Reaktion #2289925

Reaktionsgleichung

compound 5-5

1-(trans-4-(((tert-butyldimethylsilyl)oxy)carbamoyl)cyclohexyl)-N-(2-(3,5-dichloropyridin-4-yl)-2-oxoethyl)-N-(3,5-difluorobenzyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide

TBAF

→

compound

Ausbeute 23.0%

N-(2-(3,5-dichloropyridin-4-yl)-2-oxoethyl)-N-(3,5-difluorobenzyl)-1-(trans-4-(hydroxycarbamoyl)cyclohexyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide

Ausbeute 23.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with MeOH (2 mL)
2. 2
   Extraktionextracted with EtOAc (2×20 mL)
3. 3
   WaschenThe combined organic layers were washed with brine (2×10 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography (silica gel, 7% MeOH/DCM as eluent)

Vorschrift

To a stirred solution of compound 5-5 (100 mg, 0.13 mmol) in THF (8 mL) was added TBAF (1 M in THF, 0.20 mL, 0.20 mmol) dropwise and the mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with MeOH (2 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine (2×10 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 7% MeOH/DCM as eluent) to provide the compound of example 5 (19 mg, 22%) as a white solid. 1H NMR (CDCl3) rotamers present δ 8.54 and 8.48 (2H, 2×s); 7.64 and 7.60 (1H, 2×s); 6.84-6.68 (3H, m); 4.82-4.25 (5H, m); 2.23-2.04 (7H, m); 1.83-1.73 (2H, m); LCMS (APCI): 634 (M+H)+.

Quelle