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CAS No. : | 16773-42-5 | MDL No. : | MFCD00057960 |
Formula : | C7H10ClN3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IPWKIXLWTCNBKN-UHFFFAOYSA-N |
M.W : | 219.63 | Pubchem ID : | 28061 |
Synonyms : |
Ro 7-0207;NSC 95075;Tiberal;(±)-Ornidazole
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.57 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.85 |
TPSA : | 83.87 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.21 cm/s |
Log Po/w (iLOGP) : | 1.29 |
Log Po/w (XLOGP3) : | 0.6 |
Log Po/w (WLOGP) : | 0.7 |
Log Po/w (MLOGP) : | -0.1 |
Log Po/w (SILICOS-IT) : | -0.92 |
Consensus Log Po/w : | 0.31 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.58 |
Solubility : | 5.78 mg/ml ; 0.0263 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.94 |
Solubility : | 2.55 mg/ml ; 0.0116 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.08 |
Solubility : | 18.1 mg/ml ; 0.0822 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.92 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: With aluminum (III) chloride In ethyl acetate at 0℃; for 0.25 h; |
A mixture of 2-methyl-4/5-nitro-1H-imidazole (1, 39.37mmol) and anhydrous aluminium chloride (39.37mmol) were dissolved in ethylacetate (50mL) at 0°C and stirred for 15min then added (±)-epichlorohydrin (78.74mmol) to the above reaction mixture and contents were further stirred for 15–20h. After completion of reaction (as monitored by TLC) 30mL of distilled water was added and further continued the stirring for 30min and stopped the reaction. Then EtOAc (20mL) and excess water (3×30mL) was added to the reaction mixture and organic layer was separated, dried (anhyd. Na2SO4), concentrated under reduced pressure. The crude obtained was further purified by column chromatography over silica (60–120 mesh) with methanol/chloroform as eluent to get the title compounds 2 in 79percent yield as white solid. mp: 84–86°C; IR (KBr) ν (cm−1): 3400, 3110, 1540, 1360, 1150, 771; 1H NMR (400MHz, CDCl3): δ 7.72 (s, 1H), 4.92 (s, 1H), 4.63–4.60 (m, 1H), 4.19–4.16 (m, 2H), 3.73–3.63 (m, 2H), 2.45 (s, 3H); 13C (100MHz, CDCl3): δ 151.9, 138.3, 132.2, 69.8, 49.7, 46.9, 14.4; ESI-MS: m/z 220 (M+H+). |
4.8 g | With aluminum (III) chloride In ethyl acetate at 0℃; | Take 2-methyl-5-nitroimidazole 10g,After adding ethyl acetate 200ml dissolved,Then add anhydrous aluminum trichloride 10g, stirring and cooling,After cooling to 0°C, epichlorohydrin 20g was added dropwise.Insulation reaction,After the reaction is completed, the reaction solution is slowly added to water and hydrolyzed.Separate the ethyl acetate layerThe ethyl acetate layer was extracted with a 10percent hydrochloric acid solution.Finally, the acid-water layer was adjusted to pH 7 with ammonia, and a solid precipitated.Filter and dry to obtain compound 2 4.8g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.2% | With sodium hydroxide In water; acetone at 0℃; for 1h; Inert atmosphere; | 8; 9 2-Methyl-5-nitro(1-oxiranyl)-1H-imidazole A solution of 1-chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol (800 mg, 3.65 mmol) dissolved in 10 ml of acetone at 0°C Under the protection of nitrogen, a solution of sodium hydroxide (222 mg, 5.55 mmol) in water (2.6 mL) was added portionwise, and the reaction solution was stirred at room temperature for one hour. The reaction solution was filtered, and the filtrate was dispersed in 10 ml of water, extracted with 50 ml of ethyl acetate, and extracted twice. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain 650 mg of yellow solid product with a yield of 97.2%. |
91% | With sodium hydroxide In dichloromethane; water at 0℃; | 4.1.2 Synthesis of (±)-2-methyl-5-nitro-1-(oxiran-2-ylmethyl)-1H-imidazole (3) The title compound ( 3) was synthesized by dissolving compound 2 (29.68mmol) in dichlorometane (10mL) and added aqueous NaOH (29.68mmol) at 0°C. Stirred the contents for 40-45min and after completion of reaction (as monitored by TLC) contents was extracted with DCM/water and organic layer was separated, dried (anhyd. Na2SO4), concentrated under reduced pressure. The crude obtained was recrystallized with EtOAc/hexane to get the final compound ( 3) in 91% yield as white solid. mp: 113-115°C; IR (KBr) ν (cm-1): 3405, 3110, 1540, 1362, 1151; 1H NMR (400MHz, CDCl3): δ 7.92 (s, 1H), 4.85 (d/d, J=2.3 & 15.0Hz, 1H), 4.19 (d/d, J=5.8 & 15.0Hz, 1H), 3.37-3.33 (m, 1H), 2.85 (t, J=4.2Hz, 1H), 2.50 (d/d, J=2.5 & 4.4Hz, 1H), 2.47 (s, 3H); 13C (100MHz, CDCl3): δ 151.4, 138.5, 132.8, 50.3, 47.5, 45.1, 14.3; ESI-MS: m/z 184 (M+H+). |
90% | With sodium hydroxide In dichloromethane at 0℃; for 3h; | 4 2-Methyi-5-niiro-l-oxiranylmethyl-lH-imidazole(IV) was synthesized according to the following scheme. To a stirred solution of l-Chloro-3-(2-methyl-5-nitro-imidazol-l-yl)- propan-2-oI, (I) (0.5g, 2.27mmol) in dichloromethane (8ml) was added 20% Sodium hydroxide(4ml) at 0°C. The reaction mixture was stirred for 3h at 0 °C. After 3h the reaction mixture was extracted twice with dichloromethane, the organic layers were combined, washed with brine and finally dried over sodium sulphate to obtain pure product with 90% isolated yield, 1H-NMR (400 MHz, CDCl3)D 5ppm: 2.517 (3H, s, CH3), 2.52 (1H, m, CH2), 2.88 (1H, m, CH2), 3.38 (1H, m, CH), 4.17-4.23 (1H, dd, J/ - 6Hz, J2 = 15.2Hz CH2), 4.85-4.89 (1H, , d, J = 14.8 CH2). |
82% | With sodium hydroxide for 0.25h; | |
