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(4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamide → 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamide monohydrochloride

HRID 1896056
Notes
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Reaction equation

HRID 1896056 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]([NH:22][C:23]2[C:24]([O:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[N:25][C:26]([CH3:35])=[CH:27][C:28]=2[O:29][CH2:30][C:31]([F:34])([F:33])[F:32])=[O:21])[CH2:15][CH2:14]1.[ClH:42].N1C=CC=CC=1>C(O)C>[ClH:42].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([CH2:19][C:20]([NH:22][C:23]2[C:24]([O:36][CH2:37][C:38]([F:40])([F:41])[F:39])=[N:25][C:26]([CH3:35])=[CH:27][C:28]=2[O:29][CH2:30][C:31]([F:32])([F:33])[F:34])=[O:21])[CH2:17][CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10009365(4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamideHCID 10176127Pyridinium chloride

Product 1

HCID 100093642-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamide monohydrochlorideYield 74%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

After dissolving of 2-[(4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamide (1.00 g, 1.65 mmol) in ethanol (20 mL), pyridine hydrochloride (380 mg, 3.29 mmol) was added. The reaction mixture was concentrated, and to the residue, ethanol (0.5 mL) and water (5 mL) were added. A precipitate was collected by filtration to obtain 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamide monohydrochloride (786 mg, 74%) as a colorless crystalline powder. The monohydrochloride (300 mg) was suspended in water (1.5 mL), followed by heating to 80° C. to dissolve the same. After allowing the reaction mixture to cool down to room temperature, crystals were collected by filtration, washed with water (0.5 mL×2), and heated and dried at 50° C. for 7 hours under reduced pressure to obtain the title compound (84 mg, 28%) as a colorless crystalline powder.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. additionto the residue, ethanol (0.5 mL) and water (5 mL) were added
  4. filtrationA precipitate was collected by filtration

Sources & evidence

ORD record
ord-db986bb11d9e4dbca2511d5179ce0a81
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08518936B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes