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

HRID 347688Notes

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]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 0.21 g (0.44 mmol) 6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide and 1.0 ml (9.0 mmol) 1-methylpiperazine was heated at 120° C. for 2 h. After cooling to room temperature the mixture was diluted with dichloromethane and washed with water. The aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give 0.25 g of crude product. Flash chromatography gave 0.17 g (70%) of the title compound. MS m/e (%): 552 (M+H+, 100)

Workup

temperatureAfter cooling to room temperature the mixture
washwashed with water
extractionThe aqueous layer was extracted with dichloromethane
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo
customto give 0.25 g of crude product

Sources & evidence

ORD record: ord-0ea5e34bdcf54b28b7aafa3b3cb614d2
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176205B2

Reaction notes

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