Maleic Anhydride → HCID 54170922, compound

HRID 394723Notes

Reaction equation

HRID 394723 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:20]1(=[O:26])[O:25][C:23](=[O:24])[CH:22]=[CH:21]1>O1CCCC1>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:6]2[C:5]3[C:10](=[CH:11][C:2]([NH:1][C:20]([CH:21]=[CH:22][C:23]([OH:25])=[O:24])=[O:26])=[CH:3][CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazoline

Product 1

HCID 54170922HCID 54170922, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 50° C. solution of 0.158 g of 7-amino-4-(3-bromoanilino)-quinazoline (J Med Chem, 1995:3482) in 10 mL of tetrahydrofuran was added 0.059 g of maleic anhydride. The cold solution stirred for 15 minutes, and then the ice bath was removed. The reaction warmed to room temperature where it continued stirring for 15 hours. The suspension was heated under reflux for 30 minutes and then stirred at room temperature another 15 hours. Another 0.059 g of maleic anhydride and 20 mL of tetrahydrofuran were added, and the reaction was refluxed for an additional 2 hours. After another 15 hours at room temperature, the reaction was refluxed for 15 hours. The reaction was filtered, and the light tan solid was recrystallized first from dimethyl-formamide and then a second time from methanol to afford 0.036 g of the desired product.

Workup

  1. customthe ice bath was removed
  2. stirringcontinued stirring for 15 hours
  3. temperatureThe suspension was heated
  4. temperatureunder reflux for 30 minutes
  5. stirringstirred at room temperature another 15 hours
  6. additionAnother 0.059 g of maleic anhydride and 20 mL of tetrahydrofuran were added
  7. temperaturethe reaction was refluxed for an additional 2 hours
  8. waitAfter another 15 hours at room temperature
  9. temperaturethe reaction was refluxed for 15 hours
  10. filtrationThe reaction was filtered
  11. customthe light tan solid was recrystallized first from dimethyl-formamide

Sources & evidence

ORD record
ord-a7dca76a54a848ab88be31fd141e30bd
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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