2,5-Dimorpholinopyridin-3-amine → N-(2,5-di-4-morpholinyl-3-pyridinyl)-5,7-difluoro-3-methyl-2-(2-(methylsulfanyl)phenyl)-4-quinolinamine

HRID 1431303Notes

Reaction equation

HRID 1431303 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][CH3:21])[C:3]=1[CH3:22].[O:23]1[CH2:28][CH2:27][N:26]([C:29]2[C:34]([NH2:35])=[CH:33][C:32]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[CH:31][N:30]=2)[CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[N:26]1([C:29]2[C:34]([NH:35][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][CH3:21])[C:3]=3[CH3:22])=[CH:33][C:32]([N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)=[CH:31][N:30]=2)[CH2:25][CH2:24][O:23][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 596310462,5-Dimorpholinopyridin-3-amineHCID 596313634-Chloro-5,7-difluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline

Product 1

HCID 59631076N-(2,5-di-4-morpholinyl-3-pyridinyl)-5,7-difluoro-3-methyl-2-(2-(methylsulfanyl)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-(methylthio)phenyl)quinoline (75.0 mg, 0.22 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-(methylsulfanyl)phenyl)-4-quinolinamine. 1H NMR (CDCl3) δ ppm 7.83 (1H, d, J=12.1 Hz), 7.64 (1H, d, J=9.0 Hz), 7.61 (1H, d, J=2.7 Hz), 7.64 (1H, d, J=9.4 Hz), 7.43-7.50 (1H, m), 7.37-7.42 (1H, m), 7.34 (1H, td, J=7.2, 1.2 Hz), 7.25-7.30 (1H, m), 7.03 (1H, ddd, J=13.5, 8.5, 2.5 Hz), 6.42 (1H, br. s.), 3.92 (4H, br. s.), 3.73-3.83 (4H, m), 3.39 (2H, br. s.), 3.03-3.12 (4H, m), 2.85-3.03 (2H, m), 2.41 (3H, s), 1.97 (3H, s). Mass Spectrum (ESI) m/e=564.3 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0defd2ebdffd4b0a983dad52550a96b6
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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