5-Morpholinopyridin-3-amine → 7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine

HRID 1431632Notes

Reaction equation

HRID 1431632 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=2[F:22])[C:3]=1[CH3:23].[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[C:32]([NH2:36])[CH:33]=[N:34][CH:35]=2)[CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:36][C:32]3[CH:33]=[N:34][CH:35]=[C:30]([N:27]4[CH2:28][CH2:29][O:24][CH2:25][CH2:26]4)[CH:31]=3)=[C:3]([CH3:23])[C:4]([C:13]3[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=3[F:22])=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 583477375-Morpholinopyridin-3-amineHCID 596314484-Chloro-7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methylquinoline

Product 1

HCID 596312927-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Essentially prepared according to Procedure H using 4-chloro-7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methylquinoline (26.0 mg, 0.078 mmol) and 5-morpholinopyridin-3-amine in toluene to give 7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 8.58 (1H, dd, J=6.2, 2.8 Hz), 8.39 (1H, ddd, J=9.1, 4.4, 2.9 Hz), 8.11 (1H, br. s.), 8.03 (1H, dd, J=9.4, 5.9 Hz), 7.78 (2H, dd, J=9.8, 2.5 Hz), 7.64 (1H, br. s.), 7.29-7.42 (2H, m), 6.44 (1H, t, J=2.2 Hz), 3.77-3.87 (4H, m), 3.04-3.19 (4H, m), 2.19 (3H, d, J=2.3 Hz). Mass Spectrum (ESI) m/e=478.1 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-602296439e6e4419ba30d0d3f012bb0a
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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