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

HRID 1431438Notes

Reaction equation

HRID 1431438 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, chloroform-d) δ ppm 7.93 (2H, dd, J=4.3, 2.3 Hz), 7.43 (1H, ddd, J=9.5, 2.5, 1.3 Hz), 7.36 (1H, d, J=14.5 Hz), 6.99 (1H, ddd, J=13.9, 8.6, 2.5 Hz), 6.64 (1H, t, J=2.2 Hz), 4.16 (2H, br. s.), 3.77-3.89 (4H, m), 3.20-3.30 (4H, m), 2.60 (2H, t, J=7.9 Hz), 2.27 (2H, qd, J=7.5, 7.3 Hz), 2.01 (3H, s). Mass Spectrum (ESI) m/e=440.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1503e1629458426f98fa6f1d9c7f6cca
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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