Trifluoroacetic acid → HCID 67304837, compound
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=[O:24])=[CH:18][CH:17]=1)#[N:2].C(OC([N:33]([CH2:37][C:38]1[CH:39]=[C:40]([CH:42]=[C:43]([CH3:45])[CH:44]=1)[NH2:41])[CH:34]1[CH2:36][CH2:35]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH:34]1([NH:33][CH2:37][C:38]2[CH:39]=[C:40]([NH:41][C:23](=[O:24])[CH2:22][C:19]3[CH:18]=[CH:17][C:16]([O:15][C:6]4[C:5]5[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([C:1]#[N:2])[CH:4]=5)[N:9]=[CH:8][CH:7]=4)=[CH:21][CH:20]=3)[CH:42]=[C:43]([CH3:45])[CH:44]=2)[CH2:36][CH2:35]1Participants
Procedure
Using an analogous procedures to those described in Example 15, 2-[4-(6-cyano-7-methoxyquinolin-4-yloxy)phenyl]acetic acid was reacted with 3-(N-tert-butoxycarbonyl-N-cyclopropylaminomethyl)-5-methylaniline and the product was reacted with trifluoroacetic acid. The resultant product was purified by column chromatography on silica using a solvent gradient from 100:0 to 9:1 mixtures of ethyl acetate and methanol as eluent. There was thus obtained the title compound in 48% yield. A portion of the material so obtained was dissolved in methylene chloride and a solution of maleic acid (1 equivalent) in ethanol was added. The resultant solution was evaporated to provide a maleate salt of the title compound which gave the following characterising data:—1H NMR: (DMSOd6) 0.73 (m, 4H), 2.3 (s, 3H), 2.64 (m, 1H), 3.72 (s, 2H), 4.07 (s, 3H), 4.11 (s, 2H), 6.01 (s, 2H), 6.52 (m, 1H), 7.0 (s, 1H), 7.3 (d, 2H), 7.35 (s, 1H), 7.5 (d, 2H), 7.62 (s, 1H), 7.66 (s, 1H), 8.76 (m, 2H), 10.26 (s, 1H); Mass Spectrum: M+H+ 493.
Workup
- customThe resultant product was purified by column chromatography on silica using a solvent gradient from 100:0 to 9:1 mixtures of ethyl acetate and methanol as eluent
Sources & evidence
- ORD record
- ord-a08672d204974a0ab897f1b937266c16
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973164B2
Reaction notes
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