2,5-Dimorpholinobenzenamine → N-(2,5-di-4-morpholinylphenyl)-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-4-quinolinamine

HRID 1431420Notes

Reaction equation

HRID 1431420 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]([CH3:23])(=[O:22])=[O:21])[C:3]=1[CH3:24].[O:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:37]=[CH:36][C:35]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[CH:34][C:32]=2[NH2:33])[CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[N:28]1([C:31]2[CH:37]=[CH:36][C:35]([N:38]3[CH2:39][CH2:40][O:41][CH2:42][CH2:43]3)=[CH:34][C:32]=2[NH:33][C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=3[F:12])[N:5]=[C:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:20]([CH3:23])(=[O:22])=[O:21])[C:3]=2[CH3:24])[CH2:29][CH2:30][O:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 288098152,5-DimorpholinobenzenamineHCID 596310374-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline

Product 1

HCID 67509138N-(2,5-di-4-morpholinylphenyl)-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to Procedure H using 4-chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline (39.0 mg, 0.110 mmol) and 2,5-dimorpholinoaniline in toluene to give N-(2,5-di-4-morpholinylphenyl)-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-4-quinolinamine. 1H NMR (CDCl3) δ ppm 8.21 (2H, d, J=7.6 Hz), 7.78 (1H, t, J=7.6 Hz), 7.69 (1H, t, J=7.2 Hz), 7.47 (1H, d, J=9.2 Hz), 7.40 (1H, d, J=7.4 Hz), 6.98-7.09 (2H, m), 6.40 (1H, br. s.), 6.24 (1H, br. s.), 3.90 (4H, m), 3.78 (4H, m), 2.74-3.33 (8H, m), 1.95 (3H, m). Mass Spectrum (ESI) m/e=595.3 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-407bf5244b9a4546a1730d4fa4afb909
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…