4-Chlorobenzenesulfonyl chloride → [4-(4-Chloro-benzenesulfonylamino)-butyl]-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

HRID 882899Notes

Reaction equation

HRID 882899 reaction equation
[Br-:1].[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N+:7]([CH2:10][CH2:11][NH:12][C:13]([C:15]1[C:20]([NH2:21])=[N:19][C:18]([NH2:22])=[C:17]([Cl:23])[N:16]=1)=[O:14])([CH3:9])[CH3:8].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.CN1CCOCC1>CN(C=O)C>[Br-:1].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:2][CH2:3][CH2:4][CH2:5][CH2:6][N+:7]([CH2:10][CH2:11][NH:12][C:13]([C:15]2[C:20]([NH2:21])=[N:19][C:18]([NH2:22])=[C:17]([Cl:23])[N:16]=2)=[O:14])([CH3:9])[CH3:8])(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 86656640(4-Amino-butyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide2×

Product 1

HCID 57393279[4-(4-Chloro-benzenesulfonylamino)-butyl]-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4-amino-butyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide (Intermediate N) (0.25 g, 0.60 mmol), 4-chlorobenzenesulfonyl chloride (0.125 g, 0.59 mmol) and N-methylmorpholine (0.3 mL, 2.73 mmol) in DMF (5 mL) is shaken at RT for 16 h. The reaction mixture is concentrated in vacuo, and the residue is purified by chromatography (basic alumina, 0-15% methanol in DCM) to obtain the title compound. M+ 504.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe residue is purified by chromatography (basic alumina, 0-15% methanol in DCM)

Sources & evidence

ORD record
ord-f230d376d1de4ef2bc9fb3883f209a65
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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