ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
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
  1. ホーム
  2. /反応

Tetrahydrofuran → 5-{2-[2-(tert-butylthio)ethoxy]ethyl}-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1787000
ノート
印刷プレビュー

反応式

HRID 1787000 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][O:31][CH2:32]CO)[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.[CH2:35](N(CC)CC)C.[CH3:42][S:43](Cl)(=O)=O.C(=O)([O-])O.[Na+].O1[CH2:56][CH2:55][CH2:54]C1>>[C:55]([S:43][CH2:42][CH2:32][O:31][CH2:30][CH2:29][N:28]1[C:21]2[C:20]([NH:19][C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[CH:10]=4)=[C:2]([Cl:1])[CH:3]=3)=[N:25][CH:24]=[N:23][C:22]=2[CH:26]=[CH:27]1)([CH3:54])([CH3:56])[CH3:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 116846292-(2-(4-((3-chloro-4-(3-(trifluoromethyl)phenoxy)phenyl)amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethoxy)ethan-1-ol

生成物 1

HCID 67521147
5-{2-[2-(tert-butylthio)ethoxy]ethyl}-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine

実験手順

2-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethoxy}ethanol (150 mg) was dissolved in tetrahydrofuran (6.0 mL), and triethylamine (1.00 mL) and methanesulfonyl chloride (0.59 mL) were added under ice-cooling and the mixture was stirred for 1 hr. Saturated aqueous sodium hydrogen carbonate was added to this reaction solution under ice-cooling and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated, and the residue was dissolved in a mixed solvent of N,N-dimethylformamide (4.0 mL) and tetrahydrofuran (6.0 mL). Sodium 2-methylpropane-2-thiolate (220 mg) was added, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated. The residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=90:10) to give the title compound (143 mg).

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionthe residue was dissolved in a mixed solvent of N,N-dimethylformamide (4.0 mL) and tetrahydrofuran (6.0 mL)
  7. additionSodium 2-methylpropane-2-thiolate (220 mg) was added
  8. stirringthe mixture was stirred at room temperature for 1 hr
  9. additionSaturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-
  10. temperaturecooling
  11. extractionthe mixture was extracted with ethyl acetate
  12. dry with materialThe extract was dried over magnesium sulfate
  13. concentrationconcentrated
  14. customThe residue was separated
  15. custompurified by silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=90:10)

出典と根拠

ORDレコード
ord-d2507183d9084d9e93389f75e358c959
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07507740B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート