Hydrochloric Acid → HCID 178438723, Verbindung

HRID 1412346

Reaktionsgleichung

Reaktionsgleichung von HRID 1412346
[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]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866440353-Ethoxy-2-methyl-3-oxopropane-1-diazoniumHCID 178438707HCID 178438707, Verbindung

Produkt 1

HCID 178438723HCID 178438723, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178476747HCID 178476747, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a9a50712cafc4753b4540dec72285f08
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921379B2

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