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

HRID 2305407Notes

Reaction equation

HRID 2305407 reaction equation
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].Cl.[C:9](=[NH:14])(OCC)[CH3:10].[CH2:15](N)[CH2:16][CH3:17]>C(#N)C>[NH2:7][C:6]1[N:14]([CH2:15][CH2:16][CH3:17])[C:9]([CH3:10])=[N:1][C:2]=1[C:3]([NH2:5])=[O:4]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 983412-Amino-2-cyanoacetamideHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 699642055-Amino-2-methyl-1-n-propylimidazole-4-carboxamideYield 45.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-amino-2-cyanoacetamide (prepared as described in WO 94/00453; 3.6 g, 36.4 mmol) and ethyl acetimidate hydrochloride (4.50 g, 36.4 mmol) in acetonitrile (85 mL) was stirred at 50° C. for an hour, then cooled to 0° C., and stirred for a further hour. The reaction mixture was filtered, and n-propylamine (3.02 mL, 36.4 mmol) added. The solution was stirred at room temperature for an hour, and left to stand for a further 16 hours. The resulting precipitate was filtered, washed with acetonitrile, then dichloromethane and dried under vacuum to afford the title compound as a solid (3.0 g, 45%).

Workup

  1. temperaturecooled to 0° C.
  2. stirringstirred for a further hour
  3. filtrationThe reaction mixture was filtered
  4. stirringThe solution was stirred at room temperature for an hour
  5. waitleft
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with acetonitrile
  8. dry with materialdichloromethane and dried under vacuum

Sources & evidence

ORD record
ord-4dfe8c48035e4d29bf56fcc5054e907e
Source dataset
uspto-grants-2002_08
Patent number
US06440982B1

Reaction notes

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