Triethylamine → HCID 178493751, compound

Participants

Reaction Steps

To a solution of 5-methoxy-3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinic acid (150 mg, 0.35 mmol, EXAMPLE 31 Step 4) and ammonium chloride (56 mg, 1.05 mmol) in dichloromethane (5 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) (100 mg, 0.52 mmol), 1-hydroxybenzotriazole hydrate (HOBt) (53 mg, 0.35 mmol) and triethylamine (176 mg, 1.74 mmol) respectively. After being stirred at room temperature for 24 h, water was added to the mixture. The mixture was extracted with dichloromethane, and the extract was dried over sodium sulfate and concentrated in vacuo to afford an oil. The residual oil was purified by NH gel column chromatography (methanol/dichloromethane 1:30) followed by preparative high pressure liquid chromatography (prep. HPLC) (acetonitrile/0.01% aq. ammonia 96:4 to 4:96) to afford 75 mg (50%) of the title compound as an amorphous powder.

Provenance & Evidence