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

HRID 577357Notes

Reaction equation

HRID 577357 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-996e2cbea39b48c2b89c0ced3a5690a1
Source dataset
uspto-grants-2015_05
Patent number
US09040548B2

Reaction notes

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