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Cesium carbonate → 4-[5-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-2-pyrazinyloxy]benzoic acid

HRID 1443990
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인쇄 미리보기

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HRID 1443990 반응식
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(C)(C)[CH3:2].Br[C:16]1[N:17]=[C:18]([O:42][CH3:43])[C:19]([N:22](COCC[Si](C)(C)C)[S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=2[Cl:33])(=[O:25])=[O:24])=[N:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[C:6]([O:5][CH2:1][CH3:2])(=[O:14])[CH3:7].[CH3:10][CH2:9][CH2:8][CH:7]([CH3:12])[CH3:6].[Cl:33][C:27]1[C:28]([Cl:32])=[CH:29][CH:30]=[CH:31][C:26]=1[S:23]([NH:22][C:19]1[N:20]=[CH:21][C:16]([O:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]([OH:5])=[O:14])=[CH:12][CH:11]=2)=[N:17][C:18]=1[O:42][CH3:43])(=[O:25])=[O:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 117640tert-Butyl 4-hydroxybenzoateHCID 59168156N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide

생성물 2

HCID 102172984-[5-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-2-pyrazinyloxy]benzoic acidHCID 21882781Isohexane ethyl acetate

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

4-Hydroxybenzoic acid tert butyl ester (0.13 g), N-(5-bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide (Example 55 part a) (0.35 g) and caesium carbonate (0.42 g) in acetonitrile (10 mL) was heated at 50° C. After 12 h, the mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound protected with the SEM group and tert butyl group as an oil. The oil was dissolved in trifluoroacetic acid (2.0 mL) and stirred at room temperature for 3 h.

후처리

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated

출처 및 근거

ORD 기록
ord-8d80e8d66a0540ac95b0b7753090fc66
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07662825B2

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