반응 #48203

반응 방정식

benzoic acid 2-chloro-5-{[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]methyl}-phenyl ester

sodium methoxide

→

4-[(4-Chloro-3-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

용매

methanol

water

반응 조건

후처리

1. 1
   온도to reflux for 30 minutes
2. 2
   기타was removed under reduced pressure and concentrated sodium bicarbonate solution (20 mL) and ethyl acetate (50 mL)
3. 3
   workup.ADDITIONwere added
4. 4
   기타The organic layer was separated
5. 5
   건조dried over sodium sulphate
6. 6
   기타the solvent was removed under reduced pressure
7. 7
   온도The resulting white powder was refluxed in to ethyl acetate (10 mL, product
8. 8
   workup.DISSOLUTIONdid not dissolve completely)
9. 9
   온도After cooling to room temperature the product
10. 10
    여과was filtered off
11. 11
    기타dried under high vacuum

실험 절차

A solution of benzoic acid 2-chloro-5-{[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]methyl}-phenyl ester (CAB02139, 1.13 g, 2.63 mmol) and sodium methoxide (500 mg) in methanol (20 mL) and water (5 mL) was heated to reflux for 30 minutes. After cooling to room temperature most of the solvent was removed under reduced pressure and concentrated sodium bicarbonate solution (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, dried over sodium sulphate and the solvent was removed under reduced pressure. The resulting white powder was refluxed in to ethyl acetate (10 mL, product did not dissolve completely). After cooling to room temperature the product was filtered off and dried under high vacuum. Yield-412 mg (48%) white powder. 1H-NMR (400 MHz, d6-DMSO) δ=4.97 (s, 2H), 6.71-6.75 (m, 3H), 6.84 (d, J=2.0 Hz, 1H), 7.25 (d, J=8.2 Hz, 1H), 7.75 (d, J=9.0 Hz, 2H), 8.76 (s, 2H), 10.21 (s, 1H, —OH). LRMS (FAB+): 326.1 (100, [M+H]+).

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