Category: 41716-18-1

Synthetic Route of 41716-18-1, The chemical industry reduces the impact on the environment during synthesis 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

Example 11-Methyl-N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-imidazole-4-carboxamideA mixture of N-[3-(trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine (450 mg), 1-methyl-1H-imidazole-4-carboxylic acid (210 mg), EDC.HCl (320 mg), HOBt (250 mg) and acetonitrile (5 mL) was stirred at room temperature for an hour.Acetonitrile was distilled off under reduced pressure and an aqueous solution of 6 M sodium hydroxide was added.Extraction was conducted with ethyl acetate and the solvent was concentrated.The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (90 mg).

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, 1-Methyl-1H-imidazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; US2012/10414; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, A common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

1-hydroxybenzotriazole monohydrate (16 mg, 0.118 mmol), 3- (ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine (Hydrochloric Acid (1)) (35 mg, 0.183 mmol), and 1-methyl-1H-imidazole-4-carboxylic acid (15 mg, 0.119 mmol) were combined in DMF (0.2 mL) under nitrogen at room temperature and allowed to stir for 40 min. 4-(7-morpholinoquinazolin-5-yl)oxycyclohexanamine (25 mg, 0.0761 mmol) was added, and stirring was continued a further 30 min. Saturated sodium bicarbonate was added, an the mixture was extracted with EtOAc (2x). The combined organics were washed with water (2x), brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography over 4g silica gel using a 0-10% methanol / DCM gradient to yield 1- methyl-N-((1s,4s)-4-((7-morpholinoquinazolin-5-yl)oxy)cyclohexyl)-1H-imidazole-4- carboxamide (6 mg, 17%). 1H NMR (400 MHz, CDCl3) delta 9.44 (s, 1H), 9.10 (s, 1H), 7.51 (d, J = 1.3 Hz, 1H), 7.40 – 7.34 (m, 1H), 7.09 (d, J = 8.4 Hz, 1H), 6.78 (d, J = 1.9 Hz, 1H), 6.57 (d, J = 2.0 Hz, 1H), 4.74 (d, J = 3.9 Hz, 1H), 4.11 (tq, J = 9.9, 6.2, 5.3 Hz, 1H), 3.89 (dd, J = 5.9, 3.9 Hz, 4H), 3.73 (s, 3H), 3.43 – 3.33 (m, 4H), 2.29 – 2.17 (m, 2H), 2.04 – 1.73 (m, 6H). ESI-MS m/z = 433.05 (M+1)+.

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; VERTEX PHARMACEUTICALS INCORPORATED; MAXWELL, John, Patrick; JACKSON, Katrina, Lee; TANG, Qing; MORRIS, Mark, A.; RONKIN, Steven, M.; XU, Jinwang; COTTRELL, Kevin, M.; CHARIFSON, Paul, S.; (280 pag.)WO2019/143678; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, 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. 41716-18-1 name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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.

Production Example 8 N-[(2-Bromopyridin-4-yl)methyl]-N-cyclobutyl-1-methyl-1H-imidazole-4-carboxamide After a solution of methyl-1H-imidazole-4-carboxylic acid (300 mg), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (1.27 g) and diisopropylethylamine (431 mg) in dimethylformamide (7 mL) was stirred at room temperature for 15 min, N-[(2-bromopyridin-4-yl)methyl]cyclobutanamine (574 mg) was added thereto and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with chloroform, and washed with saturated aqueous sodium hydrogen carbonate solution. After extraction with chloroform, the organic phase was dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20-50:50) to afford the title compound (1.46 g). 1H NMR (600 MHz, CHLOROFORM-d) d ppm 1.55-2.26 (m, 6H), 3.60-3.81 (m, 3H), 4.56-6.50 (m, 3H), 7.04-8.29 (m, 5H) (ESI pos.) m/z: 349([M+H]+), 351([M+3]+)

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

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Moriya, Minoru; Yasuhara, Akito; Sakagami, Kazunari; Ohta, Hiroshi; Abe, Kumi; Yamamoto, Shuji; Araki, Yuko; Urabe, Hiroki; Sun, Xiang-Min; US2013/184460; (2013); 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 41716-18-1

To a solution of 1-methyl-1Himidazole-4-carboxylic acid (0.50 g, 4.0 mmol), 1-hydroxybenztriazole monohydrate (0.74 g, 4.8 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.92 g, 4.8 mmol) in acetonitrile (10 mL) was added a solution of 3-(trifluoromethoxy) benzylamine 8(0.84 g, 4.4 mmol) in acetonitrile (10 mL), and the mixture was stirred at room temperature for overnight. The reaction mixture was concentrated in vacuo, and saturated aqueous NaHCO3solution was added to the residue. After extraction with ethyl acetate, the organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (0?10percent MeOH in CHCl3) to obtain 9(1.18 g, 98percent) as a colorless powder.1H-NMR (600 MHz, CDCl3) delta: 3.73 (3 H, s), 4.62 (2 H, d, J=6.0 Hz), 7.08?7.13 (1 H, m), 7.18 (1 H, s), 7.26?7.29 (1 H, m), 7.31?7.37 (2 H, m), 7.44?7.51 (1 H, m), 7.55 (1 H, d, J=1.4 Hz); MS ESI: m/z300 [M+H]+.

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 41716-18-1.

