Hydrochloric Acid → HCID 67444486, compound

HRID 386581Notes

Reaction equation

HRID 386581 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([O:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[C:10]([C:29]#[N:30])=[N:9]2)=[C:4]([F:31])[CH:3]=1.[ClH:32].O1CCOCC1.CCOCC>C(Cl)Cl>[ClH:32].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([O:15][CH:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[C:10]([C:29]#[N:30])=[N:9]2)=[C:4]([F:31])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 44621140HCID 44621140, compound

Product 1

HCID 67444486HCID 67444486, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 4-(1-(4-bromo-2-fluorophenyl)-3-cyano-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate (493 mg, 1.0 mmol) in DCM (5 mL) at room temperature under argon was added 4 M HCl in dioxane (1.25 mL, 5.0 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, 334 mg (85%) of 1-(4-bromo-2-fluorophenyl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt was obtained as an off-white solid. MS (ESI) 393 (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-b3457ff8ce5d46d1834ca1a4983df642
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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