Ammonium Chloride → HCID 69103232, Verbindung

HRID 2217240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2217240
[NH2:1][C:2]1[C:3]([C:24](N(OC)C)=[O:25])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[CH3:30][Mg]Cl.[Cl-].[NH4+]>C1COCC1>[C:24]([C:3]1[N:4]=[C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:7][C:2]=1[NH2:1])(=[O:25])[CH3:30]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 86598207HCID 86598207, VerbindungHCID 178418332HCID 178418332, Verbindung

Produkt 1

HCID 69103232HCID 69103232, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under ice-bath cooling, to a suspension of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-N-methoxy-N-methyl-5-phenyl-2-pyrazinecarboxamide (200 mg) in THF (4.0 ml) was added 3.0M solution of methylmagnesium chloride in THF (0.85 ml) dropwise. The mixture was stirred at the same temperature for 5 hours. The mixture was poured into sat. aq ammonium chloride (20 ml) and an organic layer was extracted with EtOAc (50 ml), washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica-gel column chromatography (CH2Cl2:MeOH=50:1-15:1). The desired fraction was recrystallized from MeOH and dried in vacuo to give 5-(6-acetyl-5-amino-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (111 mg).

Aufarbeitung

  1. extractionan organic layer was extracted with EtOAc (50 ml)
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography (CH2Cl2:MeOH=50:1-15:1)
  6. customThe desired fraction was recrystallized from MeOH
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-28c4e17f3df04daf95ed99a89e105a1d
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407961B2

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