Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, 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 38993-84-9, Formula: C5H8N2O

A mixture of 4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine (100 mg, 0.33 mmol), 1-methyl-1H-imidazol-5-yl)methanol (73 mg, 0.65 mmol), diethyl azodicarboxylate (114 mg, 0.65 mmol) and triphenyl phosphine (171 mg, 0.65 mmol) in 1,4-dioxane (2 mL) was heated using microwave irradiation to 100° C. for 30 min. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC to provide Compound IIa (46 mg). 1H NMR delta (ppm) (CHCl3-d): 7.77-7.70 (4H, m), 7.56-7.46 (7H, m), 7.37 (1H, s), 5.97 (2H, s), 3.91 (3H, s). LCMS (10 cm_ESCI_Bicarb_MeCN) Rt 3.88 min; m/z 401 [M+H] 94.62percent purity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1-Methyl-1H-imidazol-5-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; BUeRLI, Roland Werner; ESMIEU, William Rameshchandra Krishna; LOCK, Christopher James; MALAGU, Karine Fabienne; OWENS, Andrew Pate; HARTE, William E.; US2014/121197; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

705-09-9, Adding a certain compound to certain chemical reactions, such as: 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]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 705-09-9.

Step 2: NaH (60%, l . lg, 45.8mmol, 1.5eq) was added protion-wise to a solution of compound Id (3.4g, 20.1mmol, l .leq) in DMF(50mL) at 0C and the mixture was stirred at r.t for 45min. Compound 5a (5.0g, 18.3mmol, leq) was added to the mixture. The mixture was stirred at r.t over weekend. Water was added and the mixture was extracted with ethyl acetate, the organic layer was washed with water for 3 times, dried, concentrated and purified by column chromatography to give 5b (3.4g, yield: 45.8%) as a white solid.’H NMR(CDC13, 300MHZ, ppm): delta 10.23(s, 1H), 7.72(d, 1H), 7.54(d, 1H)ES-MS m/z: 321(M+H+).

According to the analysis of related databases, 705-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TYROGENEX, INC.; LIANG, Congxin; WO2011/41399; (2011); A2;,
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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 16681-59-7

Step 2 To a 500 mL round flask was added N-methyl-2-bromoimidazole (6.50 g, 40 mmol),2,4-diflurophenylboronic acid (7.89g, 50 mmol), palladium(II) acetate (0.28 g, 1.25 mmol), triphenylphosphine (1.31 g, 5 mmol), sodium carbonate (14.31 g, 135 mmol), and 200 mL of DME and 100 mL of water. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 12 hours. The mixture was extracted with ethyl acetate and further purified by a silica gel column. Distillation of the product at 150 C. gave N-methyl-2-(2,4-difluorophenyl)imidazole as a colorless oil (6.60 g, 85% yield), characterized by 1H-NMR and MS.

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; Lin, Chun; Ma, Bin; Knowles, David B.; Brooks, Jason; Kwong, Raymond; US2006/8670; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 124750-92-1, 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 124750-92-1 as follows.

Step 3:; A solution of dicyclohexylcarbodiimide (DCC) (267.4 mg; 1.3 eq.) in anhydrous THF (10 ml) was added dropwise to a stirred solution of losartan acid (472 mg; 1.08 mmol) prepared as described in step 2, 5-(4-hydroxyphenyl)-3H-1,2-dithiol-3-thione (244.5 mg; 1.08 mmol) prepared as above described (step 1) and dimethylaminopyridine (DMAP, 7 mg) in 15 ml of tetrahydrofurane (THF). The reaction is performed at room temperature, stirring under nitrogen for 5 hours. At the end of the reaction the dicyclohexylurea (DCC) is removed by filtration. The solution is evaporated to dryness and the crude product was purified by column chromatography (on silica gel) eluting with CH2C12-methanol (97:3) to give an orange solid with melting point 180-185 C.

According to the analysis of related databases, 124750-92-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTG Pharma S.r.l.; EP1980559; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3034-50-2, A common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 1L three-necked round-bottomed flask with an addition funnel was added 3H-imidazole-4-carbaldehyde (4, 12 g, 0.125 mol) trityl chloride (38.3 g, 0.137 mol) and acetonitrile (400 mL). The mixture was stirred at rt to give a slurry. Triethylamine (30 mL, 0.215 mol) was added drop wise over 20 min. After the addition was complete, the reaction mixture was stirred at rt for 20 h. Hexane (40 mL) and water (400mL) were added. The slurry was stirred for 30 min and filtered. The cake was washed with water (3 × 100 mL) and dried in a vacuum oven at 50 C for 20 h to give 5 as a white solid (39.8 g, 94%).

