Ammonia → 5-(5-Methoxy-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)pyrazin-2-amine

HRID 1915029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1915029
Br[C:2]1[N:3]=[CH:4][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=3[N:10]=[C:9]2[C:19]([F:22])([F:21])[F:20])=[N:6][CH:7]=1.[NH3:23]>C(O)CO.O>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][C:12]2[N:8]([C:5]3[N:6]=[CH:7][C:2]([NH2:23])=[N:3][CH:4]=3)[C:9]([C:19]([F:22])([F:21])[F:20])=[N:10][C:11]=2[CH:16]=1

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 573569041-(5-Bromopyrazin-2-YL)-2-(trifluoromethyl)-5-methoxy-1H-benzo[D]imidazole

Produkt 1

HCID 534878715-(5-Methoxy-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)pyrazin-2-amineAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Into a 10 mL sealed tube, was placed 1-(5-bromo-pyrazin-2-yl)-5-methoxy-2-trifluoromethyl-1H-benzoimidazole (iv) (150 mg, 0.40 mmol). To this was added Cu2O (30 mg, 0.21 mmol), followed by a saturated solution of NH3 in ethylene glycol (4 ml). The resulting solution was stirred at 70° C. for 3 hours, then diluted with 30 mL of H2O and extracted three times with 20 mL of EtOAc. The organic layers were combined and dried over Na2SO4. Removal of the volatile components under reduced pressure afforded the product 5-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyrazin-2-ylamine (v) (50 mg, yield 40%) as a white solid.

Aufarbeitung

  1. customInto a 10 mL sealed tube
  2. extractionextracted three times with 20 mL of EtOAc
  3. dry with materialdried over Na2SO4
  4. customRemoval of the volatile components under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dfb9ff90c7f74adbae6e952bec028bab
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614321B2

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