Sodium hydride → 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-cyclopropyl-1H-pyrrole-3-carboxamide

Participants

Reaction Steps

Following the same procedure in Example 29, using N-cyclopropyl-1H-pyrrole-3-carboxamide (49 mg, 0.33 mmol) (see following step B for preparation), sodium hydride (100 mg, 60%, 2.5 mmol) and 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (122 mg, 0.33 mmol) in THF (6 mL) and DMF (0.5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:4) on silica gel to give 82 mg (51%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.50-0.56 (m, 2 H), 0.69-0.76 (m, 2 H), 1.40-1.57 (m, 4 H), 1.59 (s, 9 H), 2.29 (m, 1 H), 2.67-2.76 (m, 1 H), 3.24-3.34 (m, 2 H), 3.84-3.93 (m, 2 H), 4.41 (d, J=7.42 Hz, 2 H), 6.64 (dd, J=3.32, 1.56 Hz, 1 H), 7.27 (dd, J=3.32, 2.34 Hz, 1 H), 7.78-7.82 (m, 1 H), 7.90 (d, J=9.0 Hz, 1 H), 7.94 (dd, J=8.6, 1.5 Hz, 1H), 8.25 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=484.7; Anal. Calcd for C25H32N4O4S+1.10 TFA+0.10H2O (611.88): C, 53.40; H, 5.49; N, 9.16. Found: C, 53.44; H, 5.53; N, 9.18.

Provenance & Evidence