Hydrochloric Acid → 4'-{[4-(2,3-Dimethyl-1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrile

HRID 1688596노트

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HRID 1688596 반응식
O1C2(C[CH2:9][CH:8]([N:11]3[C:16](=[O:17])[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]5[C:26]([C:32]#[N:33])=[CH:27][C:28]([F:31])=[CH:29][CH:30]=5)=[CH:21][CH:20]=4)=[C:14]([CH2:34][CH2:35][CH3:36])[N:13]4[N:37]=[C:38]([CH3:40])[N:39]=[C:12]34)[CH2:7][CH2:6]2)OCC1.Cl.O1CC[CH2:44][CH2:43]1.[C:47]([O:50][CH2:51][CH3:52])(=[O:49])[CH3:48]>>[CH3:52][CH:51]1[CH:43]([CH3:44])[O:49][C:47]2([CH2:6][CH2:7][CH:8]([N:11]3[C:16](=[O:17])[C:15]([CH2:18][C:19]4[CH:20]=[CH:21][C:22]([C:25]5[C:26]([C:32]#[N:33])=[CH:27][C:28]([F:31])=[CH:29][CH:30]=5)=[CH:23][CH:24]=4)=[C:14]([CH2:34][CH2:35][CH3:36])[N:13]4[N:37]=[C:38]([CH3:40])[N:39]=[C:12]34)[CH2:9][CH2:48]2)[O:50]1

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 670100244'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrile

생성물 1

HCID 670096714'-{[4-(2,3-Dimethyl-1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrile수율 100%

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온도
70 °C

실험 절차

A mixture of 4′-{[4-(1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrile (1.1 g), 3N hydrochloric acid (30 mL) and tetrahydrofuran (30 mL) was stirred at 70° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in toluene (30 mL), 2,3-dimethylpropane-1,3-diol (0.2 g) and p-toluenesulfonic acid monohydrate (0.004 g) were added, and the mixture was subjected to an azeotropic dehydration reaction by stirring at 110° C. for 3 hr in a reaction vessel equipped with a Dean-stark trap. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.3 g, 100%).

후처리

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionThe obtained residue was dissolved in toluene (30 mL)
  5. addition2,3-dimethylpropane-1,3-diol (0.2 g) and p-toluenesulfonic acid monohydrate (0.004 g) were added
  6. customthe mixture was subjected to an azeotropic dehydration reaction
  7. stirringby stirring at 110° C. for 3 hr in a reaction vessel
  8. customequipped with a Dean-stark trap
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-004e1232ad7943748e1e4e3451402e81
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148383B2

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