Triethylamine → 2-(7-Cyano-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyanocyclobutyl)phenyl]ethyl}acetamide

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Reaction Steps

2-(7-Cyano-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyanocyclobutyl)phenyl]ethyl}acetamide is synthesized according to example 5 by mixing (7-cyano-1H-benzimidazol-1-yl)acetic acid (95.0 mg, 0.475 mmol) prepared according to scheme 3, 1-[4-(1-aminoethyl)phenyl]cyclobutanecarbonitrile (95 mg, 0.475 mmol) prepared according to scheme 9, Et3N (144 mg, 1.43 mmol, 0.199 mL) and HATU (181 mg, 0.475 mmol) in MeCN (10.0 mL). The product is purified by HPLC: Gilson prep pumps, Flow rate: 30 ml/min, Column: Gemini (5μ) 21.2×50 mm, Mobile phase: A=water (10 mM NH4CO3) B=MeCN, (34.0 mg, 0.0888 mmol, 19%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.40 (d, J=7.03 Hz, 3H) 1.89-2.05 (m, 1 H) 2.15-2.34 (m, 1H) 2.52-2.66 (m, 2H) 2.66-2.80 (m, 2H) 4.88-5.01 (m, 1H) 5.25 (dd, J=22.66, 17.58 Hz, 2H) 7.31-7.46 (m, 5H) 7.71 (dd, J=7.62, 0.78 Hz, 1H) 8.01 (dd, J=8.01, 0.78 Hz, 1H) 8.36 (s, 1H) 8.87 (d, J=7.62 Hz, 1H); MS [M+H], calcd: 384.0. found: 384.2.

Provenance & Evidence