Hydrochloric Acid → Ethyl 4-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl)-4-(3,4-dichlorobenzoylamino)butanoate

HRID 963101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963101
[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]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH:10]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:9]=1.Cl.C(=O)([O-])[OH:33].[Na+].[Cl:37][C:38]1[CH:39]=[C:40]([CH:44]=[CH:45][C:46]=1[Cl:47])[C:41](Cl)=[O:42]>C(Cl)(Cl)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]([CH2:18][CH3:19])[S:17][C:13]=1[N:12]1[C:20]([CH3:23])=[N:21][N:22]=[C:11]1[CH:10]([NH:9][C:41](=[O:42])[C:40]1[CH:44]=[CH:45][C:46]([Cl:47])=[C:38]([Cl:37])[CH:39]=1)[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:33]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 516892Sodium BicarbonateHCID 67727690ethyl 3-(4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)propionate

Produkt 1

HCID 19085272Ethyl 4-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl)-4-(3,4-dichlorobenzoylamino)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Ethyl 3-(4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)propionate (4.0 g) was added to 2M hydrochloric acid (100 ml), and the mixture was stirred at 60° C. for 1 hour. The reaction mixture was cooled to 0° C. A saturated aqueous sodium hydrogencarbonate solution, chloroform and 3,4-dichlorobenzoyl chloride (2.1 g) were added, and the mixture was stirred for 0.5 hour. The organic layer was taken out, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate) and crystallized from a mixed solvent of ethyl acetate-diisopropyl ether to give 0.56 g of ethyl 4-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl)-4-(3,4-dichlorobenzoylamino)butanoate.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 0° C
  2. stirringthe mixture was stirred for 0.5 hour
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate)
  6. customcrystallized from a mixed solvent of ethyl acetate-diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-802edad45e4246bda2847c0938b1b65b
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760032

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