Reacción #420247

Ecuación de reacción

(E)-4,4,5,5,5-Pentafluoropent-2-enoic acid

HBTU

triethylamine

N-(2-methyl-4-quinolyl)propane-1,3-diamine hydrochloride

aluminium oxide

→

(E)-4,4,5,5,5-Pentafluoro-N-[3-[(2-methyl-4-quinolyl)amino]propyl]pent-2-enamide

Disolventes

DMF

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for one hour
4. 4
   Filtraciónthe mixture was filtered
5. 5
   Otrothe filtrate was evaporated to dryness under reduced pressure
6. 6
   OtroThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
7. 7
   Otroto yield 28.4 mg (0.076 mmol, 38%)

Procedimiento

(E)-4,4,5,5,5-Pentafluoropent-2-enoic acid (38 mg, 0.2 mmol) and HBTU (76 mg, 0.2 mmol) were dissolved in a 1:1 mixture of anhydrous DMF and anhydrous acetonitrile (2 ml), after 5 minutes triethylamine (82 μl, 0.6 mmol) and N-(2-methyl-4-quinolyl)propane-1,3-diamine hydrochloride (48 mg, 0.24 mmol) was added and stirring was continued for 3 hours. To the mixture basic aluminium oxide was added, stirring was continued for one hour, the mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 28.4 mg (0.076 mmol, 38%).

Fuente