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

HRID 548781Notes

Reaction equation

HRID 548781 reaction equation
Cl.[NH2:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]([NH2:10])=[O:9].[CH3:11][O:12][C:13]([CH3:17])([CH3:16])[CH:14]=O.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH3:11][O:12][C:13]([CH3:17])([CH3:16])[CH2:14][NH:2][C:3]1[N:7]=[CH:6][NH:5][C:4]=1[C:8]([NH2:10])=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 202206772-Methoxy-2-methylpropanal2×HCID 178479549HCID 178479549, compound

Product 1

HCID 671575204-[(2-methoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamideYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Amino-4-imidazolecarboxamide hydrochloride (0.162 g, 1.0 mmol) and 2-methoxy-2-methylpropanal, which was obtained from Example 3(a) (0.204 g, 2.0 mmol) were mixed in methanol (3 mL) at r.t. Acetic acid (141 μL, 2.46 mmol) mL) was then added and the mixture was allowed to stir for 30 min followed by addition of NaCNBH3 (0.063 g, 1.0 mmol). After 3 h, additional 2-methoxy-2-methylpropanal (0.060 g, 0.59 mmol) was added. The reaction mixture was stirred at r.t. for 17 h and was then concentrated and purified by flash silica gel chromatography (CHCl3:MeOH=5:1). The title compound was obtained as an oil in 73% yield (0.155 g). MS (ESI) m/z 213 (M+1).

Workup

  1. waitAfter 3 h
  2. stirringThe reaction mixture was stirred at r.t. for 17 h
  3. concentrationwas then concentrated
  4. custompurified by flash silica gel chromatography (CHCl3:MeOH=5:1)

Sources & evidence

ORD record
ord-f7aa78645d1843c5aef1d6b7347ca0a4
Source dataset
uspto-grants-2011_05
Patent number
US07943625B2

Reaction notes

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