1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178472467, compound

Participants

Reaction Steps

Hydrazine monohydrate (32 μL, 0.65 mmol) was added in one portion to a stirred solution of ethyl cis-4-(4-{[methoxy(oxo)acetyl]amino}phenoxy)cyclohexanecarboxylate (Intermediate 108) (188 mg, 0.54 mmol) in EtOH (3 mL) and the reaction mixture was stirred at room temperature for 10 mins. EtOH (40 mL) and hydrazine monohydrate (9.0 μL, 0.18 mmol) were added and the reaction mixture was stirred for a further 20 mins. Diethylether (50 mL) was added and the mixture was filtered to leave a solid. The filtrate was concentrated in vacuo to leave a gum. The solid and the gum were combined to give the crude hydrazide that was used with no further purification; MS m/e (M−H)− 348. A solution of 2,4,5-trifluorophenyl isothiocyanate (103 mg, 0.54 mmol) in DMA (1 mL) was added in one portion to a stirred solution of the crude hydrazide (189 mg, 0.54 mmol) in DMA (4 mL) and the reaction mixture was stirred at room temperature for 1 h. EDCI (125 mg, 0.65 mmol) was added in one portion and the reaction mixture was heated to 60° C. for 2 mins and then stirred at room temperature for 60 h. The reaction mixture was concentrated in vacuo to leave an oil. Hot water was added and the residue was stirred for 5 min to give a precipitate, which was filtered to give the title compound as a light brown solid (221 mg, 81%); 1H NMR δ 1.20 (3H, t), 1.65-1.71 (4H, m), 1.76-1.85 (4H, m), 2.52 (1H, m), 4.09 (2H, q), 4.51 (1H, s), 6.96 (2H, d), 7.67-7.74 (3H, m), 8.15-8.18 (1H, m), 10.95 (1H, s), 11.05 (1H, s); MS m/e (M−H)− 503.

Provenance & Evidence