반응 #309548

반응 방정식

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

용매

DMF

반응 조건

후처리

1. 1
   온도the reaction was heated at 40° C.
2. 2
   workup.STIRRINGstirred for a further 14 days
3. 3
   기타Again no completed reaction
4. 4
   기타was obtained
5. 5
   기타The solvent was evaporated
6. 6
   세척the residue was washed with water
7. 7
   추출extracted with DCM
8. 8
   건조The organic phase was dried over sodium sulfate
9. 9
   여과filtered
10. 10
    농축concentrated in vacuo
11. 11
    기타The residue was purified by flash column chromatography
12. 12
    세척eluting with DCM/MeOH (90/10)
13. 13
    기타to give
14. 14
    기타after crystallisation from diisopropyl ether

실험 절차

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.

출처