Reacción #309548

Ecuación de reacción

1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

Intermediate 4

1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

ethyl 2-amino-1,3-oxazole-5-carboxylate

HOBt

EDCI

NEt3

EDCI

HOBt

→

Ethyl 2-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-oxazole-5-carboxylate

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction was heated at 40° C.
2. 2
   workup.STIRRINGstirred for a further 14 days
3. 3
   OtroAgain no completed reaction
4. 4
   Otrowas obtained
5. 5
   OtroThe solvent was evaporated
6. 6
   Lavadothe residue was washed with water
7. 7
   Extracciónextracted with DCM
8. 8
   SecadoThe organic phase was dried over sodium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated in vacuo
11. 11
    OtroThe residue was purified by flash column chromatography
12. 12
    Lavadoeluting with DCM/MeOH (90/10)
13. 13
    Otroto give
14. 14
    Otroafter crystallisation from diisopropyl ether

Procedimiento

A mixture of 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (Intermediate 4) (1 g, 3.4 mmol), ethyl 2-amino-1,3-oxazole-5-carboxylate (0.82 g, 5.2 mmol), HOBt (0.708 g, 5.2 mmol), EDCI (1.005 g, 5.2 mmol) and NEt3 (730 μL, 5.2 mmol) in DMF (50 mL) was stirred at room temperature for 2 days. The reaction was not completed and 2.5 eq of EDCI and HOBt were added and the reaction was heated at 40° C. and stirred for a further 14 days. Again no completed reaction was obtained. The solvent was evaporated and the residue was washed with water and extracted with DCM. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with DCM/MeOH (90/10) to give after crystallisation from diisopropyl ether, the title compound as a yellow solid (98 mg, 6%). LC/MS: m/z 424 (M+H)+. Rt: 3.17 min.

Fuente