Réaction #531904

Équation de réaction

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

EDCI

HOBt

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

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product

Rendement 35.2%

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

Rendement 35.2%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   ConcentrationSubsequently it was concentrated under reduced pressure to half the volume
2. 2
   workup.ADDITIONthe resulted solution was poured into water
3. 3
   Autreformed
4. 4
   Filtrationwas filtered
5. 5
   Lavagewashed with water

Mode opératoire

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).

Source