2,3-Diaminopyridine → tert-Butyl ((1H-imidazo[4,5-b]pyridin-2-yl)methyl)carbamate

HRID 2213149

Reaction equation

HRID 2213149 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])#[N:2].[NH2:12][C:13]1[C:18](N)=[CH:17][CH:16]=[CH:15][N:14]=1.C(N[C@H](C(O)=O)CS)(=O)C>CO>[N:2]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:1]=1[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 99562,3-DiaminopyridineHCID 12035N-Acetyl-L-CysteineHCID 545844tert-butyl N-(cyanomethyl)carbamate

Product 1

HCID 178453115tert-Butyl ((1H-imidazo[4,5-b]pyridin-2-yl)methyl)carbamateYield 87.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl cyanomethylcarbamate (1.61 g; 10 mmol), 2,3-diaminopyridine (0.56 g; 5 mmol), N-acetylcysteine (1.68 g; 10 mmol) in 10 ml of CH3OH was heated at 50° C. for 89 h. It was then concentrated, and the residue was taken up in a little CH3OH and filtered through an acidic ion exchanger (acetate on polymeric support). Renewed concentration and chromatography on silica gel (CH2Cl2/CH3OH 5%) afforded 1.09 g of the required product;

Workup

  1. concentrationIt was then concentrated
  2. filtrationfiltered through an acidic ion exchanger (acetate on polymeric support)
  3. concentrationRenewed concentration and chromatography on silica gel (CH2Cl2/CH3OH 5%)

Sources & evidence

ORD record
ord-c8b53dbe03cc4e3eb75c8e152d878f09
Source dataset
uspto-grants-2006_09
Patent number
US07105508B1

Linked notes

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