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1-Methylpiperazine → 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-[2-methyl-6'-(4-methyl-piperazin-1-yl)-[3,4']bipyridinyl-3'-yl]-isobutyramide

HRID 347680
Notes
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Reaction equation

HRID 347680 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[F:8][C:9]([F:42])([F:41])[C:10]1[CH:11]=[C:12]([C:20]([CH3:40])([CH3:39])[C:21]([N:23]([C:25]2[CH:26]=[N:27][C:28](Cl)=[CH:29][C:30]=2[C:31]2[C:32]([CH3:37])=[N:33][CH:34]=[CH:35][CH:36]=2)[CH3:24])=[O:22])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1>CN(C1C=CN=CC=1)C.COC(C)(C)C>[F:8][C:9]([F:42])([F:41])[C:10]1[CH:11]=[C:12]([C:20]([CH3:40])([CH3:39])[C:21]([N:23]([CH3:24])[C:25]2[CH:26]=[N:27][C:28]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:29][C:30]=2[C:31]2[C:32]([CH3:37])=[N:33][CH:34]=[CH:35][CH:36]=2)=[O:22])[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 531671-Methylpiperazine2×HCID 210836352-(3,5-Bis-trifluoromethyl-phenyl)-N-(6'-chloro-2-methyl-[3,4]bipyridinyl-3'-yl)-N-methyl-isobutyramide

Product 1

HCID 115560662-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-[2-methyl-6'-(4-methyl-piperazin-1-yl)-[3,4']bipyridinyl-3'-yl]-isobutyramide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 15413
tert-Butyl methyl ether
Solvent

Conditions

Temperature
140 °C

Procedure

Process variant b) describes the reaction of a compound of formula II-2 with 1-methylpiperazine to produce a compound of formula I-2. A mixture of 2-(3,5-bis-trifluoromethyl-phenyl)-N-(6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-N-methyl-isobutyramide, 1-methylpiperazine and 4-(N,N-dimethylamino)pyridine is heated at about 140° C. over night. After cooling to room temperature, the mixture is diluted with tert-butyl methyl ether and washed with water. The aqueous layer is extracted with tert-butyl methyl ether. The combined organic layers are dried and concentrated to give the compound 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-[2-methyl-6′-(4-methyl-piperazin-1-yl)-[3,4′]bipyridinyl-3′-yl]-isobutyramide of formula I-2.

Workup

  1. customto produce a compound of formula I-2
  2. temperatureAfter cooling to room temperature
  3. washwashed with water
  4. extractionThe aqueous layer is extracted with tert-butyl methyl ether
  5. customThe combined organic layers are dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-109592ad96f144f198c3d4988909188b
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