Hydrochloric Acid → HCID 59464153, compound

Participants

Reaction Steps

Methyl 4-(4-aminophenyl)butanoate (Journal of Medicinal Chemistry (1990), 33(11), 3014-19) (193 mg, 1 mmol) was stirred in dry DCM (9 mL) and PS-di-isopropylethylamine (750 mg, 3 mmol) was added. Methyl chloro(oxo)acetate (101 μl, 1.1 mmol) was added to the reaction mixture which was then stirred at room temperature for 2 h. The polymer supported base (HCl salt) was filtered off and washed with DCM (3 mL). Hydrazine monohydrate (53 μL, 1.1 mmol) was added to the stirred filtrate and a white precipitate formed after 2 h. The reaction mixture was stirred at room temperature overnight then DMF (5 mL) was added to dissolve the solid. 2-Fluorophenylisothiocyanate (0.135 mL, 1.1 mmol) was added via a pipette and the mixture stirred at room temperature for 2.5 h before adding EDAC (230 mg, 1.2 mmol). After stirring at room temperature for a further 2.5 h the mixture was heated to 50° C. and the DCM was allowed to evaporate. After 2 h the reaction had gone to completion and the mixture was concentrated in vacuo. The orange solid obtained was crystallised from water and then filtered. The solid was then washed with Et2O, EtOAc and then MeCN (1 mL) to give the title compound (174 mg, 44%) as a solid; 1H NMR δ 1.79-1.87 (2H, m), 2.31 (2H, t), 2.58 (2H, t), 3.59 (3H, s), 7.15-7.20 (3H, m), 7.25-7.34 (2H, m), 7.71 (2H, d), 8.02-8.07 (1H, m), 10.76 (1H, s), 10.95 (1H, s); MS m/e MH+ 399.

Provenance & Evidence