Tetrahydrofuran → 2-Benzyl-5-(2-ethoxybenzamido)-1-n-propylimidazole-4-carboxamide

HRID 1355558Notes

Reaction equation

HRID 1355558 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]([CH2:9][CH2:10][CH3:11])[C:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:6][C:5]=1[C:19]([NH2:21])=[O:20].[O:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH2:12]([C:7]1[N:8]([CH2:9][CH2:10][CH3:11])[C:4]([NH:3][C:26](=[O:22])[C:25]2[CH:11]=[CH:10][CH:9]=[CH:23][C:24]=2[O:20][CH2:19][CH3:5])=[C:5]([C:19]([NH2:21])=[O:20])[N:6]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 699642035-Amino-2-benzyl-1-n-propylimidazole-4-carboxamide

Product 1

HCID 699639722-Benzyl-5-(2-ethoxybenzamido)-1-n-propylimidazole-4-carboxamideYield 36%

Procedure

Sodium hydride (48 mg, 60% dispersion in mineral oil, 1.2 mmol) was added to a solution of 5-amino-2-benzyl-1-n-propylimidazole-4-carboxamide (Preparation 2; 200 mg, 0.77 mmol) in tetrahydrofuran (5 mL), and the mixture stirred for 3 hours at room temperature. The prepared solution of acid chloride (from (i) above) was then added and the reaction stirred at room temperature for 2 days. The mixture was concentrated under reduced pressure, the residue partitioned between dichloromethane and water, and the layers separated. The organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel twice, using an elution gradient of dichloromethane: methanol (100:0 to 95:5) to afford the title compound (114 mg, 36%).

Workup

  1. stirringthe reaction stirred at room temperature for 2 days
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue partitioned between dichloromethane and water
  4. customthe layers separated
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel twice

Sources & evidence

ORD record
ord-3e37b088987943469b94ee08988d96eb
Source dataset
uspto-grants-2003_07
Patent number
US06586439B2

Reaction notes

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