Category: 144689-93-0

Synthetic Route of 144689-93-0, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Imidazole 1 (2.0-8.0 g, 8.3-33.3 mmol), trityl protected tetrazolebiphenyl 2 (1.0 equivalent) and LiOH*H2O (1.0 equivalent) were stirred at ambient temperature in solvent-1 (17.5 mL/g of 1). The course of thereaction was monitored by HPLC. At partial conversion to the ester 3(when ca. 10 % of 2 was present in the reaction mixture), the temperature was raised to 40 C. When quantitative conversion to ester 3 was reached LiOH*H2O (1.5 equivalent) was added at 40 C to the reaction mixture and stirred at this temperature until the sufficient conversion to 4 was obtained. The reaction mixtures in entry 1-4 experiments were cooled to ambient temperature, in entry 5-6 experiments the temperature was maintained and reaction mixture stirred at 40 C until the reaction mixture contained less than 3% of 3. Then K2CO3 (1.1equivalent) was added followed by dropwise addition of 5 (1.23equivalent) solution in solvent-2 (2 mL/g of 1). The temperature of the reaction was raised to 50 C and mixture was stirred until quantitative conversion to 6 was obtained (if necessary, a smaller proportion of 5 was added). The reaction mixture was cooled and poured onto a mixture of ice and water, stirred for at least 0.5 h, the precipitate was filtered off and then re-slurred twice in water. The crude wet product was recrystallized from acetone and obtained precipitate was washed with a mixture of acetone/water (v/v=1/1).

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Toplak ?asar, Renata; ?asar, Zdenko; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4348 – 4359;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 144689-93-0, name: Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

EXAMPLE 2; 3-(4-Bromo-benzyl)-5-(1-hydroxy-1-methyl-ethyl)-2-propyl-3H-imidazol-4-carboxylic acid ethyl ester (IV; XBr)A mixture of a compound of formula (IX), in which R4 is ethyl (100 g, 0.417 mol), a compound of formula (X), in which X=Z=Br (107.5 g, 1.03 mol) and K2CO3 (71 g, 0.516 mol) in DMA (400 mL) is reacted at room temperature, under stirring, for 18 hours. The reaction mixture is then diluted with water and the precipitated solid is filtered and dried in a static dryer under vacuum.152 g of the title compound are obtained; yield: 89%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; US2008/76932; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144689-93-0, These common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

18(a) Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate 48 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to a solution of 0.26 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) in 5 ml of N,N-dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 0.72 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 5 ml of N,N-dimethylformamide was then added, and the reaction mixture was stirred at room temperature for 2 hours and then at 60 C. for 4 hours. At the end of this time, it was dissolved in ethyl acetate and the solution was washed three times with water. The solution was then dried over anhydrous sodium sulfate, after which it was freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.62 g of the title compound as an amorphous solid. This was crystallized from diisopropyl ether, to give the title compound as crystals, melting at 167-168 C. (with decomposition). Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 0.88 (3H, triplet, J=7 Hz); 1.08 (3H, triplet, J=7 Hz); 1.5-1.8 (2H, multiplet); 1.64 (6H, singlet); 2.52 (2H, triplet, J=8 Hz); 4.12 (2H, quartet, J=7 Hz); 5.38 (2H, singlet); 5.78 (1H, singlet); 6.7-7.6 (22H, multiplet); 7.8-8.1 (1H, multiplet).

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C12H20N2O3

Weigh 24.0 g of compound 1, 55.7 g of compound 2, And add 124g of potassium carbonate, Then 200 mL of butanone was added, Warmed to 60 C, Stir for two hours, Cool to 45 , The composite catalyst (a mixture of polyethylene glycol 400 and N, N-dimethylacetamide in a mass ratio of 5: 1) Continue stirring for 4 hours, TLC detection, Show two kinds of raw materials are not left. The reaction is over, filter, The filtrate was collected, concentrate, Get oil, A mixture of 50 mL of ethanol and water (2: 1 by volume) Stirring, A large number of solid precipitation, filter, Collect the solid, Washed with 50mL n-hexane beating, The target compound 67.3g, Yield 93.8% The HPLC purity was 99.3%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Disha Pharmaceutical Group Co., Ltd.; Zhang Zhaoxing; Zhang Hongqiang; Qin Litai; Li Wei; Li Zongwen; Xia Haijian; (6 pag.)CN103012382; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