With sodium hydroxide In dichloromethane; water at 0 - 25℃; | 28.1 Step 1: Preparation of compound 28-2 Compound 28-1 (1 g, 4.55 mmol) was dissolved in DCM (10 mL) at 0 °C, and sodium hydroxide (182.12 mg, 4.55 mmol) was slowly added to water (10 mL) at a temperature of 0-25 °C Under the conditions of reaction for 5 hours; the reaction solution was diluted with water (20mL), extracted with dichloromethane (60mL), the organic layer was washed with saturated brine (30mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain compound 28- 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With hydrogen In para-xylene at 130℃; for 24h; chemoselective reaction; | |
With hydrogenchloride; zinc In ethanol | ||
With sulfuric acid In methanol; water at 25℃; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lipase Amano PS / 384 h / Ambient temperature 2: 60 percent / conc. HCl / 5 h | ||
Stage #1: ornidazole In ethanol; water at 70℃; for 0.5h; Stage #2: With hydrazine In ethanol; water at 3℃; for 3h; | 2 example 2 Crystalline α L-ornidazole preparation method is as follows: the 5.0g dissolved in L-ornidazole 15ml75% aqueous solution of ethanol, water bath heated to 50 ±3 °C, stirring to complete dissolution, the solution is transferred to the temperature in the constant temperature water bath 20 ±2 °C 30 minutes, then agitating leng Jing devitrify 3 ±2 °C 3 hours. After filtration, the filtration cake at the hot air drying under 45 ±3 °C 8 hours to obtain 4.0g crystalline α crystals of L-ornidazole, detection HPLC purity of 99.96%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With potassium hydroxide In ethanol; water for 12h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; | 3 Bromo-acetic acid l-chloromethyl-2-(2-methyl-5-nitro-imidazol-l -yl)- ethyl ester (II) was synthesized according to the following scheme. To a stirred solution of l-Chloro-3-(2-methyl-5-nitro-imidazol-l-yl)- propan-2-ol, (I) (0.79g, 3.6mmol) in dichloromethane (10ml) was added dicyclohexylcarbadiim.de (DCC) (0.9g, 4.31mmol) followed by bromoacetic acid (0.5g, 3.6 mmol) and DMAP(0.44g, 3.6 mmol) at RT. The reaction mixture was stirred at RT for 16 h. The precipitate was removed by filtration and the organic layer was evaporated to get the crude that was purified by flash column chromatography. The final compound was eluted with 1-2 % 1 9 methanol/dichloromethane mixture. The compound was used for the next step without further characterization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃; for 16h; | Example 5: Synthesis of DART molecule 94 from Table IB Synthesis of 0-Fhioro-]-methyI-7-[4-(5-methyl-2-oxo-[l,3]dioxol-4- ylmeihyi)-piperazin~l-yi} '-4-oxo-4 H~2-lhia-8h~Qza-cycobuiQ[ ]naphth lene-3- carboxyiic acid l-chloromethyl~2-(2-meihyl~5~nitro-imidazol~l-yl)-ethyl ester (5): To a stirred solution of 6-Fluoro- l -methyl-7-[4-(5-methyl-2-oxo-[l,3]dioxol-4- ylmethyl)-piperazin-l-yl]-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3- carboxylic acid, (V) (0.5g, l .OSmmol) in DMF (20ml) was added DCC (0.3g, 1.41 mmol) and HOBt (0.146g, 1.083mmoi) followed by addition of l-Chloro-3-(2- methyl-5-nitro-imidazol-l -yl)-propan-2-ol, (I) (0.285g, 1,3 mmol) and DMAP (0.13g, 1.08 mmol) at room temperature. The reaction mixture was stirred at RT for 16 h. The precipitate was removed by filtration and the organic layer was evaporated to get the crude mass. Finally it was purified by flash column chromatography euting with 2-4 % methanol/dichloromethane mixture to obtain the pure compound, (5), i.e., Compound 94 from Table 1, with 60% isolated yield. FontWeight="Bold" FontSize="10" H-NMR (400 MHz, D SO) 6ppm: 2.03 (3H, d, J=5.6Hz, CH3), 2.12 (3H, s, CH3), 2.5 (3H, s, CH3), 2.62 (4H, m, 2 x CH2), 3.22 (4H, m, 2 x CH2), 3.95-4.06 (2H, m, CH2C1), 4.49-4.52 (1H, t, J - 10 Hz, CHN) 4.77 (1H, d, J = 13.2Hz, CHN)? 5.63(1H, d, J = 4.4Hz, CHOCO), 6.15 (1H, m, CHSN), 6.78 (1H, d, J = 7.2, Ar-H), 7.68 (1H, d, 7 = 14, Ar-H), 7.9 (1H, s, Ar-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | A mixture of 2-methyl-4/5-nitro-1H-imidazole (1, 39.37mmol) and anhydrous aluminium chloride (39.37mmol) were dissolved in ethylacetate (50mL) at 0C and stirred for 15min then added (±)-epichlorohydrin (78.74mmol) to the above reaction mixture and contents were further stirred for 15-20h. After completion of reaction (as monitored by TLC) 30mL of distilled water was added and further continued the stirring for 30min and stopped the reaction. Then EtOAc (20mL) and excess water (3×30mL) was added to the reaction mixture and organic layer was separated, dried (anhyd. Na2SO4), concentrated under reduced pressure. The crude obtained was further purified by column chromatography over silica (60-120 mesh) with methanol/chloroform as eluent to get the title compounds 2 in 79% yield as white solid. mp: 84-86C; IR (KBr) nu (cm-1): 3400, 3110, 1540, 1360, 1150, 771; 1H NMR (400MHz, CDCl3): delta 7.72 (s, 1H), 4.92 (s, 1H), 4.63-4.60 (m, 1H), 4.19-4.16 (m, 2H), 3.73-3.63 (m, 2H), 2.45 (s, 3H); 13C (100MHz, CDCl3): delta 151.9, 138.3, 132.2, 69.8, 49.7, 46.9, 14.4; ESI-MS: m/z 220 (M+H+). | |
