Reaktion #1585113

Reaktionsgleichung

NaOH

N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-ethynylimidazo[1,2-a]pyridine-3-carboxamide

azidomethyl pivalate

sodium ascorbate

→

N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-(1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Lösungsmittel

MeOH

tBuOH H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThen the reaction mixture was diluted
2. 2
   Extraktionextracted with EtOAc
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto afford a residue which
7. 7
   workup.STIRRINGthe reaction mixture was stirred for 30 minutes
8. 8
   SonstigeThe above mixture was purified by HPLC

Vorschrift

A mixture of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-ethynylimidazo[1,2-a]pyridine-3-carboxamide (53) (10 mg, 0.023 mmol), azidomethyl pivalate (3.64 mg, 0.023 mmol), CuSO4(2 μL of 0.5M aqueous solution, 0.001 mmol) and sodium ascorbate (1.4 mg, 0.007 mmol) in tBuOH/H2O (1 mL, 2:1) was stirred at room temperature overnight. Then the reaction mixture was diluted and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated to afford a residue which was dissolved in MeOH (1 mL). Aqueous NaOH (0.6 mL, 1N) was added and the reaction mixture was stirred for 30 minutes. The above mixture was purified by HPLC to give N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-(1H-1,2,3-triazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (F65). MS m/z 477.1 (M+1)+.

Quelle