o-Toluenesulfonyl chloride → HCID 131728394, compound

Participants

Reaction Steps

starting from tert-butyl (1S,4S)-5-[(5-amino-1-benzofuran-7-yl)methyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (44 mg crude starting material, 0.10 mmol; obtained in Example 118, Step 2) and o-toluenesulfonyl chloride (22 μL, 0.15 mmol). The title compound (15 mg, 31%) was obtained as an off-white solid. HPLC 98%, RT=1.37 min (System A; 10-97% MeCN over 3 min), 97%, RT=1.21 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, methanol-d4) δ ppm 2.28-2.34 (m, 1H) 2.66 (s, 3H) 2.67-2.72 (m, 1H) 3.52-3.59 (m, J=13.68, 2.64 Hz, 1H) 3.63-3.76 (m, 1H) 3.85-3.93 (m, J=12.80 Hz, 1H) 4.45-4.51 (m, 1H) 4.65 (s, 1H) 4.69-4.78 (m, 1H) 4.78-4.83 (m, 2H) 6.86 (d, J=2.26 Hz, 1H) 7.23-7.29 (m, 1H) 7.31-7.36 (m, J=7.53 Hz, 1H) 7.37-7.46 (m, 2H) 7.48 (d, J=2.26 Hz, 1H) 7.84-7.88 (m, 2H). MS (ESI+) for C21H23N3O3S m/z 398 (M+H)+.

Provenance & Evidence