18(a) Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate 48 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to a solution of 0.26 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) in 5 ml of N,N-dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 0.72 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 5 ml of N,N-dimethylformamide was then added, and the reaction mixture was stirred at room temperature for 2 hours and then at 60 C. for 4 hours. At the end of this time, it was dissolved in ethyl acetate and the solution was washed three times with water. The solution was then dried over anhydrous sodium sulfate, after which it was freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.62 g of the title compound as an amorphous solid. This was crystallized from diisopropyl ether, to give the title compound as crystals, melting at 167-168 C. (with decomposition). Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 0.88 (3H, triplet, J=7 Hz); 1.08 (3H, triplet, J=7 Hz); 1.5-1.8 (2H, multiplet); 1.64 (6H, singlet); 2.52 (2H, triplet, J=8 Hz); 4.12 (2H, quartet, J=7 Hz); 5.38 (2H, singlet); 5.78 (1H, singlet); 6.7-7.6 (22H, multiplet); 7.8-8.1 (1H, multiplet).

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144689-93-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 144689-93-0 as follows.

Example 6:; (5-MethyI-2-oxo-l,3-dioxol-4-yI)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2- (2H-tetrazoI-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate (olmesartan medoxomil) (Ie); Step I: 5-(2-Hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(N-(2-trimethylsilylethoxymethyl) tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-ethylcarboxylate (Vd); 2-Propyl-5-[(l-hydroxy-l-methyl)ethyl]-3H-imidazole-4-ethylcarboxylate (0.808 g, 0.0033675 mol) was added to the two isomers (IVb) (1.5 g, 0.0033675 mol) and K2CO3 (0.558 g, 0.0040382 mol) in anhydrous DMF (10 mL) under N2 atmosphere. The mixture was stirred at room temperature for 17 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The mixture was partitioned between water and AcOEt. The organic layer was washed with water (3 times), dried over Na2SO4 and concentrated under reduced pressure to give a residue (1.8 g) that was purified by flash chromatography on silica (cyclohexane/AcOEt 6:4) to give the isomer (Vd1) (0.499 g) and the isomer (Vd2) (0.206 g) as oils. Yield: 35%. (Vd1) (isomer with lower elution time):1H-NMR (400 MHz, CDCl3, delta): -0.03 (s, 9H, Me3Si), 0.92 (t, J=8.2Hz, 2H, SiCH2CH2O), 0.96 (t, J=7.2Hz, 3H, CH2CH2CH3), 1.18 (t, J=7.2etaz, 3H, OCH2CHi), 1.64 (s, 6eta, CMe2), 1.67-1.76 (m, 2H5 CH2CH2CH3), 2.66 (t, J=7.6Hz, 2H, CH2CH2CH3), 3.66 (t, J=8.2Hz, 2H, SiCH2CH2O), 4.22 (q, J=7.2etaz, 2H, OCH2CH3), 5.44 (s, 2H, ArCH2N), 5.78 (s, 2H, OCH2N), 6.84-6.86 (m, 2H) 7.14-7.16 (m, 2H) 7.41-7.43 (m, IH) 7.46-7.56 (m, 2H) 7.84- 7.86 (m, IH) (aromatic protons).