Month: August 2021

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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H10N2

To 2-isopropylimidazole (28mg) in dry N,N-dimethylformamide (ImI) was added sodium hydride (lOmg, 60% dispersion in mineral oil). After 30 minutes, 2-chloro-6- (4-methanesulfonyl-piperazin-l-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine, prepared via General Procedure B-3, was added and the reaction mixture was heated in the microwave for 45 minutes at 12O0C. The reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo and the residue purified using flash chromatography to yield 176. NMR (400MHz CDC13): 1.19(lH,s,CH), 1.30(6H,d(J=6.84), 2.61-2.63(4H,m,CH2), 2.74(3H,s,CH3), 3.23-3.25(4H,m,CH2), 3.79- 3.82(6H,m,CH2), 3.92-3.94(4H,m,CH2), 6.92(lH,s,ar), 7.18(lH,s,ar), 7.66(lH,d(J=1.49),ar). MH+ 506.30

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; PIRAMED LIMITED; GENENTECH, INC.; BAYLISS, Tracy; CHUCKOWREE, Irina; FOLKES, Adrian; OXENFORD, Sally; WAN, Nan, Chi; CASTANEDO, Georgette; GOLDSMITH, Richard; GUNZNER, Janet; HEFFRON, Tim; MATHIEU, Simon; OLIVERO, Alan; STABEN, Steven; SUTHERLIN, Daniel, P.; ZHU, Bing-Yan; WO2008/70740; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 72-40-2, These common heterocyclic compound, 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, 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 stirred solution of 4-aminoimidazole-5-carboxamide hydrochloride [0957] (1 g, 6.151 mmol) in N,N-dimethylformamide (5 mL) was added ethylxanthic acid potassium salt (1.479 g, 9.226) and the mixture was heated at 140 C. for 5 h. The reaction mixture was concentrated under reduced pressure. The residue was triturated with acetonitrile (20 mL). The solid was filtered, washed with acetonitrile (10 mL) and dried under vacuum to afford 2-mercapto-1,9-dihydro-6H-purin-6-one [0958] as a brown solid (0.8 g, 77%). MS(M+1)+=169.0.

The synthetic route of 72-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cadent Therapeutics, Inc.; Jefson, Martin R.; Keaney, Gregg F.; Larsen, Janus Schreiber; Lowe, III, John A.; McCall, John M.; (110 pag.)US2017/355708; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 152628-02-9, These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, 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.

The bisbenzimidazole heterocyclic compound(500 mg, 1.64 mmol) was dissolved in 20 mL of N, N-dimethylformamide,Sodium hydride (79 mg, 3.3 mmol) was added,Stirred at room temperature for 30 min,A solution of N, N-dimethylformamide (10 mL) containing N-o-methoxycarbonylphenyl-4-bromomethylindole (617 mg, 1.8 mmol) was slowly added dropwise.After dripping,The mixture was stirred at room temperature for about 2 h,TLC was monitored until the reaction was complete.Add 2M sodium hydroxide solution 2mL,Stir at room temperature for about 2 h.TLC monitoring to the reaction is complete,The pH was adjusted to 5-6 with 2M hydrochloric acid, 200 mL of dichloromethane and 200 mL of 7 K were added to the reaction solution,Take the organic phase,The aqueous phase was extracted three times with dichloromethane (150 mL X3)Combine the organic phase.The organic phase was washed four times with saturated brine (300 mL X4)Dried over anhydrous magnesium sulfate,filter,The solvent was distilled off under reduced pressure,To give a tan solid.The solid was recrystallized to give about 600 mg (yield: about 66.0%) of the off-white solid product.

Statistics shows that 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 152628-02-9.

Reference:
Patent; Chen, Zhilong; Zhu, Weibo; Ren, He; Yan, Yijia; Bao, Xiaolu; Chen, Danye; (16 pag.)CN106467521; (2017); 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., Recommanded Product: 144689-93-0

Ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate (100 gm) was dissolved in acetone (2500 ml) and then added potassium carbonate (100 gm), 5-[4′-(bromomethyl)[1,1′-biphenyl]-2-yl]-2-(triphenylmethyl)-1H-tetrazole (250 gm) and tert-butyl ammonium bromide (15 gm) under stirring at room temperature. The temperature of the reaction mass was raised to 50 to 55 C. and maintained for 15 hours at 50 to 55 C. The reaction mass was cooled to 45 C. and passed over celite bed. The collected filtrate was cooled to 0 to 5 C. and then added a solution of potassium carbonate (36 gm) in water (36 ml) for 1 hour. The temperature of the reaction mass was raised to room temperature and maintained for 16 hours at room temperature. The acetone was distilled off completely under vacuum at below 40 C. to obtain residue. To the residue was added sodium chloride solution (10%, 900 ml) and then added ethyl acetate (1500 ml). The layers were separated and the aqueous layer was extracted. Combined the both organic layers and dried over sodium sulfate. The solvent was distilled off completely to obtain a residual mass. A mixture of acetone (1200 ml), potassium carbonate (100 gm), (4-bromoethyl)-5-methyl-oxo-1,3-dioxane (105 gm) and potassium iodide (17 gm) were added under stirring at room temperature and then the contents were heated to 50 to 55 C. The solution was added to the above residual mass for 1 hour 30 minutes and maintained for 1 hour 30 minutes at 50 to 55 C. The reaction mass was cooled to 45 C. and filtered. The solvent was distilled off completely to obtain residue. Toluene (1500 ml) was added to the residue and the layers were separated. The toluene layer was dried over sodium sulfate and distilled off the layer under vacuum up to obtain clear residual mass. To the residual mass was added methanol (1500 ml) and stirred for 30 minutes at room temperature. The reaction mass was cooled to 10 to 15 C. and maintained for 1 hour 30 minutes. The separated solid was filtered and dried at 40 to 45 C. for 7 hours to obtain 270 gm of trityl olmesartan medoxomil. Trityl olmesartan medoxomil: 98.5%; Trityl olmesartan ethyl ester impurity: 0.35%; Bromo trityl olmesartan medoxomil impurity: 0.35%; Methyl trityl olmesartan medoxomil impurity: 0.34%.

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

Reference:
Patent; HETERO RESEARCH FOUNDATION; Parthasaradhi Reddy, Bandi; Rathnakar Reddy, Kura; Muralidhara Reddy, Dasari; Raji Reddy, Rapolu; Ramakrishna Reddy, Matta; Vamsi Krishna, Bandi; US2013/190506; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, 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. name: 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde

Step 3. N-(2-amino-2-oxoethyl)-N-(5-fluoro-2-((4-(7-((2-oxo-2,3-dihydro-1H- benzo[d]imidazol-5-yl)methyl)-2,7-diazaspiro[4.4]nonan-2-yl)pyrimidin-5- yl)oxy)phenyl)isobutyramide (1176) To a solution of N-(2-((4-(2,7-diazaspiro[4.4]nonan-2-yl)pyrimidin-5-yl)oxy)-5- fluorophenyl)-N-(2-amino-2-oxoethyl)isobutyramide (40 mg, crude) and 2-oxo-2,3- dihydro-1H-benzo[d]imidazole-5-carbaldehyde (Intermediate 40, 29 mg, 0.18 mmol) in anhydrous MeOH (4 mL) was added 4A-molecular sieves (50 mg), then the reaction was stirred at 50 C for 2 h under N2. After 2 h, NaBH3CN (28 mg, 0.45 mmol) was added into the solution and the reaction mixture was stirred at 50 C for 12 h. The reaction mixture was then filtered, concentrated under reduced pressure, and purified by RP- HPLC method G to afford N-(2-amino-2-oxoethyl)-N-(5-fluoro-2-((4-(7-((2-oxo-2,3- dihydro-1H-benzo[d]imidazol-5-yl)methyl)-2,7-diazaspiro[4.4]nonan-2-yl)pyrimidin-5- yl)oxy)phenyl)isobutyramide as a white solid.Yield: 7.00 mg. LCMS method E: Rt = 1.498 min, (M+H)+ = 603.3.1H NMR (CD3OD): delta 8.30 (s, 1 H), 7.76 (d, J = 2.4 Hz, 1 H), 7.52 (d, J = 8.8 Hz, 1 H), 7.15 (t, J = 8.0 Hz, 1 H), 6.87-7.03 (m, 4 H), 4.73 (dd, J = 16.4, 3.6 Hz, 1 H), 3.82 (dd, J =16.0, 4.8 Hz, 1 H), 3.56-3.85 (m, 5 H), 2.45-2.69 (m, 5 H), 1.81-1.94 (m, 5 H), 1.05 (dd, J = 36.8, 6.8 Hz, 6 H).19F NMR (CD3OD): delta -119.24.

