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 522321노트

반응식

HRID 522321 반응식
[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

참가 물질

5

반응물 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

생성물 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-one수율 94%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매

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온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-38f561c15de24ce6b72704f33c33ebb8
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328116B2

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