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3,3,3-Trifluoropropionyl chloride → 2-(4-Chloro-phenyl)-5-{3-methoxy-4-[1-(3,3,3-trifluoro-propionyl)-azetidin-3-yloxy]-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one

HRID 554877
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HRID 554877 반응식
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:17][CH2:16][C:15]4[N:18]=[C:19]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=5)[S:20][C:14]=4[C:13]3=[O:28])=[CH:8][C:7]=2[O:29][CH3:30])[CH2:2]1.[F:31][C:32]([F:38])([F:37])[CH2:33][C:34](Cl)=[O:35]>N1C=CC=CC=1>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C:19]2[S:20][C:14]3[C:13](=[O:28])[N:12]([C:9]4[CH:10]=[CH:11][C:6]([O:5][CH:3]5[CH2:4][N:1]([C:34](=[O:35])[CH2:33][C:32]([F:38])([F:37])[F:31])[CH2:2]5)=[C:7]([O:29][CH3:30])[CH:8]=4)[CH2:17][CH2:16][C:15]=3[N:18]=2)=[CH:26][CH:25]=1
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참가 물질

4

반응물 2

HCID 27833433,3,3-Trifluoropropionyl chlorideHCID 249911625-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one

생성물 1

HCID 249911672-(4-Chloro-phenyl)-5-{3-methoxy-4-[1-(3,3,3-trifluoro-propionyl)-azetidin-3-yloxy]-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one수율 70.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Dissolve 5-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (100 mg, 0.226 mmol), and 3,3,3-trifluoropropionyl chloride (137 mg, 0.905 mmol) in dry pyridine (754.3 μL). Add 4-N,N-dimethylpyridine (2.9 mg, 0.0226 mmol) and stir the solution overnight. Add NaHSO4 solution and extract with EtOAc (2×20 mL). Combine the organic portions and wash with water (10 mL). Dry the organic solution with Na2SO4, filter, and concentrate in vacuo. Purify the crude material on silica gel chromatography, using an isocratic gradient of 80% EtOAc in hexanes, to give 88 mg (70%) of the title compound as a yellow solid. ES/MS m/z (35Cl) 552.8 [M+1]−.

후처리

  1. extractionAdd NaHSO4 solution and extract with EtOAc (2×20 mL)
  2. washCombine the organic portions and wash with water (10 mL)
  3. dry with materialDry the organic solution with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude material on silica gel chromatography

출처 및 근거

ORD 기록
ord-dcbd50fd93b3469bac734452086fc183
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08049013B2

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