Author: Jessica.F

144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 144689-93-0

An eggplant flask was charged with 5- (1-hydroxy-1-methylethyl) -2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (10 g, 41.7 mmol; imidazole derivative (compound of formula (4b)), 4-bromobenzyl bromide (10.8 g, 43 mmol; dihalogen compound),Dimethylacetamide (40 ml; first reaction solvent (DMA)) was added to a mixture of potassium carbonate (7.1 g, 51.6 mmol; base) and stirred for 48 hours. After the reaction, water (120 mL) was added to the reaction solution and stirred. The precipitated crystals were filtered and recrystallized from ethyl acetate to give 3- (4-bromobenzyl) -5- (1-hydroxy-1-methylethyl) -2-propyl-3H-imidazole-4-carboxylic acid ethyl ester(A halogenated imidazole derivative (compound of the formula (1b))) 8 g (yield 47%).

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

Reference:
Patent; Tokuyama Corporation; Sekine, Masahiko; Tanaka, Kenji; (31 pag.)JP2018/154611; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33529-02-1, 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 33529-02-1 as follows.

In einem Autoklaven wurden 0,25 Mol 1-Decylimidazol, welches durch die Radziszewski-Reaktion aus Glyoxal, Formaldehyd, Ammoniak und 1-Decylamin zugaenglich ist (siehe Ullmann’s Encyclopedia of Industrial Chemistry, 6th edition, 2000 electronic release, Chapter “IMIDAZOLE AND DERIVATIVES – Production), und 0,3 Mol Dimethylcarbonat in 100 ml Methanol zusammen mit 1,5 g Kaliumcarbonat und 0,1 g 18-Krone-6 12 Stunden auf 135C erhitzt. Nach dem Abkuehlen wurde der Reaktionsaustrag filtriert und mit 150 ml 50%iger waessriger Tetrafluoroborsaeure (Fa. Acros) versetzt. Nun wurde fuer eine Stunde unter Ruehren auf 50C erwaermt und anschliebetaend die waessrige Phase abgetrennt. Die verbleibende organische Phase wurde erneut mit 100 ml 50 %iger waessriger Tetrafluoroborsaeure versetzt, fuer eine weitere Stunde unter Ruehren auf 50C erwaermt und die waessrige Phase abgetrennt. Der organische Rueckstand wurde nun zweimal mit Cyclohexan extrahiert und danach im Vakuum bei 80C von Loesungsmittelresten befreit. Es wurden 0,16 Mol 1-Decyl-3-methylimidazolium-tetrafluoroborat erhalten, was einer Ausbeute von 64 % entspricht.

According to the analysis of related databases, 33529-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; EP1398318; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 124750-59-0, name is 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C10H14N2O4

A mixture of dimethyl-2-propylimidazole-4,5-dicarboxylate compound of formula-2a (100 grams), 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide compound of formula-3 (296 grams), potassium carbonate (119 grams) in dimethyl formamide (100 ml) and acetone (500 ml) was heated to reflux temperature. The reaction mixture was stirred up to reaction completion and solvent was distilled off completely from the reaction mixture under reduced pressure at below 50C. The reaction mixture was cooled to 25-300C, acetone (150 ml) and water (1000 ml) were added to it then stirred for 60 minutes. The obtained solid was filtered, washed with water and then the wet solid was recrystallized from acetone to provide the title compound.Yield: 285 grams;Purity by HPLC: 98.15%

The synthetic route of 124750-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; NAGARAJU, Chakilam; THIRUMALAI RAJAN, Srinivasan; KODANDA RAMPRASAD, Achampeta; RAMA SUBBA REDDY, Karamala; WO2011/21224; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methyl-1H-imidazole-4-carbaldehyde

Synthesis of 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride To a suspension of 4-((1R,5S,9r)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride (100 mg, 0.32 mmol), 1-methyl-1H-imidazole-4-carboxaldehyde (70 mg, 0.64 mmol) and acetic acid (37 muL, 0.64 mmol) in dichloromethane (5 mL) was added sodium triacetoxyborohydride (203 mg, 0.96 mmol) at ambient temperature. After stirring for 16 hours, the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (*3). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica column chromatography, eluting with 2-10% methanol in dichloromethane to yield 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide (84 mg, 71% yield). To 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide (125 mg, 0.34 mmol) in ethyl acetate (10 mL) and dichloromethane (2 mL), was added 2M HCl in diethyl ether (0.17 mL, 0.34 mmol). The solvent was removed under reduced pressure. The resulting solid was triturated with diethyl ether and the liquors decanted. The solid was dried, dissolved in water and freeze-dried to yield 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride (83 mg, 60% yield). [M+H]+ 370.15. 1H NMR (400 MHz, D2O): 8.60 (d, 1H), 8.21 (s, 1H), 7.98 (s, 1H), 7.60 (d, 1H), 7.54 (s, 1H), 4.33 (s, 2H), 3.74 (s, 3H), 3.61 (d, 2H), 3.48 (d, 2H), 2.92 (s, 2H), 2.67 (s, 3H), 1.85-1.68 (m, 2H), 1.56-1.42 (m, 4H).

