Toluene → HCID 178440634, compound

HRID 519618Notes

Reaction equation

HRID 519618 reaction equation
[CH2:1]([C:5]1[N:10]2[N:11]=[C:12]([CH3:14])[N:13]=[C:9]2[N:8]([C@H:15]2[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]2)[C:7](=[O:22])[C:6]=1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:26][CH:25]=1)[CH2:2][CH2:3][CH3:4].C([O:40]C(=O)C(C)C[N+]#N)C.[C:48]1([CH3:54])[CH:53]=CC=[CH:50][CH:49]=1>C([O-])(=O)C.[Rh+]>[CH2:1]([C:5]1[N:10]2[N:11]=[C:12]([CH3:14])[N:13]=[C:9]2[N:8]([C@H:15]2[CH2:20][CH2:19][C@H:18]([O:21][CH:49]([CH3:50])[C:48]([OH:40])([CH3:54])[CH3:53])[CH2:17][CH2:16]2)[C:7](=[O:22])[C:6]=1[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:28][CH:29]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 866440353-Ethoxy-2-methyl-3-oxopropane-1-diazoniumHCID 178440633HCID 178440633, compound

Product 1

HCID 178440634HCID 178440634, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 178476747HCID 178476747, compoundCatalyst

Procedure

To a mixture of 4′-{[7-butyl-4-(trans-4-hydroxycyclohexyl)-2-methyl-5-oxo-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.45 g), rhodium(I) acetate (0.004 g) and toluene (10 mL) was added dropwise 3-ethoxy-2-methyl-3-oxopropane-1-diazonium (0.72 L) at 80° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The obtained residue was dissolved in tetrahydrofuran (10 mL), and methylmagnesium bromide (1.0 M tetrahydrofuran solution, 2.5 mL) was added at room temperature. The reaction mixture was stirred for 1 hr, 1 N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.33 g, 63%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography
  3. dissolutionThe obtained residue was dissolved in tetrahydrofuran (10 mL)
  4. additionmethylmagnesium bromide (1.0 M tetrahydrofuran solution, 2.5 mL) was added at room temperature
  5. stirringThe reaction mixture was stirred for 1 hr
  6. addition1 N hydrochloric acid was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe obtained ethyl acetate layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-69318787c32d4e8faaefc7c8f76a6d72
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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