Triethylamine → (S)-3-[5-(2,5-Dihydro-1H-pyrrol-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile

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Reaction Conditions

Reaction Steps

(S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (372 mg, 42%, slightly impure) was prepared according to the procedure in Example 25 from (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester (557.8 mg, 2.62 mmol) with isobutyl chloroformate (0.36 mL, 2.77 mmol) and triethylamine (0.73 mL, 5.2 mmol) in THF (7.5 mL). Then 3-cyano-N-hydroxy-benzamidine (424 mg, 2.6 mmol) and DMF (7 mL) were added and the mixture was heated at 120° C. for 16 h. 1H-NMR (CDCl3) was consistent with the expected product and showing a mixture of rotomers due to the Boc protecting group.

Provenance & Evidence