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

Participants

Reaction Steps

Following the same procedure in Example 29, using N-methyl-1H-pyrrole-3-carboxamide (57 mg, 0.46 mmol) (see following step B for preparation), sodium hydride (110 mg, 60%, 2.76 mmol), 2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (352 mg, 0.92 mmol) in THF (10 mL). The crude product was purified by MPLC using EtOAc on silica gel to give 134 mg (62%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.77 (t, J=7.42 Hz, 3 H), 1.40-1.56 (m, 4 H), 1.59 (s, 6 H), 1.94 (q, J=7.42 Hz, 2 H), 2.19-2.37 (m, 1 H), 2.79 (s, 3 H), 3.24-3.36 (m, 2 H), 3.84-3.94 (m, 2 H), 4.41 (d, J=7.62 Hz, 2 H), 6.63 (dd, J=3.32, 1.56 Hz, 1 H), 7.29 (dd, J=3.32, 2.34 Hz, 1 H), 7.78 (dd, J=2.15, 1.76 Hz, 1 H), 7.88-7.92 (m, 1 H), 7.92-7.98 (m, 1 H), 8.26 (dd, J=1.56, 0.59 Hz, 1 H); MS (ESI) (M+H)+=473.0; Anal. Calcd for C24H32N4O4S+1.0 TFA (586.63): C, 53.23; H, 5.67; N, 9.55. Found: C, 53.28; H, 5.77; N, 9.42.

Provenance & Evidence