Hydrazine hydrate (1:1) → HCID 73504797, compound

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Reaction Steps

(R)-1-(3-(1,3-Dioxoisoindolin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (114 mg, 0.267 mmol) was dissolved in DMA (1 mL) and methanol (1 mL), charged with powdered Selectfluor® (108 mg, 0.305 mmol), and stirred at room temperature for 20 h. The solvents were concentrated in vacuo and the residue was purified by flash chromatography (3-15% MeOH/DCM). The crude mixture obtained was then dissolved in EtOH (3 mL), charged with hydrazine hydrate (0.130 mL, 2.67 mmol), and heated to 85° C. for 30 min. The solvents were concentrated in vacuo and the residue was purified by mass-triggered reverse phase HPLC followed by purification via flash chromatography (2-10% MeOH/DCM) to give (R)-1-(3-amino-7-fluoro-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C15H15FN6O [M+1]+ 315. found 315. 1H NMR (500 MHz, DMSO-d6) δ 8.55 (s, 1H), 7.42-7.34 (m, 4H), 7.27 (m, 1H) 5.07 (q, J=6.7 Hz, 1H), 1.58 (d, J=7.0 Hz, 4H).

Provenance & Evidence