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

HRID 1431237Notes

Reaction equation

HRID 1431237 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]=[CH:17][CH:18]=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](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=3)[N:5]=[C:4]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=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 596310654-Chloro-6-fluoro-3-methyl-2-(pyridin-3-yl)quinoline

Product 1

HCID 50905051N-(2,5-Di-4-morpholinylphenyl)-6-fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to general Procedure K using 4-chloro-6-fluoro-3-methyl-2-(pyridin-3-yl)quinoline (140 mg, 0.51 mmol), 2,5-dimorpholinoaniline (135 mg, 0.51 mmol) and a 4.0M solution of HCl in dioxane (0.13 mL, 0.51 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-3-methyl-2-(3-pyridinyl)-4-quinolinamine was obtained. 1H NMR (400 MHz, chloroform-d) δ ppm 8.88 (1H, d, J=2.3 Hz), 8.72 (1H, dd, J=5.1, 2.0 Hz), 8.16 (1H, dd, J=9.0, 5.5 Hz), 7.99 (1H, dt, J=7.8, 2.2 Hz), 7.43-7.57 (3H, m), 7.16-7.20 (1H, m), 7.13 (1H, d, J=8.6 Hz), 6.46 (1H, dd, J=8.6, 2.7 Hz), 5.97 (1H, d, J=2.7 Hz), 3.87-3.99 (4H, m), 3.67-3.80 (4H, m), 3.01-3.13 (4H, m), 2.83-2.98 (4H, m), 2.33 (3H, s). Mass Spectrum (ESI) m/e=500.0 (M+1).

Workup

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

Sources & evidence

ORD record
ord-2776b7c9ee2c4fd6bda437913dbe17e5
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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