2,5-Dimorpholinopyridin-3-amine → N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(piperidin-1-yl)quinolin-4-amine

HRID 1431305Notes

Reaction equation

HRID 1431305 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][CH2:17][CH2:16][CH2:15]2)[C:3]=1[CH3:20].[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:32]([NH2:33])=[CH:31][C:30]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:29][N:28]=2)[CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:32]([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][CH2:17][CH2:16][CH2:15]4)[C:3]=3[CH3:20])=[CH:31][C:30]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[CH:29][N:28]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 596310462,5-Dimorpholinopyridin-3-amineHCID 596311534-Chloro-5,7-difluoro-3-methyl-2-(piperidin-1-yl)quinoline

Product 1

HCID 59631199N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(piperidin-1-yl)quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to Procedure H using 4-chloro-5,7-difluoro-3-methyl-2-(piperidin-1-yl)quinoline (110 mg, 0.37 mmol) and 2,5-dimorpholinopyridin-3-amine in toluene to give N-(2,5-dimorpholinopyridin-3-yl)-5,7-difluoro-3-methyl-2-(piperidin-1-yl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 7.62 (1H, br. s.), 7.53 (1H, d), 7.37 (1H, br. s.), 6.69-6.84 (1H, m), 6.29 (1H, d, J=2.3 Hz), 3.90 (4H, t, J=4.3 Hz), 3.72-3.84 (4H, m), 3.36 (4H, br. s.), 3.18 (2H, br. s.), 2.91-3.06 (4H, m), 2.09 (3H, s), 1.47-1.90 (8H, m). Mass Spectrum (ESI) m/e=525.3 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8541e3cb0f354ebca245e9aba9f5dfdb
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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