Tag: M.W=100-200

1467-16-9, 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. 1467-16-9, name is 1H-Imidazole hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

TFA (991 muIota, 13.0 mmol) was added to a solution of 3-amino-7-cyano-5-{[2- (trimethylsilyl)ethoxy]methyl}-5/-/-pyrrolo[2,3- 5]pyrazine-2-carboxylate, Intermediate 166 (150 mg, 0.43 mmol) in CH2CI2 (2 ml). The resultant mixture was stirred at RT for 4.5 h. The reaction mixture was concentrated in vacuo, azeotroped with toluene (2 x 5 ml), then dried in vacuo to afford a red/orange solid (1 14 mg). A portion (83 mg) of the solid thus obtained was dissolved in MeOH (3 ml). Aqueous NaOH solution (5.0 M, 0.67 ml, 3.4 mmol) was added then the resulting mixture was heated at 60 C for 1 h then at 80 C for 1.5 h. The reaction mixture was allowed to cool to RT then filtered. The collected solid was washed with water then dried in vacuo to afford a brown solid (60 mg). The solid thus obtained was dissolved in DMF (1 ml) then CDI (78 mg, 0.48 mmol) and imidazole hydrochloride (25 mg, 0.24 mmol) were added. The reaction was stirred at RT for 10 min. Water (3 ml) was added then the reaction was stirred at RT for 5 min. The solid was collected by filtration, washed with water, then dried in vacuo to afford a brown solid (39 mg). The solid thus obtained was dissolved in DMF (1 ml) then 2-(aminomethyl)-1 ,3- diethyl-6-methoxy-1 /-/-1 ,3-benzodiazol-3-ium iodide, Intermediate 36 (45 mg, 0.13 mmol) was added. The resultant mixture was stirred at RT for 2.5 h then concentrated in vacuo. The crude material was purified by flash column chromatography on C18 (12 g). The column was eluted with MeCNihbO + 0.1 % TFA using the following gradient (% MeCN, column volumes): 2%, 2 CV; 2-37%, 18 CV; 37-48%, 1 CV; 48-89%, 3 CV; 89-100%, 1 CV; 100% 2 CV. The desired fractions were combined and lyophilised. The material thus obtained was further purified by preparative HPLC (Method A). The desired fractions were combined and lyophilised to afford the product as a yellow solid (3.5 mg, 1.7%). 1 H NMR (500 MHz, DMSO-cfe) delta 9.41 (t, J = 5.0 Hz, 1 H), 8.34 (s, 1 H), 8.23 (s, 1 H), 7.89 (d, J = 9.1 Hz, 1 H), 7.51 (d, J = 2.3 Hz, 1 H), 7.21 (dd, J = 9.1 , 2.3 Hz, 1 H), 7.09 (s, 2H), 5.01 (d, J = 5.4 Hz, 2H), 4.66 – 4.56 (m, 4H), 3.84 (s, 3H), 1.38 – 1.28 (m, 6H). LC/MS (System C): m/z (ESI+) = 419 [M+], Rt = 1.85 min, UV purity = 99%.

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; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
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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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., 33468-69-8

l-(4-Ethynyl-2-methoxyphenyl)-4-(trifluoromethyl)-lH-imidazole. 4-Fluoro-3-methoxybenzaldehyde (2.57 g, 16.7 mmol), 4-trifluoromethylimidazole (4.54 g, 33.4 mmol), and K2CO3 (3.46 g, 25 mmol) were dissolved in 15 ml of DMF and stirred at 100 0C overnight. Cooled to room temperature and DMF removed in vacuo. The concentrated mass was taken up in EtOAc and water. Layers were separated and the aqueous layer was extracted twice with EtOAc. The organic extracts were combined, dried (Na2SO4), and concentrated. Chromatography on SiO2 (0-50% EtOAc/CH2Cl2) gave a cream-colored solid (1.67 g, 6.2 mmol, 37%). A solution of aldehyde intermediate (445 mg, 2.32 mmol) in 20 ml of MeOH was treated with K2CO3 (534 mg, 3.86 mmol) and a solution of dimethyl (l-diazo-2-oxopropyl)phosphonate (522 mg, 1.93 mmol) in 5 ml of MeOH and stirred at room temperature overnight. MeOH was removed in vacuo and the concentrated mass was dissolved in EtOAc and washed sequentially with water, sat’d NaHCO3, and water. The organic layer was dried (Na2SO4) and concentrated to a yellow solid (493.2 mg, 1.9 mmol, 96%). 1H NMR (600 MHz, CDCl3) delta 7.77 (s, 1 H), 7.51 (t, J- 1.2 Hz, 1 H), 7.22 (d, J= 7.9 Hz, 1 H), 7.18 (dd, J= 7.9, 1.4 Hz, 1 H), 7.16 (d, J= 1.5 Hz, 1 H), 3.86 (s, 3 H), 3.16 (s, 1 H); MS (EI) [M+l]+ calc’d 267.1, found 267.2.

