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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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Lithium hexamethyldisilazane → 1-(5-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide

HRID 1504545
ノート
印刷プレビュー

反応式

HRID 1504545 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18](OC4C(F)=C(F)C(F)=C(F)C=4F)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:33])[CH:7]=1.[CH3:36][O:37][C:38]1[CH:50]=[CH:49][C:41]([CH2:42][NH:43][C:44]2[CH:48]=[CH:47][O:46][N:45]=2)=[CH:40][CH:39]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([N:43]([C:44]4[CH:48]=[CH:47][O:46][N:45]=4)[CH2:42][C:41]4[CH:40]=[CH:39][C:38]([O:37][CH3:36])=[CH:50][CH:49]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:33])[CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 2733832Lithium hexamethyldisilazaneHCID 82671591N-[(4-methoxyphenyl)methyl]-1,2-oxazol-3-amineHCID 117736973Perfluorophenyl 1-(5-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

生成物 1

HCID 1177371841-(5-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide収率 70.1%

反応条件

温度
0 °C

実験手順

A flask containing perfluorophenyl 1-(5-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (3.65 g, 6.33 mmol) and N-(4-methoxybenzyl)isoxazol-3-amine (1.358 g, 6.65 mmol) was flushed with nitrogen and then charged with THF (63.3 ml) and cooled to 0° C. Lithium bis(trimethylsilyl)amide (1.0M in THF) (6.97 ml, 6.97 mmol) was added slowly, and the solution was stirred at 0° C. for 45 minutes until complete consumption of starting material. The reaction was quenched with water and extracted (×3) with EtOAc. The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude solid was triturated in IPA and filtered, washing well with IPA, to yield 1-(5-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (2.65 g, 4.44 mmol, 70.1% yield) as a white solid. m/z (ESI) 596.0 (M+H)+.

後処理

  1. customwas flushed with nitrogen
  2. additioncharged with THF (63.3 ml)
  3. customThe reaction was quenched with water
  4. extractionextracted (×3) with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude solid was triturated in IPA
  10. filtrationfiltered
  11. washwashing well with IPA

出典と根拠

ORDレコード
ord-51dbc7ee6c1441548a6df8abe2fe8946
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09212182B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート