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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247505
ノート
印刷プレビュー

反応式

HRID 1247505 の反応式
CC[N:3]=C=NCCCN(C)C.[Cl:12][C:13]1[S:39][C:16]2[NH:17][C:18]([C:20]([NH:22][CH:23]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]([CH2:33][CH:34](O)CO)[C:24]3=[O:38])=[O:21])=[CH:19][C:15]=2[CH:14]=1.ClC1SC2NC(C(NC3CC4C(=CC=CC=4)N(C[C@@H](O)CO)C3=O)=O)=CC=2C=1>C(Cl)Cl>[Cl:12][C:13]1[S:39][C:16]2[NH:17][C:18]([C:20]([NH:22][CH:23]3[CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]([CH2:33][C:34]#[N:3])[C:24]3=[O:38])=[O:21])=[CH:19][C:15]=2[CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 104771912-chloro-N-[1-[(2R)-2,3-dihydroxypropyl]-2-oxo-3,4-dihydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 117428502-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamide

生成物 1

HCID 104526402-Chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide収率 21%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

EDCI (1.09 g, 5.65 mmol) was added to a suspension of 5-Carboxy-2-chloro-6H-thieno[2,3-b]pyrrole (Method 9, 1.04 g, 5.13 mmol) and (3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetonitrile (Method 13; 1.29 g, 5.13 mmol) in DCM (30 mL) and the reaction stirred for 18 hours. The reaction was evaporated and the residue was partitioned between DCM:MeOH (9:1) (100 mL) and aqueous K2CO3 (25 mL). The organic layer was then separated, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:MeOH (9:1)) to give a brown solid. The solid was triturated with refluxing Et2O (25 mL) and the solid filtered, washed with Et2O (25 mL) then hexane (25 mL) to afford the title compound (414 mg, 21%) as a pale brown solid.

後処理

  1. customThe reaction was evaporated
  2. customthe residue was partitioned between DCM:MeOH (9:1) (100 mL) and aqueous K2CO3 (25 mL)
  3. customThe organic layer was then separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (DCM to DCM:MeOH (9:1))
  8. customto give a brown solid
  9. customThe solid was triturated with refluxing Et2O (25 mL)
  10. filtrationthe solid filtered
  11. washwashed with Et2O (25 mL)

出典と根拠

ORDレコード
ord-9c891bec6dbd494ebfa4bdc14e80f768
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07129249B2

反応ノート

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