Methyl 2,2,2-trichloroacetimidate → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-trichloromethyl-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 18582

Reaktionsgleichung

Reaktionsgleichung von HRID 18582
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:16]=[C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[O:14][N:13]=2)=[C:6]([NH2:23])[CH:5]=1.CO[C:27](=N)[C:28]([Cl:31])([Cl:30])[Cl:29]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][C:12]3[CH:16]=[C:15]([C:17]4[S:18][C:19]([Cl:22])=[CH:20][CH:21]=4)[O:14][N:13]=3)[C:27]([C:28]([Cl:31])([Cl:30])[Cl:29])=[N:23][C:6]=2[CH:5]=1)=[O:24]

Komponenten

4

Edukt 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 686173703-Amino-4-{[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-amino}-benzoic acid methyl ester

Produkt 1

HCID 686154671-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-trichloromethyl-1H-benzoimidazole-5-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

36.0 mg (0.098 mmol) 3-Amino-4-{[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-amino}-benzoic acid methyl ester were dissolved in 3 mL acetic acid. 17.4 μl (0.14 mmol) 2,2,2-trichloro-acetimidic acid methyl ester were added and the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was co-distilled twice with 15 mL toluene to give crude 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-trichloromethyl-1H-benzoimidazole-5-carboxylic acid methyl ester as a brown solid. Yield: 49 mg MS (ES+): m/e=491, chloro pattern.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-093c5128b43240c792cc6706aa41bce6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741341B2

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