2,5-Dimorpholinobenzenamine → N-(2,5-di-4-morpholinylphenyl)-5,7-difluoro-3-methyl-2-(1-piperidinyl)-4-quinolinamine

HRID 1431421Notes

Reaction equation

HRID 1431421 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]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]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]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]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 596311534-Chloro-5,7-difluoro-3-methyl-2-(piperidin-1-yl)quinoline

Product 1

HCID 50906355N-(2,5-di-4-morpholinylphenyl)-5,7-difluoro-3-methyl-2-(1-piperidinyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Essentially prepared according to Procedure H using 4-chloro-5,7-difluoro-3-methyl-2-(piperidin-1-yl)quinoline (34.0 mg, 0.120 mmol) and 2,5-dimorpholinoaniline in toluene to give N-(2,5-di-4-morpholinylphenyl)-5,7-difluoro-3-methyl-2-(1-piperidinyl)-4-quinolinamine. 1H NMR (CDCl3) δ ppm 7.97 (1H, d, J=7.6 Hz), 7.08 (1H, d, J=8.6 Hz), 6.67-6.82 (1H, m), 6.45 (1H, d, J=9.6 Hz), 6.06 (1H, d, J=2.2 Hz), 3.88 (4H, t, J=4.3 Hz), 3.70-3.82 (4H, m), 3.36 (4H, br. s.), 2.96-3.24 (4H, m), 2.70-2.97 (4H, m), 2.11 (3H, s), 1.58-1.92 (7H, m). Mass Spectrum (ESI) m/e=524.3 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-22908f01c059401cb26316e2a185e125
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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