Hydrochloric Acid → N-(2,5-Di-4-morpholinylphenyl)-6-fluoro-2-(5-fluoro-3-pyridinyl)-3-methyl-4-quinolinamine

HRID 1431239Notes

Reaction equation

HRID 1431239 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:19])[CH:18]=2)[C:3]=1[CH3:20].[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:30][C:28]=2[NH2:29])[CH2:23][CH2:22]1.Cl.O1CCOCC1>CO>[N:24]1([C:27]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[CH:30][C:28]=2[NH:29][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=3)[N:5]=[C:4]([C:13]3[CH:14]=[N:15][CH:16]=[C:17]([F:19])[CH:18]=3)[C:3]=2[CH3:20])[CH2:25][CH2:26][O:21][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 288098152,5-DimorpholinobenzenamineHCID 596310914-Chloro-6-fluoro-2-(5-fluoropyridin-3-yl)-3-methylquinoline

Product 1

HCID 50905278N-(2,5-Di-4-morpholinylphenyl)-6-fluoro-2-(5-fluoro-3-pyridinyl)-3-methyl-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to general Procedure K using 4-chloro-6-fluoro-2-(5-fluoropyridin-3-yl)-3-methylquinoline (110 mg, 0.38 mmol), 2,5-dimorpholinoaniline (120 mg, 0.38 mmol) and a 4.0M solution of HCl in dioxane (0.09 mL, 0.38 mmol) in MeOH (1.0 mL) and heating in the microwave for 2 h at 150° C. After purification N-(2,5-di-4-morpholinylphenyl)-6-fluoro-2-(5-fluoro-3-pyridinyl)-3-methyl-4-quinolinamine was obtained. 1H NMR (500 MHz, chloroform-d) δ ppm 8.70 (1H, t, J=1.7 Hz), 8.60 (1H, d, J=2.7 Hz), 8.13-8.22 (1H, m), 7.77 (1H, dt, J=8.8, 2.3 Hz), 7.44-7.55 (2H, m), 7.25 (1H, s), 7.15 (1H, d, J=8.6 Hz), 6.51 (1H, dd, J=8.8, 2.7 Hz), 6.01 (1H, dd, J=2.4, 0.5 Hz), 3.91 (4H, t, J=4.6 Hz), 3.69-3.79 (4H, m), 3.06 (4H, t, J=4.6 Hz), 2.90-2.99 (4H, m), 2.34 (3H, s). Mass Spectrum (ESI) m/e=518.1 (M+1).

Workup

  1. customPrepared
  2. customAfter purification N-(2,5-di-4-morpholinylphenyl)-6-fluoro-2-(5-fluoro-3-pyridinyl)-3-methyl-4-quinolinamine
  3. customwas obtained

Sources & evidence

ORD record
ord-390996273bbd41ed960ccf26e8ae6d1e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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