Reaktion #1112784

Reaktionsgleichung

1-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-formyl-phenyl]-3-[4-(1-hydroxy-1-methyl-ethyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide

sodium borohydride

→

1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(1-hydroxy-1-methyl-ethyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide

Ausbeute 91.2%

Lösungsmittel

methanol

dichloromethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(rotary evaporator)
2. 2
   workup.STIRRINGwater (30 ml) and shaken in a separatory funnel
3. 3
   SonstigeThe organic phase was collected
4. 4
   Extraktionthe aqueous phase was back extracted with dichloromethane (2×25 ml)
5. 5
   Trocknendried from magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   SonstigeThe crude was purified by silica gel chromatography (1 g, eluting with 7.5% methanol in dichloromethane)

Vorschrift

1-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-formyl-phenyl]-3-[4-(1-hydroxy-1-methyl-ethyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide (34 mg, 0.06 mmol) was dissolved in a solution of 1:1 methanol and dichloromethane (15 ml). To this was added a solution of sodium borohydride (11 mg, 0.29 mmol) dissolved in water (0.25 ml), via drop-wise addition. After 10 minutes stirring the volatiles were stripped (rotary evaporator) and the remainder was taken up in dichloromethane (30 ml) and water (30 ml) and shaken in a separatory funnel. The organic phase was collected and the aqueous phase was back extracted with dichloromethane (2×25 ml). The organic extracts were combined, dried from magnesium sulfate, filtered and stripped. The crude was purified by silica gel chromatography (1 g, eluting with 7.5% methanol in dichloromethane) providing the desired product 1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-3-[4-(1-hydroxy-1-methyl-ethyl)-phenylamino]-1H-pyrazole-4-carboxylic acid amide as an off-white powder (32 mg). LC/MS calcd for C32H33FN6O4 (m/e) 584.66, obsd 583 (M−H, ES−).

Quelle