Month: May 2021

Reference of 3718-04-5,Some common heterocyclic compound, 3718-04-5, name is 5-Vinyl-1H-imidazole, molecular formula is C5H6N2, 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.

Example 35 (E)-2-(4-fluorophenyl)- 1 -methyl- 1 -(4-(2-( 1 -propyl- lH-imidazol-4-yl)vinyl)phenyl)- 1.2.3.4- tetrahvdroisoquinolin-6-ol To a 30 mL vial, 4-vinyl-lH-imidazole (400 mg, 4.25 mmol) was dissolved in THF (2 mL) and the solution was cooled to 0 C. The reaction vial was charged with 60% sodium hydride in mineral oil (170 mg, 4.25 mmol) and the reaction mixture stirred for 10 min at 0 C. To the mixture was added 1-iodopropane (0.415 mL, 4.25 mmol) and the reaction was stirred overnight at room temperature. The reaction was quenched with saturated ammonium chloride (15 mL) and diluted with dichloromethane (25 mL). The organic phases were combined, passed through a phase separator and concentrated to afford the crude product. The crude material was purified by column chromatography (1-10% dichloromethane/methanol) to afford a mixture of l-propyl-4-vinyl-lH-imidazole and l-propyl-5-vinyl-lH-imidazole (511 mg, 3.72: 1). l-propyl-4-vinyl-lH-imidazole: NMR (400 MHz, CHLOROFORM-^ delta 0.83 – 0.91 (m, 3 H), 1.66 – 1.82 (m, 2 H), 3.74 – 3.90 (m, 2 H), 5.11 (dd, J=11.12, 1.52 Hz, 1 H), 5.73 – 5.87 (m, 1 H), 6.52 (dd, J=17.18, 11.12 Hz, 1 H), 6.80 (s, 1 H), 7.58 (s, 1 H). l-propyl-5-vinyl-lH-imidazole: NMR (400 MHz, CHLOROFORM-^ delta 0.78 – 0.93 (m, 3 H), 1.63 – 1.82 (m, 2 H), 3.76 – 3.90 (m, 2 H), 5.22 (d, J=11.12 Hz, 1 H), 5.57 (d, J=17.18 Hz, 1 H), 6.41 (dd, J=17.43, 11.37 Hz, 1 H), 7.17 (s, 1 H), 7.63 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Vinyl-1H-imidazole, its application will become more common.

Reference:
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
Imidazole – Wikipedia,
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. COA of Formula: C4H4N4

Example 37: General procedure for the preparation of 4-methoxy-benzoyl- imidazo[1 ,5-a]pyrimidines of general formula (I) following Scheme 1.N-[3-[8-(4-methoxy-benzoyl)-imidazo[1 ,5-a]pyrimidin-4-yl]-phenyl]-N-methyl- methanesulfonamidePart A A solution of 4-methoxy-phenyl magnesium bromide was prepared from 1.0 g (42 mmol) of magnesium and 7.9 g (42 mmol) of 1 -bromo-4-methoxy-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 1.52 g (yield 77%) of (5-amino-1 H- imidazol-4-yl)-(4-methoxy-phenyl)-methanone. 1H NMR (400 MHz, CDCI3): 3.85 (3H, s), 5.41 (1 H, b), 6.69 (2H, d, J= 8.4 Hz), 7.3 (1 H, s), 7.81 (2H, d, J= 8.4 Hz). MS (ES) m/z = 218 (MH+) HPLC = 91%

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

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

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;,
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

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

Adding a certain compound to certain chemical reactions, such as: 6478-79-1, name is 5,6-Dichloro-2-methylbenzimidazole, 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 6478-79-1, Application In Synthesis of 5,6-Dichloro-2-methylbenzimidazole

General procedure: To extend the scope of the 2-methyl-1H-benzimidazole substrates for our cascade reaction, we nextexamined the reaction of 2-fluorobenzonitrile (2a) with a variety of 2-methyl-1H-benzimidazolederivatives 1 under the conditions (Cs2CO3, DMSO, 120 C). The results are shown in Table 2. As shown in Table 2, almost all of the tested combinations successfully produced the desiredbenzimidazo[1,2-a]quinolines 8ba-8la with moderate to good isolated yields, though an undeniableamount of overreaction product 9 was isolated in most entries. Unsymmetrical 1H-benzo[d]imidazolessuch as 1b, 1e, 1f and 1g exist as an equilibrium mixture of their tautomers. Therefore, the SNAr sequenceof our cascade reaction with these substrates theoretically provides a regioisomeric mixture of thecorresponding adducts. Our survey revealed that the regiochemical outcome is highly controlled uponutilizing 1e, 1f and 1g having a substituent at the 4-position to give 8ea, 8fa and 8ga without detectingtheir regioisomers (entries 5-7). However, no reigioselectivity was observed with the cascade reactionwith 1b bearing methyl substituent at the 5-position (entry 2). These results suggest to us that the lesssterically congested nitrogen atom of 1H-benzo[d]imidazoles preferably reacted with 2-fluorobenzonitrile(2a) in the SNAr reaction. 2-Methyl-1H-benzimidazole derivatives 1h, 1i, and 1j, having an electrondonating group (-CH3, -OCH3,-SCH3), reacted with 2a to give 8ha, 8ia, and 8ja in modest yields underthe conditions, respectively (entries 8-10). When the benzimidazoles 1k and 1l possessing an electronwithdrawing group (-CN, -CO2Et) at the 2-methyl group were treated with 2a under the conditions, alarge amount of insoluble unidentified product was produced. In these reactions, the desired cascadeproduct 8la was not detected while the cascade product 8ka was isolated in a modest yield (entries 11 and12). The cascade products 8ka and 8la were obtained in good yields upon replacing Cs2CO3 with K2CO3.(entries 11 and 12). In our SNAr/Knoevenagel cascade reaction with 1k and 1l, we found the Knoevenagelcondensation between aldehydes and the active methylene of 1k and 1l occured preferably to the SNArreaction in the first step, and the desired cascade adducts could not be obtained.14 These comparativeresults indicate that the SNAr reaction occured preferably to the Dieckmann-Thorpe type reaction in thepresent cascade reaction upon fine-tuning the base used.

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; Kato, Jun-Ya; Ito, Yutaro; Ijuin, Ryosuke; Aoyama, Hiroshi; Yokomatsu, Tsutomu; Heterocycles; vol. 93; 2; (2016); p. 613 – 627;,
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. 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

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;,
Imidazole – Wikipedia,
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