Ethanolamine → HCID 57937386, 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 ethanolamine (12 uL, 12 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 1.49-1.65 (m, 2 H), 1.68 (s, 9 H), 1.70-1.86 (m, 4 H), 2.02-2.14 (m, 2 H), 2.19-2.36 (m, 1 H), 3.13 (t, J=5.57 Hz, 2 H), 3.48 (t, J=5.57 Hz, 2 H), 3.64 (dd, J=8.50, 6.35 Hz, 2 H), 3.99 (t, J=8.11 Hz, 2 H), 4.17-4.27 (m, 1 H), 4.55 (d, J=7.42 Hz, 2 H), 7.93 (dd, J=8.79, 1.76 Hz, 1 H), 8.06 (d, J=8.79 Hz, 1 H), 8.17 (d, J=1.37 Hz, 1 H); MS (ESI) (M+H)+=528.3; Anal. Calcd for C24H35F2N5O4S+0.90 TFA+1.0H2O+0.10 EtOAc (658.29): C, 47.99; H, 5.93; N, 10.64. Found: C, 47.99; H, 5.95; N, 10.68.

Provenance & Evidence