4-[5-(4-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester → N-(4-tert-Butyl-phenyl)-6-piperazin-1-yl-nicotinamide
Reaktionsgleichung
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:32])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:20](=[O:32])[C:17]2[CH:18]=[CH:19][C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:15][CH:16]=2)=[CH:27][CH:26]=1)([CH3:31])([CH3:29])[CH3:30]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
4-[5-(4-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (200 mg, 0.45 mmol) was dissolved at rt in a mixture of 30% TFA in CH2Cl2. The reaction mixture was stirred until TLC indicated consumption of starting material (30 min). The mixture was then partitioned between EtOAc and water. The water layer was basified with solid NaOH to pH 12. The organic layer was separated and the aqueous layer was extracted again with EtOAc. The combined organic layer was washed with water, dried over Na2SO4, filtered and concentrated to afford the product (89 mg, Yield: 56%). HRMS m/z calcd for C20H26N4O [M+H]+: 339.2180. Found: 339.2180.