Phenyl Isothiocyanate → HCID 178514008, compound

Participants

Reaction Steps

(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (100 mg, 0.5 mmol), isothiocyanatobenzene (60 L, 0.5 mmol), and PS-carbodiimide (769 mg, 1.01 mmol) were heated overnight at 70° C. in a sealed tube with tetrahydrofuran (10 mL). The solids were removed by filtration and the filtrate was concentrated. The organics were purified by reverse phase chromatography (Gilson) to afford, following neutralization and concentration, the title compound as a yellow solid (21%). 1H NMR (d-4 methanol): 7.73 (m, 3H), 7.29 (m, 2H), 6.98 (m, 1H), 6.44 (m, 1H), 6.40 (m, 1H), 5.31 (m, 1H), 4.88 (m, 3H), 2.98 (s, 1H), 2.89 (s, 1H), 2.73 (m, 1H), 2.37 (m, 1H), 1.57 (m, 1H), 1.30 (m, 2H). MS: 394.9 (M+H). HPLC retention time: 2.33 minutes (G Method).

Provenance & Evidence