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 347692Notes

Reaction equation

[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21](Cl)=[CH:22][C:23]=2[C:24]2[C:25]([CH3:30])=[N:26][CH:27]=[CH:28][CH:29]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>CN(C1C=CN=CC=1)C.COC(C)(C)C>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([CH3:17])[C:18]2[CH:19]=[N:20][C:21]([N:40]3[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]3)=[CH:22][C:23]=2[C:24]2[C:25]([CH3:30])=[N:26][CH:27]=[CH:28][CH:29]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 0.16 g (0.30 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-(6′-chloro-2-methyl-[3,4′]bipyridinyl-3′-yl)-N-methyl-isobutyramide, 0.67 ml (6.0 mmol) 1-methylpiperazine and 2 mg (0.02 mmol) 4-(N,N-dimethylamino)pyridine was heated at 140° C. over night. After cooling to room temperature the mixture was diluted with tert-butyl methyl ether and washed with water. The aqueous layer was extracted with two portions of tert-butyl methyl ether. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash chromatography gave 0.16 g (93%) of the title compound.

Workup

temperatureAfter cooling to room temperature the mixture
washwashed with water
extractionThe aqueous layer was extracted with two portions of tert-butyl methyl ether
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-006b540370564bdf8fa12042299d2820
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176205B2

Reaction notes

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