Author: Jessica.F

Electric Literature of 33543-78-1, 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. 33543-78-1 name is Ethyl 1H-imidazole-2-carboxylate, 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.

A solution of the required amine (0.20 mmol; 2 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is quenched by the addition of a sat. aq. KH2P04 solution and the reaction mixture is stirred at rt for 20 h. The reaction mixture is concentrated under reduced pressure and purification of the residue gives the desired product. Starting from the compound of Preparation R and ethyl imidazole-2-carboxylate and proceeding in analogy to Procedure AQ, the title compound was obtained, after purification by prep-HPLC (basic conditions), as an amorphous solid (22percent yield).MS (ESI, m/z): 340.10 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 305790-48-1, name is 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, 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 305790-48-1, Recommanded Product: 305790-48-1

A mixture of 6-bromo-l-methyl-l,3-dihydro-2H-benzo[d]imidazol-2-one (10.0 g, 44.2 mmol), l, -Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (3.6 g, 4.42 mmol), TEA (9.0 g, 88.5 mmol) in MeOH (200 mL) and DMF (10 mL) was sparged with carbon monoxide for about 10 min, placed under 4 atm carbon monoxide atmosphere, and heated to 130 C for 17 hours. The reaction mixture was cooled down to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE: EA = 2: 1 ) to give product (7.0 g, 76.9%) as a yellow solid. NMR (400 MHz, DMSO-d6) S 1 1.27 (s, 1 H), 7.77 – 7.53 (m, 2 H), 7.07 (d, J = 8.1 Hz, 1 H), 3.84 (s, 3 H), 3.33 (s, 3 H); LC/MS (ESI, m/z): [M +1]+ = 207.1.

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, 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; MAINOLFI, Nello; JI, Nan; ZHANG, Yi; WEISS, Matthew M.; (223 pag.)WO2019/60693; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 4238-71-5, name is 1-Benzyl-1H-imidazole, molecular formula is C10H10N2, 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. Computed Properties of C10H10N2

1 mol of the compound III obtained in the step (1)1 mol of benzyl chloride was dissolved in THF (tetrahydrofuran)Heated to reflux 12h,The above solution was spin-dry with a rotary evaporator,Then using 3: 1 CH 2 Cl 2 and CH 3 OH as the eluent for chromatographic separation,Obtained pale yellow oily liquid, which is Compound II;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4238-71-5, its application will become more common.

Reference:
Patent; Jiangsu Atomic Medical Institute; Lin Jianguo; Lv Gaochao; Qiu Ling; Guo Liubin; Yang Hui; Wang Tengfei; (17 pag.)CN104650155; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 15813-09-9, These common heterocyclic compound, 15813-09-9, name is 4,5-Diiodo-1H-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.

4,5-Diiodo-1H-imidazole 21 (0.50 g, 1.6 mmol) in THF (15 mL)was cooled to 0 C and NaH (60% suspension in mineral oil)(0.10 g, 2.5 mmol) was added slowly. The reaction was allowedto come to rt and stir under N2 for 30 min. 4-Methoxybenzyl chloride (0.28 mL, 2.0 mmol) was added and stirred at 50?C for 18 h.The reaction was allowed to cool to rt, quenched with water(10 mL) and extracted with EtOAc (2 10 mL). The combinedorganic solutions were washed with water (10 mL), brine(10 mL), dried (anhyd. Na2SO4) and concentrated. The resultingcrude residue was purified by column chromatography (4:6EtOAc/Hexane) to give 22 as a yellow solid (0.63 g, 91%). m.p.= 158-160?C; 1H NMR: delta = 7.55 (s, 1H), 7.10 (d, J = 8.6 Hz, 2H),6.88 (d, J = 8.6 Hz, 2H), 5.07 (s, 2H), 3.80 (s, 3H); 13C NMR:delta = 159.9, 141.2, 129.2, 126.7, 114.5, 96.1, 82.4, 55.4, 53.1; IR(cm1): 3099, 2929, 2832, 1611, 1510, 1433, 1298, 1241, 1174,1024, 816, 760, 629; HR-ESIMS (m/z): Calcd. for [M+H]+C11H11N2OI2 is 440.8955 found 440.8956.

Statistics shows that 4,5-Diiodo-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 15813-09-9.

