Cyclopropylamine → HCID 57937387, compound

Participants

Reaction Steps

Following the same procedure in Example 105, Step A, using 2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-5-[(3-isocyanatoazetidin-1-yl)sulfonyl]-1H-benzimidazole (0.095 mmol) and cyclopropylamine (13 uL, 11 mg, 0.19 mmol) in THF (6.0 mL). The crude product was purified by MPLC using EtOAc/MeOH (20:1) on silica gel to give 22 mg (44%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.29-0.40 (m, 2 H), 0.57-0.66 (m, 2 H), 1.49-1.64 (m, 2 H), 1.67 (s, 9 H), 1.70-1.86 (m, 4 H), 1.99-2.15 (m, 2 H), 2.20-2.31 (m, 1 H), 2.31-2.41 (m, 1 H), 3.65-3.78 (m, 2 H), 3.94-4.06 (m, 2 H), 4.15-4.30 (m, 1 H), 4.55 (d, J=7.42 Hz, 2 H), 7.92 (dd, J=8.69, 1.66 Hz, 1 H), 8.05 (d, J=8.79 Hz, 1 H), 8.18 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=524.3; Anal. Calcd for C25H35F2N5O3S+1.20 TFA+0.60H2O+0.40 EtOAc (711.33): C, 49.64; H, 5.75; N, 9.85. Found: C, 49.62; H, 5.71; N, 9.83.

Provenance & Evidence