Reaktion #531904

Reaktionsgleichung

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

EDCI

HOBt

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

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product

Ausbeute 35.2%

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

Ausbeute 35.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

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