Reaktion #494798

Reaktionsgleichung

103c

2-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-5-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)nicotinaldehyde

NaBH4

→

103

Ausbeute 38.0%

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

Ausbeute 38.0%

Lösungsmittel

CH3OH

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenIt was then concentrated under reduced pressure and water (10 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   ExtraktionThe resulting mixture was extracted with CH2Cl2 (10 mL×2)
4. 4
   ExtraktionThe combined CH2Cl2 extract
5. 5
   Einengenwas concentrated under reduced pressure
6. 6
   Sonstigethe residue was purified with reverse-phase prep-HPLC

Vorschrift

A mixture of 103c (120 mg, 0.18 mmol), NaBH4 (21 mg, 0.54), and CH3OH (10 mL) was stirred at 25° C. for 1 h. It was then concentrated under reduced pressure and water (10 mL) was added. The resulting mixture was extracted with CH2Cl2 (10 mL×2). The combined CH2Cl2 extract was concentrated under reduced pressure and the residue was purified with reverse-phase prep-HPLC to afford 103 (45 mg, 38%). LCMS: [M+H]+ 667. 1H NMR (500 MHz, CDCl3) δ 8.66-8.68 (m, 2H), 8.35 (s, 1H), 7.96 (d, J=3.0, 1H), 7.81 (s, 1H), 7.65 (d, J=2.5, 1H), 7.55-7.59 (m, 3H), 6.83 (d, J=8.5, 1H), 4.71-4.74 (m, 4H), 4.51-4.52 (m, 2H), 4.07-4.08 (m, 1H), 3.73 (s, 3H), 3.56 (s, 1H), 3.20-3.22 (m, 4H), 2.56-2.58 (m, 4H), 1.59 (s, 9H)

Quelle