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Benzenesulfonamide, 3-amino- → 3-((1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)amino)benzenesulfonamide

HRID 2206212
ノート
印刷プレビュー

反応式

HRID 2206212 の反応式
FC(F)(F)S(O[C:7]1[C:11]2[C:12]([O:16][CH3:17])=[N:13][CH:14]=[CH:15][C:10]=2[N:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=1)(=O)=O.[NH2:24][C:25]1[CH:26]=[C:27]([S:31]([NH2:34])(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:18]([N:9]1[C:10]2[CH:15]=[CH:14][N:13]=[C:12]([O:16][CH3:17])[C:11]=2[C:7]([NH:24][C:25]2[CH:26]=[C:27]([S:31]([NH2:34])(=[O:32])=[O:33])[CH:28]=[CH:29][CH:30]=2)=[N:8]1)([CH3:19])([CH3:20])[CH3:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 7377Benzenesulfonamide, 3-amino-HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 1179881911-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl trifluoromethanesulfonate

生成物 1

HCID 1179880393-((1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)amino)benzenesulfonamide
収率 13.9%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

To a solution of 1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl trifluoromethanesulfonate (200 mg) obtained in Step C of Example 86 in toluene (20 ml) were added 3-aminobenzenesulfonamide (146 mg), tris(dibenzylideneacetone)dipalladium (51.8 mg), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)(92.6 mg) and cesium carbonate (369 mg), and the mixture was heated overnight with reflux under nitrogen atmosphere. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (29.6 mg).

後処理

  1. temperaturethe mixture was heated overnight
  2. temperaturewith reflux under nitrogen atmosphere
  3. extractionThe reaction mixture was extracted with water and ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-2252b0063da14b7081dc5937ba38c65a
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09371320B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート