Diisopropylethylamine → 1-{[2-tert-Butyl-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 33, step A, using DIPEA (0.37 mL, 274 mg, 2.2 mmol), 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid (0.12 mmol) (see the step B in example 33 for preparation), methylamine hydrochloride (100 mg, 1.45 mmol) and HATU (150 mg, 0.40 mmol) in DMF (5 mL). The crude product was purified by MPLC using Hex/EtOAc (3:7) on silica gel to 25 mg (45%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.41-1.58 (m, 4 H), 1.61 (s, 9 H), 2.21-2.41 (m, 1 H), 2.79 (s, 3 H), 3.23-3.35 (m, 2 H), 3.83-3.96 (m, 2 H), 4.44 (d, J=7.62 Hz, 2 H), 6.63 (dd, J=3.32, 1.76 Hz, 1 H), 7.30 (dd, J=3.32, 2.34 Hz, 1H), 7.75-7.80 (m, 1 H), 7.95 (d, J=8.7 Hz, 1 H), 7.98 (dd, J=8.7, 1.5 Hz, 1 H), 8.27 (d, J=0.98 Hz, 1 H); MS (ESI) (M+H)+=458.8; Anal. Calcd for C23H30N4O4S+1.50 TFA (629.62): C, 49.60; H, 5.04; N, 8.90. Found: C, 49.53; H, 5.00; N, 9.10.

Provenance & Evidence