Ethylamine → HCID 178465147, compound

Participants

Reaction Conditions

Reaction Steps

cis-4-((E)-2-(4-Fluorobenzoylimino)-6-(piperidin-1-ylmethyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylic acid (0.025 g, 0.052 mmol) was cooled to 0° C. under nitrogen. To this mixture was added thionyl chloride (0.381 mL, 5.22 mmol), and the resulting reaction mixture was stirred for 10 minutes. The mixture was concentrated under reduced pressure and dried under high vacuum. The residue was suspended in THF (0.5 mL) and cooled to 0° C. under a nitrogen atmosphere. To this mixture was added ethanamine (2M in THF) (0.059 mL, 1.045 mmol) dropwise, and the reaction was stirred at 0° C. for 30 minutes. The reaction mixture was diluted with water (10 mL) and DCM (20 mL), and the layers were separated. The organic phase was dried over sodium sulfate, filtered, and solvent was concentrated under reduced pressure to afford (E)-N-(1-(cis-4-(ethylcarbamoyl)cyclohexyl)-6-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-2(3H)-ylidene)-4-fluorobenzamide (0.025 g, 95% yield). MS m/z=506.2 [M+H]. Calc'd for C29H36FN5O2: 505.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.14 (t, J=7.19 Hz, 3H) 1.42-1.50 (m, 2H) 1.50-1.63 (m, 4H) 1.63-1.89 (m, 4H) 2.14-2.28 (m, 2H) 2.32-2.47 (m, 4H) 2.57-2.66 (m, 1H) 2.67-2.89 (m, 2H) 3.21-3.32 (m, 2H) 3.56 (s, 2H) 4.77-5.03 (m, 1H) 7.17-7.23 (m, 1H) 7.25-7.35 (m, 2H) 7.53 (d, J=8.12 Hz, 1H) 7.63 (s, 1H) 7.83-7.94 (m, 1H) 8.29-8.43 (m, 2H) 12.79 (s, 1H).

Provenance & Evidence