Sodium cyanoborohydride → 4-({[3-Ethoxy-4-(2-ethoxyethoxy)pyridin-2-yl]methyl}amino)-1H-imidazole-5-carboxamide

HRID 912657Notes

Reaction equation

HRID 912657 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].[CH2:15]([O:17][C:18]1[C:19]([CH:30]=O)=[N:20][CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH2:26][O:27][CH2:28][CH3:29])[CH3:16]>CO>[CH2:15]([O:17][C:18]1[C:19]([CH2:30][NH:6][C:7]2[N:11]=[CH:10][NH:9][C:8]=2[C:12]([NH2:14])=[O:13])=[N:20][CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH2:26][O:27][CH2:28][CH3:29])[CH3:16]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 866311113-Ethoxy-4-(2-ethoxyethoxy)pyridine-2-carbaldehydeHCID 178479549HCID 178479549, compound

Product 1

HCID 674147844-({[3-Ethoxy-4-(2-ethoxyethoxy)pyridin-2-yl]methyl}amino)-1H-imidazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaCNBH3 (0.046 g, 0.73 mmol) was added in portions to a stirred solution of 5-amino-4-imidazolecarboxamide hydrochloride (0.150 g, 0.92 mmol) and 3-ethoxy-4-(2-ethoxyethoxy)pyridine-2-carbaldehyde (0.220 g, 0.92 mmol, obtained from Example 4(d)) in MeOH (1.5 mL) at r.t. over 10 minutes. The reaction mixture was stirred at r.t. for 2 days. The mixture was filtrated and the filtrate was evaporated in vacuo to give a crude of the title compound in quantitative yield. MS (ESI) m/z 364 (M+1).

Workup

  1. filtrationThe mixture was filtrated
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-f5f29c92bae14f44afad29ab4f3ccff8
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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