Hydrochloric Acid → 6-Chloro-N-(2,5-di-4-morpholinylphenyl)-2-(2-fluorophenyl)-3-methyl-4-quinolinamine

HRID 1431230Notes

Reaction equation

HRID 1431230 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[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>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])[C:3]([CH3:20])=[C:2]2[NH:29][C:28]1[CH:30]=[C:31]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:32]=[CH:33][C:27]=1[N:24]1[CH2:23][CH2:22][O:21][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 288098152,5-DimorpholinobenzenamineHCID 596313274,6-Dichloro-2-(2-fluorophenyl)-3-methylquinoline

Product 1

HCID 509050486-Chloro-N-(2,5-di-4-morpholinylphenyl)-2-(2-fluorophenyl)-3-methyl-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to general Procedure K using 4,6-dichloro-2-(2-fluorophenyl)-3-methylquinoline (116 mg, 0.38 mmol), 2,5-dimorpholinoaniline (100 mg, 0.38 mmol) and a 4.0M solution of HCl in dioxane (0.095 mL, 0.38 mmol) in MeOH (1.0 mL) and heating in the microwave for 2 h at 150° C. After purification 6-chloro-N-(2,5-di-4-morpholinylphenyl)-2-(2-fluorophenyl)-3-methyl-4-quinolinamine was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.10 (1H, d, J=9.0 Hz), 7.90 (1H, d, J=2.3 Hz), 7.58-7.67 (2H, m), 7.47 (1H, d, J=8.2 Hz), 7.31-7.37 (1H, m), 7.16-7.22 (1H, m), 7.13 (1H, d, J=8.6 Hz), 6.45 (1H, dd, J=8.6, 2.7 Hz), 6.00-6.08 (1H, m), 3.93 (4H, t, J=4.5 Hz), 3.76 (4H, dd, J=5.9, 3.9 Hz), 3.06 (4H, d, J=1.2 Hz), 2.91-3.02 (4H, m), 2.20 (3H, d, J=2.3 Hz). Mass Spectrum (ESI) m/e=533.2 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 6-chloro-N-(2,5-di-4-morpholinylphenyl)-2-(2-fluorophenyl)-3-methyl-4-quinolinamine
  3. customwas obtained as a yellow film

Sources & evidence

ORD record
ord-9c7900f386e94784b11a472a0c13821c
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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