3,3-Difluoroazetidine → HCID 23660484, compound

Participants

Reaction Steps

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (90 mg, 0.24 mmol), 3,3-difluoroazetidine (45 mg, 0.49 mmol) and DMAP (59 mg, 0.49 mmol) in MeCN (10 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 68 mg (66%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.46-1.63 (m, 4 H), 1.65 (s, 9 H), 2.27-2.44 (m, 1 H), 3.30-3.39 (m, 2 H), 3.89-3.98 (m, 2 H), 4.20 (t, J=12.30 Hz, 4 H), 4.51 (d, J=7.62 Hz, 2 H), 7.93 (dd, J=8.69, 1.66 Hz, 1 H), 8.05 (d, J=8.79 Hz, 1 H), 8.19 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=427.8; Anal. Calcd for C20H27F2N3O3S+1.10 TFA+0.3 CH3CN (565.26): C, 48.45; H, 5.17; N, 8.18. Found: C, 48.42; H, 4.86; N, 8.20.

Provenance & Evidence