Hydrochloric Acid → 4'-[(4-{4-[1-(1-Acetylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

HRID 2062729Notes

Reaction equation

HRID 2062729 reaction equation
[CH:1]([C:3]1([CH:7]([O:9][CH:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:21](=[O:22])[C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:26][CH:25]=4)=[C:19]([CH2:38][CH2:39][CH3:40])[N:18]4[N:41]=[CH:42][N:43]=[C:17]34)[CH2:12][CH2:11]2)[CH3:8])[CH2:6][CH2:5][CH2:4]1)=[O:2].[CH3:44][Mg]Br.O1CCCC1.Cl>O1CCCC1>[C:1]([C:3]1([CH:7]([O:9][CH:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:21](=[O:22])[C:20]([CH2:23][C:24]4[CH:25]=[CH:26][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:28][CH:29]=4)=[C:19]([CH2:38][CH2:39][CH3:40])[N:18]4[N:41]=[CH:42][N:43]=[C:17]34)[CH2:12][CH2:11]2)[CH3:8])[CH2:6][CH2:5][CH2:4]1)(=[O:2])[CH3:44]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 866440584'-[(4-{4-[1-(1-Formylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrileHCID 178420675HCID 178420675, compound

Product 1

HCID 670091324'-[(4-{4-[1-(1-Acetylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4′-[(4-{4-[1-(1-formylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (10.35 g) in tetrahydrofuran (50 mL) was added 1 M methylmagnesium bromide-tetrahydrofuran solution (27 mL), and the mixture was stirred at room temperature for 15 hr. 1 N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a solution of the residue in acetonitrile (200 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (8.48 g), and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)] to give the title compound as a colorless amorphous compound (8.32 g, 79%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additionTo a solution of the residue in acetonitrile (200 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (8.48 g)
  6. stirringthe mixture was stirred at room temperature for 2 hr
  7. additionSaturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)]

Sources & evidence

ORD record
ord-6141cd23d2344719a4a4afb7a13a37b8
Source dataset
uspto-grants-2012_10
Patent number
US08283353B2

Reaction notes

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