5-Morpholinopyridin-3-amine → 1-(5,7-Difluoro-3-methyl-4-((5-(4-morpholinyl)-3-pyridinyl)amino)-2-quinolinyl)-2-pyrrolidinone

HRID 1431439Notes

Reaction equation

HRID 1431439 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[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])[C:3]=1[CH3:20].[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:28]=[C:29]([NH2:33])[CH:30]=[N:31][CH:32]=2)[CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[F:12][C:10]1[CH:9]=[C:8]([F:13])[CH:7]=[C:6]2[C:11]=1[C:2]([NH:33][C:29]1[CH:30]=[N:31][CH:32]=[C:27]([N:24]3[CH2:25][CH2:26][O:21][CH2:22][CH2:23]3)[CH:28]=1)=[C:3]([CH3:20])[C:4]([N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19])=[N:5]2

Participants

4

Reactant 2

HCID 583477375-Morpholinopyridin-3-amineHCID 596310731-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-2-one

Product 1

HCID 596315611-(5,7-Difluoro-3-methyl-4-((5-(4-morpholinyl)-3-pyridinyl)amino)-2-quinolinyl)-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to Procedure H using 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-2-one (44.0 mg, 0.130 mmol) and 5-morpholinopyridin-3-amine in toluene to give 1-(5,7-difluoro-3-methyl-4-((5-(4-morpholinyl)-3-pyridinyl)amino)-2-quinolinyl)-2-pyrrolidinone. 1H NMR (400 MHz, MeOH) δ ppm 7.90 (1H, br. s.), 7.52-7.62 (1H, m), 7.49 (1H, ddd, J=9.6, 1.8, 1.7 Hz), 6.98-7.11 (2H, m), 3.81-3.87 (4H, m), 3.70 (2H, t, J=7.2 Hz), 3.26-3.30 (4H, m), 2.57 (2H, t, J=6.6 Hz), 2.13 (3H, s), 2.08 (2H, quin, J=6.9 Hz). Mass Spectrum (ESI) m/e=458.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2f556c9f9c5e446185eedcb9fa01998e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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