Compound 12
7-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide
From: Small-molecule inhibition of TLR8 through stabilization of its resting state
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
A mixture of acid 6 (0.1 g, 0.3 mmol) and thionyl chloride (3 mL) were refluxed in a 10 mL round bottom flask fitted with a calcium chloride guard tube. After the reaction was completed (4 hours), the excess thionyl chloride was removed by rotary evaporation. The flask was put under high vacuum for 30-60 minutes to complete thionyl chloride removal. The residue was dissolved in anhydrous DCM (3 mL), the solution was cooled in an ice bath, and then ammonia (0.5 M in THF, 4 mL, 2 mmol) was added to the chilled solution. The reaction was seated in an ice bath for an additional 30 min, then the ice bath was removed and the reaction was allowed to stir at room temperature for 3 hours. The crude product was purified by recrystallization in DCM and hexane to yield 0.067 g (67.2%) of 12 as a white solid. Purity: 90.8%. 1H NMR (400 MHz, DMSO-d6) δ 8.90 (d, J = 4.5 Hz, 1H), 8.64 (s, 1H), 8.51 (s, 1H), 8.39 (d, J = 7.9 Hz, 1H), 8.03 (d, J = 7.9 Hz, 1H), 7.89 (t, J = 7.9 Hz, 1H), 7.66 – 7.54 (m, 3H). 13C NMR (101 MHz, DMSO-d6) δ 163.02, 152.50, 147.12, 146.28, 145.97, 134.29, 131.39, 130.31, 129.50, 128.40, 126.95, 125.70, 110.16, 106.10.
- PubChemID:
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347911530
- MDL Molfile:
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