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Cesium carbonate → 3-[(7-Fluoro-5,5-dioxido-3,4-dihydro-2H-1,5-benzoxathiepin-8-yl)oxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 548654
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HRID 548654 반응식
F[C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[S:10]([CH:13]1[CH2:17][CH2:16][O:15]C1=O)(=[O:12])=[O:11].[Si]([O:26][CH2:27][C@H:28]([CH3:46])[O:29][C:30]1[CH:31]=[C:32]([CH:42]=[C:43]([OH:45])[CH:44]=1)[C:33]([NH:35][C:36]1[CH:40]=[CH:39][N:38]([CH3:41])[N:37]=1)=[O:34])(C(C)(C)C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:9][C:5]1[C:6]([O:45][C:43]2[CH:42]=[C:32]([CH:31]=[C:30]([O:29][C@@H:28]([CH3:46])[CH2:27][OH:26])[CH:44]=2)[C:33]([NH:35][C:36]2[CH:40]=[CH:39][N:38]([CH3:41])[N:37]=2)=[O:34])=[CH:7][C:2]2[O:15][CH2:16][CH2:17][CH2:13][S:10](=[O:11])(=[O:12])[C:3]=2[CH:4]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 536296323-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamideHCID 576631723-[(2,4,5-trifluorophenyl)sulfonyl]dihydrofuran-2(3H)-one

생성물 1

HCID 119612633-[(7-Fluoro-5,5-dioxido-3,4-dihydro-2H-1,5-benzoxathiepin-8-yl)oxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide수율 34.3%

시약·촉매·용매

1
HCID 6342Acetonitrile용매

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온도
150 °C

실험 절차

A solution of 3-[(2,4,5-trifluorophenyl)sulfonyl]dihydrofuran-2(3H)-one (126 mg, 0.45 mmol) and 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyloxy)-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide (203 mg, 0.50 mmol) in acetonitrile (3.5 mL) was treated with caesium carbonate (650 mg, 2.0 mmol) and heated in a microwave reactor at 150° C. for 1.5 hours. The reaction mixture was filtered and concentrated in vacuo. The residue was then chromatographed on silica, eluting with a gradient of 0 to 10% methanol in ethyl acetate, to afford the title compound (78 mg).

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was then chromatographed on silica
  4. washeluting with a gradient of 0 to 10% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-69848e2f1b9a41bab56fcd6ae1171ca3
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07943607B2

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