Cesium fluoride → HCID 68524581, 화합물

HRID 1948916

반응식

HRID 1948916 반응식
[Cl:1][C:2]1[C:3]([F:22])=[C:4]([CH:19]=[CH:20][CH:21]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[N:9]=[CH:8][N:7]=1.[N+](C1C=CC(S(O[CH:36]2[CH2:41][CH2:40][CH2:39][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:37]2)(=O)=O)=CC=1)([O-])=O.[F-].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([F:22])=[C:4]([CH:19]=[CH:20][CH:21]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([O:16][CH:40]3[CH2:41][CH2:36][CH2:37][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:39]3)[CH:14]=2)[N:9]=[CH:8][N:7]=1

참가 물질

5

반응물 3

HCID 25953Cesium fluorideHCID 57476868HCID 57476868, 화합물HCID 86600822Tert-butyl 3-[(4-nitrophenyl)sulfonyloxy]piperidine-1-carboxylate

생성물 1

HCID 68524581HCID 68524581, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Dimethylformamide (23 ml) was added to 4-(3-chloro-2-fluoroanilino)-6-hydroxy-7-methoxyquinazoline, tert-butyl 3-[(4-nitrophenyl)sulfonyloxy]piperidine-1-carboxylate (1.93 g) and cesium fluoride (2.28 g). The reaction mixture was then stirred at room temperature for 4 days. The reaction mixture was evaporated under vacuum and partitioned between methylene chloride and water. The solutions were filtered to remove insoluble solids and the methylene chloride was washed with water and saturated brine and adsorbed onto silica. The product was then purified by column chromatography on silica eluting with increasingly polar mixtures of methylene chloride/methanol (100/0 to 94/6). The fractions containing the required product were combined and evaporated under vacuum to give 4-(3-chloro-2-fluoroanilino)-6-(1-tert-butoxycarbonylpiperidin-3-yloxy)-7-methoxyquinazoline as a yellow gum (0.67 g); Mass Spectrum: (M+H)+ 503.

후처리

  1. customThe reaction mixture was evaporated under vacuum
  2. custompartitioned between methylene chloride and water
  3. filtrationThe solutions were filtered
  4. customto remove insoluble solids
  5. washthe methylene chloride was washed with water and saturated brine
  6. customThe product was then purified by column chromatography on silica eluting
  7. temperaturewith increasingly polar mixtures of methylene chloride/methanol (100/0 to 94/6)
  8. additionThe fractions containing the required product
  9. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-3465babe351542c8b5959908c6b9a417
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399667B2

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