Cyclopropanecarbonyl chloride → HCID 178516793, compound

HRID 916259Notes

Reaction equation

HRID 916259 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1.CCN(C(C)C)C(C)C>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][C:21]([CH:18]1[CH2:20][CH2:19]1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Product 1

HCID 178516793HCID 178516793, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (100.0 mg, 0.43 mmol), cyclopropanecarbonylchloride (45.0 mg, 0.43 mmol) and Hunig's base (83.0 mg, 0.64 mmol) in acetonitrile (4 mL) was heated to reflux under argon for 0.5 hr. Cooled to r.t., the reaction mixture was concentrated and the residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated and the residue was triturated with AcOEt to give a suspension. The solid was filtered to give 2-(cyclopropanecarbonyl-amino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as an oil (113.0 mg, 87.6%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 0.5 hr
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue was partitioned between EtOAc and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customthe residue was triturated with AcOEt
  8. customto give a suspension
  9. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-608f8ef03d714b5e98e1c7686031c6bf
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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