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

HRID 1431278Notes

Reaction equation

HRID 1431278 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[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:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:29][C:28]=2[NH2:39])[CH2:23][CH2:22]1.Cl.O1CCOCC1>CO>[N:24]1([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:29][C:28]=2[NH:39][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[F:12])[N:5]=[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:3]=2[CH3:20])[CH2:25][CH2:26][O:21][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 288098152,5-DimorpholinobenzenamineHCID 596314454-Chloro-5-fluoro-2-(2-fluorophenyl)-3-methylquinoline

Product 1

HCID 59631225N-(2,5-Di-4-morpholinylphenyl)-5-fluoro-2-(2-fluorophenyl)-3-methyl-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to Procedure K, Method 1 using 4-chloro-5-fluoro-2-(2-fluorophenyl)-3-methylquinoline (137 mg, 473 μmol), 2,5-dimorpholinobenzeneamine (125 mg, 473 μmol) and 4N hydrochloric acid solution in dioxane (0.12 mL, 473 μmol) in MeOH (3.00 mL) to afford product as a colorless solid after purification by chromatography on silica gel, eluting with MeOH gradient in DCM. 1H NMR (400 MHz, chloroform-d) δ ppm 8.23-8.51 (1H, m), 7.96 (1H, d, J=8.2 Hz), 7.53-7.69 (2H, m), 7.42-7.53 (1H, m, J=7.8, 7.8, 5.5, 2.0 Hz), 7.31-7.40 (1H, m), 7.13-7.26 (2H, m), 7.10 (1H, d, J=8.6 Hz), 6.47 (1H, dd, J=8.4, 2.9 Hz), 6.12-6.27 (1H, m), 3.92 (4H, t, J=4.7 Hz), 3.75-3.87 (4H, m), 3.12-3.21 (2H, m), 3.00-3.12 (4H, m), 2.69-2.98 (2H, m), 2.11 (3H, d, J=2.3 Hz). Mass Spectrum (ESI) m/e=517.3 (M+1).

Workup

  1. customPrepared
  2. customto afford product as a colorless solid
  3. customafter purification by chromatography on silica gel
  4. washeluting with MeOH gradient in DCM

Sources & evidence

ORD record
ord-eb355556c5a54c1da7f43b2f0e7f0d69
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…