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

HRID 912661Notes

Reaction equation

HRID 912661 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([NH2:9])=[O:8].[CH2:10]([C:14]1[NH:15][C:16]([Cl:21])=[C:17]([CH:19]=O)[N:18]=1)[CH2:11][CH2:12][CH3:13].[BH3-]C#N.[Na+].C(O)(=O)C>CO>[CH2:10]([C:14]1[NH:18][C:17]([CH2:19][NH:1][C:2]2[N:3]=[CH:4][NH:5][C:6]=2[C:7]([NH2:9])=[O:8])=[C:16]([Cl:21])[N:15]=1)[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 96795-Aminoimidazole-4-carboxamideHCID 551762-Butyl-5-chloro-1H-imidazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 674141614-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamideYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction mixture of 4-amino-5-imidazolecarboxamide (0.50 g, 3.96 mmol), 2-butyl-5-chloro-1H-imidazole-4-carbaldehyde (0.89 g, 4.76 mmol), and NaCNBH3 (0.25 g, 3.96 mmol) in methanol (5 mL) was stirred at r.t. over night. Acetic acid (0.24 g, 3.96 mmol) was added and the mixture was heated at 50° C. for 5 h. The mixture was concentrated in vacuo and dissolved in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol), obtaining 0.30 g (26%) of the title compound.

Workup

  1. temperaturethe mixture was heated at 50° C. for 5 h
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol)

Sources & evidence

ORD record
ord-ef92e652f2bb4a359c25e63cdfca4f47
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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