2,5-Dimorpholinopyridin-3-amine → 1-(4-((2,5-di-4-morpholinyl-3-pyridinyl)amino)-5,7-difluoro-3-methyl-2-quinolinyl)-2(1H)-pyridinone

HRID 1431422Notes

Reaction equation

HRID 1431422 reaction equation
Br[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[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=[O:20])[C:3]=1[CH3:21].[O:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:33]([NH2:34])=[CH:32][C:31]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[CH:30][N:29]=2)[CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[N:25]1([C:28]2[C:33]([NH:34][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]([N:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]4=[O:20])[C:3]=3[CH3:21])=[CH:32][C:31]([N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)=[CH:30][N:29]=2)[CH2:24][CH2:23][O:22][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 596310462,5-Dimorpholinopyridin-3-amineHCID 596311391-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2(1H)-one

Product 1

HCID 596313341-(4-((2,5-di-4-morpholinyl-3-pyridinyl)amino)-5,7-difluoro-3-methyl-2-quinolinyl)-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Essentially prepared according to Procedure H using 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2(1H)-one (50.0 mg, 0.140 mmol) and 2,5-dimorpholinopyridin-3-amine in toluene to give 1-(4-((2,5-di-4-morpholinyl-3-pyridinyl)amino)-5,7-difluoro-3-methyl-2-quinolinyl)-2(1H)-pyridinone. 1H NMR (CDCl3) δ ppm 8.29 (1H, dd, J=4.8, 1.1 Hz), 7.80-7.88 (1H, m), 7.72 (1H, d, J=10.2 Hz), 7.62 (1H, d, J=2.5 Hz), 7.27-7.33 (1H, m), 7.14-7.23 (2H, m), 6.91 (1H, ddd, J=13.3, 8.9, 2.4), 6.35 (1H, d, J=2.2 Hz), 3.92 (4H, br. s.), 3.76-3.83 (4H, m), 3.12-3.46 (4H, m), 2.98-3.07 (4H, m), 2.15 (3H, s). Mass Spectrum (ESI) m/e=535.2 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-84deaf61e27c491382464a9aa455982e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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