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

Acetamide → N-(3-{2-fluoro-6-[(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-ylmethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-acetamide

HRID 510011
ノート
印刷プレビュー

反応式

HRID 510011 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([NH:19][CH2:20][C:21]4[C:22]([O:28][CH3:29])=[N:23][CH:24]=[C:25]([F:27])[CH:26]=4)=[N:16][C:17]=3[F:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:36]([NH2:39])(=[O:38])[CH3:37].CNCCNC>O1CCOCC1.[Cl-].[Na+].O.[Cu]I.C(OCC)(=O)C>[F:18][C:17]1[C:12]([CH2:11][C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([NH:39][C:36](=[O:38])[CH3:37])[CH:3]=3)[NH:8][CH:9]=2)=[CH:13][CH:14]=[C:15]([NH:19][CH2:20][C:21]2[C:22]([O:28][CH3:29])=[N:23][CH:24]=[C:25]([F:27])[CH:26]=2)[N:16]=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

9

反応物 4

HCID 178AcetamideHCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 58259257[5-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amine

生成物 1

HCID 52935809N-(3-{2-fluoro-6-[(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-ylmethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-acetamide

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

[5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amine (P-1497, 1 equivalent) is dissolved in 25 mL of dioxane in a sealable vial. Cesium carbonate (2.1 equivalents), copper(I) iodide (1.5 equivalents), acetamide (174, 22 equivalents) and N,N′-dimethylethylenediamine (17 equivalents) are added. The vial is sealed and heated at 100° C. overnight. The reaction is added to ethyl acetate and brine and extracted. The organic layer is concentrated under vacuum and the resulting material dissolved in dichloromethane and purified by silica gel column chromatography, eluting with 0-10% methanol in dichloromethane. Appropriate fractions are concentrated, and the material dissolved in tetrahydrofuran for further purification on a C18 reverse phase column, eluting with 0-100% methanol (with 10% tetrahydrofuran)/water. Appropriated fractions are combined and concentrated under vacuum. The resulting material is triturated with methyl tert-butyl ether and filtered, washing with methyl tert-butyl ether, then heptane. The solid is dried under vacuum to provide the desired compound.

後処理

  1. customThe vial is sealed
  2. extractionextracted
  3. concentrationThe organic layer is concentrated under vacuum
  4. dissolutionthe resulting material dissolved in dichloromethane
  5. custompurified by silica gel column chromatography
  6. washeluting with 0-10% methanol in dichloromethane
  7. concentrationAppropriate fractions are concentrated
  8. dissolutionthe material dissolved in tetrahydrofuran for further purification on a C18 reverse phase column
  9. washeluting with 0-100% methanol (with 10% tetrahydrofuran)/water
  10. concentrationconcentrated under vacuum
  11. customThe resulting material is triturated with methyl tert-butyl ether
  12. filtrationfiltered
  13. washwashing with methyl tert-butyl ether
  14. customThe solid is dried under vacuum

出典と根拠

ORDレコード
ord-6e7a1fcf7490466aa8a99a95c565c5ce
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096593B2

反応ノート

読み込み中…

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