Hydrochloric Acid → 1-(4-(methylsulfonyl)phenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl

HRID 386575Notes

Reaction equation

HRID 386575 reaction equation
[C:1]([C:3]1[C:8]([O:9][CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[CH:7][C:6](=[O:23])[N:5]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[N:4]=1)#[N:2].[ClH:34].O1CCOCC1.CCOCC>C(Cl)Cl>[ClH:34].[CH3:33][S:30]([C:27]1[CH:26]=[CH:25][C:24]([N:5]2[C:6](=[O:23])[CH:7]=[C:8]([O:9][CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:3]([C:1]#[N:2])=[N:4]2)=[CH:29][CH:28]=1)(=[O:32])=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 44620998Tert-butyl 4-(3-cyano-1-(4-(methylsulfonyl)phenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 674455661-(4-(methylsulfonyl)phenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HClYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 4-(3-cyano-1-(4-(methylsulfonyl)phenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate (700 mg, 1.475 mmol) in DCM (10 mL) at room temperature under argon was added 4 M HCl in dioxane (3.69 mL, 14.75 mmol). The reaction mixture was stirred at room temperature overnight. Et2O (10 mL) was added to the reaction mixture. The solid product was collected by filtration and further washed with ether (2 mL×2). After drying under vacuum for 2 hours, 567 mg (90%) of 1-(4-(methylsulfonyl)phenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt was obtained as an off-white solid. MS (ESI) 375 (M+H).

Workup

  1. filtrationThe solid product was collected by filtration
  2. washfurther washed with ether (2 mL×2)
  3. customAfter drying under vacuum for 2 hours

Sources & evidence

ORD record
ord-83d1885289154441980614ca1ba68373
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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