p-Methylphenoxyacetic acid → 2-(4-Methylphenoxy)-1-(4-naphthalen-2-ylsulfonylpiperazin-1-yl)ethanone

HRID 517000

반응식

HRID 517000 반응식
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].[C:24]1([CH3:35])[CH:29]=[CH:28][C:27]([O:30]CC(O)=O)=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[S:11]([N:8]1[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][O:30][C:27]2[CH:28]=[CH:29][C:24]([CH3:35])=[CH:25][CH:26]=2)[CH2:6][CH2:7]1)(=[O:13])=[O:12]

참가 물질

6

반응물 4

HCID 70329p-Methylphenoxyacetic acidHCID 81531DiisopropylethylamineHCID 24058752-Chloro-1-[4-(naphthalene-2-sulfonyl)piperazin-1-yl]ethan-1-one2회HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 11515272-(4-Methylphenoxy)-1-(4-naphthalen-2-ylsulfonylpiperazin-1-yl)ethanone수율 77.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 2-chloro-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone (compound 4, 0.2 g, 0.64 mmol) and 2-(p-tolyloxy)acetic acid (106 mg, 0.64 mmol) in dry DCM (20 mL), DIPEA (495 mg, 3.86 mmol) followed by HATU (486 mg, 1.27 mmol) was added at room temperature and stirred overnight. The mixture was then diluted with DCM and washed with water (2×10 mL) & brine (2×10 mL). The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to yield the title compound (0.21 g, 77.5%) as an off-white solid.

후처리

  1. additionwas added at room temperature
  2. washwashed with water (2×10 mL) & brine (2×10 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography

출처 및 근거

ORD 기록
ord-31e27bbf07fe4a6c83d2dc5203b23350
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115086B2

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