Diisopropylethylamine → 4-[4-[(5-Cyano-furan-2-carbonyl)-amino]-3-(2,5-dimethyl-pyrrol-1-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

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Reaction Steps

Using a procedure similar to Example 4, step (c), 4-[4-amino-3-(2,5-dimethyl-pyrrol-1-yl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (30 mg, 0.8 mmol) was allowed to react with 5-cyano-furan-2-carbonyl chloride (25 mg, 0.16 mmol) in the presence of DIEA (276 mg, 1.7 mmol) to afford 14.9 mg (38%) of the title compound as a yellow solid. 1H-NMR (CDCl3, 400 MHz): 8.43 (d, 1H, J=9.3 Hz), 7.25 (s, 1H), 7.10-7.13 (m, 2H), 7.03-7.06 (m, 1H), 6.89 (s, 1H), 6.06 (s, 2H), 3.62-3.61 (m, 4H), 3.18-3.17 (m, 4H), 1.96 (s, 6H), 1.48 (s, 9H); Mass spectrum (ESI, m/z): Calcd. for C27H31N5O4, 390.1 (M-BOC+2H), found 390.1.

Provenance & Evidence