4-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline → 5,7-difluoro-N-(6'-methoxy-5-morpholino-2,3'-bipyridin-3-yl)-3-methyl-2-(2-(methylsulfonyl)-phenyl)quinolin-4-amine

HRID 1431619Notes

Reaction equation

HRID 1431619 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[C:38]([NH2:39])=[CH:37][C:36]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[CH:35][N:34]=2)=[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:39][C:38]1[C:33]([C:30]3[CH:31]=[N:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)=[N:34][CH:35]=[C:36]([N:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)[CH:37]=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 596314166'-Methoxy-5-morpholino-2,3'-bipyridin-3-amine

Product 1

HCID 596315505,7-difluoro-N-(6'-methoxy-5-morpholino-2,3'-bipyridin-3-yl)-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 6′-methoxy-5-morpholino-2,3′-bipyridin-3-amine in toluene to give 5,7-difluoro-N-(6′-methoxy-5-morpholino-2,3′-bipyridin-3-yl)-3-methyl-2-(2-(methylsulfonyl)-phenyl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 8.64 (1H, d, J=1.8 Hz), 8.20 (1H, d, J=7.2 Hz), 8.00 (1H, dd, J=8.5, 2.4 Hz), 7.94 (1H, br. s.), 7.80 (1H, td, J=7.5, 1.4 Hz), 7.70 (1H, td, J=7.7, 1.4 Hz), 7.47 (1H, ddd, J=9.4, 2.4, 1.3 Hz), 7.42 (1H, d, J=7.2 Hz), 6.92-7.04 (2H, m), 6.88 (1H, dd, J=8.6, 0.8 Hz), 6.53 (1H, br. s.), 4.00 (3H, s), 3.78 (4H, t, J=4.7 Hz), 3.02-3.27 (7H, m), 1.97 (3H, s). Mass Spectrum (ESI) m/e=618.2 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-8de393ee42d44129b0391de50c346c78
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…