Maleic Anhydride → HCID 54170922, 화합물

HRID 1698937노트

반응식

HRID 1698937 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 54170922HCID 54170922, 화합물수율 17.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 5° 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 dimethylformamide and then a second time from methanol to afford 0.036 g of the desired product.

후처리

  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 dimethylformamide

출처 및 근거

ORD 기록
ord-9aac7f90ec064227b1a2c0d01673abd2
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06344459B1

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