Hydrochloric Acid → HCID 57690954, compound

HRID 1513672Notes

Reaction equation

HRID 1513672 reaction equation
Cl.F[C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH2:18][O:19][C:20]4[C:29]5[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=5)[N:23]=[CH:22][CH:21]=4)=[N:16][N:17]=3)[CH:14]=2)[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.CS(C)=[O:41]>O1CCOCC1.C(Cl)Cl.CO>[CH3:31][O:30][C:26]1[CH:25]=[C:24]2[C:29]([C:20]([O:19][CH2:18][C:15]3[N:13]4[CH:14]=[C:9]([C:7]5[NH:8][C:3](=[O:41])[CH:4]=[CH:5][CH:6]=5)[CH:10]=[CH:11][C:12]4=[N:17][N:16]=3)=[CH:21][CH:22]=[N:23]2)=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 67502414HCID 67502414, compound

Product 1

HCID 57690954HCID 57690954, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
100 °C

Procedure

In a pressure vessel, 3N HCl (1.2 ml, 3.5 mmol) was added to 4-((6-(6-fluoropyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline (0.071 g, 0.18 mmol) in dioxane (0.60 mL). The reaction mixture was then heated at 100° C. for 3.5 h. Concentrated HCl (0.300 mL, 9.9 mmol) was added and the reaction was heated at 100° C. for 2 h. The reaction mixture was concentrated in vacuo, and then dried on high vacuum. Triethylamine (0.74 ml, 5.3 mmol) was added to the compound, and it was allowed to stir for one hour until the free base crashed out of solution. The compound was dissolved partially in DCM/MeOH, however, fully dissolved after addition of hot DMSO. The compound was purified via flash chromatograph, eluting with 0-10% MeOH/NH4OH in DCM. The compound was sonicated in DCM and filtered to remove the triethylamine-hydrochloride salt, and yielded 6-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)pyridin-2(1H)-one.

Workup

  1. temperaturethe reaction was heated at 100° C. for 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customdried on high vacuum
  4. dissolutionhowever, fully dissolved
  5. customThe compound was purified via flash chromatograph
  6. washeluting with 0-10% MeOH/NH4OH in DCM
  7. customThe compound was sonicated in DCM
  8. filtrationfiltered
  9. customto remove the triethylamine-hydrochloride salt

Sources & evidence

ORD record
ord-0a902f80406345488379755703d0941b
Source dataset
uspto-grants-2012_07
Patent number
US08217177B2

Reaction notes

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