2,5-Dimorpholinopyridin-3-amine → N-(2,5-di-4-morpholinyl-3-pyridinyl)-3-ethyl-5,7-difluoro-2-(2-pyridinyl)-4-quinolinamine

HRID 1431314Notes

Reaction equation

HRID 1431314 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][N:15]=2)[C:3]=1[CH2:20][CH3:21].[O:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:33]([NH2:34])=[CH:32][C:31]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[CH:30][N:29]=2)[CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[N:25]1([C:28]2[C:33]([NH:34][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][N:15]=4)[C:3]=3[CH2:20][CH3:21])=[CH:32][C:31]([N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)=[CH:30][N:29]=2)[CH2:24][CH2:23][O:22][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 596310462,5-Dimorpholinopyridin-3-amineHCID 596313784-Chloro-3-ethyl-5,7-difluoro-2-(pyridin-2-yl)quinoline

Product 1

HCID 50906359N-(2,5-di-4-morpholinyl-3-pyridinyl)-3-ethyl-5,7-difluoro-2-(2-pyridinyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to Procedure H using 4-chloro-3-ethyl-5,7-difluoro-2-(pyridin-2-yl)quinoline (40.0 mg, 0.131 mmol) and 2,5-dimorpholinopyridin-3-amine in toluene to give N-(2,5-di-4-morpholinyl-3-pyridinyl)-3-ethyl-5,7-difluoro-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (CDCl3) δ ppm 8.70 (1H, td, J=2.4, 1.0 Hz), 7.79-8.00 (2H, m), 7.53-7.66 (2H, m), 7.45 (1H, d, J=6.3 Hz), 7.40 (1H, ddd, J=7.3, 4.8, 1.6 Hz), 6.98 (1H, ddd, J=12.8, 8.7, 2.6 Hz), 6.43 (1H, d, J=2.3 Hz), 3.87-4.07 (4H, m), 3.73-3.82 (4H, m), 3.15-3.35 (4H, m), 2.93-3.03 (4H, m), 2.70 (2H, br. s.), 0.98 (3H, t, J=7.5 Hz). Mass Spectrum (ESI) m/e=533.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-d388c995d8a84056a373855200c3ca8c
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…