78% | With aluminum (III) chloride; In ethyl acetate; at 45 - 50℃; for 1.5h; | Add 330 g of <strong>[696-23-1]2-methyl-5-nitroimidazole</strong> and 1650 g of ethyl acetate to the reaction bottle, add the1650 g of aluminum trichloride catalyst on the macroporous resin, stirring evenly, the stirring speed is 150 rpm-200 rpm;Add 330 g of epichlorohydrin dropwise to the reaction system, the drop rate is 3-5 ml / min, and the internal temperature should not exceed 50 degrees;After dropping epichlorohydrin, keep the reaction at 45 degrees for 1.5 hours, filter, and wash the catalyst with 660 g of ethyl acetateSub-filtration and drying to be applied; the filtrate is washed with water, dried over anhydrous sodium sulfate, decolorized after decolorization of medical charcoal; added to the residueAfter heating and dissolving 330 grams of ethanol to cool down and crystallize, filter with suction and dry to obtain the finished product of ornidazole.[0040] After HPLC detection, the results are shown in FIG. 1, FIG. 1 is an HPLC chart of ornidazole prepared in Example 1 of the present invention;It can be seen that the purity of the product is 99.97%; the yield is 78%. |
4.8 g | With aluminum (III) chloride; In ethyl acetate; at 0℃; | Take <strong>[696-23-1]2-methyl-5-nitroimidazole</strong> 10g,After adding ethyl acetate 200ml dissolved,Then add anhydrous aluminum trichloride 10g, stirring and cooling,After cooling to 0C, epichlorohydrin 20g was added dropwise.Insulation reaction,After the reaction is completed, the reaction solution is slowly added to water and hydrolyzed.Separate the ethyl acetate layerThe ethyl acetate layer was extracted with a 10% hydrochloric acid solution.Finally, the acid-water layer was adjusted to pH 7 with ammonia, and a solid precipitated.Filter and dry to obtain compound 2 4.8g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.2% | With aluminum (III) chloride; In ethyl acetate; at 3 - 5℃; | 50 g of <strong>[696-23-1]2-methyl-5-nitroimidazole</strong> was added to 500 mL of ethyl acetate, and the mixture was cooled to 3 ± 1 C. Then, 90 g of aluminum trichloride was added,The reaction temperature was controlled to less than 5 ± 2 C and 85 mL of S-epichlorohydrin was added slowl. During the addition, the reaction temperature was controlled at 5 ± 2 C,Plus complete, temperature control 3 ± 1 C reaction. After completion of the reaction, the reaction solution was directly added to a 2 L ice / water mixture,The temperature was controlled to stir at 10 ± 2 C for 30 minutes,The ethyl acetate layer was separated, dried over anhydrous sodium sulfate and then dried at 45 ± 1 C,-0.08MPa ~ -0.10MPa under vacuum concentration, concentration to no droplets,Add 50mL acetone beating for 30 minutes, then add cyclohexane 500mL, precipitate the solid, filter, the filter cake at 45 ± 1 hot air drying 8 hours Ornidazole 76.2g, off-white crystals,Yield 88.2%. |
403 g | With formic acid; sulfuric acid; at -5 - 15℃; for 2h; | In a 5 L reaction flask, 3 L of formic acid was added,171 ml of concentrated sulfuric acid was added with stirring,Stirring was continued for 1 hour.And 540 g of <strong>[696-23-1]2-methyl-5-nitroimidazole</strong> was added,Stir and cool to -5 C.Slowly droppingS - (+) - epichlorohydrin 1.08 L,The reaction temperature was controlled to less than 5 C. Drop complete, stirring reaction,The temperature of the reaction solution was controlled at 10 C to 15 C, and the reaction was monitored by HPLC. After the reaction was stopped (the degree of reaction was increased by less than 0.3% in 2 hours), the formic acid in the reaction solution and the excess amount of S - (+) - epichlorohydrin were distilled off,The residue was added to a mixture of 2000 ml of ice and water,Adjusting pH to 3 ~ 4,The filtrate was extracted with ethyl acetate (2 L x 3)The combined ethyl acetate,Dried over anhydrous sodium sulfate,filter,5 L of water was added to the filtrate,And hydrochloric acid was added to adjust the pH to 1,Liquid separation,The water layer and the ammonia water were adjusted to pH 7-8,Precipitation of L-ornidazole solid.filter,The filter cake is dried at 30 ~ 40 under reduced pressure to obtain optical enantiomer of ornidazoleProduct 490g. L-ornidazole refining:Take the L-ornidazole crude 490g,Was added to a 3.4 L solution of ethanol-water (25:75)Heating dissolution,Adding 0.5% (W / V) of activated carbon decolorization at 60 for 10min, filtration, the filtrate placed crystallization.L-ornidazole refined products 403g. purity 99.92% |
3.21 kg | With boron trifluoride; In ethyl acetate; at -10 - 15℃; for 5h;Darkness; Large scale; | In the dark,In the absence of oxygen under the conditions of 50L reactor,20 L of ethyl acetate and 2 kg of <strong>[696-23-1]2-methyl-5-nitroimidazole</strong> were added,Down to -10 C,A solution of boron trifluoride in ethyl acetate (containing about 1.8 kg of boron trifluoride) was slowly added dropwise (the control temperature did not exceed 15 c)Drop finished,And then slowly dropping 2.2LS - (+) - epichlorohydrin (controlled temperature not exceeding 15 C)Drop 10 C for 5 hours,The reaction solution was slowly added to 18 kg of ice-water mixture,The temperature does not exceed 30 (: stirring reaction 5 hours,With concentrated hydrochloric acid to adjust the pH value of 1.0 or so,Points to the organic layer,The aqueous layer was adjusted to pH 7.0 with concentrated ammonia,Stirring crystallization for 24 hours,filter,Washed with water,Dried up to Orangidazole 3.21kg. |
