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 1896055Notes

Reaction equation

HRID 1896055 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-94274c01caca4e9db871637d2f01f71c
Source dataset
uspto-grants-2013_08
Patent number
US08518936B2

Reaction notes

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