Trifluoroacetic acid → HCID 86670410, compound

Participants

Reaction Steps

A 5-mL vial was charged with (R)-tert-butyl 4-(5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyrimidin-2-yl)-3-((N-phenylmethylsulfonamido)methyl)piperazine-1-carboxylate (0.214 g, 0.348 mmol, Example 233, Step 5), TFA (1.0 mL, 13 mmol) and CH2Cl2 (2 mL). The mixture was stirred at room temperature for 35 min and then concentrated. CH2Cl2 (2 mL) and triethylamine (0.50 mL, 3.6 mmol) were added and the mixture was stirred at room temperature for 10 min. 6-chloropyridine-3-sulfonyl chloride (0.0910 g, 0.429 mmol, Organic Process Research & Development 2009, 13, 875) was then added in potions and the mixture was stirred at room temperature for 1.5 h. The mixture was concentrated and purified by column chromatography (50 g of silica gel, 0 to 60% EtOAc in hexanes) to afford N-(((2R)-4-((6-chloro-3-pyridinyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-N-phenylmethanesulfonamide (0.134 g) as a white solid.

Provenance & Evidence