Reacción #531904

Ecuación de reacción

3-(3,4-difluorophenyl)-2-(4-fluorophenyl)acrylic acid

EDCI

HOBt

4-(aminomethyl)-N-(2-aminophenyl)benzamide

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product

Rendimiento 35.2%

N-(2-aminophenyl)-4-((3-(3,4-difluorophenyl)-2-(4-fluorophenyl)acrylamido)methyl)benzamide

Rendimiento 35.2%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónSubsequently it was concentrated under reduced pressure to half the volume
2. 2
   workup.ADDITIONthe resulted solution was poured into water
3. 3
   Otroformed
4. 4
   Filtraciónwas filtered
5. 5
   Lavadowashed with water

Procedimiento

To a solution of 3-(3,4-difluorophenyl)-2-(4-fluorophenyl)acrylic acid (0.5 g, 1.7 mmol) in DMF (5 mL) was added TEA (0.75 mL, 5.4 mmol), EDCI (0.68 g, 3.5 mmol), HOBt (0.25 g, 1.8 mmol) followed by the 4-(aminomethyl)-N-(2-aminophenyl)benzamide (0.52 g, 1.9 mmol). The reaction mixture was stirred at room temperature for 12 hours. Subsequently it was concentrated under reduced pressure to half the volume and the resulted solution was poured into water. Upon standing a white precipitate formed, was filtered, washed with water followed by ether gave the pure product (0.3 g, 30% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 4.41 (2H, d, CH2), 4.88 (2H, s, NH2), 6.59 (1H, t, Ar—H), 6.77 (1H, d, Ar—H), 6.88 (1H, s, Ar—H), 6.96 (2H, m, Ar—H), 7.16 (1H, d, Ar—H), 7.24-7.38 (7H, m, Ar—H), 7.47 (1H, s, ═CH), 7.92 (2H, d, Ar—H), 8.14 (1H, t, NH), 9.61 (1H, s, NH). MS m/z: 502.1 (M++1).

Fuente