1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-chloro-N-(1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6h-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178429
CCN=C=NCCCN(C)C.[C:12]([C:15]1[NH:19][C:18]2[S:20][C:21]([Cl:23])=[CH:22][C:17]=2[CH:16]=1)([OH:14])=O.[NH2:24][CH:25]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH2:35][CH2:36][S:37][CH3:38])[C:26]1=[O:39].ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[Cl:23][C:21]1[S:20][C:18]2[NH:19][C:15]([C:12]([NH:24][CH:25]3[CH2:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]([CH2:35][CH2:36][S:37][CH3:38])[C:26]3=[O:39])=[O:14])=[CH:16][C:17]=2[CH:22]=1

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 104428202-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acidHCID 219068283-amino-1-[2-(methylthio)ethyl]-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 100477312-chloro-N-(1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6h-thieno[2,3-b]pyrrole-5-carboxamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

EDCI (915 mg, 4.77 mmol) was added to a suspension of 5-Carboxy-2-chloro-6H-thieno[2,3-b]pyrrole (801 mg, 3.97 mmol), 3-amino-1-[2-(methylthio)ethyl]-3,4-dihydroquinolin-2(1H)-one (Method 16; 1.40 g, 3.97 mmol) and 1-hydroxybenzotriazole (537 mg, 3.97 mmol) in DCM (60 mL) and the reaction stirred for 18 hours. The reaction was evaporated and the residue was partitioned between DCM (100 mL) and water (25 mL). The organic layer was then separated, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:EtOAc (9:1)) to afford the title compound (660 mg, 40%) as a white solid.

Aufarbeitung

  1. customThe reaction was evaporated
  2. customthe residue was partitioned between DCM (100 mL) and water (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:EtOAc (9:1))

Quellen und Nachweise

ORD-Eintrag
ord-b56772a2667548de9d2cb22c4635203c
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276517B2

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