4-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline → 5,7-difluoro-N-(2-(6-methoxypyridin-3-yl)-5-morpholinophenyl)-3-methyl-2-(2-(methylsulfonyl)-phenyl)quinolin-4-amine

HRID 1431620Notes

Reaction equation

HRID 1431620 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].[CH3:25][O:26][C:27]1[N:32]=[CH:31][C:30]([C:33]2[CH:39]=[CH:38][C:37]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[CH:36][C:34]=2[NH2:35])=[CH:29][CH:28]=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:35][C:34]1[CH:36]=[C:37]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[CH:38]=[CH:39][C:33]=1[C:30]1[CH:31]=[N:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=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 596310374-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinolineHCID 596313512-(6-Methoxypyridin-3-yl)-5-morpholinoaniline

Product 1

HCID 596315575,7-difluoro-N-(2-(6-methoxypyridin-3-yl)-5-morpholinophenyl)-3-methyl-2-(2-(methylsulfonyl)-phenyl)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 (50.0 mg, 0.140 mmol) and 2-(6-methoxypyridin-3-yl)-5-morpholinoaniline in toluene to give 5,7-difluoro-N-(2-(6-methoxypyridin-3-yl)-5-morpholinophenyl)-3-methyl-2-(2-(methylsulfonyl)-phenyl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 8.34 (1H, d, J=2.0 Hz), 8.20 (1H, d, J=7.8 Hz), 7.73-7.83 (2H, m), 7.63-7.73 (1H, m), 7.40-7.47 (1H, m), 7.38 (1H, d, J=7.2 Hz), 7.14 (1H, d, J=8.4 Hz), 6.94 (1H, ddd, J=13.7, 8.6, 2.5 Hz), 6.86 (1H, d, J=13.7 Hz), 6.82 (1H, dd, J=8.5, 0.7 Hz), 6.55 (1H, d, J=7.4 Hz), 6.32 (1H, br. s.), 3.99 (3H, s), 3.78 (4H, t, J=4.2 Hz), 3.00-3.32 (7H, m), 1.96 (3H, s). Mass Spectrum (ESI) m/e=617.2 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-bfeee42af8834c9c812b79de25c45f2f
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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