Ethylamine hydrochloride → 1-{[2-(1,1-Dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-N-ethyl-1H-pyrazole-4-carboxamide

Participants

Reaction Steps

Following the same procedure in Example 24, Step A, using ethylamine hydrochloride (29 mg, 0.36 mmol), DIPEA (104 uL, 77 mg, 0.59 mmol), 1-{[2-(1,1-dimethylpropyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acid (0.18 mmol) and HATU (109 mg, 0.29 mmol) in DMF (3 mL). The crude product was purified by MPLC using Hex/EtOAc (1:4) on silica gel to give 53 mg (61%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.77 (t, J=7.42 Hz, 3 H), 1.15 (t, J=7.32 Hz, 3 H), 1.39-1.57 (m, 4 H), 1.58 (s, 6 H), 1.94 (q, J=7.68 Hz, 2 H), 2.19-2.37 (m, 1 H), 3.24-3.40 (m, 4 H), 3.83-3.94 (m, 2 H), 4.41 (d, J=7.23 Hz, 2 H), 7.92 (d, J=8.8 Hz, 1 H), 7.99 (dd, J=8.8, 1.4 Hz, 1 H), 8.04 (s, 1 H), 8.34 (d, J=1.17 Hz, 1 H), 8.74 (s, 1 H); MS (ESI) (M+H)+=488.0; Anal. Calcd for C24H33N5O4S+0.9 TFA+0.3H2O (595.65): C, 52.02; H, 5.84; N, 11.76. Found: C, 52.01; H, 5.66; N, 11.91.

Provenance & Evidence