Ethyl Acetate → 5-(4-chloro-phenyl)-6-(2,4-dichlorophenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-ylamine

HRID 1693495

反応式

HRID 1693495 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=O)=[CH:4][CH:3]=1.[NH2:19][C:20]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:23]=[CH:22][C:21]=1[C:31]#[N:32].CCOC(C)=O>ClC(Cl)C.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:31]([NH2:32])=[C:21]3[CH:22]=[N:23][N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:20]3=[N:19][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 792565-Amino-1-phenyl-1H-pyrazole-4-carbonitrileHCID 219848672-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)ethan-1-one

生成物 1

HCID 116196625-(4-chloro-phenyl)-6-(2,4-dichlorophenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-ylamine

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 63651,1-Dichloroethane溶媒2 回

実験手順

A solution of 2-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-ethanone (300 mg, 0.99 mmol) in dichloroethane (3 mL) is stirred at room temperature while TiCl4 (311 mg, 1.64 mmol) is added dropwise. After the addition, the mixture is stirred at room temperature for 5 minutes and a solution of 5-amino-1-phenyl-1H-pyrazole-4-carbonitrile (150 mg, 0.815 mmol) in dichloroethane (3 mL) is added dropwise. After the addition, the mixture is heated to 125° C. for 5 hours. After cooling, the mixture is poured into a mixture of ice cold saturated aqueous NaHCOs solution (30 mL) and EtOAc (30 mL). The resultant precipitate is filtered through celite and washed with EtOAc (2×10 mL). The filtrate is extracted by EtOAc (3×15 mL). The organic layers are combined and washed with brine and dried (MgSO4). After filtering off the drying agent, the filtrate is concentrated and purified by column chromatography (silica gel, 0%˜40% EtOAc/hexane) to provide the titled compound 5-(4-chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-ylamine as light yellow solid:

後処理

  1. additionis added dropwise
  2. additionAfter the addition
  3. additionAfter the addition
  4. temperaturethe mixture is heated to 125° C. for 5 hours
  5. temperatureAfter cooling
  6. filtrationThe resultant precipitate is filtered through celite
  7. washwashed with EtOAc (2×10 mL)
  8. extractionThe filtrate is extracted by EtOAc (3×15 mL)
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationAfter filtering off the drying agent
  12. concentrationthe filtrate is concentrated
  13. custompurified by column chromatography (silica gel, 0%˜40% EtOAc/hexane)

出典と根拠

ORDレコード
ord-e83f9a8350d541c59c0050f21c20238b
出典データセット
uspto-grants-2012_04
特許番号
US08158634B2

関連ノート

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