Acetic Acid → 4-{[(6-Butoxypyridin-2-yl)methyl]amino}-1H-imidazole-5-carboxamide

HRID 912701Notes

Reaction equation

HRID 912701 reaction equation
[NH2:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8].[CH2:10]([O:14][C:15]1[N:20]=[C:19]([CH:21]=O)[CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH3:13].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH2:10]([O:14][C:15]1[N:20]=[C:19]([CH2:21][NH:1][C:2]2[N:6]=[CH:5][NH:4][C:3]=2[C:7]([NH2:9])=[O:8])[CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 96795-Aminoimidazole-4-carboxamideHCID 5003444Sodium cyanoborohydrideHCID 108450736-Butoxypyridine-2-carbaldehyde

Product 1

HCID 674158084-{[(6-Butoxypyridin-2-yl)methyl]amino}-1H-imidazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Aminoimidazole-4-carboxamide (0.30 g, 2.4 mmol) was added to the solution of 6-butoxypyridine-2-carbaldehyde (0.43 mg, 2.4 mmol, obtained from Example 17(d)) in anhydrous ethanol (30 mL) and the reaction mixture was refluxed. After 2 h, the reaction mixture was concentrated in vacuo. The light pink solid was suspended in anhydrous ethanol (25 mL), and acetic acid (0.27 mL, 4.8 mmol) was added. After 1.5 h, sodium cyanoborohydride (0.30 g, 4.8 mmol) was added to the mixture. After stirring o.n. at ambient temperature, the reaction mixture was concentrated in vacuo. The resulting 1.2 g of crude title compound was used in the next step without further purification. MS (ESI) m/z 290 (M+1)

Workup

  1. temperaturethe reaction mixture was refluxed
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. waitAfter 1.5 h
  4. concentrationat ambient temperature, the reaction mixture was concentrated in vacuo
  5. customThe resulting 1.2 g of crude title compound was used in the next step without further purification

Sources & evidence

ORD record
ord-b716e8f4075b4558bffcebba3f65d85d
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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