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

Participants

Reaction Steps

Following the same procedure in Example 24, Step A, using methylamine hydrochloride (24 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) (see following Steps B and C for preparation) and HATU (109 mg, 0.29 mmol) in DMF (3 mL). The crude product was purified by MPLC using Hex/EtOAc (1:9) on silica gel to give 78 mg (92%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.78 (t, J=7.52 Hz, 3 H), 1.40-1.57 (m, 4 H), 1.59 (s, 6 H), 1.95 (q, J=7.29 Hz, 2 H), 2.21-2.37 (m, 1 H), 2.82 (s, 3 H), 3.25-3.35 (m, 2 H), 3.85-3.94 (m, 2 H), 4.42 (d, J=7.42 Hz, 2 H), 7.94 (d, J=9.0 Hz, 1 H), 8.00 (dd, J=8.8, 1.7 Hz, 1 H), 8.02 (d, J=0.59 Hz, 1 H), 8.35 (d, J=1.56 Hz, 1 H), 8.72 (d, J=0.59 Hz, 1 H); MS (ESI) (M+H)+=474.0; Anal. Calcd for C23H31N5O4S+1.10 TFA+0.4H2O (606.23): C, 49.93; H, 5.47; N, 11.55. Found: C, 49.95; H, 5.44; N, 11.48.

Provenance & Evidence