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

Participants

Reaction Steps

Following the same procedure in Example 24, Step A, using DIPLA (105 uL, 78 mg, 0.60 mmol), 1-{[2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid (0.85 mmol) (see following Steps B and C for preparation) in DMF (15 mL), HATU (582 mg, 10.53 mmol) and ethylamine hydrochloride (154 mg, 1.87 mmol). The crude product was purified by MPLC on silica gel using EtOAc to give 0.32 g (81%) of a white solid as the title compounds 1H NMR (400 MHz, CHLOROFORM-D) δ 1.19 (t, J=7.23 Hz, 3 H), 1.45-1.54 (m, 4 H), 1.56 (s, 9 H), 2.15-2.33 (m, 1 H), 3.26-3.35 (m, 2 H), 3.36-3.44 (m, 2 H), 3.93-4.03 (m, 2 H), 4.22 (d, J=7.42 Hz, 2H), 5.79 (t, J=5.66 Hz, 1 H), 6.47 (dd, J=3.22, 1.66 Hz, 1 H), 7.17 (dd, J=3.32, 2.15 Hz, 1 H), 7.41 (d, J=8.59 Hz, 1 H) 7.62 (dd, J=2.34, 1.76 Hz, 1 H), 7.76 (dd, J=8.69, 1.86 Hz, 1 H), 8.32 (d, J=1.76 Hz, 1 H); MS (ESI) (M+H)+=473.3.

Provenance & Evidence