Category: imidazoles-derivatives

Application of 1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ethylmagnesium bromide (3 M in Et2O, 0.0642 mL, 0.193 mmol) was added dropwise to a solution of 5-bromo-1-methyl-1H-imidazole (31.0 mg, 0.193 mmol) in DCM (1 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature for 15 min, then was cooled to 0 C. A solution of (2,4-dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanone (49.2 mg, 0.128 mmol, Intermediate 37, step b) in DCM (2 mL) was added via cannula. The mixture was stirred at room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous NH4Cl and was diluted with water. The mixture was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by RP-HPLC (10-90% CH3CN-H2O, 0.1% TFA) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta 8.99 (br. s., 1H), 8.39 (s, 1H), 8.10-8.25 (m, 2H), 7.83 (d, J=9.05 Hz, 1H), 7.47-7.63 (m, 3H), 7.36-7.47 (m, 2H), 7.27 (br. s., 1H), 6.38 (s, 1H), 3.52 (s, 3H), 2.24 (s, 3H); MS m/e 465.1 [M+H]+.

The synthetic route of 5-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; 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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); 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. 3034-50-2, name is Imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H4N2O

To a mixture of 1H-imidazole-4-carbaldehyde (3.71 g, 38.6 mmol), 1-chloro-4-iodobenzene(13.81 g, 57.9 mmol), (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (1.10 g, 7.72 mmol),copper(l) iodide (0.368 g, 1.93 mmol) and cesium carbonate (25.2 g, 77 mmol) was added DMF (50 mL). The reaction was sealed and heated to 110 00 for 18 hours. The reaction mixture was then cooled to room temperature and diluted with a saturated solution of NH4CI.brown solid develops. Solid was collected, washed with water and air dried. Solid materialwas then dissolved in 10%MeOH:90%DCM solution and dried (Na2504), filtered and concentrated to afford a dark brown solid 1-(4-chlorophenyl)-1 H-imidazole-4-carbaldehyde (8.55 g, 41.4 mmol, 107 % yield). Material as used without further purification. LCMS m/z 207.1 (M + H), Rt 0.58 mm.Step 1

The synthetic route of 3034-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CAFERRO, Thomas Raymond; CHEN, Zhuoliang; CHO, Young Shin; COSTALES, Abran Q.; LEVELL, Julian Roy; LIU, Gang; MANNING, James R.; SENDZIK, Martin; SHAFER, Cynthia; SHULTZ, Michael David; SUTTON, James; WANG, Yaping; ZHAO, Qian; WO2014/141104; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 32673-41-9, A common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

Step A Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title product as a white.

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6297239; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 583-39-1, 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. 583-39-1, name is 2-Mercaptobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Benzyl chloride or 1-iodopropane, 89.25 mmol, and potassium carbonate, 170.0 mmol, were added to a solution of 85.0 mmol of 1,3-dihydro-2H-benzimidazole-2-thione in 140 mL of acetone. The mixture was refluxed for 3 h with stirring and poured into water with stirring to dissolve inorganic com-ponents. The precipitate was filtered off and washed with water and methanol. Compound 1b was dried and recrystallized from 20 mL of methanol. Compound 1a required no additional purification. Compound 1a. Yield 93%, colorless crystals, mp 180-181C. 1 H NMR spectrum, delta, ppm: 4.56 s (2H, CH 2 ), 7.07 t (2H, H arom , J = 4.0 Hz), 7.21 t (1H, H arom , J = 6.8 Hz), 7.28 t (2H, H arom , J = 7.2 Hz), 7.35-7.45 m (4H, H arom ), 12.04 br.s (1H, NH). Compound 1b. Yield 55%, colorless crystals, mp 151-152C. 1 H NMR spectrum, delta, ppm: 1.07 t (3H, CH 3 , J = 7.2 Hz), 1.80 sext (2H, CH 2 , J = 6.8 Hz), 3.25 t (2H, CH 2 , J = 7.2 Hz), 7.05 s (2H, H arom ), 7.37 s (1H, H arom ), 12.27 s (1H, NH).

