Ammonium Chloride → 4'-{[4-(4-Hydroxyphenyl)-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

HRID 2048602Notes

Reaction equation

HRID 2048602 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[NH:20][N:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.N12CCCN=C1CCCCC2.[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH:47]([C:53](=O)[CH2:54][CH2:55][CH3:56])[C:48](OCC)=[O:49])=[CH:42][CH:41]=1)#[N:33].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>CCN(C1C=CC=CC=1)CC.C(OCC)(=O)C.O1CCCC1>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:48](=[O:49])[C:47]([CH2:46][C:43]3[CH:44]=[CH:45][C:40]([C:35]4[C:34]([C:32]#[N:33])=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:41][CH:42]=3)=[C:53]([CH2:54][CH2:55][CH3:56])[N:20]3[N:19]=[CH:18][CH:17]=[C:16]23)=[CH:13][CH:14]=1

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724141Tetrabutylammonium FluorideHCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 67009063N-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1H-pyrazol-5-amine

Product 1

HCID 670088984'-{[4-(4-Hydroxyphenyl)-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrileYield 79%

Reagents, catalysts & solvents 3

HCID 7061N,N-DiethylanilineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1H-pyrazol-5-amine (2.8 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.30 mL) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (7.0 g) in diethylaniline (15 mL) was stirred at 180° C. for 8 hr. The mixture was allowed to cool, tetrahydrofuran (5 mL) and tetrabutylammonium fluoride (1.0 M tetrahydrofuran solution, 5 mL) were added, and the mixture was stirred for 1 hr. To the reaction mixture were added ethyl acetate and saturated aqueous ammonium chloride solution, 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 (3.5 g, 79%).

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-11e929b8a83b4f09ba5d539fa01a744c
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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