N,N-Diisopropylmethylamine → 4-Methoxy-but-2-enoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide

HRID 1069007노트

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HRID 1069007 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)C)(C)C.[CH3:28][O:29][CH2:30]/[CH:31]=[CH:32]/[C:33](Cl)=[O:34].C(=O)(O)[O-].[Na+].[Cl-].[Na+].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:33](=[O:34])[CH:32]=[CH:31][CH2:30][O:29][CH3:28])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 547370N,N-DiisopropylmethylamineHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamineHCID 224665544-Methoxycrotonyl chlorideHCID 129703874Sodium hydrogencarbonate brine

생성물 1

HCID 543919464-Methoxy-but-2-enoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide수율 95.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a stirred solution of 1.0 g of N-(3-bromophenyl)-4,6-quinazolindiamine and 0.62 g of diisopropyl methylamine in 21 mL of tetrahydrofuran at 0° C. was added 0.62 g of 4-methoxycrotonyl chloride. The mixture was stirred at 0° C. for 1.5 hr and 10 min at room temperature. The mixture was poured into saturated sodium bicarbonate-brine and extracted with ethyl acetate. The organic solution was dried over magnesium sulfate. The solution was filtered through silica gel and the solvent was removed. The residue was recrystallized from 1-butanol to give 1.25 g of 4-Methoxy-but-2-enoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide as a yellow solid: mass spectrum (m/e): M+H 415.0.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. filtrationThe solution was filtered through silica gel
  4. customthe solvent was removed
  5. customThe residue was recrystallized from 1-butanol

출처 및 근거

ORD 기록
ord-140e71bc53c54d56aec6bd1923a12126
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251912B1

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