Hydrochloric Acid → (2S,4S)-4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-N,N-dimethylpiperidine-2-carboxamide dihydrochloride

HRID 876424Notes

Reaction equation

HRID 876424 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][N:24](C(OC(C)(C)C)=O)[C@H:23]([C:34](=[O:38])[N:35]([CH3:37])[CH3:36])[CH2:22]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(Cl)(Cl)[Cl:40].[ClH:43]>C(OCC)C>[ClH:40].[ClH:43].[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][C@H:23]([C:34]([N:35]([CH3:37])[CH3:36])=[O:38])[CH2:22]4)[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 Acid2×HCID 6212ChloroformHCID 67234046(2S,4S)-tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-(dimethylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 67234184(2S,4S)-4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-N,N-dimethylpiperidine-2-carboxamide dihydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the product from Step A (0.080 g, 0.155 mmol) was added chloroform (1.6 mL) To the resulting solution was added hydrogen chloride (0.387 mL, 1.55 mmol, 4.0 M in 1,4-dioxane) causing the solution to turn yellow. The mixture was stirred at ambient temperature for 3 hours. Additional hydrogen chloride (0.387 mL, 1.55 mmol, 4.0 M in 1,4-dioxane) was added and the reaction stirred at ambient temperature for another 3 hours. The mixture was diluted with diethyl ether (5 mL) and filtered. The product was washed with Et2O and dried in vacuo to provide 0.068 g (86%) of the desired product as a yellow solid. MS ESI (+) m/z 417.1 (M+1) detected.

Workup

  1. stirringthe reaction stirred at ambient temperature for another 3 hours
  2. filtrationfiltered
  3. washThe product was washed with Et2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bcceee89b573420183fc182e218e17cc
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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