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

Participants

Reaction Steps

Following the same procedure in Example 24, Step A, using isopropylamine (21 mg, 31 uL, 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 (1:2) on silica gel to give 67 mg (74%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.79 (t, J=7.42 Hz, 3 H), 1.20 (d, J=6.64 Hz, 6 H), 1.42-1.58 (m, 4 H), 1.61 (s, 6 H), 1.97 (q, J=7.42 Hz, 2 H), 2.22-2.41 (m, 1 H), 3.26-3.37 (m, 2 H), 3.87-3.96 (m, 2 H), 4.06-4.19 (m, 1 H), 4.43 (d, J=7.62 Hz, 2 H), 7.95 (d, J=8.8 Hz, 1 H), 7.98-8.03 (dd, J=9.0, 2.0 Hz, 1 H), 8.07 (s, 1 H), 8.36 (d, J=1.76 Hz, 1 H), 8.79 (s, 1 H); MS (ESI) (M+H)+=502.0; Anal. Calcd for C25H35N5O4S+110 TFA+0.6H2O (626.48): C, 51.76; H, 5.99; N, 11.18. Found: C, 51.77; H, 5.96; N, 11.27.

Provenance & Evidence