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; MERCK & CO., INC.; WO2008/156580; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1632-83-3, 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. 1632-83-3 name is 1-Methylbenzimidazole, 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.

General procedure: 4.3 General procedure for CuO-catalyzed arylation and alkenylation of 1,3-azole (0012) Under argon, 0.5mmol of the bromobenzene or bromoalkene was added to the reaction mixture containing 0.25mmol of the benzoxazole, 0.5mmol K2CO3, 0.025mmol CuO, and 0.075mmol PPh3, followed by the addition of 2mL dry diglyme. The sealed reaction tube was stirred at 160C for 5-24h. After cooling, the reaction mixture was centrifuged to remove solid and separated the organic phase. Then, organic phase was extracted and dried over anhydrous MgSO4, and concentrated under reduced pressure after filtered. The residue was purified by column chromatography on silica gel eluted to afford corresponding product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methylbenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Wu; Tian, Yujie; Zhao, Na; Wang, Yuanyuan; Li, Jia; Wang, Zhenghua; Tetrahedron; vol. 70; 36; (2014); p. 6120 – 6126;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

37052-78-1, Name is 5-Methoxy-1H-benzo[d]imidazole-2-thiol, 37052-78-1, 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.

EXAMPLE 3 F Preparation of 2 -(4 -morpholino-3 -chloro-2 -pyridylmethylthio)-5 -methoxy-(1H)-benzimidazole 5 N Sodium hydroxide (5.68 ml) was added dropwise to a stirred solution of 4 -morpholino-3 -chloro-2 -chloromethylpyridine hydrochloride (3.66 g) and 5 -methoxy-2 -mercaptobenzimidazole (2.33 g). After standing overnight the solution was evaporated under reduced pressure and the residue triturated with water. The solid thus obtained was recrystallized from ethanol to give 2 -(4 -morpholino-3 -chloro-2 -pyridyl-methylthio)-5 -methoxy-(1H)-benzimidazole, 4.38 g, m.p. 124-25.

Statistics shows that 5-Methoxy-1H-benzo[d]imidazole-2-thiol is playing an increasingly important role. we look forward to future research findings about 37052-78-1.

Reference:
Patent; SmithKline & French Laboratories Limited; US5250527; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

A mixture of 2-(methylthio)-4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)aniline (2. 8g, 1.05? mmol, 1. Oeq) and 5-bromo- 1-methyl- 1H- imidazole 1.1 (2.5g, 1 .58mmol, 1 .5eq.) in a mixture of dioxane (24mL) and water (6mL). Reaction mixture was degassed with argon atmosphere for 10mm. Then [1,1?- Bi s(diphenylphosphino)ferrocene]palladium(II) dichloride(0 .25 Og, 0.31 mmol, 0.03 eq) and potassium carbonate(4.3 7g,3. l6mmol,3eq) was added into it. Reaction mixture was stirred at 115c for 24h. Upon completion, reaction mixture was transferred into cold water then extracted with ethyl acetate. Organic layers were combined, dried over Na2SO4 and concentrated in vacuo to obtain crude product. This was purified by column chromatography and compound was eluted in 5% ethyl acetate in hexane as eluant to obtain pure 214.1 (1 .5g, 90.69 %). MS(ES): m/z 220.31 [M+H].

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

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (869 pag.)WO2018/75937; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

52099-72-6, 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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below.

1-Isopropyl-1,3-dihydro-benzoimidazol-2-one A mixture of 1-isopropenyl-1,3-dihydro-benzoimidazol-2-one (J. Davoll, J. Chem. Soc. 1960, 308) (6.90 g, 39.6 mmol) and 10% palladium on carbon (1.0 g) in MeOH (50 mL) was placed in a Parr shaker under hydrogen (40 psi) for 2 h. The reaction mixture was filtered through celite and evaporated to give 6.97 g (100%) of 1-isopropyl-1,3-dihydro-benzoimidazol-2-one as a white solid. 1H NMR (CDCl3) delta 1.57 (d, J=7.1 Hz, 6H), 4.70-4.81 (m, 1H), 7.02-7.10 (m, 2H), 7.10-7.20 (m, 2H); MS m/e 177 (MH+); Anal. Calcd for C10H12N2O: C, 68.16; H, 6.86; N, 15.90; Found: C, 68.05; H, 6.63; N, 15.77.

