Hydrochloric Acid → HCID 90647121, compound

Participants

Reaction Conditions

Reaction Steps

(5-Tert-butyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (US2004/0192653, which is incorporated herein by reference in its entirety; 242 mg, 0.74 mmol) was treated with a solution of Intermediate 38d (300 mg, 0.74 mmol) in 1,4-dioxane (5 mL) then DIPEA (185 μL, 1.1 mmol) was added. The mixture was stirred at 50° C. overnight. The mixture was evaporated in vacuo and the residue purified by HPLC (Method 6, 20-40% MeCN in H2O, 0.1% HCO2H over 30 min) to give a colourless glass that was dissolved in MeCN and treated with 1N HCl (550 μL, 1 eq.). The volatiles were evaporated to drieness under reduced pressure affording a colourless glass that upon trituration with ether gave a solid. The solid was collected by filtration, washed with ether and dried at 50° C. in vacuo to give the title compound as an off white solid (346 mg, 74%). LCMS (Method 5): Rt 3.01 min, m/z 586.4 [MH+]. 1H NMR (400 MHz, d6-DMSO): 1.20 (9H, s), 1.81-2.15 (5H, m), 2.16-2.24 (2H, bs), 2.42-2.52 (4H, br s, partially obscured by DMSO), 2.74-2.80 (6H, s), 3.45-3.53 (2H, m), 3.56 (3H, s), 3.97-4.06 (1H, m), 4.79-4.88 (1H, m), 5.54 (1H, t, J 4.3 Hz), 6.00 (1H, s), 7.08 (1H, d, J 8.4 Hz), 7.22-7.27 (1H, m), 7.33-7.39 (4H, m), 7.77 (1H, d, J 9.3 Hz), 8.45 (1H, bs), 8.60 (1H, s).

Provenance & Evidence