Formate → HCID 178503849, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,3S,4R,5S,6R)-2-(3-(4-(2-aminoethoxy)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (44, 31 mg, 0.057 mmol) and 3,5-dimethyl-1H-pyrazole-1-carboximidamide nitrate (23 mg, 0.11 mmol) in CH3CN was added DIPEA (30 μL, 0.17 mmol). The reaction was heated at 60° C. for 4 hours, then cooled to room temperature and concentrated under vacuum. The residue was dissolved in MeOH and treated with a few drops of NaOMe (25 wt % in MeOH) for 1 hour. The reaction was concentrated under vacuum, and the residue was purified by prep HPLC (C18 30×100 mm column, 5-40% CH3CN/10 mM aqueous ammonium formate, 45 mL/min) to give urea 46 (9 mg, 34% yield) as the formate salt. 1H NMR (400 MHz, MeOH-d4) δ ppm 7.11-7.20 (m, 3 H), 7.07 (d, J=8.6 Hz, 2 H), 6.81-6.89 (m, 2 H), 4.39 (d, J=9.3 Hz, 1 H), 4.12 (d, J=9.1 Hz, 1 H), 4.08 (t, J=4.9 Hz, 2 H), 3.94 (s, 2 H), 3.58 (t, J=5.1 Hz, 2 H), 3.34-3.48 (m, 3 H), 2.20 (s, 3 H), 2.14 (s, 3 H); MS (ES+) [M+H]+=462.

Provenance & Evidence