Hydrochloric Acid → HCID 178438723、化合物

HRID 519632

反応式

HRID 519632 の反応式
[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[C:41](=O)[CH:42](C)[CH2:43][N+:44]#N)C.[OH-:48].[Na+].Cl>O1CCCC1.CO.C([O-])(=O)C.[Rh+].C1(C)C=CC=CC=1>[C:36]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[C:10](=[O:29])[N:11]([C@H:22]3[CH2:23][CH2:24][C@H:25]([O:28][CH:42]([CH3:41])[C:43]([NH2:44])=[O:48])[CH2:26][CH2:27]3)[C:12]3[N:13]([N:18]=[C:19]([CH3:21])[N:20]=3)[C:14]=2[CH2:15][CH2:16][CH3:17])=[C:2]([F:1])[CH:3]=1)#[N:37]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866440353-Ethoxy-2-methyl-3-oxopropane-1-diazoniumHCID 178438707HCID 178438707、化合物

生成物 1

HCID 178438723HCID 178438723、化合物収率 65%

試薬・触媒・溶媒 4

HCID 178476747HCID 178476747、化合物触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 (1 g), rhodium(I) acetate (0.009 g) and toluene (20 mL) was added dropwise 3-ethoxy-2-methyl-3-oxopropane-1-diazonium (1.5 mL) at 80° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was concentrated, and the residue obtained by purification by silica gel column chromatography was dissolved in tetrahydrofuran (10 mL) and methanol (10 mL). 1N Aqueous sodium hydroxide solution (10 mL) was added, and the mixture was stirred at room temperature for 3 hr. 1 N Hydrochloric acid was added to the reaction mixture, 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 dissolved in N,N-dimethylformamide (10 mL), 1-hydroxybenzotriazole ammonium salt (0.21 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.3 g) were added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with dilute hydrochloric acid 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 solid (0.37 g, 65%).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue obtained by purification by silica gel column chromatography
  3. stirringthe mixture was stirred at room temperature for 3 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe obtained ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (10 mL)
  9. addition1-hydroxybenzotriazole ammonium salt (0.21 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.3 g) were added
  10. stirringthe mixture was stirred at room temperature for 16 hr
  11. additionThe reaction mixture was diluted with ethyl acetate
  12. washwashed with dilute hydrochloric acid
  13. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  14. customThe solvent was evaporated under reduced pressure
  15. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-efdc7fcd8d574e82aa8cca7967bb3d84
出典データセット
uspto-grants-2015_08
特許番号
US09115136B2

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