Substituted thiazolone secreted aspartic acid protease inhibitor and preparation method thereof
A technology of thiazolone and group, applied in the field of pharmaceutical compounds
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Embodiment 1
[0098] Example 1: Preparation of 1,3-diphenylthiourea (II, R 1 =H) Preparation
[0099] Weigh aniline (2.33g, 25mmol, 2equiv), carbon disulfide (1.24g, 16.25mmol, 2equiv), triethanolamine (2.5mL) and sulfur powder (100mg) in 50mL of water, stir and reflux for 6h. The reaction solution was cooled to room temperature, and a white precipitate precipitated out. Filtered and washed with cold water to obtain 1.46 g of white solid, yield: 51%. 1 H-NMR (300MHz, DMSO-d 6 )δ:9.78(s,2H,NH),7.47(m,4H,Ar-H),7.32(m,4H,Ar-H),7.11(m,2H,Ar-H).ESI-MS(m / z):229.28[M+1].
Embodiment 2
[0100] Example 2: 3-phenyl-2-(phenylimino)thiazolidin-4-one (Ⅲ, R 1 =H) Preparation
[0101] Weigh 1,3-diphenylthiourea (1.14g, 4.0mmol, 1equiv), anhydrous sodium acetate (1.64g, 20.0mmol, 5equiv), 0.85mL ethyl chloroacetate (0.98g, 8.0mmol, 2equiv) In 20 mL of absolute ethanol, the mixture was stirred at 60° C. for 6 h. The reaction solution was cooled to room temperature, and a precipitate appeared. The precipitate was filtered, washed with ethanol, and recrystallized with ethyl acetate to obtain 0.68 g of an orange solid, yield: 64%, which was directly used in the next reaction without further purification. 1 H-NMR (300MHz, DMSO-d 6 )δ:7.47-7.59(m,2H),7.37-7.46(m,3H),7.25-7.36(m,2H),7.08(t,1H,J=7.8Hz),6.81-6.92(m,2H) ,4.15(s,2H).ESI-MS(m / z):269.35[M+1].
Embodiment 3
[0102] Example 3: Ethyl 2-(2-{[4-oxo-3-phenyl-2-(phenylimino)thiazolidin-5-enylidene]methyl}phenoxy)acetate (IV, R 1 =H) Preparation
[0103] Weigh 3-phenyl-2-(phenylimino)thiazolidin-4-one (0.3g, 1.12mmol, 1equiv), ethyl 2-formylphenoxy acetate (0.28g, 1.35mmol, 1.2equiv) , piperidine (0.095g, 1.12mmol, 1equiv) in 5mL of absolute ethanol, the mixture was stirred at 60°C for 8h. Purification by flash preparative chromatography (PE-EtOAc, 5:1) gave 0.48 g of light yellow solid, yield: 95%. 1 H-NMR (300MHz, DMSO-d 6 )δ:8.07(s,1H),7.44-7.62(m,5H),7.30-7.43(m,4H),7.02-7.22(m,3H),6.90-7.01(m,2H),4.94(s, 2H), 4.16(dd, 2H, J=7.06, 14.02Hz), 1.20(t, 3H, J=7.31Hz). ESI-MS (m / z): 459.40[M+1].
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