According to the analysis of related databases, 17289-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alkermes, Inc.; Wynn, Thomas Andrew; Alvarez, Juan C.; Moustakas, Demetri Theodore; Haeberlein, Markus; Pennington, Lewis D.; US2019/241524; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 14741-71-0, A common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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.

To a solution of compound 3 (2.04 g, 0.01 mol) in ethanol (40 mL) containing piperidine (0.50 mL) ethyl orthoformate (1.48 g, 0.01 mol) and aniline oil (0.93 g, 0.01 mol) was added. The reaction mixture was heated under reflux for 3 h then poured onto ice/water mixture containing few drops of hydrochloric acid and the formed solid product was collected by filtration. Pale yellow crystals from ethanol; yield: 2.35 g (79%); m.p. >300 oC. IR, : 3471-3329 (NH), 3055 (CH aromatic), 2980, 2873 (CH3, CH2), 1699 (CO), 1643 (C=N), 1629 (C=C). 1H-NMR: : 1.15 (t, 3H, J = 7.13 Hz, CH3), 4.23 (q, 2H, J = 7.13 Hz, CH2), 6.03 (s, 1H, CH=C), 7.26-7.42 (m, 9H, C6H5, C6H4), 8.23, 8.34 (2s, 2H, 2NH, D2O exchangeable). 13C NMR (DMSO): 16.2 (ester CH3), 52.5 (ester CH2), 88.4, 90.3 (C=C), 120.6, 121.6, 123.6, 123.8, 124.1, 125.3, 126.4, 127.3, 128.8, 129.5 (C6H5, C6H4), 164.8 (CO), 173.3 (C=N), Anal. calcd for C18H17N3O2: C, 70.34; H, 5.58; N, 13.67%. Found: C, 70.29; H, 5.73; N, 13.82%. MS: m/z: (%) 307 (M+, 22%).

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
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.

Into a 100-mL two-neck flask were sequentially added imidazole 4(5 g, 21.0 mmol), bromide 3 (9.05 g, 22.3 mmol), K2CO3 (5.1 g,37.4 mmol) and MeCN (50 mL) at 25 C. The reaction mixture washeated at 84 C until completion of the reaction (18 h). Then, themixture was cooled to 25 C and filtered through Celite. TheCelite bed was washed with EtOAc (2 × 10 mL). To the combinedEtOAc layer was added H2O (100 mL). The resulting two layerswere separated and the aqueous layer was extracted with EtOAc (3× 50 mL). The combined organic layer was washed with 2% aq HCl(30 mL) followed by brine (150 mL). The organic layer was driedover Na2SO4 and concentrated under reduced pressure to give 1a;yield: 9.78 g (83%)

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:
Article; Seki, Masahiko; Synthesis; vol. 46; 23; (2014); p. 3249 – 3255;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, 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 4856-97-7, Product Details of 4856-97-7

To a solution of 1 (5.0 g, 34 mmol) in DCM was added MnO2(1.3 g, 6.8 mmol). The resulting solution was stirred at 40 C for 2 h and monitored by TLC. Aftercomplete conversion of starting material, reaction mixture was cooled to room temperature, filteredand concentrated in vacuo to obtain 2 as white solid in 85.0% yield. LC-MS m/z: 147.1 [M + H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1H-Benzoimidazol-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Wang, Shuxiang; Guan, Lihong; Zang, Jie; Xing, Kun; Zhang, Jian; Liu, Dan; Zhao, Linxiang; Molecules; vol. 24; 7; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 496-46-8, 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 496-46-8 as follows.

Synthesis of cucurbit[n]urils in methanesulphonic acid using Diethoxymethane(Ethylal)Unsubstituted glycoluril (19.94 g) and methane sulphonic acid (neat, 82 mL) were placed in a reaction flask and heated to 80 C. Ethylal (35.21 mL) was added in drop-wise and the reaction mixture was then heated to 100 C (internal temp) for 18 hours. The reaction mixture was cooled and added to acetone (410 ml) to produce a brown powder which was analysed by1H NMR.Approximate Yields b1H NMR (% of recovered product) cucurbii[5]urii 8%, cucurbit[6]uri 42%, cucurbit[7]uril 43%, cucurbit[8]uril 7%, cucurbit[9]uril 0%, cucurbit[10]uril 0%, cucurbit[ 13uril 0%.Residual formaldehyde by HPLC method was 34 ppm.