Reference:
Article; Koswatta, Panduka B.; Kasiri, Sabha; Das, Jayanta K.; Bhan, Arunoday; Lima, Heather M.; Garcia-Barboza, Beatriz; Khatibi, Nicole N.; Yousufuddin, Muhammed; Mandal, Subhrangsu S.; Lovely, Carl J.; Bioorganic and Medicinal Chemistry; vol. 25; 5; (2017); p. 1608 – 1621;,
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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., name: 1H-Benzimidazole-2-carboxylic acid

General procedure: To a solution of the commercially available L-leucine tert-butyl ester (12, 0.89mmol) in DMF (15mL) were added an appropriate carboxylic acid (8, 1.1mmol), HOBt¡¤H2O (1.1mmol), and EDC¡¤HCl (1.1mmol). The resulting solution was cooled to 0C under ice bath conditions, and TEA was added dropwise. After 5min, the ice bath was removed, and the mixture was allowed to stir for 2h at ambient temperature. DMF was removed under high vacuum, and the resulting residue was dissolved in EtOAc (30mL). The organic layer was washed with 5% citric acid (20mL¡Á2), 5% NaHCO3 (20mL¡Á2), and brine (20mL). The solution was dried over Na2SO4, filtered, and evaporated under reduced pressure to give compound 13. The resulting crude compound was purified by silica gel column chromatography using hexane-EtOAc as eluents.

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:
Article; Thanigaimalai, Pillaiyar; Konno, Sho; Yamamoto, Takehito; Koiwai, Yuji; Taguchi, Akihiro; Takayama, Kentaro; Yakushiji, Fumika; Akaji, Kenichi; Chen, Shen-En; Naser-Tavakolian, Aurash; Schoen, Arne; Freire, Ernesto; Hayashi, Yoshio; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 372 – 384;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2466-76-4 as follows. name: 1-(1H-Imidazol-1-yl)ethanone

General procedure: To a solution of N -acetylimidazole 7a (1 mmol) and a suitable Baylis-Hillman acetate 1 (1 mmol) in DMF (1 mL), K2CO3 (1 mmol) was added and the resulting mixture was stirred at room temperature until complete consumption of N -acetylimidazole 7a. The reaction mixture was then diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4 . After removal of the solvent under reduced pressure, the residue was puried by flash chromatography over silica gel with EtOAc and hexane (1:1).

According to the analysis of related databases, 2466-76-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koeseceli Oezenc, Ay?en; Celik, Ilhami; Koekten, ?ule; Turkish Journal of Chemistry; vol. 41; 3; (2017); p. 323 – 334;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 26832-08-6, name is 1H-Imidazole-4-carboxamide, 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 26832-08-6, category: imidazoles-derivatives

General procedure: To a solution of 4-imidazolecarboxamide (1.94 mmol) in DMF(3 mL) was added NaH (60% in mineral oil, 1.94 mmol) at roomtemperature and the reaction mixture was stirred for 20 min. The methanesulfonate (1.29 mmol) prepared above was added andthe resulting mixture was stirred at 85 C for 3 days. The reactionmixture was cooled, and the insoluble material was filtered andwashed thoroughly with CH2Cl2. The filtrate and washings werecombined and washed with brine. The organic layer was dried overNa2SO4 and concentrated in vacuo. The residue was purified by silicagel column chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Article; Kandalkar, Sachin R.; Ramaiah, Parimi Atchuta; Joshi, Manoj; Wavhal, Atul; Waman, Yogesh; Raje, Amol A.; Tambe, Ashwini; Ansari, Shariq; De, Siddhartha; Palle, Venkata P.; Mookhtiar, Kasim A.; Deshpande, Anil M.; Barawkar, Dinesh A.; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5799 – 5819;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, molecular formula is C5H6N2O2, 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: C5H6N2O2

a) 3-(1,2,3,4-Tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 1 ,2,3,4-tetrahydro-1-naphthol (CASNo. 529-33-9, 1.00 g, 6.74 mmol), which can be prepared as described in Ollivier, R.; et al. Journal of Medicinal Chemistry, 1997, 40, 952-960, in THF (60 ml_), at 0 0C is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 0.85 g, 6.74 mmol) and triphenylphosphine, followed by diisopropyl azodicarboxylate (1.36 g, 6.74 mmol). The cooling bath is then removed. After 16 hours, the solvent is evaporated in vacuo and the residue is purified by silica gel flash chromatography (elution with ethyl acetate) to give a partially purified product, which is dissolved in ethyl acetate and extracted with 1 M aqueous HCI. The aqueous layer is basified to a pH of ca. 9 with 2M aqueous NaOH, and then extracted three times with dichloromethane. The organic layers are combined, dried with MgSO4, filtered, and concentrated to furnish 3-(1 ,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 257.2 (M+H)+. The HNO3 salt of the title compound is prepared by dissolving the free base in methanol, followed by treatment with an excess of a 1 :1 solution of HNO3-H2O. Concentration and trituration with diethyl ether and methanol, provides the nitric acid salt of 3-(1 ,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4- carboxylic acid methyl ester; 1H NMR (400 MHz, DMSO-Cf6) delta ppm 1.66 – 1.87 (m, 2 H), 2.11 – 2.33 (m, 2 H), 2.81 (dt, J=17.2, 6.5 Hz, 1 H), 2.93 (dt, J=17.2, 6.0 Hz, 1 H), 3.87 (s, 3 H),6.33 (t, J=5.9 Hz, 1 H), 6.99 (d, J=7.6 Hz, 1 H), 7.10 – 7.21 (m, 1 H), 7.21 – 7.35 (m, 2 H),8.34 (S1 1 H), 8.58 (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 17325-26-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 288-32-4, These common heterocyclic compound, 288-32-4, name is 1H-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.

7kg concentration of 20% sodium hydride DMF solution was taken, while stirring in an ice bath at a rate of 2ml / s, while stirring 7kg 20% imidazole DMF solution was stirred at 60 C for 60min; After cooling with an ice salt bath, 5 kg of 1-chloro-4-(4-chlorophenyl)-2-butanol was slowly added, and the reaction was stirred at 60 C. for 120 min. After cooling with an ice salt bath, the reaction liquid was obtained. To the reaction solution was added 25% by weight of n-hexane, stirred at a rate of 3 revolutions per second for 15 minutes, and then added with ice water of 350% by weight of the reaction solution and stirred at 3 revolutions per second. After precipitation is stopped, the precipitate is filtered, and the cake is washed once with water that is 1/3 times the weight of the cake, and is dried at a rotation speed of 2825 r/min for 60 min, which is 2.5 times and 0.05 times the weight of the product obtained by the centrifugal drying, respectively. Ethyl acetate and activated carbon, After recrystallization at -5C for 13 hours, the recrystallized product was dried at 50C to obtain 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1H-imidazole. The purity is 99.31%. The 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1-hydro-imidazole was used as a raw material in Example 6.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhuzhou Qianjin Pharmaceutical Co., Ltd.; Peng Kaifeng; Wen Fengqiu; Bai Lu; Li Sanxin; Gong Yun; Li Fujun; (12 pag.)CN105198816; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole, 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. COA of Formula: C9H7N3O2

Benzyl bromide (712 muIota_, 6 mmol) and 4-nitrophenylimidazole (222 mg, 1 .2 mmol.) were stirred in 10 ml of anhydrous THF under reflux for 45 h and under inert atmosphere. The precipitate was then filtered, washed with THF and dried under reduced pressure to give 393 mg (91 %) of 1-benzyl-3-(4-nitrophenyl)imidazolium bromide (Example 1) as an off white powder. 1H NMR (DMSO-d6, 400.13 MHz): delta 10.37 (t, 1 H, J = 1.5 Hz, N-CH-N), 8.57 (1 H, m, H(imidazolium backbone)), 8.55 (2H, m, H(nitrobenzyl)), 8.19 (1 H, m, H(imidazolium backbone)), 8.17 (2H, m, H(nitrophenyl)), 7.64-7.58 (2H, m, Hm(benzyl)), 7.52-7.43 (3H, m, Hp + Ho(benzyl)), 5.61 (2H, s, CH2). 13C NMR (DMSO-d6,100.16 MHz): delta 147.7 (carbene), 139.5, 134.4, 129.1 , 129.0, 128.9, 125.7, 123.7, 123.2, 121.8, 52.7 (CH2). MS (ES+) calcd for (M-Bn+H)+ 190.1 (100%), 191 .1 (1 1 %) (M-Br)+: 280.1 (100%), 281 .1 (18.7%), (2M-Br)+: 639.1 (100%), 641.1 (95%), 640.1 (36%), 642.1 (36%) Found (M- Bn+H)+ 190.0 (100%) (M-Br)+: 280.1 (100%), 280.8 (18.9%), (2M-Br)+: 639.0 (95 %), 641 .0(100%)

The synthetic route of 2301-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); CHU NANTES; UNIVERSITE DE NANTES; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S); FAIVRE-CHAUVET, Alain; RAJERISON, Holisoa; GESTIN, Jean-Francois; WO2013/171224; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem