Sodium Carbonate → 2-amino-5-(3-bromophenyl)-5-(1-ethyl-5-propionyl-1H-pyrrol-3-yl)-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 2220474Notes

Reaction equation

HRID 2220474 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[C:9]([C:11]2C=[C:14]([C:16](=O)CC)[N:13]([CH2:20]C(F)(F)F)[CH:12]=2)=O)[CH:5]=[CH:6][CH:7]=1.[CH3:26][NH:27][C:28]([NH2:30])=[NH:29].[C:31](=[O:34])([O-])[O-].[Na+].[Na+].CCO[C:40]([CH3:42])=O.[CH2:43]([OH:45])C>C(O)C>[NH2:30][C:28]1[N:27]([CH3:26])[C:43](=[O:45])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)([C:9]2[CH:11]=[C:12]([C:31](=[O:34])[CH2:40][CH3:42])[N:13]([CH2:14][CH3:16])[CH:20]=2)[N:29]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 21584252Ethanol ethylacetateHCID 597727141-(3-bromo-phenyl)-2-[5-propionyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-3-yl]-ethane-1,2-dioneHCID 178485088HCID 178485088, compound

Product 1

HCID 159497442-amino-5-(3-bromophenyl)-5-(1-ethyl-5-propionyl-1H-pyrrol-3-yl)-3-methyl-3,5-dihydro-4H-imidazol-4-oneYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3-bromo-phenyl)-2-[5-propionyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-3-yl]-ethane-1,2-dione (4.5 g, 0.0108 mol), methylguanidine (2.36 g, 0.0216 mol) and sodium carbonate (2.28 g, 0.0216 mol) in 100 ml ethanol is heated to reflux for three hours. The solvent is evaporated to dryness and the residue is flash chromatographed on silica gel with eluent EtOAc/Ethanol (containing 2 mol ammonia) to afford the product 3.8 gram (75%) as an off-white solid, mp 100-102° C.,

Workup

  1. temperatureis heated
  2. temperatureto reflux for three hours
  3. customThe solvent is evaporated to dryness

Sources & evidence

ORD record
ord-3d6fc21eb5b045828b640ca9d790f444
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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