Реакция #48203

Уравнение реакции

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

Растворители

methanol

water

Условия реакции

Обработка

1. 1
   Температураto reflux for 30 minutes
2. 2
   Другоеwas removed under reduced pressure and concentrated sodium bicarbonate solution (20 mL) and ethyl acetate (50 mL)
3. 3
   workup.ADDITIONwere added
4. 4
   ДругоеThe organic layer was separated
5. 5
   Сушкаdried over sodium sulphate
6. 6
   Другоеthe solvent was removed under reduced pressure
7. 7
   ТемператураThe resulting white powder was refluxed in to ethyl acetate (10 mL, product
8. 8
   workup.DISSOLUTIONdid not dissolve completely)
9. 9
   ТемператураAfter cooling to room temperature the product
10. 10
    Фильтрацияwas filtered off
11. 11
    Другоеdried under high vacuum

Методика

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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