4-Piperidinecarboxylic acid → HCID 21183970, compound
Reaction equation
Cl[C:2]1[CH:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([Cl:22])[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]#[N:24])[CH:8]=2)[N:3]=1.[NH:25]1[CH2:33][CH2:32][CH:28]([C:29]([OH:31])=[O:30])[CH2:27][CH2:26]1.CN1CC[CH2:37][C:36]1=O>O>[CH2:36]([O:30][C:29]([CH:28]1[CH2:32][CH2:33][N:25]([C:2]2[CH:11]=[C:10]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([Cl:22])[CH:15]=3)[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:23]#[N:24])[CH:8]=3)[N:3]=2)[CH2:26][CH2:27]1)=[O:31])[CH3:37]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture comprising 750 mg of 2-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanoquinoline, 1.6 ml of isonipecotic acid and 5 ml of N-methyl-2-pyrrolidone was heated on an oil bath at 130° C. for 3 hours and cooled, followed by the addition of water. The resulting mixture was extracted with ethyl acetate and the ethyl acetate layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (20 to 40% ethyl acetate/hexane) and thereafter recrystallized from ethyl acetate/hexane to give 860 mg of the title compound.
Workup
- temperaturecooled
- extractionThe resulting mixture was extracted with ethyl acetate
- washthe ethyl acetate layer was washed with water
- dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
- concentrationconcentrated
- customrecrystallized from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-5df99ca976c34a3ba37ba53792a54278
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06262059B1
Reaction notes
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