Hydrochloric Acid → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((cis)-3-fluoropiperidin-4-yloxy)quinoline dihydrochloride

HRID 876485Notes

Reaction equation

HRID 876485 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][C@H:21]4[CH2:26][CH2:25][NH:24][CH2:23][C@H:22]4[F:27])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[ClH:28].O1CCOCC1>CO>[ClH:28].[ClH:28].[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][C@H:21]4[CH2:26][CH2:25][NH:24][CH2:23][C@H:22]4[F:27])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 672309412-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((cis)-3-fluoropiperidin-4-yloxy)quinoline

Product 1

HCID 672349172-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((cis)-3-fluoropiperidin-4-yloxy)quinoline dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Non-racemic 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-((cis)-3-fluoropiperidin-4-yloxy)quinoline (20 mg, 0.055 mmol) was dissolved in MeOH (2 mL) and treated with 4M HCl in dioxane (1 mL, 4 mmol). The mixture was stirred for 5 minutes then concentrated in vacuo. The residue was dissolved in fresh MeOH and concentrated in vacuo three times to a pale yellow solid (20.7 mg, 86%). Specific rotation: [α]20D=+26° (c=0.45, 1:1 water/95% ethanol).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in fresh MeOH
  3. concentrationconcentrated in vacuo three times to a pale yellow solid (20.7 mg, 86%)

Sources & evidence

ORD record
ord-30951e6add064d31a791c81134cd7c10
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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