Triethylamine → 7-Chloro-2-(4-methoxyphenylthiocarbamoyl)-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide

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Reaction Steps

A suspension of 7-chloro-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide trifluoroacetic acid salt (50 mg, Reference Example 1) in dry dichloromethane (5 mL) was treated with dry triethylamine (54 μL), then with a solution of 4-methoxyphenyl isothiocyanate (18 μL) in dry dichloromethane (5 mL). After stirring at room temperature for a further 3 hours the reaction mixture was further treated with dichloromethane (10 mL) and then washed three times with water (5 mL). The organic phase was dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica eluting with a mixture of pentane and ethyl acetate (1:1, v/v) to give 7-chloro-2-(4-methoxyphenylthiocarbamoyl)-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide (40 mg) as a white solid, m.p. 176–178° C. MS: 443 [MH]+, 441 [MH]+.

Provenance & Evidence