Ethylamine → HCID 57937301, compound

Participants

Reaction Steps

A solution of 2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-5-[(3-isocyanatoazetidin-1-yl)sulfonyl]-1H-benzimidazole in THF (4.0 mL, 0.095 mmol) (see following step B for preparation) was added to a solution of ethylamine (100 uL, 2.0 M in THF, 0.2 mmol) in THF (2.0 mL). The reaction mixture was stirred for 4 h at room temperature, diluted with EtOAc (50 mL), washed with NaHCO3 (2×5 mL) and dried over Na2SO4. The crude product was purified by MPLC using EtOAc/MeOH (20:1) on silica gel to give 21 mg (44%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.02 (t, J=7.13 Hz, 3 H), 1.51-1.64 (m, 2 H), 1.66 (s, 9 H), 1.69-1.87 (m, 4 H), 2.01-2.15 (m, 2 H), 2.21-2.37 (m, 1 H), 3.04 (q, J=7.16 Hz, 2 H), 3.62 (dd, J=8.11, 6.74 Hz, 2 H), 3.99 (t, J=8.10 Hz, 2 H), 4.16-4.29 (m, 1 H), 4.54 (d, J=7.62 Hz, 2 H), 7.90 (dd, J=8.59, 1.56 Hz, 1 H), 8.03 (d, J=8.59 Hz, 1 H), 8.17 (d, J=1.76 Hz, 1 H); MS (ESI) (M+H)+=512.3; Anal. Calcd for C24H35F2N5O3S+1.40 TFA+0.50H2O (680.28): C, 47.32; H, 5.54; N, 10.29. Found: C, 47.36; H, 5.57; N, 10.32.

Provenance & Evidence