Dimethyl Sulfoxide → HCID 136146879, 화합물

HRID 1674308노트

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HRID 1674308 반응식
[Cl-].[OH:2][NH3+:3].[C:4](=[O:7])([O-])O.[Na+].CS(C)=O.[Si]([O:20][CH:21]1[CH2:26][CH2:25][CH:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([N:34]3[C:39](=[O:40])[C:38]([CH2:41][C:42]4[CH:47]=[CH:46][C:45]([C:48]5[C:49]([C:54]#[N:55])=[CH:50][CH:51]=[CH:52][CH:53]=5)=[CH:44][CH:43]=4)=[C:37]([CH2:56][CH2:57][CH3:58])[N:36]=[C:35]3[CH2:59][F:60])=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)(C(C)(C)C)(C)C>C(OCC)(=O)C>[F:60][CH2:59][C:35]1[N:34]([C:31]2[CH:32]=[CH:33][C:28]([O:27][CH:24]3[CH2:25][CH2:26][CH:21]([OH:20])[CH2:22][CH2:23]3)=[CH:29][CH:30]=2)[C:39](=[O:40])[C:38]([CH2:41][C:42]2[CH:43]=[CH:44][C:45]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[C:54]3[NH:55][C:4](=[O:7])[O:2][N:3]=3)=[CH:46][CH:47]=2)=[C:37]([CH2:56][CH2:57][CH3:58])[N:36]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 57460961HCID 57460961, 화합물

생성물 1

HCID 136146879HCID 136146879, 화합물수율 6.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

A mixture of hydroxylammonium chloride (0.16 g), sodium hydrogen carbonate (0.23 g) and dimethyl sulfoxide (3 mL) was stirred at 40° C. for 30 min, 4′-{[1-{4-[(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)oxy]phenyl}-2-(fluoromethyl)-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (0.18 g) was added, and the mixture was stirred at 90° C. for 12 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (2 mL). N,N′-carbonyldiimidazole (0.07 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.06 mL) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous potassium hydrogen sulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (1 mL), tetrabutylammonium fluoride tetrahydrofuran solution (1 mol/L, 0.1 mL) was added, and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated from the reaction mixture under reduced pressure. The residue was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.01 g, 6%).

후처리

  1. stirringthe mixture was stirred at 90° C. for 12 hr
  2. washwashed with water
  3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in tetrahydrofuran (2 mL)
  6. additionN,N′-carbonyldiimidazole (0.07 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.06 mL) were added
  7. stirringthe mixture was stirred at room temperature for 2 hr
  8. additionThe reaction mixture was diluted with ethyl acetate
  9. washwashed with saturated aqueous potassium hydrogen sulfate solution
  10. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. dissolutionThe residue was dissolved in tetrahydrofuran (1 mL)
  13. additiontetrabutylammonium fluoride tetrahydrofuran solution (1 mol/L, 0.1 mL) was added
  14. stirringthe mixture was stirred at room temperature for 3 hr
  15. customThe solvent was evaporated from the reaction mixture under reduced pressure
  16. additionThe residue was diluted with ethyl acetate
  17. washwashed with water
  18. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  19. customThe solvent was evaporated under reduced pressure
  20. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-aeba4872331348c591347f0675cd3007
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998968B2

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