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Pyridine → 1-(6-Chloronaphthalen-2-ylsulfonyl)-4-[6-(4-methyl-hexahydro-1,4-diazepin-1-yl)pyridazin-3-ylcarbonyl]-piperazine Hemihydrate

HRID 1372884
Notes
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Reaction equation

HRID 1372884 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][N:18]([C:21]([C:23]3[N:24]=[N:25][C:26](Cl)=[CH:27][CH:28]=3)=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[CH3:30][N:31]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.N1C=CC=CC=1>CS(C)=O.C(OCC)(=O)C>[OH2:13].[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][N:18]([C:21]([C:23]3[N:24]=[N:25][C:26]([N:34]4[CH2:35][CH2:36][CH2:37][N:31]([CH3:30])[CH2:32][CH2:33]4)=[CH:27][CH:28]=3)=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[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][N:18]([C:21]([C:23]3[N:24]=[N:25][C:26]([N:34]4[CH2:35][CH2:36][CH2:37][N:31]([CH3:30])[CH2:32][CH2:33]4)=[CH:27][CH:28]=3)=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 2283491-MethylhomopiperazineHCID 210726741-(6-Chloronaphthalene-2-sulfonyl)-4-(6-chloropyridazin-3-ylcarbonyl)piperazine

Product 1

HCID 877961221-(6-Chloronaphthalen-2-ylsulfonyl)-4-[6-(4-methyl-hexahydro-1,4-diazepin-1-yl)pyridazin-3-ylcarbonyl]-piperazine HemihydrateYield 62.9%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(6-chloronaphthalene-2-sulfonyl)-4-(6-chloropyridazin-3-ylcarbonyl)piperazine (0.2 g, 0.443 mmol), 1-methylhexahydro-1,4-diazepine (0.166 mL, 1.33 mmol) and pyridine (0.11 mL, 1.33 mmol) in DMSO (5 mL) was heated in a sealed tube at 80° C. overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (500 mL), washed with saturated sodium bicarbonate (200 mL), water (2×150 mL) and brine, and dried over sodium sulfate. After filtration and evaporation of the solvent, the residue was purified by flash chromatography over silica, eluting with 5–7% methanol/methylene chloride, to afford the title compound (0.1 g, 43%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with saturated sodium bicarbonate (200 mL), water (2×150 mL) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and evaporation of the solvent
  5. customthe residue was purified by flash chromatography over silica
  6. washeluting with 5–7% methanol/methylene chloride

Sources & evidence

ORD record
ord-bd384395b9c442e0a2c6f565caed977e
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07160878B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes