Methylamine → HCID 23660829, compound

Participants

Reaction Steps

Following the same procedure in Example 24, Step A, using HATU (37 mg, 0.09 mmol), methylamine in THF (0.07 mL, 2M, 0.14 mmol), DIPEA (0.02 mL, 0.10 mmol) and 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acid (40 mg, 0.09 mmol) (see following step B for preparation) in DMF (5 mL). The crude product was purified by MPLC on silica gel using EtOAc/DCM (1:1) to provide the title compound as a white solid. The product was converted to its TFA salt. Yield: 15 mg (29%); 1H NMR (400 MHz, CD3OD) δ 1.38-1.46 (m, 2 H), 1.46-1.54 (m, 2 H), 1.54-1.59 (s, 9 H), 2.22-2.36 (m, 1 H), 2.83 (s, 3 H), 3.25-3.35 (m, 2 H), 3.89 (dd, J=11.43, 3.61 Hz, 2 H), 4.36 (d, J=7.42 Hz, 2 H), 7.79 (d, J=8.59 Hz, 1 H), 7.90 (dd, J=8.69, 1.86 Hz, 1 H), 8.01 (s, 1 H), 8.29 (d, J=1.95 Hz, 1 H), 8.72 (s, 1 H); MS (ESI) (M+H)+=459.8; Anal. Calcd for C22H29N5O4S+0.1H2O: C, 57.27; H, 6.38; N, 15.18. Found: C, 57.49; H, 6.55; N, 14.34.

Provenance & Evidence