Reaktion #2021773

Reaktionsgleichung

thiophene

compound 37

2-(2-amino-1-methylpropyl)-4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

benzaldehyde

→

4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[2-[(phenylmethyl)amino]-1-methylpropyl]-3H-1,2,4-triazol-3-one

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationAfter uptake of hydrogen, the catalyst was filtered off
2. 2
   Sonstigethe filtrate was evaporated
3. 3
   SonstigeThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2)
4. 4
   SonstigeThe pure fractions were collected
5. 5
   Sonstigethe solvent was evaporated
6. 6
   SonstigeThe residue was triturated in DIPE and 2-propanol
7. 7
   Filtrationfiltered off
8. 8
   Sonstigedried

Vorschrift

A mixture of compound 37 (0.0029 mol) and benzaldehyde (0.0029 mol) in methanol (250 ml) was hydrogenated at 50° C. overnight with Pd on activated carbon 10% (2 g) as a catalyst in the presence of thiophene solution (2 ml). After uptake of hydrogen, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated. The residue was triturated in DIPE and 2-propanol, filtered off and dried, yielding 1.1 g (48%) of [2S-[2α,4α(S*,R*)]]-4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[2-[(phenylmethyl)amino]-1-methylpropyl]-3H-1,2,4-triazol-3-one (compound 106; mp. 154.3° C.).

Quelle