Ethylmorpholine → 4-[2-(4-Methoxy-piperidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]([OH:19])=O)[C:12]2[C:7](=[CH:8][C:9]([CH3:20])=[CH:10][CH:11]=2)[N:6]=1)=[O:4].FC1C(O)=C(F)C(F)=C(F)C=1F.[CH3:33][O:34][CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.C(N1CCOCC1)C>CN(C=O)C.C(Cl)Cl.C(Cl)CCl>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]([N:38]2[CH2:39][CH2:40][CH:35]([O:34][CH3:33])[CH2:36][CH2:37]2)=[O:19])[C:12]2[C:7](=[CH:8][C:9]([CH3:20])=[CH:10][CH:11]=2)[N:6]=1)=[O:4]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 1000 mg 4-Carboxymethoxy-7-methyl-quinoline-2-carboxylic acid methyl ester in 5 ml DMF were added 956 mg pentafluorophenol and 994 mg EDC. The mixture was stirred under exclusion of moisture until LCMS indicated complete conversion to the corresponding pentafluorophenolester. 4-methoxypiperidine (379 mg) was mixed with 1.3 ml N-ethylmorpholine and 10 ml DMF and this mixture added dropwise to the solution of the pentafluorophenolester. After 12 h the reaction mixture was diluted with DCM and washed with aqueous LiCl (4%) and saturated aqueous NaHCO3. The crude product obtained after evaporation of the solvent was purified by flash chromatography on silica eluting with ethyl acetate/heptane gradient. Yield: 980 mg.
Workup
- additionthis mixture added dropwise to the solution of the pentafluorophenolester
- washwashed with aqueous LiCl (4%) and saturated aqueous NaHCO3
Sources & evidence
- ORD record
- ord-18599ad156ef427f913668484b8efc07
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669266B2
Reaction notes
Loading…