2-[4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamide → 2-[4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamide hydrochloride

HRID 2354015Notes

Reaction equation

HRID 2354015 reaction equation
[F:1][C:2]1[C:42]([F:43])=[CH:41][C:5]2[N:6]=[C:7]([S:9][CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]([NH:21][C:22]4[C:23]([O:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[N:24][C:25]([CH3:34])=[CH:26][C:27]=4[O:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[O:20])[CH2:14][CH2:13]3)[NH:8][C:4]=2[CH:3]=1.[ClH:44].N1C=CC=CC=1>C(O)C>[ClH:44].[F:1][C:2]1[C:42]([F:43])=[CH:41][C:5]2[N:6]=[C:7]([S:9][CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][N:15]([CH2:18][C:19]([NH:21][C:22]4[C:23]([O:35][CH2:36][C:37]([F:38])([F:39])[F:40])=[N:24][C:25]([CH3:34])=[CH:26][C:27]=4[O:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[O:20])[CH2:16][CH2:17]3)[NH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 100097592-[4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamideHCID 10176127Pyridinium chloride

Product 1

HCID 100097582-[4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamide hydrochlorideYield 74.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After dissolving 2-[4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-pyridyl]acetamide (1.00 g, 1.56 mmol) in ethanol (20 mL), pyridine hydrochloride (360 mg, 3.12 mmol) was added. The reaction mixture was concentrated, and the residue was recrystallized from ethanol to obtain the title compound (787 mg, 78%; including 40% equivalent of ethanol as determined by 1H-NMR) as a colorless crystalline powder.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-80d87660f0034a3b9e268d22450ad310
Source dataset
uspto-grants-2010_07
Patent number
US07750150B2

Reaction notes

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