Reaktion #2289928

Reaktionsgleichung

compound 8-3

ethyl trans-4-(4-((3,5-difluorobenzyl)(2-oxo-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)ethyl)carbamoyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)cyclohexanecarboxylate

HCl

→

compound

Ausbeute 17.3%

trans-4-(4-((3,5-difluorobenzyl)(2-oxo-2-(1H-pyrazol-3-yl)ethyl)carbamoyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)cyclohexanecarboxylic acid

Ausbeute 17.3%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in 1,4-dioxane (2 mL)
3. 3
   workup.ADDITIONNH4OH (0.5 mL) was added
4. 4
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 2 h
5. 5
   SonstigeThe solvent was removed under reduced pressure
6. 6
   Sonstigethe residue was purified by reverse phase column chromatography (C18 silica gel, 70% CH3CN/water as eluent)

Vorschrift

To a stirred solution of compound 8-3 (75 mg, 0.107 mmol) in 1,4-dioxane (2 mL) was added HCl (12 M, 0.5 mL). The mixture was stirred at 80° C. for 2 h. The solvent was removed under reduced pressure. The residue was dissolved in 1,4-dioxane (2 mL) and NH4OH (0.5 mL) was added. The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure and the residue was purified by reverse phase column chromatography (C18 silica gel, 70% CH3CN/water as eluent) to provide the compound of example 8 (10 mg, 16%) as a white solid. 1H NMR (CD3OD) rotamers present δ 7.74-7.50 (2H, m); 6.98-6.95 (1H, m); 6.87-6.78 (3H, m); 5.00 and 4.78 (2H, 2×s); 4.74 and 4.64 (2H, 2×s); 4.28-4.21 (1H, m); 2.36-2.28 (1H, m); 2.17-2.09 (2H, m); 2.02-1.93 (4H, m); 1.62-1.55 (2H, m); LCMS (APCI): 540 (M+H)+.

Quelle