2,5-Dimorpholinopyridin-3-amine → 1-(4-((2,5-Di-4-morpholinyl-3-pyridinyl)-amino)-5,7-difluoro-3-methyl-2-quinolinyl)-2-piperidinone

HRID 1431318Notes

Reaction equation

HRID 1431318 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][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[CH2:19][CH2:18][CH2:17][CH2:16][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 596315521-(4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one

Product 1

HCID 509065731-(4-((2,5-Di-4-morpholinyl-3-pyridinyl)-amino)-5,7-difluoro-3-methyl-2-quinolinyl)-2-piperidinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to Procedure H using 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one (35.0 mg, 0.113 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-piperidinone. 1H NMR (CDCl3) δ ppm 8.01 (1H, br. s.), 7.60 (1H, d, J=2.5 Hz), 7.47 (1H, d, J=9.8 Hz), 6.99 (1H, ddd, J=13.7, 8.6, 2.5 Hz), 6.51 (1H, br. s.), 4.33 (1H, br. s.), 3.83-4.01 (4H, m), 3.77-3.83 (4H, m), 3.48-3.59 (1H, m), 3.41 (2H, br. s.), 3.16 (4H, br. s,), 2.89-3.07 (2H, m), 2.50-2.61 (2H, m), 1.88-2.19 (7H, m). Mass Spectrum (ESI) m/e=539.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-55162ab3f3ca455188fc64489794597e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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