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

HRID 1431233Notes

Reaction equation

HRID 1431233 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[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]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[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 596311684-Chloro-2-(2-fluorophenyl)-3-methylquinoline

Product 1

HCID 50905050N-(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-chloro-2-(2-fluorophenyl)-3-methylquinoline (103 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-4-quinolinamine was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.29 (1H, d, J=8.6 Hz), 7.93 (1H, d, J=8.2 Hz), 7.68-7.76 (1H, m), 7.65 (1H, td, J=7.4, 1.6 Hz), 7.40-7.55 (3H, m), 7.34 (1H, t, J=7.4 Hz), 7.19 (1H, t, J=9.0 Hz), 7.11 (1H, d, J=8.6 Hz), 6.47 (1H, dd, J=8.8, 2.9 Hz), 6.06-6.20 (1H, m), 3.85-4.00 (4H, m), 3.67-3.80 (4H, m), 3.01-3.17 (4H, m), 2.88-3.00 (4H, m), 2.21 (3H, d, J=2.3 Hz). Mass Spectrum (ESI) m/e=499.2 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 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-a41e411a1ef848b2b831d0c8f3f5d341
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…