4-(4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)morpholine → N-(5-(3,6-dihydro-2H-pyran-4-yl)-pyridin-3-yl)-5,7-difluoro-3-methyl-2-morpholinoquinolin-4-amine

HRID 1431618Notes

Reaction equation

HRID 1431618 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]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:3]=1[CH3:20].[O:21]1[CH2:26][CH:25]=[C:24]([C:27]2[CH:28]=[C:29]([NH2:33])[CH:30]=[N:31][CH:32]=2)[CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[O:21]1[CH2:22][CH:23]=[C:24]([C:27]2[CH:28]=[C:29]([NH:33][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]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[C:3]=3[CH3:20])[CH:30]=[N:31][CH:32]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 596310604-(4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)morpholineHCID 596311705-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-amine

Product 1

HCID 59631497N-(5-(3,6-dihydro-2H-pyran-4-yl)-pyridin-3-yl)-5,7-difluoro-3-methyl-2-morpholinoquinolin-4-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Essentially prepared according to Procedure H using 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)morpholine (40.0 mg, 0.130 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-morpholinoquinolin-4-amine. 1H NMR (CDCl3) δ ppm 8.28 (1H, d, J=2.0 Hz), 8.07 (1H, d, J=2.5 Hz), 7.32 (1H, ddd, J=10.0, 2.5, 1.4 Hz), 7.03 (1H, t, J=2.2 Hz), 6.94 (1H, d, J=12.7 Hz), 6.81 (1H, ddd, J=13.9, 8.6, 2.5 Hz), 6.11-6.19 (1H, m), 4.32 (2H, q, J=2.7 Hz), 3.93 (2H, t, J=5.5 Hz), 3.83-3.90 (4H, m), 3.34-3.43 (4H, m), 2.42-2.51 (2H, m), 2.06 (3H, s). Mass Spectrum (ESI) m/e=439.1 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-f33576d8627e43eda3bc072c8c21741a
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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