Toluene → HCID 25235944, compound

Participants

Reaction Conditions

Reaction Steps

A 20% solution of phosgene in toluene (163 uL, 0.310 mmol) was added dropwise to a solution of pyrrolidine (51 uL, 0.620 mmol) in THF (2 mL) and EDIPA (216 uL, 1.24 mmol) at 0° C. under N2. The reaction was stirred for 20 min before the addition of 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (100 mg, 0.310 mmol) and NMP (1 mL). The ice bath was removed after 2 hr and the reaction allowed to stir overnight. The reaction was heated to 60° C. for 1.5 hr before being concentrated. The concentrate was added to a microwave vial charged with Burgess reagent (220 mg, 0.930 mmol) and the mixture heated to 150° C. for 15 min by microwave irradiation. The reaction was partitioned between EtOAc and H2O. The organic phase was concentrated and purified by reverse phase HPLC (25-50% ACN/H2O+5 mM NH4OH) to afford the title compound: 1H NMR (400 MHz, MeOD) δ ppm 2.05-2.14 (m, 4H) 3.58-3.67 (m, 4H) 7.55-7.64 (m, 3H) 7.79 (br. s., 1H) 7.94 (d, J=8.34 Hz, 1H) 8.19 (br. s., 1H); MS m/z=400.1 (M+1).

Provenance & Evidence