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

Participants

Reaction Steps

To a suspension of 109b (95 mg, 0.106 mmol) at 0° C. in methanol (5 mL) was added sodium borohydride (24 mg, 0.636 mmol) and the mixture was stirred for 30 minutes. Then the reaction mixture was quenched with water (1.0 mL) and concentrated. The residue was purified by reverse-phase prep-HPLC to afford 109 (13.5 mg, 18.7%). LCMS: [M+H]+ 681. 1H NMR (500 MHz, CDCl3) δ 8.76 (s, 1H), 8.65 (d, J=2.0, 1H), 8.61 (s, 1H), 8.32 (d, J=2.5, 1H), 7.96 (d, J=3.0, 1H), 7.82 (s, 1H), 7.56-7.58 (m, 2H), 7.40 (d, J=2.0, 1H), 7.28-7.31 (m, 1H), 6.81 (d, J=9.0, 1H), 4.61-4.70 (m, 4H), 4.43 (s, 2H), 3.95 (s, 1H), 3.72 (s, 3H), 3.45-3.53 (m, 2H), 3.07 (t, J=5.25, 2H), 2.43-2.56 (m, 3H), 2.18-2.22 (m, 1H), 1.43 (s, 9H), 0.99 (d, J=6.5, 3H)

Provenance & Evidence