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

Reference:
Article; Kharaneko; Russian Journal of Organic Chemistry; vol. 54; 9; (2018); p. 1363 – 1368; Zh. Org. Khim.; vol. 54; 9; (2018); p. 1350 – 1354,5;,
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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone

1,8-diazabicyclo[5.4.0]undec-7-enium 5′-O-(tert-butyldiphenylsilyl)-2′-O-(tert-butyldimethylsilyl)uridine-3′-yl phosphonate (8u) (100 mumol) are dried by repeated co-evaporation with anhydrous pyridine and then dissolved in anhydrous pyridine (1 mL). N,N’-bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride (BopCl; 500 mumol) is added and the mixture is allowed to stir for 5 minutes.To the mixture, a solution of amino alcohol (L-2) (100 mumol) dissolved in anhydrous pyridine (1 mL) was added dropwise by syringe and the mixture was stirred for 5 min under argon. 2′,3′-O-bis((tert-butyldimethylsilyl)uridine 9u is dried using repeated co-evaporation with anhydrous pyridine and dissolved in 100 mumol pyridine. Thereafter, the mixture is added via cannula to a solution of 2′,3′-O-bis(tert-butyldimethylsilyl)uridine 9u (100 mumol). After 10 minutes N-trifluoroacetylimidazole (CF3COIm; 200 mumol) is added. After an additional 30 seconds N,N’-dimethylthiuram disulfide (DTD; 120 mul) is added. After a further 3 minutes the mixture is dried in vacuo. Concentrated NH3-EtOH (3: 1, v / v, 10 mL) is added to the residue and the mixture is allowed to stir for 12 hours, then concentrated to dryness under reduced pressure. Thereafter, the mixture is diluted with CHCl3 (5 mL) and washed with 0.2 M phosphate buffer (pH 7.0, 5 mL). The aqueous layer is back-extracted with CHCl3 (2 × 5 mL). The organic layers are combined, dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The residue is purified by preparative TLC. The product was dissolved in CHCl3 (5 mL), washed with 0.2 M 1,8-diazabicyclo [5.4.0] undec-7-enium bicarbonate buffer (5 mL) and washed with CHCl3 (2 × 5 mL) Back extracted. Combine the organic layers, dry over Na2SO4, filter, concentrate and dry to give (SP)-10uu.

According to the analysis of related databases, 1546-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONTORII INCORPORATED; VERDINE, GREGORY L; MEENA, MEENA; IWAMOTO, NAOKI; (250 pag.)JP2015/205910; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 89532-38-7, A common heterocyclic compound, 89532-38-7, name is 2-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.

To a mixture of ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (455 mg, 1.0 mmol) and 2-cyclopropyl-1H-imidazole (17-3) (324 mg, 3.0 mmol, 3.0 eq.) in NMP (4 ml) was added 8-hydroxyquinoline (22 mg, 0.15 mmol, 0.15 eq.), Cu2O (282 mg, 0.1 mmol) and K2CO3 (166 mg, 1.2 mmol) and PEG-2000 (50 mg). The resulting mixture under N2 was irradiated under microwave at 128 C for 6.0 h, cooled to room temperature and diluted with THF (10 ml) and water (10 ml). The mixture was filtered and the resulting aqueous layer was extracted with EA (30 ml x 5). The combined organic layers were washed with brine (20 ml), dried over MgSO4, filtered, concentrated and purified by silica gel column chromatography (MeOH : CH2Cl2 = 1 : 15) to afford the desired compound as a yellow solid (190 mg, yield 39%).

