Aniline → HCID 23659490, compound

Participants

Reaction Steps

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (76 mg, 0.20 mmol), aniline (46 uL, 47 mg, 0.50 mmol) and DMAP (82 mg, 0.67 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 43 mg (50% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.40-1.58 (m, 4 H), 1.61 (s, 9 H), 2.21-2.38 (m, 1 H), 3.29-3.35 (m, 2 H), 3.85-3.93 (m, 2 H), 4.45 (d, J=7.62 Hz, 2 H), 6.96-7.04 (m, 1 H), 7.04-7.11 (m, 2 H), 7.11-7.21 (m, 2 H), 7.84-7.89 (m, 1 H), 7.91-7.98 (m, 1 H), 8.06 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=428.0; Anal. Calcd for C23H29N3O3S+1.10 TFA+0.30 EtOAc+0.2H2O (583.03): C, 54.39; H, 5.69; N, 7.21. Found: C, 54.43; H, 5.68; N, 7.22.

Provenance & Evidence