Cesium fluoride → HCID 68524581、化合物

HRID 1948916

反応式

HRID 1948916 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 68524581HCID 68524581、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3465babe351542c8b5959908c6b9a417
出典データセット
uspto-grants-2013_03
特許番号
US08399667B2

関連ノート

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