1,4-Dideoxy-1,4-iminothreitol → 4-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

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A solution of 4-fluoro-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 1.1, 60 mg, 0.13 mmol), (3S,4S)-pyrrolidine-3,4-diol (28.2 mg. 0.273 mmol) and TEA (76 μL, 0.546 mmol) in DMSO (103 μL) was stirred at 105° C. for 90 h. The solvent was evaporated off under reduced pressure and the crude product was purified by preparative SFC (Column Diol, from 22% to 27% in 10 min) to afford the title compound as a yellow powder. UPLC-MS (Condition 1) tR=2.18 min, m/z=466.0 [M+H]+, m/z=464.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.86 (d, J=10.51 Hz, 2H) 3.36 (dd, J=10.51, 3.67 Hz, 2H) 3.90 (br. s, 2H) 5.05 (br. s, 2H) 6.93 (d, J=8.80 Hz, 1H) 7.33 (d, J=8.56 Hz, 2H) 7.78-7.98 (m, 5H) 9.16 (s, 1H) 10.12 (s, 1H).

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