Ethanol → HCID 178424571, compound

Participants

Reaction Steps

A solution of 100 mg (0.171 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-tert-butylsulfamoyl-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in the previous step) in CH2Cl2 (10 mL) was treated with 62.0 μL EtOH, 67.0 μL (0.616 mmol) of anisole, and TFA (750 μL) at RT for 18 h. EtOH (3 mL) was added, the mixture was concentrated, the residue was subjected again to the conditions above except that 900 μL of TFA was used, and then was subjected a third time with 1.70 mL of TFA. Solvents were evaporated in vacuo. Purification of the residue by RP-HPLC (C18) with 20-100% CH3CN in 0.1% TFA/H2O over 30 min afforded 27.7 mg (41%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.40 (d, 1H, J=8.8 Hz), 7.92 (s, 1H), 7.71 (dd, 1H, J=8.8, 2.4 Hz), 7.62 (d, 1H, J=2.4 Hz), 5.80-5.73 (m, 1H), 2.30-2.21 (m, 2H), 2.08-1.99 (m, 2H), 1.60-1.50 (m, 2H), 1.02 (s, 6H).

Provenance & Evidence