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N,N'-Dimethylethylenediamine → 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-methanesulfonyl-pyridin-3-yl)-cyclopropyl]-amide

HRID 2172978
ノート
印刷プレビュー

反応式

HRID 2172978 の反応式
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]2([NH:11][C:12]([C:14]3[C:15]4[CH:22]=[N:21][N:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[C:16]=4[CH:17]=[N:18][CH:19]=3)=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:30][S:31]([O-:33])=[O:32].[Na+].CNCCNC.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C.[I+].[Cu+]>[CH3:30][S:31]([C:2]1[N:7]=[CH:6][C:5]([C:8]2([NH:11][C:12]([C:14]3[C:15]4[CH:22]=[N:21][N:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[C:16]=4[CH:17]=[N:18][CH:19]=3)=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)(=[O:33])=[O:32]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 25517Ammonium ChlorideHCID 2733271Sodium methanesulfinateHCID 529167991-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide

生成物 1

HCID 529168001-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-methanesulfonyl-pyridin-3-yl)-cyclopropyl]-amide

試薬・触媒・溶媒 3

HCID 178505377HCID 178505377、化合物触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
130 °C

実験手順

A solution of 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide (72.7 mg, 0.161 mmol), sodium methanesulfinate (32.8 mg, 0.321 mmol) and copper (I) iodine (61.2 mg, 0.321 mmol) in DMSO (1 mL) is evacuated and purged with argon three times and heated at 130° C. After 45 minutes, the reaction is cooled to room temperature and N,N′-dimethylethylenediamine (69 μL, 0.64 mmol) is added. The mixture is stirred for 30 minutes, diluted with ethyl acetate (20 mL) and stirred for 15 minutes. A saturated aqueous solution of ammonium chloride (20 mL) is added; the resulting mixture is sonicated for 30 minutes, and diluted with ethyl acetate (100 mL). Phases are separated and the aqueous layer is extracted with ethyl acetate (3×20 mL). The combined organic layers are washed with saturated aqueous ammonium chloride (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated. The resulting residue is purified by silica gel chromatography eluting with a gradient of 0-8% methanol in methylene chloride to afford the title compound as a solid.

後処理

  1. custompurged with argon three times
  2. temperaturethe reaction is cooled to room temperature
  3. stirringstirred for 15 minutes
  4. customthe resulting mixture is sonicated for 30 minutes
  5. customPhases are separated
  6. extractionthe aqueous layer is extracted with ethyl acetate (3×20 mL)
  7. washThe combined organic layers are washed with saturated aqueous ammonium chloride (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), brine (50 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting residue is purified by silica gel chromatography
  12. washeluting with a gradient of 0-8% methanol in methylene chloride

出典と根拠

ORDレコード
ord-950ce9b8c8d845dbbebad6346a89ab8b
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056858B2

反応ノート

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