Category: imidazoles-derivatives

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;,
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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;,
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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

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

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

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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., Safety of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

4-Nitrophenol (162 mg, 1.17 mmol) is dissolved in methylene chloride (2 mL). To the solution is added (3-methyl-2-nitro-3H-imidazol-4-yl)-methanol (115 mg, 0.732 mmol) and triphenylphosphine (211 mg, 0.805 mmol). The mixture is stirred at room temperature until a solution is achieved. The solution is then cooled in an ice bath and treated with diisopropyl azodicarboxylate, DIAD (158 uL, 0.805 mmol). After 1 hour the ice bath is removed and the mixture is stirred overnight at room temperature. Crude product is purified on a silica gel column to isolate the product mixed with triphenylphosphine oxide. The solids are triturated with t-butyl methyl ether to remove the triphenylphosphine oxide to afford l-methyl-2-mtro-5- (4-nitro-phenoxymethyl)-lH-imidazole. MS (ESI+) for C11H10N4O5 m/z 279.1 (M+H)+.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 118469-15-1, The chemical industry reduces the impact on the environment during synthesis 118469-15-1, name is 5-Fluoro-2-methyl-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

In a 150 mL round bottom flask, intermediate VI-13 2-methyl 5-fluorobenzimidazole (0.31 g, 2.04 mmol) was added, and potassium carbonate was used as a base (0.30 g, 2.20 mmol), and acetonitrile was stirred at 50 C as a solvent. After 40 minutes, after cooling to room temperature, intermediate V (0.43 g, 1.70 mmol) was added and the mixture was warmed to 75 C. After concentration, extraction, column chromatography separation, drying, etc., the intermediate X-13 (0.48 g) is obtained in a yield of 77.8%; white solid

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Fluoro-2-methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei·lamohan·laao·yadafu; Wang Juan; (39 pag.)CN110305064; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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. Computed Properties of C5H6N2O2

Examples; CRYSTAL FORMS OF ZOLEDRONIC ACID (ZLD-Ac); Preparation of ZLD-AC crystal form I; General procedure for the preparation of ZLD-AC crystal form I starting from 1- Imidazoleacetic acid (IAA), Phosphorous acid (H3PO3) and Phosphorous oxychloride (POC13) (Examples 1-9, see Table 1) :; A cylindrical reactor equipped with a mechanical stirrer, a thermometer, a reflux condenser and a dropping funnel, is loaded with 1-IMIDAZOLEACETIC acid (IAA), Phosphorous acid and a diluent (Toluene/Chlorobenzene/PEG-400/Silicon oil). The obtained suspension is heated to 75C-80C and Phosphorous oxychloride is added drop- wise. The reaction mixture is then heated to 75C-100C for 1-34 hours. Then water is added at 80C-100C. The mixture is stirred vigorously for about 15 minutes. [In some cases, when Silicon oil is used as a diluent, there is a need to add Toluene in order to improve the separation between the oily phase and the aqueous phase]. Then the phases are separated. The aqueous phase is put in a clean reactor and heated to 95C-100C for 13.5-19 hours. Then it is cooled to 5C and absolute Ethanol is added to obtain a precipitate after stirring at 5C for 2.5-4 hours [In some cases a precipitate of Zoledronic acid is obtained without adding absolute Ethanol as an anti-solvent]. The white product is then filtered, washed with absolute Ethanol and dried in a vacuum oven at 50C for 17-24 hours to obtain Zoledronic acid crystal form I (LOD BY TGA=6. 3%-9. 3%).; ZLD HPLC METHOD: COLUMN: PHENOMENEX PHENYL-HEXYL 5UM, 250X4.6MM MOBILE PHASE: 40MM OCTANSULFONIC ACID SODIUM SALT IN 1% HCLO4, 0.2% H3PO4 : METHANOL (85:15) DETECTION: 220NM STABILITY WAS MEASURED VERSUS THE PRESENCE OF FORM II. P THE STABILITY DATA FOR EXAMPLE 4 IN THE TABLE ABOVE IS:

The synthetic route of 22884-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/5447; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3034-38-6,Some common heterocyclic compound, 3034-38-6, name is 5-Nitro-1H-imidazole, molecular formula is C3H3N3O2, 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.

Step A: To a mixture of 4-nitro-lH-imidazole (1.5 g, 13.27 mmol) and TEA (2 mL, 14.59 mmol) in DMF (12 mL) at 0 C was added trityl chloride (3.7 g, 13.27 mmol). The mixture was allowed to warm to rt and was stirred for 1 h. The mixture was poured onto ice and 1 N aq NaOH (2 mL) was added. The solid was collected by filtration washing with water to afford 4-nitro-l -trityl- lH-imidazole as a solid (4.58 g, 96%).

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMBIT BOISCIENCES CORPORATION; HADD, Michael, J.; WO2012/30914; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 120781-02-4, These common heterocyclic compound, 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-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.

(1) 2-bromo-3-methyl -3H- to imidazole-4-carboxylic acid methyl ester (800mg) 4-(trifluoromethyl)benzeneboronic acid(1.04g), tetrakis(triphenylphosphine)palladium(422mg) And as a solvent was stirred in tetrahydrofuran (9), saturated sodium carbonate (3), was added water (1.5), and microwave irradiation for 30 minutes at 120 . After the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (n- hexane: ethyl acetate) [(trifluoromethyl) 4-phenyl] After purification, 3-methyl-2–3H- imidazole-4-carboxylic acid methyl ester ( It was obtained 980mg) as a yellow solid.

Statistics shows that Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 120781-02-4.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; Watanabe, Masayuki; Furukawa, Hiroyuki; Hamada, Maiko; Fuji, Naoto; Ushio, Hiroyuki; Takashima, Toru; (81 pag.)KR2015/2661; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem