Hydrochloric Acid → 4'-[(4-{4-[1-(1-Acetylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

HRID 519795ノート

反応式

HRID 519795 の反応式
[CH:1]([C:3]1([CH:7]([O:9][CH:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:21](=[O:22])[C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:26][CH:25]=4)=[C:19]([CH2:38][CH2:39][CH3:40])[N:18]4[N:41]=[CH:42][N:43]=[C:17]34)[CH2:12][CH2:11]2)[CH3:8])[CH2:6][CH2:5][CH2:4]1)=[O:2].[CH3:44][Mg]Br.O1CCCC1.Cl>O1CCCC1>[C:1]([C:3]1([CH:7]([O:9][CH:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:21](=[O:22])[C:20]([CH2:23][C:24]4[CH:25]=[CH:26][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:28][CH:29]=4)=[C:19]([CH2:38][CH2:39][CH3:40])[N:18]4[N:41]=[CH:42][N:43]=[C:17]34)[CH2:12][CH2:11]2)[CH3:8])[CH2:6][CH2:5][CH2:4]1)(=[O:2])[CH3:44]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 866440584'-[(4-{4-[1-(1-Formylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrileHCID 178420675HCID 178420675、化合物

生成物 1

HCID 670091324'-[(4-{4-[1-(1-Acetylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4′-[(4-{4-[1-(1-formylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (10.35 g) in tetrahydrofuran (50 mL) was added 1 M methylmagnesium bromide-tetrahydrofuran solution (27 mL), and the mixture was stirred at room temperature for 15 hr. 1 N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a solution of the residue in acetonitrile (200 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (8.48 g), and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)] to give the title compound as a colorless amorphous compound (8.32 g, 79%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. additionTo a solution of the residue in acetonitrile (200 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (8.48 g)
  6. stirringthe mixture was stirred at room temperature for 2 hr
  7. additionSaturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→60/40 (volume ratio)]

出典と根拠

ORDレコード
ord-7db99a61b12c42c1a527509377d0271e
出典データセット
uspto-grants-2015_08
特許番号
US09115136B2

反応ノート

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