تفاعل #309548

معادلة التفاعل

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

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction was heated at 40° C.
2. 2
   workup.STIRRINGstirred for a further 14 days
3. 3
   أخرىAgain no completed reaction
4. 4
   أخرىwas obtained
5. 5
   أخرىThe solvent was evaporated
6. 6
   غسيلthe residue was washed with water
7. 7
   استخلاصextracted with DCM
8. 8
   تجفيفThe organic phase was dried over sodium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated in vacuo
11. 11
    أخرىThe residue was purified by flash column chromatography
12. 12
    غسيلeluting with DCM/MeOH (90/10)
13. 13
    أخرىto give
14. 14
    أخرىafter crystallisation from diisopropyl ether

الإجراء التجريبي

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.

المصدر