Ammonia → Ethyl (2-amino-6-bromo-3-nitropyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate

HRID 629935Notes

Reaction equation

HRID 629935 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=2)[C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:5]=[C:4]([Br:33])[N:3]=1.[NH3:34].CO>C1COCC1>[NH2:34][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:11]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][P:25]([O:27][CH2:28][CH3:29])([O:30][CH2:31][CH3:32])=[O:26])=[CH:22][CH:23]=2)[C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:5]=[C:4]([Br:33])[N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86667761Ethyl (2,6-dibromo-3-nitropyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate

Product 1

HCID 86667762Ethyl (2-amino-6-bromo-3-nitropyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamateYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (2,6-dibromo-3-nitropyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate (1 equiv.) in THF (0.40 M) was added a 7 M solution of ammonia in methanol (5 equiv.). The reaction mixture was then allowed to stir at room temperature for 48 h. At this point the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH™ system using a gradient of 0-5% MeOH/DCM to provide the title compound (68%) 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-00ee9269b30d4e769732ec3b9d8e9947
Source dataset
uspto-grants-2016_04
Patent number
US09315530B2

Reaction notes

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