Ethyl Acetate → 4'-({4-[4-(1-Methylethoxy)phenyl]-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile

HRID 1412561Notes

Reaction equation

HRID 1412561 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:3].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:49](=O)[CH2:50][CH2:51][CH3:52])[C:44](OCC)=[O:45])=[CH:38][CH:37]=1)#[N:29].C(OCC)(=O)C>CCN(C1C=CC=CC=1)CC.O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:44](=[O:45])[C:43]([CH2:42][C:39]3[CH:40]=[CH:41][C:36]([C:31]4[C:30]([C:28]#[N:29])=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:37][CH:38]=3)=[C:49]([CH2:50][CH2:51][CH3:52])[N:16]3[N:15]=[CH:14][CH:13]=[C:12]23)=[CH:9][CH:10]=1)[CH3:1]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 67009388N-[4-(1-methylethoxy)phenyl]-1H-pyrazol-5-amine

Product 1

HCID 670091114'-({4-[4-(1-Methylethoxy)phenyl]-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrileYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7061N,N-DiethylanilineSolvent

Procedure

N-[4-(1-Methylethoxy)phenyl]-1H-pyrazol-5-amine (0.37 g) and a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.051 mL) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (1.2 g) in diethylaniline (5 mL) were stirred at 180° C. for 1 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 (0.76 g, 89%).

Workup

  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

Sources & evidence

ORD record
ord-8b3f98411b69445a9a556de471519ae4
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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