Cyanogen Bromide → HCID 178473435, compound

HRID 2361902Notes

Reaction equation

HRID 2361902 reaction equation
[N:1]#[C:2]Br.[NH2:4][C:5]1[C:6]([Cl:18])=[CH:7][C:8]([NH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:9][C:10]=1[NH2:11]>C(O)C>[CH2:16]([O:15][C:13](=[O:14])[NH:12][C:8]1[N:9]=[C:10]2[NH:11][C:2]([NH2:1])=[N:4][C:5]2=[C:6]([Cl:18])[CH:7]=1)[CH3:17]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 418338HCID 418338, compound

Product 1

HCID 178473435HCID 178473435, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyanogen bromide (0.55 g, 5.2 mmol) was added to a stirred solution of ethyl 5,6-diamino-4-chloro-2-pyridinecarbamate (intermediate for the preparation of 1, 1.00 g, 4.3 mmol) in 20 mL of ethanol at room temperature. The solution was stirred for 3 h and then at 60° C. for 3 h. The precipitate was filtered and washed with diethyl ether to give (2-amino-7-chloro-3H-imidazo[4,5-b]pyridin-5-yl)-carbamic acid ethyl ester (0.55 g, 38%) as a yellow powder. 1H NMR confirmed the structure.

Workup

  1. waitat 60° C. for 3 h
  2. filtrationThe precipitate was filtered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-34c4b74cf9af4e41b0214fc7e8d838dc
Source dataset
uspto-grants-2014_04
Patent number
US08691814B2

Reaction notes

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