Réaction #71640

Équation de réaction

D2

N-(4-Fluorophenyl)-4-piperidinamine

trisamine

isocyanate

D48

2-{4-[((3R,5S)-4-{[(1,1-Dimethylethyl)oxy]carbonyl}-3,5-dimethyl-1-piperazinyl)methyl]phenyl}-2-methylpropanoic Acid

DCC

1-hydroxybenzotriazole

→

1,1-dimethylethyl (2R,6S)-4-{[4-(2-{4-[(4-fluorophenyl)amino]-1-piperidinyl}-1,1-dimethyl-2-oxoethyl)phenyl]methyl}-2,6-dimethyl-1-piperazinecarboxylate

Solvants

DMF DCM

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was shaken for 2 h
2. 2
   Filtrationfiltered
3. 3
   Concentrationconcentrated

Mode opératoire

A mixture of D48 (100 mg, 0.256 mmol), polymer-supported DCC (296 mg, 1.3 mmol/g, 0.385 mmol) and 1-hydroxybenzotriazole (18 mg, 0.128 mmol) in 1:4 DMF/DCM (5 ml) was treated with D2 (50 mg, 0.256 mmol) and the mixture stirred overnight. Scavenger resins (PS-trisamine, PS-isocyanate and Si-carbonate) were added, the mixture was shaken for 2 h and then filtered and concentrated to give 1,1-dimethylethyl (2R,6S)-4-{[4-(2-{4-[(4-fluorophenyl)amino]-1-piperidinyl}-1,1-dimethyl-2-oxoethyl)phenyl]methyl}-2,6-dimethyl-1-piperazinecarboxylate, MS (ES): MH+ 567. This whole was treated with 4M HCl in 1,4-dioxane (2 ml) for 1 h. The solvents were removed in vacuo to give the dihydrochloride salt of the title compound (115 mg). MS (ES): MH+ 467.

Source