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; DIEC, David; NOGUEIRA, Guilherme; GERARDUS DE ROOIJ, Johannes; (23 pag.)WO2018/115822; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-53-1, 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 68282-53-1 as follows.

COMPOUND 12.1. 53: NN-DIETHYL-4- {6-METHOXY-2- [4-METHYL-lH- IMIDAZOL-5-YL)METHYL]-7-NITRO-1,2,3,4-TETRAHYDROISOQUINOLIN-1- YLdBENZAMIDE; To a solution of INTERMEDIATE 9.2. 2 (1.16 g, 3.00 mmole) and 4-methyl-5- imidazolecarboxaldehyde (0.31 g, 2.8 mmole) in 1,2-dichloromethane (25 mL) was added sodium triacetoxyborohydride (1.65 g, 7.8 mmole) and the resulting solution was stirred at room temperature for 18 h. Sodium hydroxide (1M, 100 mL) was added and the mixture extracted with ethyl acetate (3 x 100 mL). The organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (ethyl acetate/10% methanol in chloroform, 2/8) to give COMPOUND 12.1. 53 (1.12 g, 78%) as a yellow amorphous solid. 1H NMR (500 MHz, CDC13) : 5 1.12, 1.23 (2 br s, 6H), 2.05 (s, 3H), 2.55 (m, 1H), 2.82 (dd, J3. 5,13 Hz, 1H), 3.02 (m, 1H), 3.12 (m, 1H), 3. 26 (br s, 2H), 3.30 (d, J 13.5 Hz, 1H), 3.54 (br s, 2H), 3.56 (d, J 13.5 Hz, 1H), 3.91 (s, 3H), 4.56 (s, 1H), 6.73 (br s, 2H), 6. 80 (s, 1H), 7.20 (s, 1H), 7.30 (m, 5H); 13C NMR (125 MHz, CDC13) : 8 10.76, 12.82, 14.13, 29.35, 39.39, 43.45, 46.11, 49.33, 56.46, 67.12, 113. 00, 126.13, 126.59, 127.03, 129.45, 129.50, 130.33, 133.05, 136.52, 137.67, 142.46, 144.01, 151.23, 171.07 ; (+) LRESIMS m/z 478 [M+H] +.

According to the analysis of related databases, 68282-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89830-98-8, A common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

General procedure: A mixture of 9-(2-methyloxazol- 4-yl)-3,4,7,8-tetrahydro-[1 ,4]diazepino[7,1-a]isoquinoline-2,5-dione (140 mg, 0.45 mmol) in DCE (10 mL) was treated with POCI3 (84 mu, 0.91 mmol) and heated to 100 °C for 1 h. The mixture was then allowed to cool to RT, poured onto cold H20 and extracted with DCM. The org. phases were dried over Na2SO,, filtered and concentrated in vacuo. The brown residue obtained was taken up in DCE (5 mL) and 4-cyclopropyl-1H-imidazole (59 mg, 0.54 mmol) and pyridine (110 mu, 1.36 mmol) were then added. The mixture was heated to 100 DC for 1 h, and then allowed to cool to RT, poured onto H20 and extracted with DCM. The org. layers were then dried over Na2S04. filtered and concentrated in vacuo. Purification by SFC (column: 2-Ethylpyridine 5 muetaiota, 250 x 30 mm, 60A, Princeton; eluent: 10percent MeOH/C02 for 1 min, then from 10percent MeOH/C02 to 15percent MeOH/C02 in 6 min; then from 15percent MeOH/C02 to 50percent MeOH/C02 in 1 min; flow 100 mL/min; UV detection at 220 nm) afforded the title compound (42 mg) as beige powder. UPLC-MS: MS 400.2 (M+H+); UPLC rt 0.86 min. 1H NMR (400 MHz, CHLOROFORM- : delta ppm 0.61 – 0.82 (m, 2 H); 0.82 – 0.91 (mr 2 H); 1.78 – 1.96 (m, 1 H); 2.56 (s, 3 H); 3.16 (t, J=6.02 Hz, 2 H); 3.89 (t, J=6.15 Hz, 2 H); 4.37 (br. s., 2 H); 6.62 (s, 1 H); 7.19 (d, J=1.25 Hz, 1 H); 7.38 – 7.48 (m, 1 H); 7.63 – 7.70 (m, 2 H); 7.78 (dd, J=7.65, .13 Hz, 1 H); 7.89 (d, J=1.26 Hz, 1 H).

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; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; WO2014/30128; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem