Formaldehyde → HCID 77776214, compound

Participants

Reaction Steps

A mixture of [2S-[2α,4α(R*,S*)]]+[2S-[2α,4α(S*,R*)]]-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-2-[2-[[1-(phenylmethyl)-4-piperidinyl]amino]-1-methylpropyl]-3H-1,2,4-triazol-3-one (0.006 mol) in THF (250 ml) was hydrogenated for 3 days with Pd on activated carbon 10% (2 g) as a catalyst. Then paraformaldehyde (0.006 mol) and thiophene solution 4% (2 ml) were added. Hydrogenation was continued at 50° C. After uptake of H2, the mixture was cooled. The catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanol. The precipitate was filtered off and dried, yielding 3.2 g (68%) of [2S-[2α,4α(R*,S*)]]+[2S-[2α,4α(S*,R*)]]-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-2-[2-[(1-methyl-4-piperidinyl)amino]-1-methylpropyl]-3H-1,2,4-triazol-3-one (compound 64).

Provenance & Evidence