Chloroform → Ethyl 2-(4-(3-(2-chlorobenzoyl)-5-methylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate

HRID 963066

Reaktionsgleichung

Reaktionsgleichung von HRID 963066
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH3:18])[S:17][C:13]=2[N:12]2[C:19]([CH3:22])=[N:20][N:21]=[C:11]2[CH2:10][N:9]=1.C(Cl)(Cl)Cl.C(=O)([O-])[OH:28].[Na+].[CH2:32]([O:34][C:35]([CH2:37][N:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[C:39]1[C:47](Cl)=[O:48])=[O:36])[CH3:33]>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:14]1[CH:15]=[C:16]([CH3:18])[S:17][C:13]=1[N:12]1[C:19]([CH3:22])=[N:20][N:21]=[C:11]1[CH2:10][NH:9][C:47]([C:39]1[N:38]([CH2:37][C:35]([O:34][CH2:32][CH3:33])=[O:36])[C:46]2[C:41]([CH:40]=1)=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:48])=[O:28]

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 124343244-(2-Chlorophenyl)-2,9-dimethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepineHCID 190851631-Ethoxycarbonylmethylindole-2-carbonyl chloride

Produkt 1

HCID 22439218Ethyl 2-(4-(3-(2-chlorobenzoyl)-5-methylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetateAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-(2-Chlorophenyl)-2,9-dimethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (4.15 g) was dissolved in 5% hydrochloric acid (50 ml), and the solution was stirred at 60° C. for 4 hours. The reaction mixture was cooled in a water bath, and chloroform (60 ml) and sodium hydrogencarbonate (12.6 g) were added with vigorous stirring. Then, 1-ethoxycarbonylmethylindole-2-carbonyl chloride (3.52 g) was added, and the mixture was stirred for 1 hour. The chloroform layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate and methanol as eluent and crystallized from a mixed solvent of ethyl acetate and hexane to give 6.23 g of ethyl 2-(4-(3-(2-chlorobenzoyl)-5-methylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled in a water bath
  2. stirringthe mixture was stirred for 1 hour
  3. washThe chloroform layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography
  7. customcrystallized from a mixed solvent of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-0b71b69418774cd3a9613a0c3385e719
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760032

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