Silane, bromotriethyl- → N-(2,3-Dioxo-7-nitro-1,2,3,4-tetrahydroquinoxalin-5-ylmethyl)-alpha-(ethylamino)ethylphosphonic acid hydrobromide

HRID 1953774Notes

Reaction equation

HRID 1953774 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([N:8]=[C:9]([O:16]C)[C:10]([O:14]C)=[N:11]2)=[C:6]([CH2:18][N:19]([CH2:28][CH3:29])[CH:20]([P:22](=[O:27])([O:25]C)[O:23]C)[CH3:21])[CH:5]=1)([O-:3])=[O:2].C([Si](CC)(CC)[Br:33])C>ClCCl>[BrH:33].[O:14]=[C:10]1[C:9](=[O:16])[NH:8][C:7]2[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[CH2:18][N:19]([CH2:28][CH3:29])[CH:20]([P:22](=[O:23])([OH:25])[OH:27])[CH3:21])[NH:11]1

Participants

4

Reactant 2

HCID 70680Silane, bromotriethyl-HCID 23298022dimethyl N-(7-nitro-2,3-dimethoxyquinoxalin-5-ylmethyl)-alpha-(ethylamino)ethylphosphonate

Product 1

HCID 17967587N-(2,3-Dioxo-7-nitro-1,2,3,4-tetrahydroquinoxalin-5-ylmethyl)-alpha-(ethylamino)ethylphosphonic acid hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

160 mg (0.37 mmol) of dimethyl N-(7-nitro-2,3-dimethoxyquinoxalin-5-ylmethyl)-α-(ethylamino)ethylphosphonate are dissolved in 8 ml of dichloromethane and stirred at room temperature for one hour with 0.19 ml (4 eq.) of triethylbromosilane. The solvent and excess reagent are evaporated and the residue is briefly dried in a high vacuum, dissolved in 5 ml of an about 33% hydrogen bromide solution in acetic acid, and stirred at room temperature for 18 hours. The reaction mixture is diluted with diethyl ether, and the solid is filtered off, washed with diethyl ether and dried. The title compound is obtained as a beige solid; m.p.=191° (dec.).

Workup

  1. customThe solvent and excess reagent are evaporated
  2. customthe residue is briefly dried in a high vacuum
  3. dissolutiondissolved in 5 ml of an about 33% hydrogen bromide solution in acetic acid
  4. additionThe reaction mixture is diluted with diethyl ether
  5. filtrationthe solid is filtered off
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-805450e2d57f40898fcf73124a490141
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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