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

HRID 1431614Notes

Reaction equation

HRID 1431614 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]([CH3:23])(=[O:22])=[O:21])[C:3]=1[CH3:24].[O:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:32]=[C:33]([NH2:37])[CH:34]=[N:35][CH:36]=2)[CH2:27][CH2:26]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:37][C:33]1[CH:34]=[N:35][CH:36]=[C:31]([N:28]3[CH2:29][CH2:30][O:25][CH2:26][CH2:27]3)[CH:32]=1)=[C:3]([CH3:24])[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([CH3:23])(=[O:22])=[O:21])=[N:5]2

Participants

4

Reactant 2

HCID 583477375-Morpholinopyridin-3-amineHCID 596310374-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline

Product 1

HCID 596315665,7-difluoro-3-methyl-2-(2-(methylsulfonyl)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-(methylsulfonyl)phenyl)quinoline (75.0 mg, 0.20 mmol) and 5-morpholinopyridin-3-amine in toluene to give 5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 8.19 (1H, dd, J=7.9, 1.3 Hz), 7.89 (1H, d, J=2.3 Hz), 7.86 (1H, d, J=2.3 Hz), 7.78 (1H, td), 7.68 (1H, td, J=7.7, 1.2 Hz), 7.49 (1H, ddd, J=9.4, 2.4, 1.3 Hz), 7.42 (1H, dd, J=7.5, 1.3 Hz), 7.02-7.15 (2H, m), 6.55 (1H, t, J=2.3 Hz), 3.79 (4H, t, J=4.8 Hz), 3.09-3.22 (7H, m), 1.88 (3H, s). Mass Spectrum (ESI) m/e=511.1 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-143d146758db4cf4b75a66f3a45d28e7
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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