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1-Methylpiperazine → 2-Methyl-6'-(4-methyl-piperazin-1-yl)-[3,4']bipyridinyl-3'-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide

HRID 347681
Notes
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Reaction equation

HRID 347681 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8]([C:10]1[CH:11]=[N:12][C:13](Cl)=[CH:14][C:15]=1[C:16]1[C:17]([CH3:22])=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:9].[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>ClCCl>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8]([C:10]1[CH:11]=[N:12][C:13]([N:38]2[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]2)=[CH:14][C:15]=1[C:16]1[C:17]([CH3:22])=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 586945956'-Chloro-2-methyl-[3,4']bipyridinyl-3'-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide

Product 1

HCID 115196362-Methyl-6'-(4-methyl-piperazin-1-yl)-[3,4']bipyridinyl-3'-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

2-Methyl-6′-(4-methyl-piperazin-1-yl)-[3,4′]bipyridinyl-3′-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide of formula I-1 is prepared as follows: A mixture of 6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide and 1-methylpiperazine is heated at about 120° C. for 2 h. After cooling to room temperature the mixture is diluted with dichloromethane and washed with water. The aqueous layer is worked up in conventional manner to give the compound 2-methyl-6′-(4-methyl-piperazin-1-yl)-[3,4′]bipyridinyl-3′-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide of formula I-1.

Workup

  1. custom2-Methyl-6′-(4-methyl-piperazin-1-yl)-[3,4′]bipyridinyl-3′-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide of formula I-1 is prepared
  2. temperatureAfter cooling to room temperature the mixture
  3. washwashed with water

Sources & evidence

ORD record
ord-f4c496e24bd34beda743e5f2d26936e3
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176205B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes