1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 69211211, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pent-4-enoic acid (361 mg), EDAC.HCl (408 mg), and dimethyl aminopyridine (8 mg) in DCM (4 ml) at −20° C. under N2 was added a solution of N-[(1S)-1-phenylprop-2-en-1-yl]cyclopentanamine in DCM (3 ml). The mixture was allowed to stir at −20° C. for 1 hr then RT overnight. The next day the reaction was diluted with DCM and extracted with 0.1 N HCl. The aqueous layer was back extracted with DCM (×2). All organics were combined, dried (Na2SO4), filtered and evaporated. The resulting residue was purified by column chromatography (10% EtAOc/Hexane) to afford a mixture (85:15) (SS:RS) of the title compound and it's diasteromer (2R)-N-cyclopentyl-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-[(1S)-1-phenylprop-2-en-1-yl]pent-4-enamide (249 mg) as determined by NMR. 1H NMR (300 MHz, d6-DMSO at 110° C.) δ 1.10-2.12 (m, H9), 2.38-3.15 (m, 2H), 4.88-5.21 (m, 4H), 5.30-5.45 (m, 3H), 5.70-5.90 (m, 1H), 6.00-6.18 (m, 1H), 6.21-6.38 (m, 0.17H), 6.95-7.12 (m, 1H), 7.19-7.41 (m, 5H), 7.18-7.95 (m, 4H). MS APCI, m/z=429 (M+1), LC/MS, 3.04 min.

Provenance & Evidence