Diethylamine → 1-(6-Amino-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-quinolin-4-one
Reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[C:15]([C:24](=[O:34])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([CH3:33])[CH:26]=3)=[CH:14]2)[N:7]=1)=O.C(NCC)C>CO>[NH2:5][C:6]1[N:7]=[C:8]([CH2:12][N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[C:15]([C:24](=[O:34])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([CH3:33])[CH:26]=3)=[CH:14]2)[CH:9]=[CH:10][CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 212 mg (0.43 mmol) 2,2,2-Trifluoro-N-{6-[3-(4-methoxy-3-methyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridin-2-yl}-acetamide, excess diethylamine and 5 mL of methanol were heated at 45° C. overnight. The solid was collected by filtration and purified by reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 32.4 mg of 1-(6-Amino-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-quinolin-4-one. LC-MSD, m/z for C24H21N3O3 [M+H]: 400.16 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 1.5 min.