Hydrochloric Acid → HCID 67444435, compound

HRID 386570Notes

Reaction equation

HRID 386570 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:25]=[N:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=2)[N:4]=1)#[N:2].[ClH:32].O1CCOCC1.CCOCC>C(Cl)Cl>[ClH:32].[C:30]([C:27]1[N: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)#[N:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 44621043HCID 44621043, compound

Product 1

HCID 67444435HCID 67444435, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 4-(3-cyano-1-(6-cyanopyridin-3-yl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate (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, 17.3 mg (100%) of 1-(6-cyanopyridin-3-yl)-6-oxo-4-(piperidin-4-yloxy)-1,6-dihydropyridazine-3-carbonitrile HCl salt was obtained as an off-white solid. MS (ESI) 323 (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-aaeed157b119469bbe6e0408c1718b4d
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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