The synthetic route of 106429-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); A1;,
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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 60-56-0

Example 257 7-{1-[(1-Methyl-1H-imidazol-2-yl)thio]ethyl}-2-(1,3-thiazol-2-yl)-1H-indole A solution of 1-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]ethanol (0.089 g), 1-methyl-1H-imidazole-2-thiol (0.046 g) and tributylphosphine (0.458 g) in tetrahydrofuran (7 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.584 g) was added, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate_hexane=30:70 – 70:30) to give the title compound (0.110 g, yield 89%) as colorless crystals. MS m/z 341 (M+H+).

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1873144; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, 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 28890-99-5, Formula: C13H9N3

Example 4 a) 7.78 g (25 mmol) 1-bromo-3-iodo-benzene, 16.3 g (50.0 mmol) caesium carbonate, 1.24 g (6.50 mmol) copper(I) iodide and 1.50 g (13.0 mmol) L-proline are added to 5.18 g (25.0 mmol) mmol) 5H-benzimidazo[1,2-a]benzimidazole in 100 ml dimethylsulfoxide (DMSO) under nitrogen. The reaction mixture is stirred for 18 h at 100 C. The reaction mixture is poured into water. The organic phase is extracted with dichloromethane. The organic phase is dried with magnesium sulfate. The solvent is distilled of. Column chromatography on silica gel with toluene gives the product. Yield 8.35 g (92%).1H NMR (400 MHz, CDCl3): delta 8.25 (s, 1H), 7.90-8.05 (m, 3H), 7.95-8.05 (m, 3H), 7.71 (d, J=7.9 Hz, 1H), 7.65 (d, J=7.9 Hz, 1H). 7.50-7.65 (m, 2H), 7.26-7.45 (m, 4H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; US2012/241681; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.

Ethyl magnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a few minutes to a clear colorless solution of 5-bromo-1-methyl-1H-imidazole (10.4 g, 64.4 mmol) in THF (100 mL) under a nitrogen atmosphere in an ice bath. A white precipitate formed during the addition. The mixture was removed from the ice bath and was stirred for 20 minutes, then was again cooled in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, Intermediate 22: step a). The resulting white suspension was stirred overnight at room temperature. The reaction was quenched by addition of saturated aqueous NH4Cl and diluted with water. The mixture was partially concentrated to remove THF and was diluted with DCM. The mixture was acidified to pH 1 with 1 N aqueous HCl, then neutralized with saturated aqueous NaHCO3. The phases were separated and the aqueous phase was further extracted with DCM. The organic extracts were washed with water, then were dried (Na2SO4), filtered, and concentrated, affording a white solid. The crude product was triturated with a mixture of EtOAc:heptanes (1:1, 150 mL). The precipitated solid was collected by vacuum filtration, washing with heptanes, to afford the title compound.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); 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. 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, A new synthetic method of this compound is introduced below., Quality Control of 4-Amino-1H-imidazole-5-carboxamide

To a solution of 5-amino-lH-imidazole-4-carboxylic acid amide (lOg, 79.36 mmol) and DMAP (291 mg, 2.38 mmol) in anhydrous pyridine (200 mL) was slowly added 2,2- dimethyl-propionyl chloride (10.74 mL, 87.30 mmol) and the reaction mixture was stirred at 80 C for 8 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water (50 mL). The precipitate was filtered, washed with water (30 mL) and dried to get yield the title compound (9 g, 54 %) as ash-color solid. MS(m/e): 211.4 (M+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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BENDELS, Stefanie; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; WO2014/177490; (2014); 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. 50995-95-4, name is 2-Propylimidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Propylimidazole

General procedure: A solution of imidazole 4-13, benzimidazole 40, 41, pyridoimidazole 42 or benzotriazole 43 (23 mmol) in dry DMF (15 mL) and K2CO3 (11.5 mmol) was stirred for 10 min at 0-5 C, under nitrogen atmosphere. After this time, appropriate 1-aryl-2-bromo-ethanone 18-21 (23 mmol) was added and the mixture was stirred for 1.5 h then poured into ice water. The resulting crude material was extracted with dichloromethane (3 × 50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure; the obtained residue were purified by means of flash chromatography performed using silica gel 60 (230-400 mesh) and a mixture of ethyl acetate/methanol 8:2 v/v or dichloromethane/methanol 9.5/0.5 v/v (only for purification of 25 and 26, 49 and 51, 50 and 52, respectively) as eluent.

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; Salerno, Loredana; Modica, Maria N.; Romeo, Giuseppe; Pittala, Valeria; Siracusa, Maria A.; Amato, Maria E.; Acquaviva, Rosaria; Di Giacomo, Claudia; Sorrenti, Valeria; European Journal of Medicinal Chemistry; vol. 49; (2012); p. 118 – 126;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem