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

Sodium hydride → (Z)-N,N-Dicyclopropyl-4-(4,4-dimethoxy-1-(methylthio)-3-oxobut-1-enylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

HRID 220399
ノート
印刷プレビュー

反応式

HRID 220399 の反応式
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:22][CH3:23])[C:11]([C:13]([N:15]([CH:19]3[CH2:21][CH2:20]3)[CH:16]3[CH2:18][CH2:17]3)=[O:14])=[CH:12][C:7]2=[C:6]2[N:24]([CH3:27])[CH:25]=[N:26][C:5]=12.[CH3:28][O:29][CH:30]([O:39][CH3:40])[C:31](=[O:38])[CH:32]=[C:33](SC)[S:34][CH3:35]>CN(C=O)C.C(OCC)(=O)C>[CH:16]1([N:15]([CH:19]2[CH2:21][CH2:20]2)[C:13]([C:11]2[N:10]([CH2:22][CH3:23])[C:8]3=[N:9][C:4]([NH:3]/[C:33](/[S:34][CH3:35])=[CH:32]/[C:31](=[O:38])[CH:30]([O:29][CH3:28])[O:39][CH3:40])=[C:5]4[N:26]=[CH:25][N:24]([CH3:27])[C:6]4=[C:7]3[CH:12]=2)=[O:14])[CH2:18][CH2:17]1
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 3

HCID 24758Sodium hydrideHCID 111603891,1-Dimethoxy-4,4-bis(methylsulfanyl)but-3-en-2-oneHCID 581805034-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

生成物 1

HCID 58180627(Z)-N,N-Dicyclopropyl-4-(4,4-dimethoxy-1-(methylthio)-3-oxobut-1-enylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide収率 80%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium hydride (142 mg, 3.55 mmol) was added to 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 1J, 400 mg, 1.182 mmol) in DMF (7 mL) at room temperature and the mixture stirred for 30 min, 1,1-dimethoxy-4,4-bis(methylthio)but-3-en-2-one (394 mg, 1.773 mmol) was added and stirring continued overnight. The reaction mixture was diluted with ethyl acetate and washed with water, 10% lithium chloride and water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (80 g column, eluting with 2-5% methanol/dichloromethane). (Z)-N,N-Dicyclopropyl-4-(4,4-dimethoxy-1-(methylthio)-3-oxobut-1-enylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (484 mg, 0.944 mmol, 80% yield) was obtained as a yellow solid.

後処理

  1. stirringstirring continued overnight
  2. washwashed with water, 10% lithium chloride and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel using
  7. washan automated ISCO system (80 g column, eluting with 2-5% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-e1d3ec3b736c4652b8f7f13a5fac34a9
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202881B2

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