4-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline → N-(5-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-yl)-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-quinolin-4-amine

HRID 1431615Notes

Reaction equation

HRID 1431615 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][CH:29]=[C: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>[O:25]1[CH2:26][CH:27]=[C:28]([C:31]2[CH:32]=[C:33]([NH:37][C:2]3[C:11]4[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=4[F:12])[N:5]=[C:4]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[S:20]([CH3:23])(=[O:22])=[O:21])[C:3]=3[CH3:24])[CH:34]=[N:35][CH:36]=2)[CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 596310374-Chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinolineHCID 596311705-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-amine

Product 1

HCID 59631238N-(5-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-yl)-5,7-difluoro-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 5-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-amine in toluene to give N-(5-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-yl)-5,7-difluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-quinolin-4-amine. 1H NMR (CDCl3) δ ppm 8.23 (2H, d, J=2.2 Hz), 8.20 (1H, dd, J=8.0, 1.2 Hz), 7.75-7.82 (1H, m), 7.68 (1H, td, J=7.7, 1.4 Hz), 7.50 (1H, ddd, J=9.3, 2.5, 1.3 Hz), 7.42 (1H, dd, J=7.6, 1.2 Hz), 7.15 (1H, d, J=13.7 Hz), 7.01-7.11 (2H, m), 6.22 (1H, dt, J=2.9, 1.4 Hz), 4.28 (2H, q, J=2.6 Hz), 3.89 (2H, td, J=5.4, 2.1 Hz), 3.14 (3H, s), 2.33-2.58 (2H, m), 1.86 (3H, s). Mass Spectrum (ESI) m/e=508.1 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-82ac4eaebab5402eaa765e68a82458a2
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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