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

HRID 1431607Notes

Reaction equation

HRID 1431607 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[CH2:19][CH2:18][CH2:17]C[C:15]2=[O:20])[C:3]=1[CH3:21].[O:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([NH2:34])[CH:31]=[N:32][CH:33]=2)[CH2:24][CH2:23]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:34][C:30]1[CH:31]=[N:32][CH:33]=[C:28]([N:25]3[CH2:26][CH2:27][O:22][CH2:23][CH2:24]3)[CH:29]=1)=[C:3]([CH3:21])[C:4]([N:14]1[CH2:19][CH2:18][CH2:17][C:15]1=[O:20])=[N:5]2

Participants

4

Reactant 2

HCID 583477375-Morpholinopyridin-3-amineHCID 596310611-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-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

Essentially prepared according to Procedure H using 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one (75.0 mg, 0.21 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, CDCl3) δ ppm 7.90 (1H, d, J=2.5 Hz), 7.86 (1H, d, J=2.3 Hz), 7.46 (1H, ddd, J=9.6, 2.5, 1.4 Hz), 7.24 (1H, d, J=14.1 Hz), 6.99 (1H, ddd, J=13.9, 8.6, 2.5 Hz), 6.54 (1H, t, J=2.4 Hz), 4.22-4.33 (1H, m), 3.82 (4H, t, J=4.8 Hz), 3.48-3.58 (1H, m), 3.13-3.28 (4H, m), 2.50-2.58 (2H, m), 2.07-2.14 (1H, m), 1.95-2.04 (3H, m), 1.94 (3H, s).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-57f4575ee6e64729985d153470018737
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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