تفاعل #48203

معادلة التفاعل

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

المذيبات

methanol

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto reflux for 30 minutes
2. 2
   أخرىwas removed under reduced pressure and concentrated sodium bicarbonate solution (20 mL) and ethyl acetate (50 mL)
3. 3
   workup.ADDITIONwere added
4. 4
   أخرىThe organic layer was separated
5. 5
   تجفيفdried over sodium sulphate
6. 6
   أخرىthe solvent was removed under reduced pressure
7. 7
   درجة الحرارةThe resulting white powder was refluxed in to ethyl acetate (10 mL, product
8. 8
   workup.DISSOLUTIONdid not dissolve completely)
9. 9
   درجة الحرارةAfter cooling to room temperature the product
10. 10
    ترشيحwas filtered off
11. 11
    أخرىdried under high vacuum

الإجراء التجريبي

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]+).

المصدر