Toluene → HCID 178438717, 화합물

HRID 1412334

반응식

HRID 1412334 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:30]2[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[C:10](=[O:29])[N:11]([C@H:22]2[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]2)[C:12]2[N:13]([N:18]=[C:19]([CH3:21])[N:20]=2)[C:14]=1[CH2:15][CH2:16][CH3:17].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+]>[F:1][C:2]1[CH:3]=[C:4]([C:30]2[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]1[C:10](=[O:29])[N:11]([C@H:22]2[CH2:23][CH2:24][C@H:25]([O:28][CH:49]([CH3:50])[C:48]([OH:40])([CH3:54])[CH3:53])[CH2:26][CH2:27]2)[C:12]2[N:13]([N:18]=[C:19]([CH3:21])[N:20]=2)[C:14]=1[CH2:15][CH2:16][CH3:17]

참가 물질

5

반응물 3

HCID 1140TolueneHCID 866440353-Ethoxy-2-methyl-3-oxopropane-1-diazoniumHCID 178438707HCID 178438707, 화합물

생성물 1

HCID 178438717HCID 178438717, 화합물수율 50%

시약·촉매·용매 1

HCID 178476747HCID 178476747, 화합물촉매

실험 절차

To a mixture of 3′-fluoro-4′-{[4-(trans-4-hydroxycyclohexyl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.46 g), rhodium(I) acetate (0.004 g) and toluene (10 mL) was added dropwise 3-ethoxy-2-methyl-3-oxopropane-1-diazonium (0.69 mL) at 80° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was concentrated, 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 (0.27 g, 50%).

후처리

  1. concentrationThe reaction mixture was concentrated
  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

출처 및 근거

ORD 기록
ord-a940c9328a4f48898a3c453208e9f79c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921379B2

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