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

HRID 1069007ノート

反応式

HRID 1069007 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-140e71bc53c54d56aec6bd1923a12126
出典データセット
uspto-grants-2001_06
特許番号
US06251912B1

反応ノート

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