Ammonium Acetate → 6-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl ester

HRID 417448Notes

Reaction equation

HRID 417448 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][C:9](=[O:11])[N:8]2[CH:12]([C:15](=O)[NH:16][CH2:17][C:18]([C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=3)=O)[CH2:13][CH2:14][CH:7]2[CH2:6]1)=[O:4].C([O-])(=O)C.[NH4+:32]>>[CH3:1][O:2][C:3]([N:5]1[CH2:10][C:9](=[O:11])[N:8]2[CH:12]([C:15]3[NH:32][C:18]([C:20]4[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=4)=[CH:17][N:16]=3)[CH2:13][CH2:14][CH:7]2[CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 666208976-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 666206156-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl esterYield 60%

Conditions

Temperature
130 °C

Procedure

A mixture of 6-[2-(4-bromo-phenyl)-2-oxo-ethylcarbamoyl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl ester (110 mg, 0.25 mmol), ammonium acetate (193 mg, 2.5 mmol) and xylenes (8 mL) was heated to 130° C. After 1 hour the mixture was cooled and the xylenes were removed under reduced pressure. Dichloromethane was added to the resulting residue and the mixture was filtered. The solvent was removed under reduced pressure from the filtrate and the resulting residue was subjected to flash chromatography with eluent of (10% methanol in ethyl acetate) and hexane. The product-containing fractions were combined and the solvent was removed under reduced pressure to provide 6-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl ester (65 mg, 0.15 mmol, 60%). C18H19BrN4O3 calculated 418.1 observed [M+1]+419.1; rt=1.50 min.

Workup

  1. temperatureAfter 1 hour the mixture was cooled
  2. customthe xylenes were removed under reduced pressure
  3. additionDichloromethane was added to the resulting residue
  4. filtrationthe mixture was filtered
  5. customThe solvent was removed under reduced pressure from the filtrate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a5c2c4e66a8342e18c372b089f425a28
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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