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

HRID 1178419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178419
ON1C2C=CC=CC=2N=N1.[Cl:11][C:12]1[S:41][C:15]2[NH:16][C:17]([C:19]([NH:21][CH:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:32][C@H:33]4COC(C)(C)O4)[C:23]3=[O:40])=[O:20])=[CH:18][C:14]=2[CH:13]=1.ClC1S[C:46]2[NH:47][C:48](C(NC3CC4C(=CC=CC=4)N(CC(O)CO)C3=O)=O)=CC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Cl:11][C:12]1[S:41][C:15]2[NH:16][C:17]([C:19]([NH:21][CH:22]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:32][CH2:33][N:47]([CH3:48])[CH3:46])[C:23]3=[O:40])=[O:20])=[CH:18][C:14]=2[CH:13]=1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 103442072-Chloro-N-{1-[(2,2-dimethyl-1,3-dioxolan-4(S)-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3(R,S)-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 103646262-Chloro-N-{1-[2-(dimethylamino)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamideAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

1-Hydroxybenzotriazole (0.69 g, 0.51 mmol) was added to a solution of 3-amino-1-[2-(dimethylamino)ethyl]-3,4-dihydroquinolin-2(1H)-one (Method 10, 100 mg, 0.427 mmol) in DMF (3 mL) followed by 2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid (Method 9, 86 mg, 0.42 mmol) and EDCI (0.98 g, 0.51 mmol). The reaction was diluted with EtOAc (40 mL) and sat. aqueous NaHCO3 (20 mL) and the separated organic layer was dried (MgSO4), filtered and evaporated to dryness. Purification by column chromatography (MeOH:DCM 1:9) afforded the title compound (70 mg, 56%) as a yellow solid.

Aufarbeitung

  1. dry with materialthe separated organic layer was dried (MgSO4)
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customPurification by column chromatography (MeOH:DCM 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-a02d7889a50d4ac3989014fab87f1eab
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276517B2

Notizen zur Reaktion

Wird geladen…