Succinic anhydride → N-(2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl)-succinic acid amide

HRID 1422246Notes

Reaction equation

HRID 1422246 reaction equation
C(N(CC)CC)C.[C:8]1(=[O:14])[O:13][C:11](=[O:12])[CH2:10][CH2:9]1.[NH2:15][CH2:16][C:17]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[C:23]2[C:18]=1[N:19]=[C:20]([O:32][CH3:33])[C:21]([O:30][CH3:31])=[N:22]2>COC(C)(C)C>[CH3:31][O:30][C:21]1[C:20]([O:32][CH3:33])=[N:19][C:18]2[C:23](=[CH:24][C:25]([N+:27]([O-:29])=[O:28])=[CH:26][C:17]=2[CH2:16][NH:15][C:11](=[O:12])[CH2:10][CH2:9][C:8]([OH:13])=[O:14])[N:22]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 179152965-Aminomethyl-2,3-dimethoxy-7-nitro-quinoxaline

Product 1

HCID 70272034N-(2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl)-succinic acid amide

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

55 μl (0.397 mmol) of triethylamine and 40 mg (0.397 mmol) of succinic anhydride are added to a suspension of 100 mg (0.378 mmol) of 5-aminomethyl-2,3-dimethoxy-7-nitro-quinoxaline in 2 ml of tert-butyl methyl ether and the mixture is stirred for 3 hours at room temperature. The mixture is then filtered and the residue is washed twice with tert-butyl methyl ether. The filter residue is chromatographed on silica gel with dichloromethane/methanol/acetic acid (95:4.5:0.5). The title compound is obtained in the form of a beige powder.

Workup

  1. filtrationThe mixture is then filtered
  2. washthe residue is washed twice with tert-butyl methyl ether
  3. customThe filter residue is chromatographed on silica gel with dichloromethane/methanol/acetic acid (95:4.5:0.5)

Sources & evidence

ORD record
ord-537b3ffc34ed46dc9454a2629976c075
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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