Tag: M.W=100-200

Reference of 7189-69-7,Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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 20-mL vial was charged with N-(4-methoxybenzyl)-6-methylpyrimidin-4-amine (Preparation 7i, 500 mg, 2.181 mmol) and l,r-sulfonylbis(lH-imidazole) (864 mg, 4.36 mmol) then purged with nitrogen. 2-Methyltetrahydrofuran (10.0 mL) and a solution of lithium hexamethyldisilazide in THF (1.0 M, 4.27 mL, 4.27 mmol) were added via syringe to the stirred reaction mixture. The vial was sealed with a Teflon coated cap and the reaction was warmed to 90 C and stirred vigorously. After 1 h, the red reaction mixture was allowed to cool to ambient temperature. The reaction mixture was diluted with water (25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 20 to 80% 3:1 EtOAc/EtOH in heptane with DCM as a 10% additive) to afford N-(4-methoxybenzyl)-N-(6-methylpyrimidin-4-yl)-1H-imidazole-1-sulfonamide (0.64 g, 1.78mmol, 82 % yield) as a reddish oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1′-Sulfonyldiimidazole, its application will become more common.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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Imidazole | C3H4N2 – PubChem

Related Products of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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 dry round-bottom flask was added 1.0 g of imidazole-4,5-dicarboxylic acid (10, 1 mmol) and 10 mL of toluene. To this stirred suspension were added 3.0 mL of thionyl chloride (6.5 mmol) and 0.250 mL of DMF (catalytic). The resulting mixture was refluxed for 16 h. After the mixture was cooled in ice bath, the solid product was collected by vacuum filtration, washed with two 20 mL portions of toluene, and dried under vacuum to yield 0.95 g of crude 11 (Yield: 95%) as a yellow solid. This product was used further without characterization.

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Saudi, Milind; Zmurko, Joanna; Kaptein, Suzanne; Rozenski, Jef; Neyts, Johan; Van Aerschot, Arthur; European Journal of Medicinal Chemistry; vol. 87; (2014); p. 529 – 539;,
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Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 57667-50-2, name is 1-Propyl-1H-benzo[d]imidazol-2-amine, 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 57667-50-2, name: 1-Propyl-1H-benzo[d]imidazol-2-amine

General procedure: 6.1.2. Method BTo a solution of 1-(un)substituted-2-aminobenzimidazole (0.01 mol) in dry acetonitrile (50 ml) was added anhydrous potassium carbonate (2.7 g, 0.02 mol) and tetrabutyl ammonium bromide (TBAB) (0.9 g, 0.003 mol) and 0.02 mol of the halogen organic reagent was dropped by cooling. The mixture was stirred for 2-5 h vigorously at 25 C and monitored by TLC over the reaction period. After completion of the reaction, the mixture was filtered to separate the solid K2CO3, and the organic solvent was evaporated. The residue was then crystallized from appropriate solvent to give products 4-8.

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:
Article; Mavrova, Anelia Ts.; Wesselinova, Diana; Vassilev, Nikolay; Tsenov, Jordan A.; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3362 – 3367;,
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Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 5098-11-3, name is 5-Amino-1H-imidazole-4-carbonitrile, molecular formula is C4H4N4, 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. Application In Synthesis of 5-Amino-1H-imidazole-4-carbonitrile

Example 46: General procedure for the preparation of 4-fluoro-benzoyl- imidazo[1 ,5-a]pyrimidines of general formula (I) following Scheme 1. N-[3-[8-(4-fluoro-benzoyl)-imidazo[1 ,5-a]pyrimidin-4-yl]-phenyl]-N-methyl- methanesulfonamide Part A EPO A solution of 4-fluoro-phenyl magnesium bromide was prepared from 1.0 g ( 42 mmol) of magnesium and 7.9 g (42 mmol) of 1-bromo-4-fluoro-benzene in 40 ml of dry tetrahydrofuran.To the solution of the Grignard reagent, cooled by an ice-salt bath, a mixture of 1 g (9.3 mmol)of 5-amino-1 H-imidazole-4-carbonitrile and 20 ml of dry tetrahydrofuran was slowly added with stirring. After standing at room temperature for 2 hours, the mixture was cooled and decomposed by adding, with stirring, 40 ml of 3M hydrochloric acid. When the decomposition was completed (1 hour at a temperature between 90-950C), the reaction mixture was basified to ph 10 with 25% ammonium hydroxide and was extracted with methylene chloride. The solution was dried with anhydrous sodium sulfate and the methylene chloride was distilled under diminished pressure to yield an oil which was chromatographied (silica gel) using methylene chloride/methanol as eluent to produce 1.16 g (yield 62%) of (5-amino-1 H- imidazol-4-yl)-(4-fluoro-phenyl)-methanone.1H NMR (400 MHz, DMSO): 6.86 (2H, b), 7.14-7.29 (3H, m), 8.44 (2H, b),11.56 (1 H, b).MS (ES) m/z = 206 (MH+)HPLC = 96.8%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5098-11-3, its application will become more common.

