Acetic Acid → 4-[(2-ethoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamide

HRID 548777Notes

Reaction equation

HRID 548777 reaction equation
[BH3-]C#N.[Na+].Cl.[NH2:6][C:7]1[NH:11][CH:10]=[N:9][C:8]=1[C:12]([NH2:14])=[O:13].C(O)(=O)C.[CH2:19]([O:21][C:22]([CH3:26])([CH3:25])[CH:23]=O)[CH3:20]>CO>[CH2:19]([O:21][C:22]([CH3:26])([CH3:25])[CH2:23][NH:6][C:7]1[N:11]=[CH:10][NH:9][C:8]=1[C:12]([NH2:14])=[O:13])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 147678152-Ethoxy-2-methylpropanal3×HCID 178479549HCID 178479549, compound

Product 1

HCID 671575334-[(2-ethoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaCNBH3 (0.077 g, 1.23 mmol) was added to 5-amino-4-imidazolecarboxamide hydrochloride (0.200 g, 1.23 mmol) and acetic acid (141 μL, 2.46 mmol) in methanol (1.5 mL). 2-Ethoxy-2-methylpropanal (0.286 g, 2.46 mmol) obtained from Example 1(b) was added drop by drop. After 1.5 h more 2-Ethoxy-2-methylpropanal (0.300 g, 2.58 mmol) was added followed by more 2-Ethoxy-2-methylpropanal after 0.5 h (0.424 mg, 3.65 mmol). The reaction mixture was stirred at r.t. 17 h after which it was concentrated and purified by flash silica gel chromatography (CHCl3/MeOH; 20:1-9.1), to give the title compound as an oil in 90% yield (0.251 g). MS (ESI) m/z 227 (M+1).

Workup

  1. concentration17 h after which it was concentrated
  2. custompurified by flash silica gel chromatography (CHCl3/MeOH; 20:1-9.1)

Sources & evidence

ORD record
ord-23889d980de24cddb8c3f1278147947a
Source dataset
uspto-grants-2011_05
Patent number
US07943625B2

Reaction notes

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