Dimethylacetamide → N-Methyl-N-(2-{5-[2-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-1,3-thiazol-2-yl}-1H-indol-7-yl)thiophene-2-sulfonamide

HRID 1851554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851554
[NH:1]([C:3](=[O:30])[CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:20]([CH3:29])[S:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[N:8][CH:7]=1)[NH2:2].[C:31](N1C=CN=C1)(N1C=CN=C1)=[O:32].CN(C)C(=O)C>O>[CH3:29][N:20]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[NH:12][C:11]([C:9]1[S:10][C:6]([CH2:5][CH2:4][C:3]3[O:30][C:31](=[O:32])[NH:2][N:1]=3)=[CH:7][N:8]=1)=[CH:19]2)[S:21]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)(=[O:23])=[O:22]

Komponenten

5

Edukt 3

HCID 31374DimethylacetamideHCID 682631,1'-CarbonyldiimidazoleHCID 57901791N-{2-[5-(3-hydrazino-3-oxopropyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

Produkt 1

HCID 57901682N-Methyl-N-(2-{5-[2-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-1,3-thiazol-2-yl}-1H-indol-7-yl)thiophene-2-sulfonamideAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of N-{2-[5-(3-hydrazino-3-oxopropyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide (0.29 g), 1,1′-carbonylbis-1H-imidazole (0.22 g) and N,N-dimethylacetamide (15 mL) was stirred at room temperature for 2 hr. Water was added to the reaction mixture and the resulting crystals were collected by filtration, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (0.20 g, yield 65%) was obtained as yellow crystals from a fraction eluted with tetrahydrofuran-hexane (2:1, volume ratio). The crystals were recrystallized from ethyl acetate. melting point 255-256° C.

Aufarbeitung

  1. filtrationthe resulting crystals were collected by filtration
  2. washwashed with water
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b1ddb83b45fa4b16b00d9ab47d8f1d6c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957070B2

Notizen zur Reaktion

Wird geladen…