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

HRID 1431301Notes

Reaction equation

HRID 1431301 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][N:15]=2)[C:3]=1[CH3:20].[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:30][C:28]=2[NH2:29])[CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[N:24]1([C:27]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[CH:30][C:28]=2[NH:29][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][N:15]=3)[C:3]=2[CH3:20])[CH2:25][CH2:26][O:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 288098152,5-DimorpholinobenzenamineHCID 596310254-Chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline

Product 1

HCID 59631120N-(2,5-di-4-morpholinylphenyl)-5,7-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to Procedure H using 4-chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (39.8 mg, 0.137 mmol) and 2,5-dimorpholinoaniline in toluene to give N-(2,5-di-4-morpholinylphenyl)-5,7-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (CDCl3) δ ppm 8.71 (1H, d, J=4.7 Hz), 8.15 (1H, d, J=10.2 Hz), 7.82-7.97 (2H, m), 7.64 (1H, d, J=9.4 Hz), 7.38 (1H, ddd, J=6.7, 4.7, 2.3 Hz), 7.10 (1H, d, J=8.6 Hz), 6.99 (1H, ddd, J=13.3, 8.6, 2.7 Hz), 6.48 (1H, dd, J=8.4, 2.5 Hz), 6.22 (1H, d, J=2.3 Hz), 3.90 (4H, t, J=4.3 Hz), 3.76-3.85 (4H, m), 3.05-3.19 (4H, m), 2.92 (4H, br. s.), 2.22 (3H, s). Mass Spectrum (ESI) m/e=518.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9c8838c245554225bf9d14f1b7832aeb
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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