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; Suryadevara, Praveen Kumar; Racherla, Kishore Kumar; Olepu, Srinivas; Norcross, Neil R.; Tatipaka, Hari Babu; Arif, Jennifer A.; Planer, Joseph D.; Lepesheva, Galina I.; Verlinde, Christophe L.M.J.; Buckner, Frederick S.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 23; (2013); p. 6492 – 6499;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4856-97-7, These common heterocyclic compound, 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, 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.

The resulting solid (1H-benzimidazol-2-yl) methanol (34 mmol) was dissolved in 250 mL of dichloromethane and stirredFollowed by addition of manganese dioxide (0.68 mmol). The temperature was raised to 40 C and stirring was continued for 2 hours to monitor the reaction. After the reaction is complete, the product is evaporated to drynessDichloromethane, 150 mL of tetrahydrofuran was added. Directly to the next step

Statistics shows that (1H-Benzoimidazol-2-yl)methanol is playing an increasingly important role. we look forward to future research findings about 4856-97-7.

Reference:
Patent; Shenyang Pharmaceutical University; Zhao Linxiang; Liu Dan; Li Kun; Ma Tianyi; Jing Yongkui; (13 pag.)CN107118249; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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 1615-14-1, HPLC of Formula: C5H8N2O

Example 10: 2-Imidazol-l-ylethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)- quinoIine-3-carboxyIate. To a suspension of 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)-quinoline-3- carboxylic acid (1.0 g, 2.8 mmol) in dry tetrahydrofuran (15 mL) at 0 0C under nitrogen atmosphere was added l-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (2.0 g, 11.2 mmol), hydroxybenzotriazole (HOBt, 0.64 g, 4.84 mmol), triethylamine (3.2 mL, 2.3 mmol) and 2-hydroxyethylimidazole (0.65 g, 3.4 mmol). The reaction mixture was slowly brought to room temperature and stirred for 12 hours. The reaction mixture was concentrated in vacuo and after aqueous work up, extracted with dichloromethane, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified on column (flash chromatography on alumina gel, chloroform/methanol 99.8 : 0.2) to give 0.25 g (23 % yield) of 2-imidazol-l-ylethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate as a pale yellow solid. LC-MS (m/z) 446.2 (M+l). 1H NMR delta (CDCl3) 10.65 (s, IH), 9.16 (s, IH), 8.05 (dd, IH, J1 = 8.7 Hz, J2 = 1.8 Hz), 7.97 (d, IH, J= 8.7 Hz), 7.84 (s, IH), 7.76 (s, IH), 7.22-7.10 (m, 3H), 7.08 (s, IH), 6.97 (d, 2H, J= 9.0 Hz), 5.67 (broad s, IH), 4.75 – 4.60 (m, 2H), 4.50-4.35 (m, 2H), 3.87 (s, 3H), 2.88 (s, 3H).

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, 2-(1H-Imidazol-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CLANOTECH AB; MALM, Johan; RINGOM, Rune; CALDIROLA, Patrizia; WESTMAN, Jacob; WO2010/133669; (2010); A1;,
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. 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Difluoromethyl)-1H-benzo[d]imidazole

Preparation Example 1 To a solution of 4,6-dichloro-2-(methylsulfanyl)pyrimidine (5 g) in N,N-dimethylformamide (50 mL) were added potassium carbonate (5.3 g) and 2-(difluoromethyl)-1H-benzimidazole (3.9 g), and the mixture was stirred at room temperature for 5 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain 1-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]-2-(difluoromethyl)-1H-benzimidazole (5.49 g) as a white powder.

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; Astellas Pharma Inc.; TAKAHASHI, Fumie; IMADA, Sunao; ASANO, Toru; KOZUKI, Yoshihiro; MAEDA, Junko; KATO, Koji; FUKAHORI, Hidehiko; SHIWAKU, Masahiko; US2013/150364; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 39070-14-9, 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 39070-14-9 as follows.

A mixture of 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-ethanol (1.32 mmol) and 1-fluoro- 3 -nitrobenzene (1.67 mmol) and K2C03(465 mg, 3.36 mmol) in DMF (5 mL) was stirred 2 hours at ambient temperature followed by heating. The reaction was worked-up by extraction. The residue was purified by prep-HPLC with the following condition: column: XBridge preparative CI 8 OBD column 19x 150 mm, 5 um; mobile phase A: water (10 mmol/L NH4HCO3), mobile phase B: ACN; flow rate: 20 mL/min; gradient elution. The product-containing fractions were collected and then lyophilized to give l-methyl-5-nitro-2-(3-nitro-phenoxymethyl)-lH- imidazole. LC-MS: (ES, m/z) 279.07 (M+H)+; analysis: C, 47.53; H, 3.69; N, 20.24; O, 28.85.

According to the analysis of related databases, 39070-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); 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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 57090-88-7

General procedure: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

The synthetic route of 57090-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem