Toluene → HCID 178438766, 화합물

HRID 519611

반응식

HRID 519611 반응식
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[C:10](=[O:28])[N:11]([CH:21]3[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]3)[C:12]3[N:13]([N:18]=[CH:19][N:20]=3)[C:14]=2[CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1[C:29]1[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=1.[N+](=CC(OCC)=[O:41])=[N-].[C:45]1([CH3:51])[CH:50]=CC=C[CH:46]=1>C([O-])(=O)C.[Rh+]>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[C:10](=[O:28])[N:11]([C@H:21]3[CH2:22][CH2:23][C@H:24]([O:27][CH2:46][C:45]([OH:41])([CH3:51])[CH3:50])[CH2:25][CH2:26]3)[C:12]3[N:13]([N:18]=[CH:19][N:20]=3)[C:14]=2[CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1[C:29]1[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 12192Ethyl diazoacetateHCID 670098682'-Fluoro-4'-{[4-(4-hydroxycyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

생성물 1

HCID 178438766HCID 178438766, 화합물수율 23%

시약·촉매·용매 1

HCID 178476747HCID 178476747, 화합물촉매

실험 절차

To a mixture of 2′-fluoro-4′-{[4-(4-hydroxycyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.95 g), rhodium(I) acetate (0.007 g) and toluene (20 mL) was added dropwise ethyl diazoacetate (0.96 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 (15 mL), and methylmagnesium bromide (1.0 M tetrahydrofuran solution, 5.8 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 (0.25 g, 23%).

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 (15 mL)
  4. additionmethylmagnesium bromide (1.0 M tetrahydrofuran solution, 5.8 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-e82d8ceb8aa84a49a219c9e78b8d933d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115136B2

연결된 노트

불러오는 중…