1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500660, compound

Participants

Reaction Conditions

Reaction Steps

3-Pyridyl isothiocyanate (41 mg, 0.3 mmol) was added in one portion to a suspension of methyl [trans-4-(4-{[hydrazino(oxo)acetyl]amino}-phenyl)cyclohexyl]acetate (Intermediate 43, 100 mg, 0.3 mmol) in CH3CN (5 mL) and the reaction mixture was heated at 80° C. for 10 minutes in the microwave and then cooled to room temperature. EDCI (58 mg, 0.3 mmol) was added in one portion and the reaction mixture was heated to 90° C. for 20 minutes. The mixture was cooled to room temperature and filtered to leave a solid. The solid was washed with CH3CN (5 mL) to give the title compound (90 mg, 69%) as a solid; 1H NMR δ 1.12-1.18 (2H, m), 1.45 (2H, q), 1.80 (5H, m), 2.24-2.26 (2H, d), 2.42-2.48 (1H, m), 3.61 (3H, s), 7.23 (2H, d), 7.43-7.46 (1H, m), 7.69-7.71 (2H, m), 8.06-8.09 (1H, m), 8.28-8.29 (1H, m), 8.78 (1H, d), 10.95 (1H, s), 11.22 (1H, s); MS m/e MH+ 436.

Provenance & Evidence