Sulfuric acid magnesium salt (1:1) → HCID 73505017, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-1-(3-amino-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (52.9 mg, 0.179 mmol), cyclopentane-1,3-dione (34.1 mg, 0.348 mmol) and MgSO4 (167.7 mg, 1.393 mmol) in toluene (2 ml) was heated in a sealed 5 ml microwave vial to 150° C. for 1 hr. LCMS shows formation of product. The mixture was poured directly onto silica gel and purified via flash chromatography (Biotage SNAP 10 g, 0-20% MeOH/DCM) to provide (R)-1-(3-((3-oxocyclopent-1-en-1-yl)amino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (3.11 mg, 8.26 μmol, 4.63% yield) as a yellow solid. MS ESI calc'd. For C20H21N6O2 [M+H]+ 377. found 377. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 12.49 (s, 1H), 10.39 (s, 1H), 8.99 (s, 1H), 8.87 (s, 1H), 7.77 (br s, 1H), 1.53 (s, 1H), 7.34 (m, 5H), 7.23 (s, 1H), 6.11 (br s, 1H), 4.86 (t, J=6.5 Hz, 1H), 3.32 (s, 3H, overlaps with H2O peak), 2.81 (s, 2H), 2.26 (s, 2H), 1.40 (d, J=6.8 Hz, 3H).

Provenance & Evidence