Ethylenediamine → 3-[3-(4,5-dihydro-1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one

HRID 522321ノート

反応式

HRID 522321 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH3:15])[CH3:14])=[C:11]([N:16]3[CH2:20][CH2:19][CH:18]([N:21]4[C:25]5=[N:26][CH:27]=[CH:28][CH:29]=[C:24]5[C:23]([C:30]#[N:31])=[N:22]4)[C:17]3=[O:32])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:33](N)[CH2:34][NH2:35]>CC(O)=O.CCO>[NH:31]1[CH2:33][CH2:34][N:35]=[C:30]1[C:23]1[C:24]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:21]([CH:18]2[CH2:19][CH2:20][N:16]([C:11]3[CH:10]=[N:9][N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[C:12]=3[CH:13]([CH3:14])[CH3:15])[C:17]2=[O:32])[N:22]=1

参加物

5

反応物 2

HCID 3301EthylenediamineHCID 867230351-[1-[1-(4-Fluorophenyl)-5-isopropyl-pyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-b]pyridine-3-carbonitrile

生成物 1

HCID 867230363-[3-(4,5-dihydro-1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one収率 94%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-[1-[1-(4-fluorophenyl)-5-isopropyl-pyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]pyrazolo[3,4-b]pyridine-3-carbonitrile (0.082 g, 0.19 mmol) in ethane-1,2-diamine (1 mL), HOAc (0.1 mL) and EtOH (2.5 mL) was stirred at 100° C. for 1 hr. The mixture was then cooled to room temperature, quenched with saturated aqueous NaHCO3 (50 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-[3-(4,5-dihydro-1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.085 g, 94%).

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. customquenched with saturated aqueous NaHCO3 (50 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-38f561c15de24ce6b72704f33c33ebb8
出典データセット
uspto-grants-2016_05
特許番号
US09328116B2

反応ノート

読み込み中…