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

HRID 882900Notes

Reaction equation

HRID 882900 reaction equation
[Br-:1].[NH2:2][CH2:3][CH2:4][N+:5]([CH2:8][CH2:9][NH:10][C:11]([C:13]1[C:18]([NH2:19])=[N:17][C:16]([NH2:20])=[C:15]([Cl:21])[N:14]=1)=[O:12])([CH3:7])[CH3:6].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][S:30](Cl)(=[O:32])=[O:31])=[CH:25][CH:24]=1.CN1CCOCC1>CN(C=O)C>[Br-:1].[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][S:30]([NH:2][CH2:3][CH2:4][N+:5]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[C:18]([NH2:19])=[N:17][C:16]([NH2:20])=[C:15]([Cl:21])[N:14]=2)=[O:12])([CH3:6])[CH3:7])(=[O:32])=[O:31])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 227304(4-Chlorophenyl)methanesulfonyl chlorideHCID 86656647(2-Amino-ethyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide2×

Product 1

HCID 86656646[2-(4-Chloro-phenylmethanesulfonylamino)-ethyl]-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2-amino-ethyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide (Intermediate K) (0.3 g, 0.78 mmol), (4-chloro-phenyl)-methanesulfonyl chloride (0.18 g, 0.78 mmol) and N-methylmorpholine (0.35 mL, 3.18 mmol) in DMF (5 mL) is shaken at RT for 16 h. After this time the solvent is removed in vacuo and the residue is subjected to chromatography (basic alumina, 0-15% methanol in DCM) to yield the title compound. M+ 490.

Workup

  1. customAfter this time the solvent is removed in vacuo

Sources & evidence

ORD record
ord-ede6fa6295394d45b054ef61111b69eb
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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