Hydrochloric Acid → HCID 11431024, compound

HRID 1684993Notes

Reaction equation

HRID 1684993 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:33]([S:36](Cl)(=[O:38])=[O:37])[CH2:34][CH3:35].Cl>ClCCl>[F:23][C:22]([F:25])([F:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]([N:11]1[CH2:10][CH2:9][N:8]([C:5]2[N:6]=[N:7][C:2]([NH:1][S:36]([CH2:33][CH2:34][CH3:35])(=[O:38])=[O:37])=[CH:3][CH:4]=2)[CH2:13][CH2:12]1)=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Product 1

HCID 11431024HCID 11431024, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of [4-(6-amino pyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone (0.10 g, 0.285 mmol) and triethyl amine (0.037 g, 0.371 mmol) in 10 mL of dichloromethane at 0° C. was added n-propylsulphonyl chloride (0.044 g, 0.313 mmol). The reaction mixture was stirred at room temperature for 4 hours and then dilute hydrochloric acid solution was added (20 mL). The mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulphate, the concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a white solid (46.3 mg, 35.5% yield). 1H NMR (400 MHz, CDCl3) δ 7.75, 7.63-7.66, 7.56-7.59, 7.37, 7.25, 6.99, 4.04-4.07, 3.85-3.89, 3.71-3.78, 3.35, 1.96-2.00, 1.1.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationthe concentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ff088ae924d14f278e56f46c3382eb85
Source dataset
uspto-grants-2012_04
Patent number
US08148378B2

Reaction notes

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