Hydrochloric Acid → 1(3,4-dichlorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carboxylic acid HCl salt

HRID 386559Notes

Reaction equation

HRID 386559 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:16]([C:30]([OH:32])=[O:31])=[N:17][N:18]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[C:19](=[O:21])[CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.CCOCC>C(Cl)Cl>[ClH:28].[Cl:29][C:24]1[CH:23]=[C:22]([N:18]2[C:19](=[O:21])[CH:20]=[C:15]([O:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:16]([C:30]([OH:32])=[O:31])=[N:17]2)[CH:27]=[CH:26][C:25]=1[Cl:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 670726944-(1-(Tert-butoxycarbonyl)piperidin-4-yloxy)-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

Product 1

HCID 670726151(3,4-dichlorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carboxylic acid HCl saltYield 181.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylic acid (from example 15 step A) (105 mg, 0.217 mmol) in DCM (2 mL) at room temperature under argon was added 4 M HCl in dioxane (0.271 mL, 1.1 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 (5 mL×2). After drying under reduce pressure over night, 83 mg (100%) of 1(3,4-dichlorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carboxylic acid HCl salt was obtained as an off-white solid. MS (ESI) 384 (M+H).

Workup

  1. filtrationThe solid product was collected by filtration
  2. washfurther washed with ether (5 mL×2)
  3. customAfter drying

Sources & evidence

ORD record
ord-fa65acf5be4a4eeaa8a848ef17bf6024
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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