Propylamine → 5-Amino-2-benzyl-1-n-propylimidazole-4-carboxamide

HRID 1357556Notes

Reaction equation

HRID 1357556 reaction equation
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].Cl.[C:9]1([CH2:15][C:16](=[NH:20])OCC)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:21](N)[CH2:22][CH3:23]>C(#N)C>[NH2:7][C:6]1[N:20]([CH2:21][CH2:22][CH3:23])[C:16]([CH2:15][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:1][C:2]=1[C:3]([NH2:5])=[O:4]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 983412-Amino-2-cyanoacetamideHCID 12218775Ethyl 2-phenylacetimidate hydrochloride

Product 1

HCID 699642035-Amino-2-benzyl-1-n-propylimidazole-4-carboxamideYield 21.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-amino-2-cyanoacetamide (prepared as described in WO 94/00453; 250 mg, 2.5 mmol) in acetonitrile (6 mL) was added to ethyl 2-phenylethanimidoate hydrochloride (prepared as described in J. Med. Chem. 38 (18), 3676 (1995); 500 mg, 2.5 mmol), and the suspension stirred at room temperature for an hour, then cooled in an ice-bath. The resulting precipitate was filtered off, n-propylamine (160 μL, 2.5 mmol) added to the filtrate and the solution stirred at room temperature for 72 hours. The reaction mixture was concentrated under reduced pressure, and the residue purified by column chromatography on silica gel using dichloromethane:methanol (95:5) as eluant to afford the title compound as a tan coloured solid (136 mg, 21%).

Workup

  1. temperaturecooled in an ice-bath
  2. filtrationThe resulting precipitate was filtered off
  3. stirringthe solution stirred at room temperature for 72 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7950b61bb25f4eac9cccdebe141da9fe
Source dataset
uspto-grants-2003_07
Patent number
US06593332B2

Reaction notes

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