(Vd2) (isomer with higher elution time): 1H-NMR (400 MHz, CDCl3, delta): -0.10 (s, 9H, Me3Si), 0.70 (t, J=8.4Hz, 2H, SiCH2CH2O), 0.92 (t, J=7.4Hz, 3H, CH2CH2CH5), 1.13 (t, J=7.0etaz, .3eta, OCH2CH3), 1.60 (s, 6eta, CMe2), 1.62-1.71 (m, 2H, CH2CH2CH3), 2.58 (t, J=7.8Hz, 2H, CH2CH2CH3), 3.39 (t, J=8.4Hz, 2H, SiCH2CH2O), 4.17 (q, J=7.2etaz, 2H, OCH2CH3), 5.05 (s, 2H, ArCH2N), 5.38 (s, 2H, OCH2N), 6.81-6.83 (m, 2H) 7.05-7.07 (m, 2H) 7.49-7.52 (m, 2H) 7.55-7.57 (m, IH) 7.61- 7.65 (m, IH) (aromatic protons). Step II: 5-(2-Hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(N-(2-trimethylsilylethoxymethyl) tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylic acid (Ve i); A solution of NaOH (0.052 g, 0.001311 mol> in water (1 mL) was added to compound (VdO (0.262 g, 0.0004337 mol) in THF (1 mL). The mixture was stirred at room temperature for 23 hrs (TLC monitoring: CH2Cl2/MeOH/AcOH 85:10:5). HCl IN was added until pH 4 was reached. The mixture was extracted with AcOEt. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to give the compound (Vei) (0.261 g) as a white solid, m.p. 68-69C. Yield: 99%. 1H-NMR (400 MHz, CDCl3, delta): -0.05 (s, 9H, Me3Si), 0.86 (t, J-7.2Hz, 3H, CH2CH2CH3), 0.89 (t, J=8.1etaz, 2H, SiCH2CH2O), 1.54-1.60 (m, 2H, CH2CH2CH3) 1.67 (s, 6H, CMe2), 2.94 (t, J-7.2Hz, 2H, CH2CH2CH3), 3.65 (t, J=8.1Hz, 2H, SiCH2CH2O), 5.75 (s, 2eta, ArCH2N), 5.79 (s, 2H, OCH2N), 6.97-6.99 (m, 2H) 7.12-7.14 (m, 2H) 7.35-7.38 (m, IH) 7.44-7.53 (m, 2H) 7.83-7.85 (m, IH) (aromatic protons). Step III: 4-Bromomethyl-5-methyl~l,3-dioxol~2-one; A mixture of 4,5-dimethyl-l,3-dioxol-2-one (1.5 g, 0.013158 mol), NBS (2.34 g, 0.013158 mol) and benzoyl peroxide (0.089 g, 0.0003684 mol) in CCl4 (20 mL) was stirred at 77C for 6 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The solution was treated with an aqueous solution OfNaHCO3 and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to give 4-bromomethyl-5 -methyl- 1,3- dioxol-2-one (2.34 g). Yield: 92%.1H-NMR (400 MHz, CDCl3, delta): 2.13 (s, 3H, CH3), 4.18 (s, 2H, CH2Br). Stp IV: (5-Methyl-2-oxo-l,3-dioxol-4-yl)methyl 5-(2~hydroxypropan-2-yl)-2-propyl-3-[[4- [2-(N-(2-trimethylsilylethoxymethyl)tetrazol-5-yl)pherpsil]phenyl]methyl]imidazole-4- carboxylate (Vf1); A mixture of the compound (Ve1) (0.260 g, 0.0004516 mol), 4-bromomethyl-5-methyl-l,3- dioxol-2-one (0.1 g, 0.000518 mol) and K2CO3 (0.033 g, 0.000239 mol) in anhydrous DMF (1.5 mL) was stirred for 1.5 hrs at room temperature under N2 atmosphere (TLC monitoring: CH2Cl2/Me0H/Ac0H 85:10:5). The mixture was partitioned between a saturated solution of NaHCO3 and AcOEt. The organic phase was washed with water (3 times), dried over Na2SO4 and concentrated under reduced pressure to give the compound (Vf1) (0.3042g) as a yellow oil. Yield: 98%.1H-NMR (400 MHz, CDCl3, delta): -0.02 (s, 9H, Me3Si), 0.92 (t, J=8.1Hz, 2H, SiCH2CH2O), 0.98 (t, J=7.2Hz, 3H, CH2CH2CH3), 1.64 (s, 6eta, CMe2), 1.70-1.80 (m, 2H, CH2CH2CH3), 2.07 (s, 3H, CH3C=C), 2.76 (m, 2H, CH2CH2CH3), 3.67 (t, J=8.1Hz, 2H, SiCH2CH2O), 4.89 (s, 2eta, COOCH2), 5.41 (s, 2H, ArCH2N), 5.79 (s, 2H, OCH2N), 6.80-6.82 (m, 2H) 7.14-7.16 (m, 2H) 7.44-7.52 (m, 2H) 7.54-7.58 (m, IH) 7.85-7.87 (m, IH) (aromatic protons). Step V: (5-Methyl-2-oxo-l,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)~2~propyl~3-[[4- [2~(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate (olmesartan medo…

