Methylamine → 3-methyl-1-(4-(4-propionylpiperazin-1-yl)-3-(trifluoromethyl)phenyl)-9-(quinolin-3-yl)pyrimido[5,4-c]quinoline-2,4(1H,3H)-dione
Reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[C:30]4[C:29]5[CH:28]=[C:27]([C:31]6[CH:32]=[N:33][C:34]7[C:39]([CH:40]=6)=[CH:38][CH:37]=[CH:36][CH:35]=7)[CH:26]=[CH:25][C:24]=5[N:23]=[CH:22][C:21]=4[C:20](=[O:41])[O:19][C:18]3=O)=[CH:13][C:12]=2[C:43]([F:46])([F:45])[F:44])[CH2:7][CH2:6]1)(=[O:4])[CH2:2][CH3:3].[CH3:47][NH2:48]>C1COCC1.C(Cl)Cl>[CH3:47][N:48]1[C:20](=[O:41])[C:21]2[CH:22]=[N:23][C:24]3[CH:25]=[CH:26][C:27]([C:31]4[CH:32]=[N:33][C:34]5[C:39]([CH:40]=4)=[CH:38][CH:37]=[CH:36][CH:35]=5)=[CH:28][C:29]=3[C:30]=2[N:17]([C:14]2[CH:15]=[CH:16][C:11]([N:8]3[CH2:7][CH2:6][N:5]([C:1](=[O:4])[CH2:2][CH3:3])[CH2:10][CH2:9]3)=[C:12]([C:43]([F:46])([F:44])[F:45])[CH:13]=2)[C:18]1=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of compound 5.6 1-(4-(4-propionylpiperazin-1-yl)-3-(trifluoromethyl)phenyl)-9-(quinolin-3-yl)-1H-[1,3]oxazino[5,4-c]quinoline-2,4-dione (20 mg, 0.032 mmol, 1 equiv.) in THF/CH2Cl2 (5 mL, 1:1) at room temperature was added MeNH2 (5 mg, 0.16 mmol, 5 equiv.). The resulting solution was heated to 40° C. and stirred for 2 h. Upon concentration, the mixture was purified via preparative LC-MS (CH3CN:H2O) to furnish the desired compound 5.7 3-methyl-1-(4-(4-propionylpiperazin-1-yl)-3-(trifluoromethyl)phenyl)-9-(quinolin-3-yl)pyrimido[5,4-c]quinoline-2,4(1H,3H)-dione (3 mg). LC-MS (M+H): 639.49
Workup
- concentrationUpon concentration
- customthe mixture was purified via preparative LC-MS (CH3CN:H2O)
Sources & evidence
- ORD record
- ord-190e665f54c04ffd8629fd554c74391e
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394818B2
Reaction notes
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