N,N-二异丙基甲胺 → 4-Methoxy-but-2-enoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide

HRID 1069007笔记

反应方程式

HRID 1069007 反应方程式
[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

参与物

6

反应物 4

HCID 547370N,N-二异丙基甲胺HCID 5328042N4-(3-溴苯基)喹唑啉-4,6-二胺HCID 224665544-Methoxycrotonyl chlorideHCID 129703874Sodium hydrogencarbonate brine

产物 1

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

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
0 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-140e71bc53c54d56aec6bd1923a12126
来源数据集
uspto-grants-2001_06
专利号
US06251912B1

反应笔记

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