customto give a yellow oil which
  7. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-05fa853db1424d82be2a0ff768e827c8
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07700599B2

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