Hydrochloric Acid → N-(2,5-di-4-Morpholinylphenyl)-8-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine

HRID 1431225Notes

Reaction equation

HRID 1431225 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:3]=1[CH3:19].[O:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:29][C:27]=2[NH2:28])[CH2:22][CH2:21]1.Cl.O1CCOCC1>CO>[N:23]1([C:26]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:29][C:27]=2[NH:28][C:2]2[C:11]3[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:3]=2[CH3:19])[CH2:24][CH2:25][O:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 288098152,5-DimorpholinobenzenamineHCID 596313584-Chloro-8-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

Product 1

HCID 50908278N-(2,5-di-4-Morpholinylphenyl)-8-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to general Procedure K using 4-chloro-8-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (95 mg, 0.348 mmol), 2,5-dimorpholinoaniline (92 mg, 0.348 mmol) and a 4.0M solution of HCl in dioxane (0.09 mL, 0.348 mmol) in MeOH (2.0 mL) and heating in the microwave for 2 h at 150° C. After purification N-(2,5-di-4-morpholinylphenyl)-8-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.72 (1H, dd, J=4.7, 1.6 Hz), 7.87-8.00 (2H, m), 7.64-7.71 (1H, m), 7.31-7.45 (4H, m), 7.11 (1H, d, J=8.6 Hz), 6.47 (1H, d, J=7.4 Hz), 6.04 (1H, br. s.), 3.90 (4H, t, J=4.9 Hz), 3.68-3.79 (4H, m), 2.99-3.14 (4H, m), 2.86-2.98 (4H, m), 2.42 (3H, s). Mass Spectrum (ESI) m/e=500.2 (M+1).

Workup

  1. customPrepared
  2. customAfter purification N-(2,5-di-4-morpholinylphenyl)-8-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine
  3. customwas obtained as a yellow film

Sources & evidence

ORD record
ord-6ccae34209fb426293c5a2f3f9685aa6
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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