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; Yu, Kuo-Long; Wang, Xiangdong; Sun, Yaxiong; Cianci, Christopher; Thuring, Jan Willem; Combrink, Keith; Meanwell, Nicholas; Zhang, Yi; Civiello, Rita L.; US2003/207868; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

7189-69-7, 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. 7189-69-7 name is 1,1′-Sulfonyldiimidazole, 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.

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1′-Sulfonyldiimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-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 1003-21-0.

Intermediate 66: step b (1-methyl-1H-imidazol-5-yl)(pyrimidin-2-yl)methanone 5-Bromo-l-m.ethyl-lH-im.idazole (6.66 g, 41 ,4 mmol) was added to a round bottom flask followed by tetrahydrofuran (150 mL) under an N2atmosphere. The contents were cooled to 0 C in an ice water bath. EtMgBr (3.0 M solution in THF, 13.3 mL, 39.8 mmol) was added slowly via syringe over approximately 5 minutes, then the ice bath was removed and the contents allowed to warm and stirred at room temperature for approximately 30 minutes. The vessel was then re-cooled to 0 C and a solution of N-methoxy-N-methylpyrimidine-2-carboxamide (3.09 g, 15.9 mmol, Intermediate 66: step a) in THF (20 mL) was cannulated into the reaction vessel. The contents were allowed to stir at 0 C, then slowly warmed to room temperature, then heated to 40 C in an oil bath for approximately 36 hours. The contents were then cooled to 0 C, quenched with a saturated aqueous NH4CI solution, diluted with ethyl acetate and transferred to a separatory funnel. The aqueous layer was separated, extracted twice with EtOAc, then the combined organic phases were dried over MgS04, filtered, then distilled under reduced pressure to yield an amber oil. The crude product was purified by flash column chromatography (silica gel, 0-10% DCM / (10% of a 2 M N MeOH in DCM)) to provide the title compound.

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-Bromo-1-methyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

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; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

98873-55-3, 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. 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, A new synthetic method of this compound is introduced below.

EXAMPLE 7 Synthesis of 2-(1-imidazolyl)-2-[4 (2-chlorophenyl)1,3-dithiolan-2-ylidene]acetonitrile (Compound Nos. 34 and 35) To a mixed solution of 2.2 g (0.02 mole) of 1cyanomethylimidazole, 1.60 g (0.02 mole) of carbon disulfide and 10 ml of dimethyl sulfoxide wa added 3.0 g (0.05 mole) of potassium hydroxide powder, and the reaction was carried out with stirring at room temperature for 1 hour. Then, 6.0 g (0.02 mole) of 2′-chloro-(1,2-dibromoethyl)benzene was added dropwise with stirring, and the resulting solution was subjected to reaction for another 2 hours. After completion of the reaction, 20 ml of water was added to the reaction solution, after which the resulting mixture was subjected to extraction with ethyl acetate, and the organic layer was washed with water and dried. The solvent was distilled off and the residue was purified by silia gel chromatography to obtain 0.3 g of the Z isomer and 1.3 g of the E isomer individually in the form of light-yellow crystals. The Z isomer: melting point 119.4 C., yield 5%. The E isomer: melting point 141.5 C., yield 20%.

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; Nihon Nohyaku Co., Ltd.; US4636519; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life.

4-Iodoimidazole (0101-1) (10.0 g, 51.6 mmol, 1.0 eq.)Dissolved in 150 ml of tetrahydrofuran,Triphenylmethyl chloride (17.2 g, 61.7 mmol, 1.2 equivalents) andTriethylamine (14.5 ml, 10.4 mmol, 2.0 eq),Heat to 80C and react overnight.Cooled to room temperature, concentrated under reduced pressure, added ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Methanol and a small amount of dichloromethane were added and stirred for half an hour. The solid was collected by suction, washed twice with methanol, and vacuum dried. ,4-Iodo-1-trityl-1H-imidazole (16 g, yield: 71%) was obtained as a white solid.

The chemical industry reduces the impact on the environment during synthesis 5-Iodo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem