Acetic Acid → N-(2-hydroxyethyl)-2-(2-(4-((methylamino)methyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

Participants

Reaction Steps

2-(2-(4-Formyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (100 mg, 0.225 mmol), Methylamine (2 M in THF, 0.45 mL, 0.90 mmol) and DCM (3 mL) were treated with acetic acid (13.51 mg, 0.225 mmol) to give pH 4-5 and the solution stirred at RT for 20 min. 10% Pd/C (20 mg) was added as a slurry in DCM and the mixture stirred under 4 barr hydrogen overnight. The mixture was taken into a 20 mL syringe and the residue of the flask washed with MeOH/DCM and also taken into the syringe. The mixture was filtered through a filter tip and concentrated to give a yellow oil (˜200 mg). Purification was achieved on silica eluting with 4% 2 M NH3 in MeOH/DCM and the product obtained as a light yellow glass (74.2 mg, 0.160 mmol, 71%).

Provenance & Evidence