Hydrochloric Acid → N-(5-Bromo-2-morpholinophenyl)-2-(2-fluorophenyl)-3-methylquinolin-4-amine

HRID 1431292Notes

Reaction equation

HRID 1431292 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].[Br:20][C:21]1[CH:22]=[CH:23][C:24]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[C:25]([NH2:27])[CH:26]=1.Cl.O1CCOCC1>CN1C(=O)CCC1>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([N:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)=[C:25]([NH:27][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])[CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 49618715-Bromo-2-morpholin-4-ylanilineHCID 596311684-Chloro-2-(2-fluorophenyl)-3-methylquinoline

Product 1

HCID 59631162N-(5-Bromo-2-morpholinophenyl)-2-(2-fluorophenyl)-3-methylquinolin-4-amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Prepared according to Procedure K, Method 2 using 4-chloro-2-(2-fluorophenyl)-3-methylquinoline (230 mg, 848 μmol), 5-bromo-2-morpholinobenzenamine (109 mg, 424 μmol) and 4N hydrochloric acid solution in dioxane (0.011 mL, 42 μmol) in NMP (0.50 mL) to afford a colorless solid upon purification by chromatography on silica gel, eluting with EtOAc gradient in hexane. Mass Spectrum (ESI) m/e=492.1 & 494.1 (M+1).

Workup

  1. customPrepared
  2. customto afford a colorless solid
  3. customupon purification by chromatography on silica gel
  4. washeluting with EtOAc gradient in hexane

Sources & evidence

ORD record
ord-0c5e0b2cb0294ce08f567127d1bc22a7
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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