3.21 kg | With boron trifluoride; In ethyl acetate; at -10 - 15℃; for 5h;Darkness; Large scale; | In a 50L reaction vessel in dark, anaerobic conditions,20 L of ethyl acetate and 2 kg of <strong>[696-23-1]2-methyl-5-nitroimidazole</strong> were added, the temperature was lowered to -10C, and a solution of boron trifluoride in ethyl acetate (about 1.1 kg containing boron trifluoride) was slowly added dropwise (control) The temperature does not exceed 15C. After adding dropwise, 2.2LS-(+)-epichlorohydrin is slowly added dropwise (control temperature does not exceed 15C), and the reaction is completed at 10C for 5 hours.The reaction solution was slowly added to a mixture of 18 kg ice water, the temperature does not exceed 30 C stirred for 5 hours, with concentrated hydrochloric acid to adjust the pH value of about 1.0, the organic layer was separated, the aqueous layer was adjusted to pH 7.0 with concentrated ammonia, stirring crystallization 24 hours, filtered, washed with water and dried to obtain 3.21 kg of L-ornidazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; | In the water bath conditions, Na-t-butoxycarbonyl-arginine hydrochloride (22 mmol, 7.23 g) N,N'-dicyclohexylcarbodiimide (4.4 mmol, 0.91 mg), 4-dimethylamino-pyridine (2.2 mmol, 0.3 g), And stirred with anhydrous dichloromethane (30 ml). Followed by addition of L-ornidazole (26 mmol, 5.7 g) and stirred overnight at room temperature. Filtering to remove the solid insoluble matter, the filtrate evaporated solvent; add ether to the residue, The insoluble impurities in the solution were removed by filtration. The filtrate was concentrated and the column was rapidly passed through ether and the product fractions were collected. The product was concentrated under reduced pressure.The product was concentrated under reduced pressure. The obtained product was directly added with 4MHC1 / dioxane solution (20 ml), and the reaction was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure and concentrated to dryness. The residue was isolated by HPLC (TFA) to give the product 3. 8 g; the yield of compound 7 was 66.6percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.4% | In the water bath, N-t-butoxycarbonyl-Nim-triphenylmethyl-histidine (22 mmol, 7.6 g) N,N'-dicyclohexylcarbodiimide (4. 4 mmol, 0.91 g), 4-dimethylamino-pyridine (2. 2 mmol, 0.3 g) And stirred with anhydrous dichloromethane (30 ml). Followed by the addition of L-ornidazole (26mmol, 5.7g) and stirred overnight at room temperature. The insoluble matter was removed by filtration, and the filtrate was evaporated to dryness. The ether was added to the residue and the insoluble impurities in the solution were removed by filtration. The filtrate was concentrated and the column was rapidly passed through ether and the product fractions were collected. The product was concentrated under reduced pressure. The resulting product was added directly to 4MHC1 / dioxane Ring solution (10ml), stirring at room temperature 1h. The solvent was distilled off under reduced pressure and concentrated to dryness. The residue was purified by HPLC (TFA) system to give product 4.3 g; compound 8 yield 75. 4percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In propan-1-ol for 64h; Reflux; | Preparation of 1-(3'-arylamino-2'-hydroxypropyl)-2-methyl-5-nitroimidazoles 4: General procedure General procedure: A mixture of 1-(3'-chloro-2'-hydroxypropyl-2-methyl-4-nitroimidazole (0.004 mol, 1.04 g) and appropriately substituted aniline (0.004 mol, 0.45 ml) in 10 ml of n-propanol was refluxed for 64 hr. The solvent was removed under vaccum. 10 ml of chloroform was added to the sticky residue and off-white coloured precipitate was obtained which was filtered, dried and recrystallized from ethyl acetate:ethanol mixture to yield off-white coloured crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In propan-1-ol for 64h; Reflux; | Preparation of 1-(3'-arylamino-2'-hydroxypropyl)-2-methyl-5-nitroimidazoles 4: General procedure General procedure: A mixture of 1-(3'-chloro-2'-hydroxypropyl-2-methyl-4-nitroimidazole (0.004 mol, 1.04 g) and appropriately substituted aniline (0.004 mol, 0.45 ml) in 10 ml of n-propanol was refluxed for 64 hr. The solvent was removed under vaccum. 10 ml of chloroform was added to the sticky residue and off-white coloured precipitate was obtained which was filtered, dried and recrystallized from ethyl acetate:ethanol mixture to yield off-white coloured crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | In propan-1-ol for 64h; Reflux; | Preparation of 1-(3'-arylamino-2'-hydroxypropyl)-2-methyl-5-nitroimidazoles 4: General procedure General procedure: A mixture of 1-(3'-chloro-2'-hydroxypropyl-2-methyl-4-nitroimidazole (0.004 mol, 1.04 g) and appropriately substituted aniline (0.004 mol, 0.45 ml) in 10 ml of n-propanol was refluxed for 64 hr. The solvent was removed under vaccum. 10 ml of chloroform was added to the sticky residue and off-white coloured precipitate was obtained which was filtered, dried and recrystallized from ethyl acetate:ethanol mixture to yield off-white coloured crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In propan-1-ol for 64h; Reflux; | Preparation of 1-(3'-arylamino-2'-hydroxypropyl)-2-methyl-5-nitroimidazoles 4: General procedure General procedure: A mixture of 1-(3'-chloro-2'-hydroxypropyl-2-methyl-4-nitroimidazole (0.004 mol, 1.04 g) and appropriately substituted aniline (0.004 mol, 0.45 ml) in 10 ml of n-propanol was refluxed for 64 hr. The solvent was removed under vaccum. 10 ml of chloroform was added to the sticky residue and off-white coloured precipitate was obtained which was filtered, dried and recrystallized from ethyl acetate:ethanol mixture to yield off-white coloured crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In propan-1-ol for 64h; Reflux; | Preparation of 1-(3'-arylamino-2'-hydroxypropyl)-2-methyl-5-nitroimidazoles 4: General procedure General procedure: A mixture of 1-(3'-chloro-2'-hydroxypropyl-2-methyl-4-nitroimidazole (0.004 mol, 1.04 g) and appropriately substituted aniline (0.004 mol, 0.45 ml) in 10 ml of n-propanol was refluxed for 64 hr. The solvent was removed under vaccum. 10 ml of chloroform was added to the sticky residue and off-white coloured precipitate was obtained which was filtered, dried and recrystallized from ethyl acetate:ethanol mixture to yield off-white coloured crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In propan-1-ol for 64h; Reflux; | Preparation of 1-(3'-arylamino-2'-hydroxypropyl)-2-methyl-5-nitroimidazoles 4: General procedure General procedure: A mixture of 1-(3'-chloro-2'-hydroxypropyl-2-methyl-4-nitroimidazole (0.004 mol, 1.04 g) and appropriately substituted aniline (0.004 mol, 0.45 ml) in 10 ml of n-propanol was refluxed for 64 hr. The solvent was removed under vaccum. 10 ml of chloroform was added to the sticky residue and off-white coloured precipitate was obtained which was filtered, dried and recrystallized from ethyl acetate:ethanol mixture to yield off-white coloured crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.5% | With potassium carbonate In ethanol for 6h; Reflux; | 1 1-(2-Methyl-5-nitro-1hydro-imidazol-1-yl)-3-morpholinepropan-2-ol Add chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol (500 mg,2.28 mmol), potassium carbonate (380 mg, 2.75 mmol) and morpholine (320 mg, 3.67 mmol) were added to ethanol (10 mL), and the mixed system was refluxed for 6 hours. The temperature of the reaction solution was lowered, and the ethanol was spun off and purified by column chromatography (eluent: dichloromethane/methanol=10/1) to obtain1-(2-Methyl-5-nitro-1H-imidazol-1-yl)-3-ol (330 mg, 53.5%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With trichlorophosphate In acetonitrile Reflux; | 3 Example 3: Preparation of nitroimidazole compound II racemate Add 100ml of acetonitrile, 17g of phosphorus oxychloride and 50g of ornidazole to the reaction flask.Turn on the stirring, heat to reflux and react for 4-8 hours. After the reaction is over,Concentrate under reduced pressure until there is no dripping, put the residue on a chromatography column, and elute with dichloromethane: methanol (2:1).After the elution is completed, the target eluate is concentrated to 1/3 of the total volume, the temperature is lowered to -5°C to 0°C, and crystallization is performed for 8 to 12 hours.After filtering, the filter cake is placed in a blast drying box, and the temperature is controlled at 20°C to 30°C and dried for 2 to 4 hours to obtain 43.5 g of nitroimidazole compound II racemate, with a yield of 87.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With fac-tris(2-phenylpyridinato-N,C2')iridium(III); sodium acetate In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; | General procedure for the fluoroalkylation of nitroimidazoles 3 and 5. General procedure: To a 10 mL Schlenk tube equipped with a Teflon septum and magnetic stir bar were added nitroimidazole (0.3 mmol, 1 equiv.), fac-Ir(ppy)3 (1 mol %) and NaOAc (0.6 mmol, 2 equiv.). The tube was evacuated and backfilled with Ar three times. DMSO (2 mL) and fluoroalkylated agent (0.9 mmol, 3 equiv.) were subsequently added under Ar. The reaction was then irradiated with 5 W blue LEDs at room temperature. After being stirred for 24 h, the mixture was diluted with ethylacetate (5 mL × 3). The combined organic layers were washed with brine three times, dried over anhydrous Na2SO4, and concentrated. The crude product was further purified by silica gel chromatography to afford pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With fac-tris(2-phenylpyridinato-C<SUP>2</SUP>,N)iridium(III); anhydrous Sodium acetate In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; | General procedure for the fluoroalkylation of nitroimidazoles 3 and 5. General procedure: To a 10 mL Schlenk tube equipped with a Teflon septum and magnetic stir bar were added nitroimidazole (0.3 mmol, 1 equiv.), fac-Ir(ppy)3 (1 mol %) and NaOAc (0.6 mmol, 2 equiv.). The tube was evacuated and backfilled with Ar three times. DMSO (2 mL) and fluoroalkylated agent (0.9 mmol, 3 equiv.) were subsequently added under Ar. The reaction was then irradiated with 5 W blue LEDs at room temperature. After being stirred for 24 h, the mixture was diluted with ethylacetate (5 mL × 3). The combined organic layers were washed with brine three times, dried over anhydrous Na2SO4, and concentrated. The crude product was further purified by silica gel chromatography to afford pure product. |
53% | With anhydrous potassium acetate In dimethyl sulfoxide at 20℃; for 24h; Irradiation; Inert atmosphere; Green chemistry; | General procedure for the trifluoromethylated compounds 3 General procedure: To a 10 mL Schlenk tube equipped with a Teflon septum and magnetic stir bar were added nitroimidazole 1 (0.2 mmol, 1 equiv.), Togni’s reagent 2a (0.3 mmol, 1.5 equiv.) and KOAc (0.4 mmol, 2.0 equiv.). The tube was evacuated and backfilled with Ar for three times. Anhydrous DMSO (2 mL) was subsequently added under Ar. The reaction was then irradiated with 5 W cold white LED at room temperature for 24 h. The mixture was diluted with ethyl acetate (5 mL × 3). The combined organic layers were washed with brine three times, dried over anhydrous Na2SO4, and concentrated. The crude product was further purified by silica gel chromatography to afford pure product. |
