4-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline → N-(2,5-di-4-morpholinyl-3-pyridinyl)-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-4-quinolinamine

HRID 1431309Notes

Reaction equation

HRID 1431309 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[C:36]([NH2:37])=[CH:35][C:34]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[CH:33][N:32]=2)[CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[N:28]1([C:31]2[C:36]([NH:37][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]([CH3:23])(=[O:22])=[O:21])[C:3]=3[CH3:24])=[CH:35][C:34]([N:38]3[CH2:39][CH2:40][O:41][CH2:42][CH2:43]3)=[CH:33][N:32]=2)[CH2:27][CH2:26][O:25][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 596310374-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinolineHCID 596310462,5-Dimorpholinopyridin-3-amine

Product 1

HCID 59631443N-(2,5-di-4-morpholinyl-3-pyridinyl)-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 (70.0 mg, 0.190 mmol) and 2,5-dimorpholinopyridin-3-amine in toluene to give N-(2,5-di-4-morpholinyl-3-pyridinyl)-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-4-quinolinamine. 1H NMR (CDCl3) δ ppm 8.21 (1H, d, J=7.8 Hz), 7.84 (1H, d, J=11.7.0 Hz), 7.80 (1H, td, J=7.5, 1.4 Hz), 7.70 (1H, td, J=7.7, 1.4 Hz), 7.54 (1H, br. s.), 7.50 (1H, d, J=9.4), 7.41 (1H, d, J=7.4 Hz), 7.06 (1H, ddd, J=13.5, 8.6, 2.5 Hz), 6.52 (1H, br. s.), 3.84-4.03 (4H, m), 3.70-3.83 (4H, m), 3.32-3.56 (2H, m), 2.87-3.19 (9H, m), 1.92 (3H, s). Mass Spectrum (ESI) m/e=596.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-d8ec6cd4606f4e1fafaec4810603edc9
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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