The synthetic route of 89532-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Xicheng; Qiu, Jian; Strong, Sarah A.; Green, Louis S.; Wasley, Jan W.F.; Blonder, Joan P.; Colagiovanni, Dorothy B.; Mutka, Sarah C.; Stout, Adam M.; Richards, Jane P.; Rosenthal, Gary J.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5849 – 5853;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2034-22-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2034-22-2 name is 2,4,5-Tribromoimidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1. 2,4,5-Tribromo-l-methyl-lH-imidazole (0975) [00314] To a suspension of sodium hydride (0.787 g, 19.69 mmol) in DMF (15 mL) was added 2, 4, 5-tribromo-lH-imidazole (5 g, 16.41 mmol) in DMF (10 mL) at ambient temperature. The mixture was stirred at 50 C for 1 h, cooled to 0 C, and treated with methyl iodide (1.128 ml, 18.05 mmol). The mixture was warmed to 50 C and stirred 16 h, the DMF was removed under reduced pressure and EtOAc was added. The mixture was washed with water, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (eluting with a gradient of 10-80% EtOAc/hexanes) afforded 4.87 g (94%) of 2,4,5-tribromo-l -methyl- lH-imidazole. 1H MR (300 MHz, CDC13) delta 3.62 (s, 3H). MS (ESI) m/z 316.77 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4,5-Tribromoimidazole, and friends who are interested can also refer to it.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5465-29-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5465-29-2 name is 2-Propylbenzimidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a stirred solution of 22 (65 mg, 0.18 mmol) and 2-propylbenzo[d]imidazole (32 mg, 0.20 mmol) in DMF (1.5 mL) was added potassiumcarbonate (125 mg, 0.908 mmol), and the solution was stirredfor 4 h at 60 C. After the consumption of the starting material, thereaction mixture was poured into water and extracted twice with ethylacetate. The combined organic layers were washed with brine, driedover sodium sulfate, and filtered. The organic layer was concentrated togive the residue. The obtained residue was then purified by flashcolumn chromatography on silica gel (100:0 to 50:50 hexane/ethylacetate) to give 25 (63 mg, 79%) as an amorphous. 1H NMR (300 MHz,CDCl3): delta 0.98 (t, J=7.4 Hz, 3H), 1.71-1.93 (m, 2H), 2.23 (s, 3H),2.74-2.91 (m, 2H), 4.73 (d, J=12.4 Hz, 1H), 5.23-5.38 (m, 3H),6.72-6.85 (m, 2H), 6.90-7.18 (m, 7H), 7.39-7.47 (m, 1H). LC/MS (ESI,[M+H]+, m/z) 438.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Propylbenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yamamoto, Keisuke; Tamura, Tomohiro; Nakamura, Rina; Hosoe, Shintaro; Matsubara, Masahiro; Nagata, Keiko; Kodaira, Hiroshi; Uemori, Takeshi; Takahashi, Yuichi; Suzuki, Michihiko; Saito, Jun-ichi; Ueno, Kimihisa; Shuto, Satoshi; Bioorganic and Medicinal Chemistry; vol. 27; 22; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 71759-87-0, name is 4-Iodo-1-methyl-1H-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 71759-87-0, Formula: C4H5IN2

Preparation 78tert-butyl (3S,4R)-4-{[3-carbamoyl-5-( 1-methyl-i H-imidazol-4-yl) pyridin-2-ylloxy}-3-fluoropiperidine- 1 -carboxylate To a solution of tert-butyl (3S,4R)-4-{[3-carbamoyl-5-(4,4, 5, 5-tetramethyl- 1, 3,2-dioxaborolan-2- yl) pyridin-2-yl]oxy}-3-fluoropiperidine- 1 -carboxylate (Preparation 99, 900 mg, 1.94 mmol) and 4- iodo-i-methyl-1H-imidazole (403 mg, 1.94 mmol) in DMF (15 mL) was added a solution of potassium carbonate (534 mg, 3.87 mmol) in water (2 mL) and the mixture degassed with argon for 15 minutes. i,i-bis(diphenylphosphino)ferrocene palladium (II) dichloride (79 mg, 0.097mmol) was added and the reaction heated to 100C for 16 hours. The reaction was cooled, diluted with EtOAc, washed with water, brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 3-5% MeOH in DCM to afford the title compound (400 mg, 49%).1H NMR (400 MHz, DMSO-d6): O ppm 1.41 (5, 9H), 1.81-1.86 (m, 1H), 1.96-1.99 (m, 1H), 2.95-3.30 (m, 2H), 3.68 (5, 3H), 3.98-4.03 (m, 1H), 4.10-4.21 (m, 1H), 5.00 (d, 1H), 5.42-5.50 (m, 1H),7.53 ( br 5, 1 H), 7.67 (5, 1 H), 7.69 (5, 1 H), 7.82 (br 5, 1 H), 8.54 (d, 1 H), 8.63 (d, 1 H). MS mlz 420 [M+H]

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; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57090-88-7, 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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A flask charged with imidazole-4-carbonitrile (0.50 g, 5.2 mmol) (Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 10 h at RT. The mixture was diluted with ethyl acetate (EtOAc) (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer was dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30percent EtOAc/hexane to give 0.80 g (70percent) of the title compound as a colorless oil. Mass spectrum (CI (CH4), m/z) Calcd. for C10H17N3OSi, 224.1 (M+H), found 224.1.

The chemical industry reduces the impact on the environment during synthesis 1H-Imidazole-4-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; DesJarlais, Renee Louise; Meegalla, Sanath K.; Wall, Mark; Wilson, Kenneth; US2007/249649; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem