N-substituted imidazole formate derivative and application thereof
An unsubstituted and deuterated technology, applied in the field of medicinal chemistry, can solve problems such as not found
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Embodiment 1
[0227] Embodiment 1 Preparation of Compound 1 of the present invention
[0228]
[0229] 1. Preparation of (R)-1-(1-Phenylethyl)-1H-imidazole-5-carbonyl chloride (1b)
[0230]
[0231] In an ice-water bath at 0°C, inject (COCl) 2 (2 mL) was slowly added to a solution of 1b-2 (200 mg, 0.92 mmol) in dichloromethane (20 mL) at a rate of 1 mL / min, and reacted at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure to obtain white solid 1b (220 mg, crude product).
[0232] 2. Preparation of target compound 1
[0233]
[0234] In an ice-water bath at 0°C, the 1b prepared in the previous step was added to (S)-5-hydroxymethyldihydrofuran-2-one (107mg, 0.92mmol) and triethylamine (2.81g, 27.8mmol) dichloro methane (30 mL) solution, after the addition was completed, the reaction was continued for 1 hour. The reaction solution was concentrated under reduced pressure to obtain the crude product, which was separated by silica gel column ch...
Embodiment 2
[0236] Embodiment 2 Preparation of Compound 2 of the present invention
[0237]
[0238] In an ice-water bath at 0°C, add (S)-(-)-4-hydroxymethyl-2(5H)-furanone (65mg, 0.56mmol) and triethylamine (113mg, 1.12 mmol) in dichloromethane (5mL) solution, the reaction was continued for 1 hour after the addition was complete. The reaction solution was concentrated under reduced pressure to obtain the crude product, which was separated by silica gel column chromatography, using any ratio of ethyl acetate / petroleum ether (v / v) in the range of 1 / 10 to 1 / 1 as the eluent, TLC (acetic acid Ethyl ester / petroleum ether (v / v)=1 / 1) was detected, and the fraction with Rf=0.4-0.5 was collected to obtain colorless oily compound 2 (20 mg, two-step reaction yield 12%). ESI[M+H] + =313.2
[0239] 1 H NMR (400MHz, d 6 -DMSO)δ8.34(s,1H),7.73–7.71(d,J=0.8Hz,1H),7.59(s,1H),7.36–7.32(m,2H),7.29–7.27(m,1H) ,7.17–7.15(m,2H),6.24–6.22(m,1H),6.18–6.16(m,1H), 5.47(d,J=1.6Hz,1H),4.57(dd,J=12.0,3.2Hz ...
Embodiment 3
[0240] Embodiment 3 Preparation of Compound 3 of the present invention
[0241]
[0242] Compound 3 was prepared by using compound 1b (234 mg, 1.0 mmol) and (S)-3-hydroxy-γ-butyrolactone (102 mg, 1.0 mmol) as raw materials, and compound 3 was synthesized according to the method of Example 1. ESI[M+H] + =301.2
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