2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride → 2-tert-Butyl-5-[(3-methyl-1H-pyrazol-1-yl)sulfonyl]-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole

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 (371 mg, 1.0 mmol), 3-methyl-1H-pyrazole (164 mg, 2.0 mmol) and DMAP (367 mg, 3.0 mmol) in MeCN (10 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 116 mg (28%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.39-1.57 (m, 4 H), 1.59 (s, 9 H), 2.17 (s, 3 H), 2.23-2.33 (m, 1 H), 3.27-3.36 (m, 2 H), 3.88 (m, 2 H), 4.42 (d, J=7.62 Hz, 2 H), 6.31 (d, J=2.54 Hz, 1 H), 7.88-7.99 (m, 2 H), 8.18 (d, J=2.73 Hz, 1 H), 8.28 (d, J=1.76 Hz, 1 H); MS (ESI) (M+H)+=416.8.

Provenance & Evidence