Hydrochloric Acid → 4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-12-(1H-pyrazol-5-yl)-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene

HRID 1530558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530558
Cl.O1CCCCC1[N:8]1[C:12]([C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][CH:26]=2)[C:23]2[N:19]([CH:20]=[C:21]([C:27]4[N:31]([CH:32]([CH3:34])[CH3:33])[N:30]=[CH:29][N:28]=4)[N:22]=2)[CH2:18][CH2:17][O:16]3)=[CH:11][CH:10]=[N:9]1>C(OCC)(=O)C>[CH3:34][CH:32]([N:31]1[C:27]([C:21]2[N:22]=[C:23]3[N:19]([CH:20]=2)[CH2:18][CH2:17][O:16][C:15]2[C:24]3=[CH:25][CH:26]=[C:13]([C:12]3[NH:8][N:9]=[CH:10][CH:11]=3)[CH:14]=2)=[N:28][CH:29]=[N:30]1)[CH3:33]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 6831314112-[1-(oxan-2-yl)-1H-pyrazol-5-yl]-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene

Produkt 1

HCID 683130694-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-12-(1H-pyrazol-5-yl)-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaeneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of 3N HCl in ethyl acetate at −20° C. (100 mL) was added dropwise a solution of 12-[1-(oxan-2-yl)-1H-pyrazol-5-yl]-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (2.20 g, 6.09 mmol) in ethyl acetate (20.0 mL). After being stirred at this temperature for 1 h, the reaction mixture was warmed to room temperature and stirred for 3 hr. After removal of the solvent, the residue was treated with water and basified to pH around 10. The aqueous layer was then extracted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated to afford 4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-12-(1H-pyrazol-5-yl)-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (1.4 g, 78% yield) as pale yellow solid. LCMS (ESI) m/z: 362.0 [M+H+].

Aufarbeitung

  1. stirringstirred for 3 hr
  2. customAfter removal of the solvent
  3. additionthe residue was treated with water and basified to pH around 10
  4. extractionThe aqueous layer was then extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1ce78408bb3c48b7a2c02ffa40cf1a10
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090628B2

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