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3-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)prop-2-yn-1-ol → 3-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)propan-1-ol

HRID 1627285
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HRID 1627285 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][C:28]([C:32]#[C:33][CH2:34][OH:35])=[CH:27][C:26]=3[F:36])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:37][CH3:38]>CO.O=[Pt]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:26]([F:36])=[CH:27][C:28]([CH2:32][CH2:33][CH2:34][OH:35])=[CH:29][C:30]=3[F:31])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:37][CH3:38]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 1

HCID 667400453-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)prop-2-yn-1-ol

생성물 1

HCID 667411903-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)propan-1-ol수율 77.3%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 887Methanol용매

실험 절차

A solution of 3-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenyl)prop-2-yn-1-ol (714 mg, 1.28 mmol) in MeOH (75 mL) was sparged with argon, charged with PtO2 (30 wt %, 214 mg) and then pressurized to 65 psi under hydrogen atmosphere in a Parr shaker for 36 h. The reaction was monitored by LCMS and upon completion the mixture was filtered through Celite™ to remove the catalyst. The filtrate was concentrated and purified by flash chromatography (80% EtOAc/Hex) to yield the title compound (560 mg, 0.99 mmol). MS (EI) m/z 561 (MH+).

후처리

  1. filtrationwas filtered through Celite™
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography (80% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-026885158dbb442290c025590fa1b0f7
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785488B2

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