1,4-Dioxane hydrochloride → HCID 86628816, compound

HRID 2244660Notes

Reaction equation

HRID 2244660 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:22]=3[CH:23]=[CH:24][N:25]4[CH2:30][C:31]([N:33]3[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]3)=[O:32])[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][C@@H:10]([CH3:15])[C:11]([F:14])([F:13])[F:12].[ClH:48].O1CCOCC1>C(Cl)Cl>[ClH:48].[O:32]=[C:31]([N:33]1[CH2:34][CH2:35][NH:36][CH2:37][CH2:38]1)[CH2:30][N:25]1[C:26]2[C:22](=[C:21]([C:18]3[N:17]=[C:16]([C:5]4[CH:6]=[CH:7][C:8]([O:9][C@@H:10]([CH3:15])[C:11]([F:12])([F:13])[F:14])=[C:3]([C:2]([F:47])([F:46])[F:1])[CH:4]=4)[O:20][N:19]=3)[CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:24]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59214215HCID 59214215, compound

Product 1

HCID 86628816HCID 86628816, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tertiary-butyl 4-{[4-(5-{3-(trifluoromethyl)-4-[(1S)-2,2,2-trifluoro-1-methylethoxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]acetyl}piperazine-1-carboxylate (70.7 mg) in methylene chloride (1 ml) was added dropwise 10 equivalents of 4M HCl/dioxane, followed by stirring at room temperature for 3 hours. After 5 hours, the reaction solution was concentrated. With addition of diisopropyl ether, a white solid was precipitated. The white solid was washed with IPE to obtain 1-(2-oxo-2-piperazin-1-ylethyl)-4-(5-{3-(trifluoromethyl)-4-[(1S)-2,2,2-trifluoro-1-methylethoxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole hydrochloride (58.9 mg) as a pale red solid.

Workup

  1. waitAfter 5 hours
  2. concentrationthe reaction solution was concentrated
  3. additionWith addition of diisopropyl ether
  4. customa white solid was precipitated
  5. washThe white solid was washed with IPE

Sources & evidence

ORD record
ord-aa2146e4299b41cda5c989dec281276d
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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