Reference:
Patent; FERRER INTERNACIONAL, S. A.; WO2006/84835; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 177760-04-2, name is Ethyl 2-amino-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. Formula: C7H11N3O2

To a solution of sodium nitrite (18.3 g, 266 mmol) in water (55 mL)cooled around 5 C in an ice-salt bath, was added dropwise asolution of the amino ester 4 (6.42 g, 38.0 mmol) in acetic acid (42 mL). The temperature was allowed to rise gradually to rt and the reaction mixture was stirred overnight. The reaction mixturewas extracted with dichloromethane (3 50 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using cyclohexane/ethyl acetate (7/3,v/v) as eluent. After concentration under vacuum, the residue was washed with water (2 50 mL). The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure to yield nitro ester 5 as yellow crystals (5.67 g, 28.5 mmol). Yield 75%; mp 56-58 C (Lit. 56-58 C [40] and 65-66 C [37]); Rf 0.40(SiO2, cyclohexane/ethyl acetate, 7/3, v/v); IR (ATR) n cm1 1723,1552, 1486, 1519, 1364, 1233, 767; 1H NMR (CDCl3, 300 MHz) delta 7.70(s, 1H, CHAr), 4.39 (q, 2H, 3J 7.1 Hz, OCH2CH3), 4.31 (s, 3H, NCH3),1.39 (t, 3H, 3J 7.1 Hz, OCH2CH3); 13C NMR (DMSO-d6, 126 MHz) delta 158.71 (CO), 147.61 (CArNO2), 133.70 (CHAr), 126.07 (CArCO), 61.34(OCH2), 35.14 (NCH3), 13.91 (CH2CH3).

The synthetic route of Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
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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. 7164-98-9, name is 1-Phenyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Phenyl-1H-imidazole

General procedure: Under nitrogen atmosphere, to the solution of 1,3-di-imidazolylbenzene (2.0126 g, 10 mmol) in dry THF (150 mL) cooled to ?78Cwas added dropwise with N, N, N, N-tetramethylethylenediamine(TMEDA, 3.0 mL, 20 mmol) and n-BuLi (2.5 M in hexane, 8.8 mL,22 mmol). The obtained mixture after stirring vigorously for 1 h,chlorodiphenylphosphine (PPh2Cl, 4.953 g, 22 mmol) was addeddropwise. The resultant mixture was stirred overnight with thereaction temperature increasing to ambient. After quenchingexcess n-BuLi with deionized water, the obtained oily mixture wasremoved of solvent in vacuo. The residue was purified by columnchromatography on silica gel, using CH2Cl2/ethyl acetate (30:1)as an eluent, to yield L1 as a white solid (2.53 g, 44percent).1H NMR(400 MHz, , ppm, CD3CN): = 7.47 (t, J = 8 Hz, 1H, HPh), 7.32?7.36(m, 24H, HPh + imi), 7.26 (s, 2H, Himi), 7.18 (s, 1H, HPh).31P NMR(162 MHz, , ppm, CDCl3): = ?28.2 (s, PPh2). The31P NMR signalof L1 ( = ?28.2 ppm) observed herein was consistent to the onereported by Chauvin [24] with two phosphine fragments located intrans-position but different to the one reported by us [30] with twophosphine fragments located in cis-position.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7164-98-9.

Reference:
Article; Zhang, Heng; Li, Yong-Qi; Wang, Peng; Lu, Yong; Zhao, Xiao-Li; Liu, Ye; Journal of Molecular Catalysis A: Chemical; vol. 411; (2016); p. 337 – 343;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 4919-00-0,Some common heterocyclic compound, 4919-00-0, name is Methyl 5-amino-1H-imidazole-4-carboxylate, molecular formula is C5H7N3O2, 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.

Description 18 (0.98 g, 6.95 mmol) and 4-chlorophenyl isothiocyanate (1.29 g, 7.65 mmol) were stirred in pyridine (5 ml) at 100 C. After 15 h additional 4chlorophenyl isothiocyanate (0.12 g, 0.70 mmol) was added and heating continued for a further 4 h. The reaction was cooled, poured onto ice and the resultant solid, methyl 5-({[(4-chlorophenyl)amino]carbonothioyl}amino)-1H-imidazole-4carboxylate, was collected by filtration and dried (0.42 g, 20 %). Without purification, the solid was slurried in 1 % aqueous sodium hydroxide solution (10 ml) and heated at 80 C for 2 h. The reaction was cooled and filtered to remove unreacted starting material. The filtrate was acidified to pH 5 using acetic acid, causing a fine white precipitate to form. The solid was collected, rinsed with water and dried to give the title compound as a fine white solid (0. 28 g, 73 %). 1H NMR (360 MHz, DMSO)8 13.72 (2H, brs), 8.18(1H, s), 7.55 (2H, m), 7.30 (2H, m). Mlz (ES+) 279,281 (M+H+).

