Diisopropylethylamine → {2-[(6-Amino-5-nitro(2-pyridyl))amino]ethyl}[6-(2,4-dichlorophenyl)-5-nitro(2-pyridyl)]amine

HRID 31948Notes

Reaction equation

HRID 31948 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11](Cl)[N:10]=1.[NH2:19][CH2:20][CH2:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25]([NH2:32])[N:24]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[NH2:32][C:25]1[N:24]=[C:23]([NH:22][CH2:21][CH2:20][NH:19][C:11]2[CH:12]=[CH:13][C:14]([N+:15]([O-:17])=[O:16])=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:10]=2)[CH:28]=[CH:27][C:26]=1[N+:29]([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 221423802,6-Diamino-N2-(2-aminoethyl)-5-nitropyridineHCID 221429302-(2,4-Dichlorophenyl)-6-chloro-3-nitropyridine

Product 1

HCID 22142421{2-[(6-Amino-5-nitro(2-pyridyl))amino]ethyl}[6-(2,4-dichlorophenyl)-5-nitro(2-pyridyl)]amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 mmol of 2-(2,4-dichlorophenyl)-6-chloro-3-nitropyridine was taken with 2 mmol of (2-aminoethyl)(6-amino-5-nitro(2-pyridyl))amine and 3 mmol of N,N-diisopropylethylamine in 2 ml of DMF at 80° C. for two hours. The reaction mixture was concentrated in vacuo and diluted with water and ethyl acetate. The solution was extracted three times with ethyl acetate, dried over sodium sulfate, and purified by column chromatography eluting with 5-10% methanol/methylene chloride.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water and ethyl acetate
  3. extractionThe solution was extracted three times with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. custompurified by column chromatography
  6. washeluting with 5-10% methanol/methylene chloride

Sources & evidence

ORD record
ord-540f91fafa474bc3b55d882a4392de1f
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Reaction notes

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