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N,N-Diethylethylenediamine → (S)-N-[(2-{[2-(diethylamino)ethyl]amino}-2-oxoethyl)(oxo)phenyl-lambda6-sulfanylidene]-5-[(3-hydroxyphenyl)ethynyl]nicotinamide

HRID 607400
ノート
印刷プレビュー

反応式

HRID 607400 の反応式
C([C@H:3]([S:7]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[N:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[CH:17]=1)=[O:11])=[O:8])[C:4]([O-:6])=O)C.[CH2:33]([N:35]([CH2:39][CH3:40])[CH2:36][CH2:37][NH2:38])[CH3:34]>CO>[CH2:33]([N:35]([CH2:39][CH3:40])[CH2:36][CH2:37][NH:38][C:4](=[O:6])[CH2:3][S@:7](=[O:8])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[N:9][C:10](=[O:11])[C:12]1[CH:17]=[C:16]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[CH:15]=[N:14][CH:13]=1)[CH3:34]
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 2

HCID 60993N,N-DiethylethylenediamineHCID 86629474(S)-Ethyl[N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate

生成物 1

HCID 24954918(S)-N-[(2-{[2-(diethylamino)ethyl]amino}-2-oxoethyl)(oxo)phenyl-lambda6-sulfanylidene]-5-[(3-hydroxyphenyl)ethynyl]nicotinamide収率 60.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
30 °C

実験手順

(S)-Ethyl[N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate (73 mg, 0.16 mmol) in anhydrous MeOH (1.5 mL) was added N,N-diethylethylenediamine (0.12 mL, 0.84 mmol) dropwise. The reaction mixture was heated at 30° C. for 4 hours. The reaction mixture was evaporated and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed once with brine, dried (anhydrous Na2SO4), concentrated. The residue was purified by chromatography (silica gel, 50:1 CHCl3:MeOH to 10:1 CHCl3:MeOH). The product containing fractions were concentrated to give the title compound as a foamy solid (50 mg, 59%).

後処理

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. washThe organic layer was washed once with brine
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, 50:1 CHCl3:MeOH to 10:1 CHCl3:MeOH)
  7. additionThe product containing fractions
  8. concentrationwere concentrated

出典と根拠

ORDレコード
ord-58740cf5ba7344e0b3dc77ceec184c34
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07915443B2

反応ノート

読み込み中…

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