The synthetic route of 4919-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; HOLLINGWORTH, Gregory, John; JONES, A., Brian; SPAREY, Timothy, Jason; WO2005/49613; (2005); 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. 109012-23-9, name is Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate

Im-2 (0.4 g) in ETOH/ETHYL acetate (1: 1,14 mL) and Pd/C (10%, 0.3 g) were stirred under a slight positive pressure of hydrogen (ca 1.1 atm) for 3-4 hr. The reaction mixture was filtered using celite and solvent evaporated on the rotary. The remaining solid was freeze dried to yield a slightly yellow product. Yield (0.38 g, 95%). 1H NMR (DMSO): 8 6.45 (s, 1H), 4.5 (bs, 2H, NH2), 4.2 (q, 2H, J=7 Hz), 3.76 (s, 3H), 1.24 (t, 3H, J=7. 9 Hz).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 109012-23-9.

Reference:
Patent; UNIVERSITY OF WESTERN SYDNEY; WO2005/33077; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 15965-57-8, 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. 15965-57-8 name is 2-Chloro-7-methyl-1H-benzo[d]imidazole, 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 2-chloro-7-methyl-1H-benzo[d]imidazole (0.65 g, 3.9 mmol) from example 10, step A, in THF (35 mL) was added n-butyllithium (1.6 mL, 3.9 mmol) dropwise at -78C. After 45 minutes, a solution of racemic (1′-azaspiro[oxirane-2,3′-bicyclo[2.2.2]octan]-1′-yl-4-ium)trihydroborate (0.66 g, 4.29 mmol) from the reference example, in THF (10 mL) was added dropwise at -78C. The cooling bath ws removed and the reaction mixture warmed to room temperature. After 15 minutes, the mixture was heated to 75C for 2 hours and then cooled to room temperature. The reaction was quenched with water and the product was extracted with ethyl acetate (100 mL). The organics were dried with MgSO4, filtered and the solvent was removed to yield the crude product. The crude material was purified by chromatography (Biotage) to yield racemic (8-methyl-3H-1′-azaspiro[benzo[4,5]imidazo[2,1-b]oxazole-2,3′-bicyclo[2.2.2]octan]-1′-yl-10-ium)trihydroborate (0.40 g, 1.4 mmol, 52%). The 5-methyl regioisomer product was not observed. MS (LC/MS) R.T. = 1.90; [M+1-BH3]+ = 270.07.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-7-methyl-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Article; Cook, James; Zusi, F. Christopher; Hill, Matthew D.; Fang, Haiquan; Pearce, Bradley; Park, Hyunsoo; Gallagher, Lizbeth; McDonald, Ivar M.; Bristow, Linda; Macor, John E.; Olson, Richard E.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5002 – 5005;,
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Imidazole | C3H4N2 – PubChem

Related Products of 66247-84-5, 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. 66247-84-5, name is (1H-Imidazol-4-yl)methanamine hydrochloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

N,N-Diisopropylethylamine (0.24 mL, 1.389 mmol) was added to 2-chloro-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile 4 (105.8 mg, 0.278 mmol) in 1,4-dioxane (1.3 mL) and dimethyl sulfoxide (1.3 mL) at room temperature, followed by(1H-imidazol-4-yl)methanamine dihydrochloride 5d (71 mg,0.417 mmol) and the solution was heated to 100 °C and stirred forsixteen hours. The reaction mixture was poured into ether, washed with water, dried over magnesium sulfate, filtered, and concentrated.The residue was purified by silica gel chromatography,eluting with methanol:ethyl acetate (1:24) to give 2-(((1H-imidazol-4-yl)methyl)amino)-4-((2-fluoro-6-(trifluoromethyl)benzyl)amino)quinazoline-8-carbonitrile 6d (73.1 mg, 0.157 mmol, 56.6percentyield). 1H NMR (400 MHz, CD3SOCD3) d 11.82 (br s, 0.6H), 11.71(br s, 0.4H), 8.38?8.14 (m, 2H), 8.02?7.92 (m, 1H), 7.70?6.80 (m,7H), 4.86?4.68 (m, 2H), 4.51 (d, 0.8H, J = 6 Hz), 4.45 (d, 1.2H, J = 6Hz); LC?MS (LC?ES) M+H = 442.

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, (1H-Imidazol-4-yl)methanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Deaton, David N.; Haffner, Curt D.; Henke, Brad R.; Jeune, Michael R.; Shearer, Barry G.; Stewart, Eugene L.; Stuart, J. Darren; Ulrich, John C.; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2107 – 2150;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem