1-Methylpiperazine → N-(3,5-Dimethylphenyl)-2-[2-(4-methylpiperazin-1-yl)pyridin-4-ylmethylthio]pyridine-3-carboxamide

HRID 1984712Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]([C:19]2[C:20]([S:25][CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29](F)[CH:28]=3)=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1>C(OCC)(=O)C>[CH3:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]([C:19]2[C:20]([S:25][CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)[CH:28]=3)=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

Conditions

Temperature: 150 °C

Procedure

N-Methylpiperazine (2.0 mL) was added to N-(3,5-dimethylphenyl)-2-(2-fluoropyridin-4-ylmethylthio)pyridine-3-carboxamide (Reference compound No. 3-1, 100 mg, 0.27 mmol) at room temperature, then the vessel was sealed and the reaction mixture was stirred for 3 hours at 150° C. The mixture was cooled to room temperature, ethyl acetate (20 mL) was added to the reaction mixture, and then the whole was washed with brine (20 mL) and dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure, and the resulting solid was filtered off with ethyl acetate to give 39 mg of the target compound as a colorless crystal. (Yield 32%)

Workup

custom3-1, 100 mg, 0.27 mmol) at room temperature, then the vessel was sealed
temperatureThe mixture was cooled to room temperature
washthe whole was washed with brine (20 mL)
dry with materialdried over anhydrous magnesium sulfate
customThe organic layer was evaporated under reduced pressure
filtrationthe resulting solid was filtered off with ethyl acetate

Sources & evidence

ORD record: ord-4397937542924180b56feeef81aa8a17
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544703B2

Reaction notes

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