1,2-Dichloroethane → HCID 178522613, compound

Participants

Reaction Steps

A round bottom flask under nitrogen atmosphere was charged with cis-4-((E)-2-(4-fluorobenzoylimino)-6-(piperidin-1-ylmethyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylic acid (50 mg, 0.104 mmol), N,N-dimethylpyridin-4-amine (31.9 mg, 0.261 mmol), thiazol-2-amine (15.69 mg, 0.157 mmol), and DMF (2 mL). To this mixture was added EDC (40.1 mg, 0.209 mmol), and the reaction was stirred for 48 hours. The resulting mixture was diluted with water (10 mL) and DCM (30 mL). The organic layer was collected, dried over sodium sulfate and concentrated to afford a brown oil. The residual oil was purified by HPLC (10-70% ACN/H2O; 0.1% TFA) to afford (E)-4-fluoro-N-(6-(piperidin-1-ylmethyl)-1-(cis-4-(thiazol-2-ylcarbamoyl)cyclohexyl)-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide (0.027 g, 46.1% yield). MS m/z=561.2 [M+H]. Calc'd for C30H33FN6O2S: 560.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23-1.36 (m, 1H) 1.36-1.48 (m, 2H) 1.50-1.60 (m, 4H) 1.68-1.84 (m, 2H) 1.86-2.01 (m, 2H) 2.26-2.37 (m, 2H) 2.40-2.50 (m, 3H) 2.75-2.90 (m, 2H) 2.98-3.10 (m, 1H) 3.63 (s, 2H) 4.77-5.08 (m, 1H) 7.18-7.24 (m, 1H) 7.24-7.32 (m, 2H) 7.36 (d, J=3.62 Hz, 1H) 7.52-7.59 (m, 2H) 7.66 (s, 1H) 8.30-8.42 (m, 2H) 12.21 (s, 1H) 12.83 (s, 1H).

Provenance & Evidence