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Hydrochloric Acid → 1-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt

HRID 386569
Notes
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Reaction equation

HRID 386569 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:8][C:7](=[O:24])[N:6]([C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([F:33])[CH:26]=2)[N:5]=1)(=O)[NH2:2].[ClH:34].O1CCOCC1.CCOCC>C(Cl)Cl>[ClH:34].[C:31]([C:28]1[CH:29]=[CH:30][C:25]([N:6]2[C:7](=[O:24])[CH:8]=[C:9]([O:10][CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:4]([C:1]#[N:2])=[N:5]2)=[CH:26][C:27]=1[F:33])#[N:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 67445416tert-Butyl 4-(3-carbamoyl-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate

Product 1

HCID 674470261-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl saltYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 4-(3-cyano-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate (example 34) (22 mg, 0.050 mmol) in DCM (3 mL) at room temperature under argon was added 4 M HCl in dioxane (0.375 mL, 1.5 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, 19 mg (100%) of 1-(4-cyano-3-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt was obtained as an off-white solid. MS (ESI) 340 (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-736e5b60b2b9431eb66248be4cd7047a
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372837B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes