Phosphorus pentachloride → HCID 59799749, compound

Participants

Reaction Steps

2-(4-Ethoxy-phenyl)-N-{2-[2-(1-methyl-pyrrolidin-2-yl)-ethylamino]-5-nitro-phenyl}-acetamide 33 (60 mg, 0.141 mmol), Phosphorous pentachloride (33 mg, 0.158 mmol) were dissolved in anhydrous chloroform (10 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. The solution was heated to reflux in an oil bath for 4.5 hours and cooled to room temperature overnight. The mixture was diluted with H2O and chloroform and 2M ammonium hydroxide solution added to adjust pH to 9-10. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with chloroform and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated to afford crude. The product was purified using silica gel column chromatography eluting with a solvent system of 5% 2M NH3 in methanol/95% dichloromethane to afford a pale yellow solid 34 2-(4-Ethoxy-benzyl)-1-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-5-nitro-1H-benzimidazole Yield: 22 mg (38.3%). 1H NMR (DMSO) δ; 1.29 (t, 3H, J=7.0), 1.38-1.51 (m, 2H), 1.51-1.70 (m, 3H), 1.75-1.87 (m, 1H), 1.96-2.05 (m, 2H), 2.07 (s, 3H), 2.85-2.95 (m, 1H), 3.97 (q, 2H, J=7.0), 4.21 (t, 2H, J=7.9), 4.32 (s, 2H), 6.87 (d, 2H, J=8.5), 7.19 (d, 2H, J=8.5), 7.70 (d, 1H, J=9.0), 8.14 (dd, 1H, J=8.9, 2.1), 8.47 (d, 1H, J=2.1); MS (ESI): 409 (MH+, 100%).

Provenance & Evidence