2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride → HCID 23659908, 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 (1.46 g, 3.93 mmol), tert-butyl 1H-pyrazol-3-ylcarbamate (0.80 g, 4.33 mmol) (see following step B for preparation), and DMAP (1.47 g, 12.0 mmol) in MeCN (40 mL). The crude product was purified by MPLC using EtOAc on silica gel to give 0.31 g (19%) of a white solid as the title compound. 1H NMR (400 MHz, DMSO-D6) δ 1.25-1.44 (m, 4 H), 1.46 (s, 9 H), 2.05-2.24 (m, 1 H), 3.15 (m, 2 H), 3.77 (m, 2 H), 4.28 (d, J=7.03 Hz, 2 H), 5.38 (s, 2 H), 5.78 (d, J=2.93 Hz, 1 H), 7.63 (dd, J=8.79, 1.76 Hz, 1 H), 7.82 (d, J=8.59 Hz, 1 H), 7.97 (d, J=1.76 Hz, 1 H), 8.00 (d, J=2.93 Hz, 1 H); MS (ESI) (M+H)+=417.8; Anal. Calcd for C20H27N5O3S+1.30 TFA+0.10 EtOAc (575.78): C, 48.19; H, 5.09; N, 12.16. Found: C, 48.12; H, 5.02; N, 12.29.

Provenance & Evidence