Stannous chloride dihydrate → 5-(4-(4-Methoxybenzylamino)-5-aminopyridin-2-ylamino)pyrazine-2-carbonitrile

HRID 40654

Reaktionsgleichung

Reaktionsgleichung von HRID 40654
O.O.[Sn](Cl)Cl.[CH3:6][O:7][C:8]1[CH:33]=[CH:32][C:11]([CH2:12][NH:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([NH:23][C:24]3[N:25]=[CH:26][C:27]([C:30]#[N:31])=[N:28][CH:29]=3)[CH:15]=2)=[CH:10][CH:9]=1>CCO>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][NH:13][C:14]2[C:19]([NH2:20])=[CH:18][N:17]=[C:16]([NH:23][C:24]3[N:25]=[CH:26][C:27]([C:30]#[N:31])=[N:28][CH:29]=3)[CH:15]=2)=[CH:32][CH:33]=1

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 670174595-(4-(4-Methoxybenzylamino)-5-nitropyridin-2-ylamino)pyrazine-2-carbonitrile

Produkt 1

HCID 670174745-(4-(4-Methoxybenzylamino)-5-aminopyridin-2-ylamino)pyrazine-2-carbonitrileAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Tin(II)chloride dihydrate (1.59 g, 7.04 mmol) was added portionwise to 5-(4-(4-methoxybenzylamino)-5-nitropyridin-2-ylamino)pyrazine-2-carbonitrile (531 mg, 1.41 mmol) in absolute EtOH (10 mL) at room temperature. The mixture was heated at 70° C. for 2 hours before being concentrated in vacuo. The residue was suspended in a mixture of ethyl acetate and saturated sodium bicarbonate solution, then filtered to remove insoluble material. The solids were then washed with EtOAc. The aqueous phase was re-extracted with ethyl acetate and the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to give crude title compound (415 mg) as a brown solid. The product was 50% pure by LCMS analysis and was used without further purification. LCMS (2) Rt=1.73 min; m/z (ESI−) 346 (M−H); (ESI+) 348 (MH+).

Aufarbeitung

  1. concentrationbefore being concentrated in vacuo
  2. additionThe residue was suspended in a mixture of ethyl acetate and saturated sodium bicarbonate solution
  3. filtrationfiltered
  4. customto remove insoluble material
  5. washThe solids were then washed with EtOAc
  6. extractionThe aqueous phase was re-extracted with ethyl acetate
  7. washthe combined organic extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e36368421b644ea4978d29fcd96850ef
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530468B2

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