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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1247505
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
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Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9c891bec6dbd494ebfa4bdc14e80f768
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07129249B2

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