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

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Reaction Steps

2-(7-acetyl-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyano-1-methylethyl)phenyl]ethyl}acetamide is synthesized according to example 5 by mixing 7-acetyl-1H-benzimidazol-1-ylacetic acid (90.0 mg, 0.413 mmol) prepared according to scheme 4, 2-[4-(1-aminoethyl)phenyl]-2-methylpropanenitrile (77.6 mg, 0.413 mmol) prepared according to scheme 6 and Et3N (125 mg, 1.24 mmol, 0.173 mL) and HATU (157 mg, 0.413 mmol) in dry MeCN (10.0 mL). The product is purified by reverse phase HPLC: Gilson prep pumps; Flow rate: 30 ml/min; Column: Synergi Polar (4μ) 21.2×50 mm; Mobile phase: A=water (0.05% TFA) B=MeCN (49.5 mg, 0.128 mmol, 31.0%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.35 (d, J=7.03 Hz, 3H) 1.66 (s, 6H) 2.38 (s, 3H) 4.74-4.87 (m, J=7.23, 7.23 Hz, 1H) 5.14 (s, 2H) 7.26 (t, J=7.81 Hz, 1H) 7.35 (d, J=8.40 Hz, 2H) 7.45 (d, J=8.40 Hz, 2H) 7.71 (d, J=7.62 Hz, 1H) 7.85 (d, J=8.01 Hz, 1H) 8.21 (s, 1H) 8.65 (d, J=7.81 Hz, 1H); MS [M+H] calcd.: 389.19. found: 389.09.

Provenance & Evidence