Acetic Acid → 1207830-66-7

Temperatur

22 °C

1M TBAF in THF (5.11 mL, 5.11 mmol) was added to (2S)-2-(1-(2-chloro-6-cyanophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-methylpyrazin-2-yl)-3-((R)-1-(triisopropylsilyloxy)propan-2-yloxy)propanamide (Intermediate AZ1) (3.4 g, 5.11 mmol) and acetic acid (0.307 g, 5.11 mmol) in THF (35 mL). The resulting solution was stirred at 22° C. for 20 hours. It was quenched with NH4Cl solution (sat., 25 mL) and diluted with EtOAc (50 mL). The organic phase was washed with saturated sodium bicarbonate (25 mL), water (20 mL), brine (20 mL), dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with EtOAc to afford the product (2.23 g, 85%). This was crystallised from EtOAc (10 mL) and iso-hexane (6 mL) to give the desired product as a white crystalline powder (1.9 g, 73%) confirmed to be of the same crystalline form as that described previously.

1. customIt was quenched with NH4Cl solution (sat., 25 mL)
2. additiondiluted with EtOAc (50 mL)
3. washThe organic phase was washed with saturated sodium bicarbonate (25 mL), water (20 mL), brine (20 mL)
4. dry with materialdried (MgSO4)
5. customevaporated
6. customThe crude product was purified by flash silica chromatography
7. washeluting with EtOAc

ORD-Eintrag

ord-251ce15b4f5b46e28d96471dce28fb07

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08143263B2