5-Morpholinopyridin-3-amine → 5,7-difluoro-3-methyl-2-(2-(methylsulfinyl)phenyl)-N-(5-morpholinopyridin-3-yl)quinolin-4-amine

HRID 1431637Notes

Reaction equation

HRID 1431637 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]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([CH3:22])=[O:21])[C:3]=1[CH3:23].[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[C:32]([NH2:36])[CH:33]=[N:34][CH:35]=2)[CH2:26][CH2:25]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:36][C:32]1[CH:33]=[N:34][CH:35]=[C:30]([N:27]3[CH2:28][CH2:29][O:24][CH2:25][CH2:26]3)[CH:31]=1)=[C:3]([CH3:23])[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([CH3:22])=[O:21])=[N:5]2

Participants

4

Reactant 2

HCID 583477375-Morpholinopyridin-3-amineHCID 596315004-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfinyl)phenyl)quinoline

Product 1

HCID 596315115,7-difluoro-3-methyl-2-(2-(methylsulfinyl)phenyl)-N-(5-morpholinopyridin-3-yl)quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Essentially prepared according to Procedure H using (+/−)-4-chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfinyl)phenyl)quinoline (30.0 mg, 0.085 mmol) and 5-morpholinopyridin-3-amine in toluene to give 5,7-difluoro-3-methyl-2-(2-(methylsulfinyl)phenyl)-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 8.22 (1H, dd, J=7.9, 1.1 Hz), 7.96 (1H, d, J=2.3 Hz), 7.81 (1H, d, J=2.2 Hz), 7.73 (1H, td, J=7.7, 1.3 Hz), 7.63 (1H, td, J=7.5, 1.3 Hz), 7.50 (1H, ddd, J=9.2, 2.5, 1.4 Hz), 7.39 (1H, dd, J=7.6, 1.2 Hz), 7.20 (1H, d, J=14.1 Hz), 7.08 (1H, ddd, J=13.9, 8.4, 2.5 Hz), 6.60 (1H, t, J=2.2 Hz), 3.80-3.93 (4H, m), 3.12-3.28 (4H, m), 2.87 (3H, s), 1.98 (3H, s). Mass Spectrum (ESI) m/e=495.2 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-fbca634074c04a6c9d18b49f0dadeb26
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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