Ethyl (2,3-diamino-6-(2-methoxyethoxy)pyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate → diethyl 4-((4-amino-6-(2-methoxyethoxy)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)methyl)benzylphosphonate

HRID 629938Notes

Reaction equation

HRID 629938 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([N:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][P:23]([O:28][CH2:29][CH3:30])([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:17]=2)[C:10](=[O:14])OCC)[CH:5]=[C:4]([O:31][CH2:32][CH2:33][O:34][CH3:35])[N:3]=1>CC(O)=O>[NH2:1][C:2]1[C:7]2[NH:8][C:10](=[O:14])[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][P:23](=[O:24])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])=[CH:18][CH:17]=3)[C:6]=2[CH:5]=[C:4]([O:31][CH2:32][CH2:33][O:34][CH3:35])[N:3]=1

Participants

3

Reactant 1

HCID 86667764Ethyl (2,3-diamino-6-(2-methoxyethoxy)pyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate

Product 1

HCID 86667765diethyl 4-((4-amino-6-(2-methoxyethoxy)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)methyl)benzylphosphonateYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of ethyl (2,3-diamino-6-(2-methoxyethoxy)pyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate (1 equiv.) in AcOH (0.15 M) was heated in a microwave at 100° C. for 5 min. At this point the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH™ system using a gradient of 0-10% MeOH/DCM to provide the title compound (63% over two steps) as a solid.

Workup

  1. customAt this point the volatiles were removed in vacuo
  2. customThe resulting residue was purified by a COMBIFLASH™ system

Sources & evidence

ORD record
ord-8cc4358855714ccbac4939b1ef113394
Source dataset
uspto-grants-2016_04
Patent number
US09315530B2

Reaction notes

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