Trifluoroacetic acid methylene chloride → HCID 57991855, compound

Participants

Reaction Steps

A 50% TFA/DCM mixture (2 mL) was added to tert-butyl (S)-1-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-yloxy)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate. After 30 minutes, the reaction mixture was concentrated. The residue was purified by reverse phase C-18 HPLC chromatography to provide (2S)-1-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-yloxy)-3-(4-(trifluoromethyl)phenyl)propan-2-amine (50 mg, 42% over two steps). LCMS 431 (M+H) calc. for C21H18F3N4OS 431.1. 1H NMR (400 MHz, CDCl3): δ ppm 3.14 (d, J=6.46 Hz, 2H) 3.81-3.88 (m, 2H) 3.95-4.00 (m, 1H) 7.43 (d, J=8.02 Hz, 2H) 7.60 (d, J=8.22 Hz, 2H) 8.03 (d, J=6.26 Hz, 1H) 8.17 (s, 1H) 8.22-8.28 (m, 2H) 8.62 (d, J=6.26 Hz, 1H) 9.58 (s, 1H). 2H not detected.

Provenance & Evidence