(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 2354016Notes

Reaction equation

HRID 2354016 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

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 702EthanolSolvent

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-b8b3f9caa1c246e59810f86d805a28f3
Source dataset
uspto-grants-2010_07
Patent number
US07750150B2

Reaction notes

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