1-((6-Chloronaphthalen-2-yl)sulfonyl)piperazine → 1-(6-Chloronaphthalene-2-sulfonyl)-4-(6-chloropyridazin-3-ylcarbonyl)piperazine

HRID 1372883Notes

Reaction equation

HRID 1372883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[Cl:21][C:22]1[N:27]=[N:26][C:25]([C:28](Cl)=[O:29])=[CH:24][CH:23]=1>C(Cl)Cl.N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:16][CH2:17][N:18]([C:28]([C:25]3[N:26]=[N:27][C:22]([Cl:21])=[CH:23][CH:24]=3)=[O:29])[CH2:19][CH2:20]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

6

Reactant 2

HCID 113588251-((6-Chloronaphthalen-2-yl)sulfonyl)piperazineHCID 217811856-Chloropyridazine-3-carbonyl chloride

Product 1

HCID 210726741-(6-Chloronaphthalene-2-sulfonyl)-4-(6-chloropyridazin-3-ylcarbonyl)piperazineYield 76.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolvent2×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(6-chloronaphthalen-2-ylsulfonyl)-piperazine (0.450 g, 1.45 mmol) in methylene chloride (100 mL) and pyridine (0.154 mL) was added dropwise 6-chloropyridazine-3-carbonyl chloride (1.74 mmol). After the addition of the acid chloride, pyridine (0.154 mL) was added, and the reaction mixture was stirred overnight. The reaction mixture was diluted with chloroform (500 mL), washed with saturated sodium bicarbonate (200 mL), water (200 mL),and brine and dried over MgSO4. After filtration and evaporation of the solvent, trituration of the residue with ethyl acetate and filtration gave the product as a white powder (0.5 g, 76%)

Workup

  1. additionwas added
  2. washwashed with saturated sodium bicarbonate (200 mL), water (200 mL),and brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration and evaporation of the solvent, trituration of the residue
  5. filtrationwith ethyl acetate and filtration

Sources & evidence

ORD record
ord-c2732702d5f64975b55e9c81357befb9
Source dataset
uspto-grants-2007_01
Patent number
US07160878B2

Reaction notes

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