1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(cyclopropylmethyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-(1-phenylprop-2-en-1-yl)pent-4-enamide

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Reaction Conditions

Reaction Steps

To a solution of (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pent-4-enoic acid (4b) (166 mg) in DCM (1 mL) at −20° C. under N2 was added a mixture of EDAC.HCl (156 mg) and DMAP (3 mg) in DCM (1 mL) portionwise. This mixture stirred for ten min. before N-(cyclopropylmethyl)-1-phenylprop-2-en-1-amine (4a) (127 mg) in DCM (0.5 mL) was added dropwise. The reaction mixture was stirred for 1 h at −20° C. and 3 h at RT, then diluted with DCM (50 mL) and washed with 0.2 N HCl, saturated NaHCO3, brine, dried (Na2SO4), filtered, and evaporated. The crude product was purified via flash chromatography (5% then 10% EtOAc/hexanes) to give the desired product (214 mg, 76%). 1H NMR (300 MHz) The NMR of this compound in both CDCl3 and DMSO-d6 (with elavated temperatures) was complex, thus limiting interpretation. MS APCI, m/z=415 (M+1). LC/MS 2.86 min., Method A.

Provenance & Evidence