2,5-Dimorpholinopyridin-3-amine → (+/-)-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(2-(methylsulfinyl)phenyl)quinolin-4-amine
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([CH3:22])=[O:21])[C:3]=1[CH3:23].[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[C:35]([NH2:36])=[CH:34][C:33]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:32][N:31]=2)[CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[C:35]([NH:36][C:2]3[C:11]4[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=4[F:12])[N:5]=[C:4]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[S:20]([CH3:22])=[O:21])[C:3]=3[CH3:23])=[CH:34][C:33]([N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)=[CH:32][N:31]=2)[CH2:26][CH2:25]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Essentially prepared according to Procedure H using (+/−)-4-chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfinyl)phenyl)quinoline (22.0 mg, 0.063 mmol) and 2,5-dimorpholinopyridin-3-amine in toluene to give (+/−)-N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(2-(methylsulfinyl)phenyl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 8.21 (1H, d, J=8.0 Hz), 7.91 (1H, br. s.), 7.76 (1H, td, J=7.6, 1.4 Hz), 7.66-7.71 (1H, m), 7.65 (1H, d, J=2.5 Hz), 7.54 (1H, d, J=8.6 Hz), 7.39 (1H, d, J=7.6 Hz), 7.08 (1H, ddd, J=13.5, 8.5, 2.4 Hz), 6.38 (1H, br. s.), 3.92 (4H, br. s.), 3.84 (4H, t, J=4.8 Hz), 3.19-3.54 (3H, m), 3.00-3.18 (5H, m), 2.55-2.97 (3H, m), 2.01 (3H, br. s.). Mass Spectrum (ESI) m/e=580.3 (M+1).
Workup
- customEssentially prepared
Sources & evidence
- ORD record
- ord-e6c77bcd7bf84b18a8d07bb2aee69fe5
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940724B2
Reaction notes
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