Cyclopropanecarbonyl chloride → HCID 57937330, compound

Participants

Reaction Steps

Cyclopropane carbonylchloride (16 uL, 19 mg, 0.18 mmol) was added to a solution of 1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)azetidin-3-amine (52 mg, 0.12 mmol) (see Example 102 for preparation) and DIPEA (41 uL, 31 mg, 0.24 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred for 4 h at room temperature, diluted with EtOAc (50 mL), washed with NaHCO3 (2×10 mL) and dried over Na2SO4. The crude product was purified by MPLC using Hex/EtOAc (1:4) on silica gel to give 60 mg (99%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.66-0.71 (m, 2 H), 0.71-0.77 (m, 2 H), 1.38-1.48 (m, 1 H), 1.51-1.64 (m, 2 H), 1.65 (s, 9 H), 1.68-1.86 (m, 4 H), 1.99-2.13 (m, 2 H), 2.19-2.35 (m, 1 H), 3.67 (dd, J=8.69, 6.15 Hz, 2 H), 4.00 (dd, J=8.8, 7.8 Hz, 2 H), 4.23-4.37 (m, 1 H), 4.53 (d, J=7.62 Hz, 2 H), 7.90 (dd, J=8.79, 1.76 Hz, 1 H), 8.03 (d, J=8.59 Hz, 1 H), 8.16 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=509.3; Anal. Calcd for C25H34F2N4O3S+1.20 TFA+0.1H2O (647.26): C, 50.85; H, 5.51; N, 8.66. Found: C, 50.81; H, 5.52; N, 8.43.

Provenance & Evidence