Ammonium Hydroxide → 7-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-5-one

HRID 1910955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910955
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]23[N:24]([C:25]([C:27]4[C:28]([CH3:32])=[N:29][O:30][CH:31]=4)=[O:26])[CH2:23][CH2:22][N:10]2[C:11](=[O:21])[C:12]2[N:13]([CH:15]=[C:16]([N+:18]([O-])=O)[CH:17]=2)[CH2:14]3)=[CH:5][CH:4]=1.[OH-].[NH4+]>CO.O.S([O-])([O-])(=O)=O.O.O.O.O.O.O.O.[Fe+2]>[NH2:18][C:16]1[CH:17]=[C:12]2[C:11](=[O:21])[N:10]3[CH2:22][CH2:23][N:24]([C:25]([C:27]4[C:28]([CH3:32])=[N:29][O:30][CH:31]=4)=[O:26])[C:9]3([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:14][N:13]2[CH:15]=1

Komponenten

6

Edukt 2

HCID 14923Ammonium HydroxideHCID 5337344110a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-nitro-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

Produkt 1

HCID 533733037-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-5-oneAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 62662Ferrous sulfate heptahydrateKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-nitro-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (107 mg, 0.24 mmol) in MeOH (2.4 mL) was added Iron(II) heptahydrate sulfate (544 mg, 2 mmol) in water (2.4 mL). A solution of ammonium hydroxide (28%, 0.7 mL) was added and the mixture was heated at 50° C. for 45 min. The reaction mixture was then partially concentrated in vacuo (half volume), neutralized with a saturated aqueous solution of NH4Cl and then extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtrated and concentrated in vacuo to give a residue that was purified by flash chromatography (Biotage SP4 gradient 0-7% MeOH in EtOAc) to give 7-amino-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (111) (38 mg, yield 39%).

Aufarbeitung

  1. concentrationThe reaction mixture was then partially concentrated in vacuo (half volume)
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customto give a residue that
  7. customwas purified by flash chromatography (Biotage SP4 gradient 0-7% MeOH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-5209477f32d94e249fa6118732b60b37
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604034B2

Notizen zur Reaktion

Wird geladen…