Triethylamine → N-(2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl)-valeric acid amide

HRID 1422244Notes

Reaction equation

HRID 1422244 reaction equation
C(N(CC)CC)C.[CH3:8][CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13].[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.ClCCl>[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:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH3:8])[N:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 179152965-Aminomethyl-2,3-dimethoxy-7-nitro-quinoxaline

Product 1

HCID 54181386N-(2,3-Dimethoxy-7-nitro-quinoxalin-5-ylmethyl)-valeric acid amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

79 μl (0.567 mmol) of triethylamine and 55 μl (0.454 mmol) of n-valeroyl chloride 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 at room temperature for 16 hours. The mixture is then taken up in dichloromethane, washed with 1 N hydrochloric acid and with 1 N sodium hydroxide solution, dried over sodium sulfate and concentrated by evaporation. The title compound is obtained in the form of a yellowish powder.

Workup

  1. washwashed with 1 N hydrochloric acid and with 1 N sodium hydroxide solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-affe4107c7964e84a88b14953e47736f
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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