1,4-Dioxane hydrochloride → HCID 86628815, compound

HRID 2244659Notes

Reaction equation

HRID 2244659 reaction equation
[Cl:1][C:2]1[N:6]2[C:7]([C:11]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:28])[C:24]([F:27])([F:26])[F:25])=[C:18]([C:29]([F:32])([F:31])[F:30])[CH:17]=4)[O:13][N:12]=3)=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.Cl.O1CCOCC1>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[N:6]2[C:7]([C:11]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:28])[C:24]([F:25])([F:26])[F:27])=[C:18]([C:29]([F:32])([F:30])[F:31])[CH:17]=4)[O:13][N:12]=3)=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59214416HCID 59214416, compound

Product 1

HCID 86628815HCID 86628815, compoundYield 190.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}imidazo[1,2-a]pyridine (150 mg) in ethanol was added NCS (67 mg) at room temperature, followed by stirring at 80° C. for 15 hours. To the reaction solution was added water, followed by extraction with EtOAc. The organic layer was washed with saturated brine, dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. It was purified by silica gel column chromatography (n-hexane:EtOAc=90:10 to 75:25) to obtain 3-chloro-5-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}imidazo[1,2-a]pyridine (110.4 mg) as a white solid. To a solution of 3-chloro-5-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}imidazo[1,2-a]pyridine (100 mg) in methylene chloride (2 ml) was added dropwise 10 equivalents of 4M HCl/dioxane at room temperature. After stirring at room temperature as it was for 1 hour, it was concentrated under reduced pressure. It was powdered/washed with diisopropyl ether, and then collected by filtration to obtain 3-chloro-5-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}imidazo[1,2-a]pyridine hydrochloride (102.6 mg) as a white solid.

Workup

  1. concentrationit was concentrated under reduced pressure
  2. washIt was powdered/washed with diisopropyl ether
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a8a07337a3f94289b3d516b0098146d0
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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