Hydrochloric Acid → Methyl 6-[1-(6-cyanopyridin-3-yl)-1H-pyrazol-5-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate

HRID 1640691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640691
C(O[CH:4](OCC)[C:5]#[C:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10](=[O:17])[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:8]=1[CH3:28])C.FC(F)(F)C(O)=O.[NH:39]([C:41]1[CH:42]=[CH:43][C:44]([C:47]#[N:48])=[N:45][CH:46]=1)[NH2:40].Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[C:47]([C:44]1[N:45]=[CH:46][C:41]([N:39]2[C:6]([C:7]3[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[C:10](=[O:17])[N:9]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[CH:19]=4)[C:8]=3[CH3:28])=[CH:5][CH:4]=[N:40]2)=[CH:42][CH:43]=1)#[N:48]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59564940Methyl 6-(3,3-diethoxyprop-1-ynyl)-5-methyl-3-oxo-4-(3-(trifluoromethyl)phenyl)-3,4-dihydropyrazine-2-carboxylateHCID 667386805-Hydrazinopyridine-2-carbonitrile trifluoroacetate

Produkt 1

HCID 66738829Methyl 6-[1-(6-cyanopyridin-3-yl)-1H-pyrazol-5-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylateAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Methyl 6-(3,3-diethoxyprop-1-ynyl)-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (0.073 g, 0.17 mmol) and 5-hydrazinopyridine-2-carbonitrile trifluoroacetate (0.050 g, 0.20 mmol) in dioxane (3 ml) were placed in a vial. 2M HCl (0.188 ml) was added and the mixture was stirred at 55° C. for 15 min. After cooling, NaHCO3 (0.048 g) was added and the mixture was extracted with DCM and water. The combined organic phases were washed with water, brine, dried (Na2SO4) and evaporated. The residue was dissolved in acetic acid (10 ml) and the vial was sealed. The solution was stirred at 90° C. for 10 h. After evaporation, the residue was purified by preparative HPLC to give 0.023 g (28%) of the title compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with DCM and water
  3. washThe combined organic phases were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in acetic acid (10 ml)
  7. customthe vial was sealed
  8. stirringThe solution was stirred at 90° C. for 10 h
  9. customAfter evaporation
  10. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-51f7e1bed9a84366bf7c550c4efdfa4f
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114881B2

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