Cyclobutanecarbonyl chloride → HCID 23659909, compound

Participants

Reaction Steps

Cyclobutanecarbonyl chloride (30 mg, 30 uL, 0.26 mmol) was added to a solution of 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazol-3-amine (37 mg, 0.087 mmol) (see Example 21 for preparation) and DIPEA (34 mg, 46 uL, 0.26 mmol) in CH2Cl2 (10 mL). The reaction mixture was stirred overnight at room temperature. After evaporation of the solvent, the crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 14.3 mg (33%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.41-1.56 (m, 4 H), 1.59 (s, 9 H), 1.76-1.88 (m, 1 H), 1.91-2.01 (m, 1 H), 2.06-2.18 (m, 2 H), 2.17-2.27 (m, 2 H), 2.26-2.37 (m, 1 H), 3.10-3.24 (m, 1 H), 3.25-3.35 (m, 2 H), 3.84-3.95 (m, 2 H), 4.41 (d, J=7.62 Hz, 2 H), 6.87 (d, J=2.93 Hz, 1 H), 7.88 (d, J=8.9 Hz, 1 H), 7.92 (dd, J=8.8, 1.5 Hz, 1 H), 8.18 (d, J=2.93 Hz, 1 H), 8.25 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=499.8; Anal. Calcd for C25H33N5O4S+0.80 TFA+0.20 EtOAc+0.10H2O (612.68): C, 54.11; H, 5.86; N, 11.43. Found: C, 54.12; H, 5.92; N, 11.34.

Provenance & Evidence