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; S.I.M.S. S.r.l. – SOCIETA ITALIANA MEDICINALI SCANDICCI; WO2008/12852; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 144689-93-0

Preparation of Olmesartan Medoxomil Example 1 17.3 g (124.8 mmol) of K2CO3, 15 g (62.4 mmol) ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (III) and 38.3 g (68.7 mmol) 4-[2-(trityltetrazol-5-yl)phenyl]-benzyl bromide (IVa) were suspended in 750 ml of acetonitrile. The suspension was then heated under reflux until the reaction was completed (7 h). 510 ml of acetonitrile were distilled off and the concentrate was cooled to 23 to 25 C. The mixture was stirred at this temperature overnight, then the suspension was cooled to 0 C. and stirred at this temperature for 1 h. The crude product (Va) was filtered off and washed 2* with 20 ml of cooled acetonitrile. Wet product was suspended in 450 ml of water, stirred for 1.5 h and after that filtered off. The mass of dried product (Va) was 39.5 g (89%). T=165-169 C. IR: 1666, 1525, 1291, 1446, 1177, 881, 756, 699, 640

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KRKA; US2009/131680; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Synthesis of 1 was achieved by literature known method [1, 2]. To a solution of 1 (5 g, 20.82 mmol) in ethanol (50 mL), hydrazine hydrate (3.03 mL, 62.46 mmol) was added. The reaction mixture was refluxed for 16 h for completion of the reaction which was monitored by TLC. Solvent was removed under reduced pressure and cooled by adding ice cold water. The resulting precipitate was filtered, washed with cold water and recrystallized from ethanol to get the desired compound 2.

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumara; Suhas; Suyoga Vardhan; Shobha; Channe Gowda; Bioorganic Chemistry; vol. 86; (2019); p. 34 – 38;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, Adding a certain compound to certain chemical reactions, such as: 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 144689-93-0.

20L reactor was added 300.0g (1.25mol) imidazole mono-, 1043.6g (1.87mol) BBTT, 44.8g (1.87mol) of lithium hydroxide and 7kg acetonitrile. The reaction system was increased to 70-75 5h, TLC or HPLC in control, raw reaction was complete. After cooling to 30-45 system To the system was added in portions 280.6g (5.0mol) of potassium hydroxide and 700g of water to form a solution. Plus complete, insulation reaction 4-5h, TLC or HPLC in control, raw reaction was complete. After 300g of water added to the system dropwise acetic acid adjusted to pH 5.5 to 6.5. After stirring for 1h incubation continued cooling to room temperature, filtered, the filter cake washed with a small amount of acetone to obtain 777.4g of intermediate 5 run. HPLC: 95.9%,Yield: 90.4%.

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Bang Pharmaceutical Co., Ltd.; Zhao, Guangrong; Huan, Shuang; Zhao, Huayang; Liu, Liping; Chen, Guoping; Tang, Jingyu; (19 pag.)CN105481842; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, The chemical industry reduces the impact on the environment during synthesis 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

400 ml of acetone was added to a 1 L glass reaction flask, and 111. 4 g of N-(triphenylmethyl)-5-(4′-bromomethylbiphenyl-2-yl)tetrazole, 48.0 of ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazol-5-carboxylate was added with stirring, 55.2 g of potassium carbonate, 6.4 g of tetrabutylammonium bromide, heated to 50-60 C, After the incubation reaction for 20 hours, the temperature was lowered to 20-30 C, 200 ml of water was added, stirred for 30 minutes, and filtered, and the filter cake was successively rinsed with 200 ml of water and 200 ml of acetone. The filter cake was air-dried at 40-50 C for 12 hours to give a white solid, 130.0 g ( Intermediate 1), yield: 90.7%, HPLC: 98.6%.

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Jiashi (Hunan) Pharmaceutical Technology Co., Ltd.; Dai Yongzhi; Liu Hu; Zhu Laifa; Cai Jian; (8 pag.)CN108341804; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem