Hydrochloric Acid → N-(2,5-Di-4-morpholinylphenyl)-2-(2-fluorophenyl)-3-methyl-7-(trifluoromethyl)-4-quinolinamine

HRID 1431231Notes

Reaction equation

HRID 1431231 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:3]=1[CH3:23].[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:33][C:31]=2[NH2:32])[CH2:26][CH2:25]1.Cl.O1CCOCC1>CO>[N:27]1([C:30]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)=[CH:33][C:31]=2[NH:32][C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=3)[N:5]=[C:4]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:3]=2[CH3:23])[CH2:28][CH2:29][O:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 288098152,5-DimorpholinobenzenamineHCID 596315924-Chloro-2-(2-fluorophenyl)-3-methyl-7-(trifluoromethyl)quinoline

Product 1

HCID 50905049N-(2,5-Di-4-morpholinylphenyl)-2-(2-fluorophenyl)-3-methyl-7-(trifluoromethyl)-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to general Procedure K using 4-chloro-2-(2-fluorophenyl)-3-methyl-7-(trifluoromethyl)quinoline (129 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 N-(2,5-di-4-morpholinylphenyl)-2-(2-fluorophenyl)-3-methyl-7-(trifluoromethyl)-4-quinolinamine was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.49 (1H, s), 8.04 (1H, d, J=8.6 Hz), 7.58-7.72 (2H, m), 7.46-7.54 (1H, m, J=7.9, 7.9, 5.4, 2.0 Hz), 7.30-7.40 (2H, m), 7.17-7.24 (1H, m), 7.13 (1H, d, J=8.6 Hz), 6.47 (1H, dd, J=8.6, 2.7 Hz), 6.04 (1H, d, J=0.8 Hz), 3.92 (4H, t, J=4.7 Hz), 3.69-3.80 (4H, m), 3.06 (4H, br. s.), 2.82-3.00 (4H, m), 2.24 (3H, s). Mass Spectrum (ESI) m/e=567.3 (M+1).

Workup

  1. customPrepared
  2. customAfter purification N-(2,5-di-4-morpholinylphenyl)-2-(2-fluorophenyl)-3-methyl-7-(trifluoromethyl)-4-quinolinamine
  3. customwas obtained as a yellow film

Sources & evidence

ORD record
ord-039fcbaafc344055b25e17a846c3795b
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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