Water → HCID 67385665, compound

Participants

Reaction Steps

250 mg (0.62 mmol) of (E)-methyl 3-(3-amino-4-(2-(diethylamino)ethylthio)-phenyl)acrylate was suspended in acetonitrile (5 mL) and to this solution, 3-phenylpropionaldehyde (108 mg, 0.8 mmol) was added under stirring. Then, sodium triacetoxyborohydride (636 mg, 3 mmol) was added and the resulted mixture was stirred at room temperature for 3-60 hours. Water and ethyl acetate was added after removing the solvent—acetonitrile. Collecting organic layers and drying it, 229 mg of (E)-methyl 3-(4-(2-(diethylamino)ethylthio)-3-(3-phenylpropylamino)phenyl)acrylate was obtained in a form of an oily product after being purified by chromatography. Yield: 86.6%. TLC: Rf=0.6 (DCM:MeOH=9:1). HPLC: 91%; tR=9.90 min (LC/PDA: Diamonsil C18.5μ 150×4.6 mm, flow rate 1.0 mL/min, grade: 10-100% B, 18 minutes; mobile phase A: H2O; mobile phase B: acetonitrile; UV254). MS (m/z): 427 (MH)+.

Provenance & Evidence