Hydrochloric Acid → N-(5-Bromo-2-morpholinophenyl)-7-fluoro-3-methyl-2-(pyridin-2-yl)-quinolin-4-amine

HRID 1431272Notes

Reaction equation

HRID 1431272 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][N:14]=2)[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.CO>[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][C:8]([F:12])=[CH:9][CH:10]=3)[N:5]=[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:3]=2[CH3:19])[CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 49618715-Bromo-2-morpholin-4-ylanilineHCID 596310754-Chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

Product 1

HCID 59631314N-(5-Bromo-2-morpholinophenyl)-7-fluoro-3-methyl-2-(pyridin-2-yl)-quinolin-4-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Prepared according to Procedure K, Method 1 using 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (131 mg, 480 μmol), 5-bromo-2-morpholinobenzenamine (124 mg, 480 μmol) and 4.0N hydrochloric acid (0.12 mL, 480 μmol) solution in dioxane in MeOH (1.50 mL) to afford a yellow solid after purification by chromatography on silica gel, eluting with EtOAc-hexane solvent mixture. Mass Spectrum (ESI) m/e=493.0 & 495.0 (M+1).

Workup

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

Sources & evidence

ORD record
ord-25e468bbaacf48c3b20ad818ebde2b4e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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