Sodium borohydride → (R)-6-tert-Butyl-8-fluoro-2-(3-(hydroxymethyl)-4-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazine-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)phthalazin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 106b (90.0 mg, 0.13 mmol) in MeOH (10 mL) was added NaBH4 (15.0 mg, 0.39 mmol). The mixture was stirred at 20° C. for 2 h. It was then evaporated and the residue was purified by reverse-phase prep-HPLC to afford 106 (7.3 mg, 8%) as a white solid. LCMS: (M+H)+ 681.4. 1H NMR (500 MHz, DMSO) δ 8.63 (d, J=2.5, 1H), 8.57 (d, J=5.0, 1H), 8.54 (d, J=2.0, 1H), 8.47 (s, 1H), 7.91 (s, 1H), 7.86 (d, J=3.0, 1H), 7.78 (d, J=12.5, 1H), 7.53 (d, J=5.0, 1H), 7.47 (d, J=2.0, 1H), 7.36-7.39 (m, 1H), 7.25 (d, J=9.5, 1H), 4.90 (s, 1H), 4.54-4.58 (m, 2H), 4.47 (t, J=6.0, 1H), 4.39-4.43 (m, 3H), 3.69 (s, 1H), 3.61 (s, 3H), 3.37-3.42 (m, 1H), 3.09-3.11 (m, 1H), 2.95 (t, J=9.0, 1H), 2.54-2.56 (m, 1H), 2.30-2.37 (m, 2H), 2.19 (t, J=8.0, 1H), 1.39 (s, 9H), 0.94-0.93 (d, J=6.5, 3H)

Provenance & Evidence