Morpholine → N-(2,5-di-4-morpholinyl-3-pyridinyl)-5,8-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine

HRID 1431312Notes

Reaction equation

HRID 1431312 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:14][C:15]2[C:24]3[C:19](=[C:20]([F:26])[CH:21]=[CH:22][C:23]=3[F:25])[N:18]=[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[C:16]=2[CH3:33])[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C1(C)C=CC=CC=1>[N:8]1([C:5]2[C:4]([NH:14][C:15]3[C:24]4[C:19](=[C:20]([F:26])[CH:21]=[CH:22][C:23]=4[F:25])[N:18]=[C:17]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[C:16]=3[CH3:33])=[CH:3][C:2]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:7][N:6]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 59631425N-(5-bromo-2-morpholinopyridin-3-yl)-5,8-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine

Product 1

HCID 50906358N-(2,5-di-4-morpholinyl-3-pyridinyl)-5,8-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to Procedure H using N-(5-bromo-2-morpholinopyridin-3-yl)-5,8-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine (40.0 mg, 0.131 mmol) and morpholine in toluene to give N-(2,5-di-4-morpholinyl-3-pyridinyl)-5,8-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (CDCl3) δ ppm 8.68 (1H, d, J=3.9 Hz), 8.00 (1H, d, J=7.8 Hz), 7.78-7.96 (2H, m), 7.63 (1H, d, J=2.3 Hz), 7.34-7.44 (1H, m), 7.28-7.34 (1H, m), 7.11 (1H, ddd, J=12.8, 8.7, 3.9 Hz), 6.47 (1H, d, J=2.3 Hz), 3.87-4.01 (4H, m), 3.76-3.87 (4H, m), 3.15-3.49 (4H, m), 2.98-3.13 (4H, m), 2.26 (3H, s). Mass Spectrum (ESI) m/e=519.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-82db8e0e36b54455b8dcef9756e891d2
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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