Hydrochloric Acid → 6-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)-5-(piperidin-4-yloxy)pyridazin-3(2H)-one HCl salt

HRID 386578Notes

Reaction equation

HRID 386578 reaction equation
[OH:1][CH2:2][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.[ClH:34].O1CCOCC1.CCOCC>C(Cl)Cl>[ClH:34].[OH:1][CH2:2][C:3]1[C:8]([O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:7][C:6](=[O:23])[N:5]([C:24]2[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=2)[N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 67072635Tert-butyl 4-(3-(hydroxymethyl)-1-(4-(methylsulfonyl)phenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 670726116-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)-5-(piperidin-4-yloxy)pyridazin-3(2H)-one HCl saltYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 4-(3-(hydroxymethyl)-1-(4-(methylsulfonyl)phenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate (200 mg, 0.417 mmol) in DCM (3 mL) at room temperature under argon was added 4 M HCl in dioxane (0.521 mL, 2.085 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, 171 mg (100%) of 6-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)-5-(piperidin-4-yloxy)pyridazin-3(2H)-one HCl salt was obtained as an off-white solid. MS (ESI) 380 (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-d6067dd9c16848b68c47710a0d614b32
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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