With anhydrous potassium acetate In dimethyl sulfoxide at 20℃; for 24h; Irradiation; Inert atmosphere; Green chemistry; | General procedure for the trifluoromethylated compounds 3 General procedure: To a 10 mL Schlenk tube equipped with a Teflon septum and magnetic stir bar were added nitroimidazole 1 (0.2 mmol, 1 equiv.), Togni’s reagent 2a (0.3 mmol, 1.5 equiv.) and KOAc (0.4 mmol, 2.0 equiv.). The tube was evacuated and backfilled with Ar for three times. Anhydrous DMSO (2 mL) was subsequently added under Ar. The reaction was then irradiated with 5 W cold white LED at room temperature for 24 h. The mixture was diluted with ethyl acetate (5 mL × 3). The combined organic layers were washed with brine three times, dried over anhydrous Na2SO4, and concentrated. The crude product was further purified by silica gel chromatography to afford pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.6% | With triethylamine In dichloromethane at 5 - 20℃; for 2h; | 1-8 Example 1 Add 10.0g ornidazole and 60ml dichloromethane to the 250ml three-necked flask, stir and dissolve at room temperature completely, add 5.1g triethylamine, cool down to 0°C and slowly add 3.9g acetyl chloride dropwise, and stir at 5°C after the dropwise addition. 2h, TLC detection, after the reaction of ornidazole is complete, concentrate under reduced pressure, add 30ml of ethanol to the concentrated residue, stir to dissolve, slowly add 90ml of water dropwise, stir and crystallize at 0 °C for 2h, the system has a large amount of solid precipitation, suction filtration , the wet product was obtained and dried at 60°C to obtain a white powdery solid, which was ornidazole impurity 9.84g, purity 99.9%, and yield 82.6%. It can be used directly as an impurity reference. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27.3% | Stage #1: thiazolidine-2,4-dione With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 0.5h; Stage #2: ornidazole In N,N-dimethyl-formamide at 80℃; for 16h; | 3 Example 3, preparation of intermediate IV: Thiazolidinedione (2.0 g, 1.71 mmol) and potassium carbonate (3.54 g, 2.56 mmol) of N, N-dimethylformamide (30 mL) solution was stirred at 50 °C for 30 min, ornidazole (5.63 g, 2.56 mmol) was added, and the reaction was heated to 80 °C for 16 h. After the end of the reaction, it was cooled to room temperature, the solution was extracted with dichloromethane (3×100mL), and the lower organic phase was distilled under reduced pressure to obtain a crude product, and the yellow solid intermediate IV 1.40g was purified by column chromatography, with a yield of 27.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With 1,3-dibromo-5,5-dimethylhydantoin; 3-Nitrobenzenesulfonic acid at 60℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34.8% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 3 Preparation of compound I-1 In a 100 mL round bottom flask, intermediate III-1 (400 mg, 1.35 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (446 mg, 2.03 mmol),Potassium carbonate (373 mg, 2.7 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-1 (224 mg, 0.47 mmol), yield: 34.8%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42.9% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 4 Preparation of compound I-2 In a 100 mL round bottom flask, intermediate III-2 (400 mg, 1.19 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (391 mg, 1.78 mmol),Potassium carbonate (328 mg, 2.38 mmol) in acetonitrile (8 mL) as solvent,The reaction was carried out at 80 °C for 12 h, followed by thin layer chromatography until the end of the reaction.It was cooled to room temperature, and the solvent was removed to obtain compound I-2 (265 mg, 0.51 mmol), yield: 42.9%;Yellow solid; melting point: 224.8-225.1°C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 5 Preparation of compound I-3 In a 100 mL round bottom flask, intermediate III-3 (400 mg, 1.09 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (361 mg, 1.64 mmol),Potassium carbonate (301 mg, 2.18 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound 1-3 (269 mg, 0.49 mmol),Yield: 45.0%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.1% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 6 Preparation of compound I-4 In a 100 mL round bottom flask, intermediate III-4 (400 mg, 0.89 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (293 mg, 1.34 mmol),Potassium carbonate (246 mg, 1.78 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-4 (259 mg, 0.41 mmol), yield: 46.1%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.2% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 7 Preparation of compound I-5 In a 100 mL round bottom flask, intermediate III-5 (400 mg, 1.24 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (410 mg, 1.87 mmol),Potassium carbonate (342 mg, 2.48 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-5 (308 mg, 0.61 mmol), yield: 49.2%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.6% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 8 Preparation of compound I-6 In a 100 mL round bottom flask, intermediate III-6 (400 mg, 1.14 