Ethyl Acetate → 4'-{[7-Butyl-4-(1,4-dioxaspiro[4.5]dec-8-yl)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}-2'-fluorobiphenyl-2-carbonitrile

HRID 1688809노트

반응식

HRID 1688809 반응식
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][C:12]3[NH:16][N:15]=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH:43]([C:48](=O)[CH2:49][CH2:50][CH2:51][CH3:52])[C:44](OC)=[O:45])=[CH:38][C:37]=1[F:54])#[N:29].C(OCC)(=O)C>CCN(C1C=CC=CC=1)CC.O>[CH2:49]([C:48]1[N:16]2[N:15]=[CH:14][CH:13]=[C:12]2[N:11]([CH:8]2[CH2:7][CH2:6][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:10][CH2:9]2)[C:44](=[O:45])[C:43]=1[CH2:42][C:39]1[CH:40]=[CH:41][C:36]([C:31]2[C:30]([C:28]#[N:29])=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:37]([F:54])[CH:38]=1)[CH2:50][CH2:51][CH3:52]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67009202Methyl 2-[(2'-cyano-2-fluorobiphenyl-4-yl)methyl]-3-oxoheptanoateHCID 67009993N-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amine

생성물 1

HCID 670085724'-{[7-Butyl-4-(1,4-dioxaspiro[4.5]dec-8-yl)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}-2'-fluorobiphenyl-2-carbonitrile수율 88.2%

시약·촉매·용매 2

HCID 962Water용매HCID 7061N,N-Diethylaniline용매

실험 절차

A solution of N-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amine (2.2 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.30 mL) and methyl 2-[(2′-cyano-2-fluorobiphenyl-4-yl)methyl]-3-oxoheptanoate (6.4 g) in diethylaniline (10 mL) was stirred at 180° C. for 2 hr. The mixture was allowed to cool, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (4.7 g, 87%).

후처리

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e0635bcfbdcd441da27a9ee541aea462
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148383B2

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