7-Benzyloxy4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride → 4-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-quinazolinol

HRID 238086Notes

Reaction equation

HRID 238086 reaction equation
Cl.C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=3[F:28])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:29][CH3:30])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:14]2[C:13]3[C:18](=[CH:19][C:10]([OH:9])=[C:11]([O:29][CH3:30])[CH:12]=3)[N:17]=[CH:16][N:15]=2)=[C:22]([F:28])[CH:23]=1

Participants

3

Reactant 1

HCID 187534737-Benzyloxy4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride

Product 1

HCID 1355038524-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-quinazolinolYield 82%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride (9.4 g, 19.1 mmol) in TFA (90 ml) was heated at reflux for 50 minutes. The mixture was allowed to cool and was poured on to ice. The resulting precipitate was collected by filtration and dissolved in methanol (70 ml). The solution was adjusted to pH9-10 with concentrated aqueous ammonia solution. The mixture was concentrated to half initial volume by evaporation. The resulting precipitate was collected by filtration, washed with water and then ether, and dried under vacuum to give 4-(4-bromo-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (5.66 g, 82%).

Workup

  1. temperatureat reflux for 50 minutes
  2. temperatureto cool
  3. additionwas poured on to ice
  4. filtrationThe resulting precipitate was collected by filtration
  5. dissolutiondissolved in methanol (70 ml)
  6. concentrationThe mixture was concentrated to half initial volume
  7. customby evaporation
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with water
  10. dry with materialether, and dried under vacuum

Sources & evidence

ORD record
ord-cc9142326d4d4772b2e73fc2da36c22e
Source dataset
uspto-grants-2014_02
Patent number
US08642608B2

Reaction notes

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