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (377 mg, 1.72 mmol),Potassium carbonate (315 mg, 2.28 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-6 (319 mg, 0.60 mmol), yield: 52.6%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.9% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 9 Preparation of compound I-7 In a 100 mL round bottom flask, intermediate III-7 (400 mg, 1.10 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (363 mg, 1.65 mmol),Potassium carbonate (304 mg, 2.20 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound 1-7 (306 mg, 0.56 mmol),Yield: 50.9%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 10 Preparation of compound I-8 In a 100 mL round bottom flask, intermediate III-8 (400 mg, 1.28 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (423 mg, 1.93 mmol),Potassium carbonate (353 mg, 2.56 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-8 (361 mg, 0.73 mmol), yield: 57.0%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.2% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 11 Preparation of compound I-9 In a 100 mL round bottom flask, intermediate III-9 (400 mg, 1.23 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (405 mg, 1.84 mmol),Potassium carbonate (339 mg, 2.46 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-9 (320 mg, 0.63 mmol), yield: 51.2%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.3% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 12 Preparation of compound I-10 In a 100 mL round bottom flask, intermediate III-10 (400 mg, 1.07 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (353 mg, 1.61 mmol),Potassium carbonate (295mg, 2.14mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-10 (319 mg, 0.56 mmol), yield: 52.3%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.7% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 13 Preparation of compound I-11 In a 100 mL round bottom flask, intermediate III-11 (400 mg, 1.23 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (405 mg, 1.84 mmol),Potassium carbonate (339 mg, 2.46 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-11 (361 mg, 0.71 mmol), yield: 57.7%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.4% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 14 Preparation of compound I-12 In a 100 mL round bottom flask, intermediate III-12 (400 mg, 1.13 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (371 mg, 1.69 mmol),Potassium carbonate (312 mg, 2.26 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-12 (355 mg, 0.66 mmol), yield: 58.4%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.2% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 15 Preparation of compound I-13 In a 100 mL round bottom flask, intermediate III-13 (400 mg, 1.09 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (358 mg, 1.63 mmol),Potassium carbonate (301 mg, 2.18 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-13 (320 mg, 0.58 mmol),Yield: 53.2%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.1% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 16 Preparation of compound I-14 In a 100 mL round bottom flask, intermediate III-14 (400 mg, 1.35 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (445 mg, 2.02 mmol),Potassium carbonate (373 mg, 2.70 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-14 (331 mg, 0.69 mmol),Yield: 51.1%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.4% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 17 Preparation of compound I-15 In a 100 mL round bottom flask, intermediate III-15 (400 mg, 1.18 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (387 mg, 1.76 mmol),Potassium carbonate (326 mg, 2.36 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound 1-15 (398 mg, 0.76 mmol),Yield: 64.4%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.8% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 18 Preparation of compound I-16 In a 100 mL round bottom flask, intermediate III-16 (400 mg, 1.18 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (389 mg, 1.77 mmol),Potassium carbonate (326 mg, 2.36 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature, and the solvent was removed to obtain compound I-16 (313 mg, 0.60 mmol), yield: 50.8%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61.7% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 19 Preparation of compound I-17 In a 100 mL round bottom flask, intermediate III-17 (400 mg, 1.07 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (354 mg, 1.61 mmol),Potassium carbonate (295mg, 2.14mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-16 (366 mg, 0.66 mmol), yield: 61.7%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.6% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 20 Preparation of compound I-18 In a 100 mL round bottom flask, intermediate III-18 (400 mg, 1.04 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (343 mg, 1.56 mmol),Potassium carbonate (287mg, 2.08mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-18 (353 mg, 0.62 mmol), yield: 59.6%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.7% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 21 Preparation of compound I-19 In a 100 mL round bottom flask, intermediate III-19 (400 mg, 0.96 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (316 mg, 1.44 mmol),Potassium carbonate (265mg, 1.92mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-19 (384 mg, 0.64 mmol), yield: 