Reaktion #87815

Reaktionsgleichung

2-fluoro benzoic acid

thionyl chloride

5-(5-(aminomethyl)-2-chloro-4-fluorophenyl)-2-(4-chlorophenyl)-2H-1,2,4-triazol-3 (4H)-one

DIPEA

→

desired product

Ausbeute 9.5%

N-(4-Chloro-5-(1-(4-chlorophenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)-2-fluorobenzamide

Ausbeute 9.5%

Lösungsmittel

DMF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 5 h and excess of solvent
2. 2
   Sonstigewas removed under reduced pressure
3. 3
   Sonstigeto obtain crude product
4. 4
   SonstigeThe obtained crude product
5. 5
   SonstigeAfter completion of reaction, reaction mass
6. 6
   Sonstigewas quenched with water
7. 7
   Extraktionextracted with ethyl acetate
8. 8
   SonstigeThe organic layer was separated
9. 9
   Einengenconcentrated

Vorschrift

A mixture of 2-fluoro benzoic acid (0.400 g), thionyl chloride (20 mL) and DMF (cat. amt.) was refluxed for 5 h and excess of solvent was removed under reduced pressure to obtain crude product. The obtained crude product was added to the solution of 5-(5-(aminomethyl)-2-chloro-4-fluorophenyl)-2-(4-chlorophenyl)-2H-1,2,4-triazol-3 (4H)-one (Intermediate-78, 0.250 g) and DIPEA (1.0 mL) in THF (20 mL) and the reaction mass was stirred for 3 h. After completion of reaction, reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was separated, concentrated to afford 0.032 g of the desired product. 1H NMR (300 MHz, DMSO): δ 4.53 (br s, 2H), 7.29 (m, 2H), 7.70 (m, 3H), 7.78 (m, 3H), 7.95 (br s, 2H), 8.94 (br s, 1H), 12.63 (br s, 1H); MS (m/z): 475.39 (M+H)+.

Quelle