Ethyl Acetate → HCID 178438719, compound

HRID 1688790Notes

Reaction equation

HRID 1688790 reaction equation
C(OC(=O)[CH2:5][O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:18](=[O:19])[C:17]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]#[N:34])=[CH:23][C:22]=3[F:35])=[C:16]([CH2:36][CH2:37][CH3:38])[N:15]3[N:39]=[CH:40][CH:41]=[C:14]23)[CH2:9][CH2:8]1)C.[CH3:43][Mg]Br.C([O:49][CH2:50][CH3:51])(=O)C>O1CCCC1>[F:35][C:22]1[CH:23]=[C:24]([C:27]2[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:25]=[CH:26][C:21]=1[CH2:20][C:17]1[C:18](=[O:19])[N:13]([C@H:10]2[CH2:9][CH2:8][C@H:7]([O:6][CH2:5][C:50]([OH:49])([CH3:51])[CH3:43])[CH2:12][CH2:11]2)[C:14]2[N:15]([N:39]=[CH:40][CH:41]=2)[C:16]=1[CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 178418573HCID 178418573, compoundHCID 178438732HCID 178438732, compound

Product 1

HCID 178438719HCID 178438719, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl[(trans-4-{6-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-5-oxo-7-propylpyrazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexyl)oxy]acetate (0.40 g) in tetrahydrofuran (4 mL) was added dropwise methylmagnesium bromide (1 M tetrahydrofuran solution, 0.71 mL) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture were added ethyl acetate and then saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with 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 (0.26 g, 88%).

Workup

  1. extractionsaturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d2d2b00d15c7458b9630dc0fa684adb0
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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