2,5-Dimorpholinopyridin-3-amine → N-(2,5-dimorpholinopyridin-3-yl)-7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methylquinolin-4-amine

HRID 1431633Notes

Reaction equation

HRID 1431633 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[C:35]([NH2:36])=[CH:34][C:33]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:32][N:31]=2)[CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[C:35]([NH:36][C:2]3[C:11]4[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=4)[N:5]=[C:4]([C:13]4[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=4[F:22])[C:3]=3[CH3:23])=[CH:34][C:33]([N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)=[CH:32][N:31]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 596310462,5-Dimorpholinopyridin-3-amineHCID 596314484-Chloro-7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methylquinoline

Product 1

HCID 59631298N-(2,5-dimorpholinopyridin-3-yl)-7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methylquinolin-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 (150.0 mg, 0.45 mmol) and 2,5-dimorpholinopyridin-3-amine in toluene to give N-(2,5-dimorpholinopyridin-3-yl)-7-fluoro-2-(2-fluoro-5-nitrophenyl)-3-methylquinolin-4-amine. 1H NMR (CDCl3) δ ppm 8.58 (1H, dd, J=6.2, 2.8 Hz), 8.39 (1H, ddd, J=9.0, 4.3, 2.9 Hz), 7.89 (1H, dd, J=9.0, 5.9 Hz), 7.79 (1H, dd, J=9.8, 2.5 Hz), 7.64 (1H, d, J=2.7 Hz), 7.32-7.44 (2H, m), 6.90 (1H, br. s.), 6.26 (1H, d, J=1.2 Hz), 3.94 (4H, t, J=4.6 Hz), 3.69-3.85 (4H, m), 3.13-3.32 (4H, m), 2.90-3.03 (4H, m), 2.19 (3H, d, J=2.0 Hz). Mass Spectrum (ESI) m/e=563.3 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-c8d28eecc6f14020b4e953dd787984c3
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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