Acetic Acid → HCID 19106907, compound

HRID 248638Notes

Reaction equation

HRID 248638 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH:11]2[CH2:13][CH2:12]2)[NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C(O)(=O)C.[CH2:18]([CH2:22][C:23](=O)[CH3:24])[C:19]([CH3:21])=O>C(O)C>[CH:11]1([C:4]2[NH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:2]([N:1]3[C:23]([CH3:24])=[CH:22][CH:18]=[C:19]3[CH3:21])[N:3]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 19106922HCID 19106922, compound

Product 1

HCID 19106907HCID 19106907, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of methyl 4-amino-2-cyclopropylimidazole-5-carboxylate (Example 40, 5.72 g, 0.032 mol) in ethanol (40 mL) was treated with acetic acid (25 mL) and the mixture refluxed to effect solution. To the hot solution was added acetonylacetone (5.41 g, 0.047 mol) and the whole stirred and refluxed for 18 hours. The solvent was removed under reduced pressure and the residue purified by flash chromatography eluting with a gradient of CH2Cl2 to 20% EtOAc in CH2Cl2 to afford 7.93 g of the title compound methyl 2-cyclopropyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)imidazole-5-carboxylate. 1H-NMR (CDCl3) 5.85 (s, 2H), 3.68 (s, 3H), 2.0 (s, 6H), 1.80-2.0 (m, 1H), 1.0-1.18 (m, 4H).

Workup

  1. temperaturethe mixture refluxed
  2. temperaturerefluxed for 18 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by flash chromatography
  5. washeluting with a gradient of CH2Cl2 to 20% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-a57834ba3fc5474385031c805b284b53
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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