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 1753177Notes

Reaction equation

HRID 1753177 reaction equation
[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

Participants

6

Reactant 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

Product 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-oneYield 39%

Reagents, catalysts & solvents 3

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-0dceadee34ec46ba88e7f1d2b6977a61
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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