Hydrochloric Acid → 1-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

HRID 1959717Notes

Reaction equation

HRID 1959717 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([CH2:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)=[N:13][N:14]=2)[N:11]=1)=[CH2:5])C.Cl.C([O-])(O)=O.[Na+]>CO>[N:22]1[C:23]2[C:18](=[CH:17][C:16]([CH2:15][C:12]3[N:10]4[N:11]=[C:6]([C:4](=[O:3])[CH3:5])[CH:7]=[CH:8][C:9]4=[N:14][N:13]=3)=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 698109446-((6-(1-Ethoxyvinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

Product 1

HCID 581904611-(3-(Quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanoneYield 51.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-((6-(1-ethoxyvinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline in MeOH (30 mL) was added excess 3N HCl solution. The solution was stirred at rt overnight and neutralized with saturated NaHCO3 solution. Organic solvent was evaporated and the residue was extracted with EtOAc three times. Organic layers were combined, washed with brine and dried over Na2SO4. Solvent was evaporated and the crude was purified by column chromatography (DCM:MeOH=95:5) to give the title compound as yellow solid (51.3%). LCMS (method B): [MH]+=304.1, tR=1.708 min.

Workup

  1. customOrganic solvent was evaporated
  2. extractionthe residue was extracted with EtOAc three times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customSolvent was evaporated
  6. customthe crude was purified by column chromatography (DCM:MeOH=95:5)

Sources & evidence

ORD record
ord-65a0ff50833d44508c8434f8b444aa59
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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