66.7%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.5% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 22 Preparation of compound I-20 In a 100 mL round bottom flask, intermediate III-20 (400 mg, 0.96 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (316 mg, 1.44 mmol),Potassium carbonate (265mg, 1.92mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound 1-20 (366 mg, 0.61 mmol),Yield: 63.5%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.8% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 23 Preparation of compound I-21 In a 100 mL round bottom flask, intermediate III-21 (400 mg, 1.02 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (336 mg, 1.53 mmol),Potassium carbonate (282 mg, 2.04 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-21 (356 mg, 0.62 mmol), yield: 60.8%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55.9% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 24 Preparation of compound I-22 Intermediate III-22 (400 mg, 1.02 mmol) was added to a 100 mL round bottom flask,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (336 mg, 1.53 mmol),Potassium carbonate (282 mg, 2.04 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound 1-22 (325 mg, 0.57 mmol),Yield: 55.9%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.5% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 25 Preparation of compound I-23 In a 100 mL round bottom flask, intermediate III-23 (400 mg, 0.94 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (310 mg, 1.41 mmol),Potassium carbonate (260 mg, 1.88 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-23 (334 mg, 0.55 mmol),Yield: 58.5%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.1% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 26 Preparation of compound I-24 In a 100 mL round bottom flask, intermediate III-24 (400 mg, 1.07 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (353 mg, 1.61 mmol),Potassium carbonate (296 mg, 2.14 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound 1-24 (337 mg, 0.60 mmol),Yield: 56.1%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.8% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 27 Preparation of compound I-25 In a 100 mL round bottom flask, intermediate III-25 (400 mg, 1.02 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (336 mg, 1.53 mmol),Potassium carbonate (282 mg, 2.04 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-25 (345 mg, 0.62 mmol), yield: 60.8%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.2% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 28 Preparation of compound I-26 In a 100 mL round bottom flask, intermediate III-26 (400 mg, 1.02 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (336 mg, 1.53 mmol),Potassium carbonate (282 mg, 2.04 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-26 (354 mg, 0.61 mmol), yield: 60.2%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.8% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 29 Preparation of compound I-27 In a 100 mL round bottom flask, intermediate III-27 (400 mg, 1.15 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (378 mg, 1.72 mmol),Potassium carbonate (317 mg, 2.30 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-27 (292 mg, 0.55 mmol), yield: 47.8%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.4% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 30 Preparation of compound I-28 In a 100 mL round bottom flask, intermediate III-28 (400 mg, 1.05 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (347 mg, 1.58 mmol),Potassium carbonate (290 mg, 2.10 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound 1-28 (304 mg, 0.54 mmol),Yield: 51.4%;s |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55.5% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 31 Preparation of compound I-29 In a 100 mL round bottom flask, intermediate III-29 (400 mg, 1.10 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (362 mg, 1.65 mmol),Potassium carbonate (304 mg, 2.20 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound 1-29 (334 mg, 0.61 mmol),Yield: 55.5%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.9% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 32 Preparation of compound I-30 Intermediate III-30 (400 mg, 1.06 mmol) was added to a 100 mL round bottom flask,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (348 mg, 1.59 mmol),Potassium carbonate (293 mg, 2.12 mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-30 (309 mg, 0.55 mmol),Yield: 51.9%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.9% | With potassium carbonate In acetonitrile at 80℃; for 12h; | 33 Preparation of compound I-31 In a 100 mL round bottom flask, intermediate III-31 (400 mg, 0.96 mmol) was added,1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (318 mg, 1.45 mmol),Potassium carbonate (265mg, 1.92mmol),Using acetonitrile (8 mL) as solvent, react at 80 °C for 12 h,Thin-layer chromatography was followed until the end of the reaction, cooled to room temperature,The solvent was removed to obtain compound I-31 (269 mg, 0.45 mmol), yield: 46.9%; |
Tags: 16773-42-5 synthesis path| 16773-42-5 SDS| 16773-42-5 COA| 16773-42-5 purity| 16773-42-5 application| 16773-42-5 NMR| 16773-42-5 COA| 16773-42-5 structure
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P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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