Sulfuric acid magnesium salt (1:1) → Dimethyl N-(2,3-dimethoxy-7-nitroquinoxalin-5-ylmethyl)-beta-aminopropylphosphonate

HRID 1953783Notes

Reaction equation

HRID 1953783 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:18][CH3:19])[C:7]([O:16][CH3:17])=[N:8]2.S([O-])([O-])(=O)=O.[Mg+2].O=[C:27]([CH3:35])[CH2:28][P:29](=[O:34])([O:32][CH3:33])[O:30][CH3:31].C([BH3-])#N.[Na+]>ClCCl.C(O)(=O)C.CO>[CH3:17][O:16][C:7]1[C:6]([O:18][CH3:19])=[N:5][C:4]2[C:9](=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:3]=2[CH2:2][NH:1][CH:27]([CH3:35])[CH2:28][P:29](=[O:34])([O:32][CH3:33])[O:30][CH3:31])[N:8]=1

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 5003444Sodium cyanoborohydrideHCID 179152965-Aminomethyl-2,3-dimethoxy-7-nitro-quinoxaline

Product 1

HCID 23298051Dimethyl N-(2,3-dimethoxy-7-nitroquinoxalin-5-ylmethyl)-beta-aminopropylphosphonate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

200 mg (0.757 mmol) of 5-aminomethyl-7-nitro-2,3-dimethoxyquinoxaline, 547 mg (4.5 eq.) of magnesium sulfate and 163 mg (1.3 eq.) of dimethyl 2-oxopropylphosphonate are stirred at room temperature for 20 hours in 8 ml of dichloromethane. 4 ml of methanol, 0.095 ml of acetic acid and 52 mg (1.1 eq.) of sodium cyanoborohydride are then added and stirred for 4 hours. The reaction mixture is then filtered and the filtrate is extracted with water and brine. The organic phases are combined, dried over magnesium sulfate and evaporated. The title compound is obtained as a brown oil.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. extractionthe filtrate is extracted with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-334cfcc977314de598a322b4776a869b
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

Loading…