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Hydrochloric Acid → N-(5-Bromo-2-morpholinophenyl)-7-fluoro-2-(2-fluorophenyl)-3-methylquinolin-4-amine

HRID 1431270
Notes
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Reaction equation

HRID 1431270 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][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].[Br:21][C:22]1[CH:23]=[CH:24][C:25]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[C:26]([NH2:28])[CH:27]=1.Cl>O1CCOCC1.CO>[Br:21][C:22]1[CH:23]=[CH:24][C:25]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)=[C:26]([NH:28][C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=3)[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])[CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 49618715-Bromo-2-morpholin-4-ylanilineHCID 596313954-Chloro-7-fluoro-2-(2-fluorophenyl)-3-methylquinoline

Product 1

HCID 59631174N-(5-Bromo-2-morpholinophenyl)-7-fluoro-2-(2-fluorophenyl)-3-methylquinolin-4-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 31275
1,4-Dioxane
Solvent

Procedure

Prepared according to Procedure K, Method 1 using 4-chloro-7-fluoro-2-(2-fluorophenyl)-3-methylquinoline (118 mg, 407 μmol), 5-bromo-2-morpholinobenzenamine (105 mg, 407 μmol) and 4.0N hydrochloric acid (0.10 mL, 407 μmol) in 1,4-dioxane in MeOH (1.00 mL) to afford a yellow solid after purification by chromatography on silica gel, eluting with EtOAc-DCM-hexane solvent mixture. Mass Spectrum (ESI) m/e=510.0 & 512.0 (M+1).

Workup

  1. customPrepared
  2. customto afford a yellow solid
  3. customafter purification by chromatography on silica gel
  4. washeluting with EtOAc-DCM-hexane solvent mixture

Sources & evidence

ORD record
ord-899b24140db54eba883e62db19c0be7b
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08940724B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes