Triethylamine → HCID 73335129, compound

Participants

Reaction Steps

The regioisomer mixture obtained above (66 mg, approx 0.25 mmol total) was combined with 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid (67 mg, 0.275 mmol), HATU (114 mg, 0.3 mmol), and Et3N (52 μL, 0.38 mmol) in THF (1 mL). After 90 minutes the reaction slurry was diluted with EtOAc, washed with H2O, and concentrated. The residue was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provide two regioisomers. First eluting, Compound A: 1-[1-(4-chlorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-[4-chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone was isolated as a white solid (1.7 mg). 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.36 (s, 0.8H), 7.59 (s, 0.2H), 7.43 (s, 4H), 5.24 (s, 0.4H), 5.13 (s, 1.6H), 3.92 (m, 0.4H), 3.85 (m, 1.6H), 2.90 (m, 1.8H), 2.77 (m, 0.2H), 2.34 (s, 2.4H), 2.32 (s, 0.6H), 2.13 (m, 1.5H), 2.05 (m, 0.5H); MS: (ES) m/z calculated for C19H17Cl2F3N5O [M+H]+ 458.1, found 458.0. Second eluting, Compound B: 1-(2-(4-chlorophenyl)-6,7-dihydro-2H-pyrazolo[4,3-b]pyridin-4(5H)-yl)-2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethanone was isolated as a white solid (31.0 mg). 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 7.56 (m, 2H), 7.36 (m, 2H), 5.16 (s, 2H), 3.84 (s, 2H), 2.93 (t, J=6.6 Hz, 2H), 2.32 (s, 3H), 2.19 (m, 2H); MS: (ES) m/z calculated for C19H17Cl2F3N5O [M+H]+ 458.1, found 458.0.

Provenance & Evidence