Toluene → HCID 178440634、化合物

HRID 1412332

反応式

HRID 1412332 の反応式
[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]

参加物

5

反応物 3

HCID 1140TolueneHCID 866440353-Ethoxy-2-methyl-3-oxopropane-1-diazoniumHCID 178440633HCID 178440633、化合物

生成物 1

HCID 178440634HCID 178440634、化合物収率 63%

試薬・触媒・溶媒 1

HCID 178476747HCID 178476747、化合物触媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-82d40d8fd547442998a1b9ed81cf6ab7
出典データセット
uspto-grants-2014_12
特許番号
US08921379B2

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