Dimethylformamide → 2-(cyclohexylamino)-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-6-piperidin-1-ylnicotinamide

HRID 426018Notes

Reaction equation

[CH:1]1([NH:7][C:8]2[N:28]=[C:27](F)[CH:26]=[CH:25][C:9]=2[C:10]([NH:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][C:19](=[O:24])[N:20]3[CH3:23])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH:1]1([NH:7][C:8]2[N:28]=[C:27]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:26]=[CH:25][C:9]=2[C:10]([NH:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][C:19](=[O:24])[N:20]3[CH3:23])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-(cyclohexylamino)-6-fluoro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)nicotinamide (150 mg), piperidine (64 mg), potassium carbonate (63 mg) and DMF was stirred at 60° C. for 18 hours. Then, water was added, followed by extraction with ethyl acetate. After drying the organic layer with magnesium sulfate, the solution was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (basic silica gel, hexane:ethyl acetate, 2:1 to 1:1) to obtain 2-(cyclohexylamino)-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-6-piperidin-1-ylnicotinamide (138 mg) as a solid.

Workup

extractionfollowed by extraction with ethyl acetate
dry with materialAfter drying the organic layer with magnesium sulfate
concentrationthe solution was concentrated under a reduced pressure
customthe residue was purified by silica gel column chromatography (basic silica gel, hexane:ethyl acetate, 2:1 to 1:1)

Sources & evidence

ORD record: ord-4557bc6f5a474e7d91e026d5bbf10d5d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106190B2

Reaction notes

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