Reference:
Article; Yamamoto, Shuji; Ohta, Hiroshi; Abe, Kumi; Kambe, Daiji; Tsukiyama, Naohiro; Kawakita, Yasunori; Moriya, Minoru; Yasuhara, Akito; Chemical and Pharmaceutical Bulletin; vol. 64; 11; (2016); p. 1630 – 1640;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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. SDS of cas: 41716-18-1

To a stirred solution of 11-3 (0.23g, 0.4mMol), HOBT (0.06g, 0.45mMol), and 1- methyl-lH-imidazole-4-carboxylic acid (0.06g, 0.45mMol) in anhydrous DMF (2mL) was added DIEA (0.13mL, 0.8mMol) followed by EDC (0.09g, 0.5mMol). The solution was heated in the microwave reactor for 15 minutes at 800C. Solution was then treated with 0.2mL of acetic acid and was heated to 800C in the microwave reactor for 20 minutes. Upon cooling to room temperature, the solution was passed through a syringe filter and purified on a C18 reverse phase HPLC to give 12-1 as a solid. Mass (M+l) calculated: 632.2742 observed: 632.274 EPO

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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. category: imidazoles-derivatives

To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC ACID (11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added drop-wise a solution of lithium aluminium hydride [(1 M] in THF, [117ML,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour Water (3 [ML)] was added followed by [NA2SO4] and the mixture was filtered through [CELITETM.] The filtrate was concentrated under reduced pressure to afford the title compound as a solid [(8G,] 78.95percent) ;’H NMR (300 MHz, [CDCI3)] 6 ppm: 7.25 (s, 1 H), 6. 7 (s, 1H), 5.25 (m, 1H), 4.4 (s, 2H), 3.45 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41716-18-1, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13138; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1,Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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.

1-Methyl-4-imidazolecarboxylic acid (4-1) (265 mg, 2.1 mmol)Was dissolved with N, N-dimethylformamide (12 mL)N-Methylmorpholine (850 mg, 8.4 mmol) was added with stirring,The reaction solution was placed in an ice water bath and slowly stirred for 10 minutes,Trimethylacetyl chloride (277 mg, 2.3 mmol) was then slowly added dropwise,Complete addition the reaction was stirred for 30 minutes under ice-water bath maintained;After the anhydride is completely formed,Under ice-cooling, a solution of 1- (4-methoxyphenyl) -3-methyl-2-piperazinone hydrochloride (4 -2) (462 mg, 1.8 mmol)Plus,The reaction was stirred at room temperature for 1 hour, followed by monitoring the reaction; After the reaction was completed, quenched with water, the reaction was concentrated in vacuo, the concentrate was extracted with dichloromethane, and then washed with saturated brine, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure.The concentrate was subjected to column chromatography to obtain a white solid1- (4-methoxyphenyl) -3-methyl-4- (1-methyl- 4- carbonylimidazole) piperazin- 2-one (compound- 4),Yield 70percent,

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujian Jinle Pharmaceutical Technology Co., Ltd.; Zhou Zhongxiang; Xing Yuanyuan; Chen Yingzhong; Deng Chengjun; Deng Honggui; Xue Wanhua; Zhang Shuzu; Chen Weipeng; Li Fang; (27 pag.)CN107174584; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC ACID (11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added drop-wise a solution of lithium aluminium hydride [(1 M] in THF, [117ML,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour Water (3 [ML)] was added followed by [NA2SO4] and the mixture was filtered through [CELITETM.] The filtrate was concentrated under reduced pressure to afford the title compound as a solid [(8G,] 78.95percent) ;’H NMR (300 MHz, [CDCI3)] 6 ppm: 7.25 (s, 1 H), 6. 7 (s, 1H), 5.25 (m, 1H), 4.4 (s, 2H), 3.45 (s, 3H).

The synthetic route of 1-Methyl-1H-imidazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13138; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 41716-18-1,Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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.

The complex 1 was obtained during attempted 1:2CuSO4.5H2O and L1H in methanol/water (2:1 v/v) solution atroom temperature under continuous stirring. After stirring for20 min, the solution that resulted from the mixture was filteredoff and allowed to evaporate at room temperature. Blue blockcrystals of 1 formed in about 5 days. Elemental analysis for 1,Anal. Calcd. (percent): C, 31.13; H, 4.70; N, 14.52. Found: C, 31.17;H, 4.73; N, 14.59.

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Li-Jing; Song, Wen-Tao; Luo, Yang-Hui; Sun, Bai-Wang; Inorganic and Nano-Metal Chemistry; vol. 47; 4; (2017); p. 493 – 499;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, 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 41716-18-1 as follows.

To a solution of tert-butyl (1-(4-(5-hydrazono-3-phenyl-5,6,7,8-tetrahydro-1,6- naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (22mg, 0.04 mmol) in dry DMF (1 ml_) was added EDCI (11 mg, 0.06 mmol), HOBt.H20(8 mg, 0.06 mmol) and 1-methyl-1H- imidazole-4-carboxylic acid (8 mg, 0.06 mmol) under nitrogen. The reaction mixture was heated at 60 °C overnight. After cooled down to room temperature, the mixture was partitioned between saturated NaHC03 solution and ethyl acetate. The layers were separated and the organic phase washed with water and brine, dried over Na2S04, filtered and concentrated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (method G, gradient 5 to 95percent 0.1percentFA/ACN in0.1percentFA/H2O) to give the title compound (1 mg, 5percent). NMR (500 MHz, CDCI3): 8.49 (1 H, s), 7.74 (1 H, s), 7.54 (1H, s), 7.38 (2H, d), 7.31 (2H, d), 7.28-7.23 (5H, m), 5.01 (1 H, br s), 4.94 (2H, t), 3.81 (3H, s), 3.49 (2H, t), 2.60-2.30 (4H, m), 2.10-2.01 (1 H, m), 1.85- 1.76 (1 H, m), 1.45-1.20 (9H, br).

According to the analysis of related databases, 41716-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ZHANG, Lixin; TREVITT, Graham, Peter; MIEL, Hughes; BURKAMP, Frank; HARRISON, Timothy; WILKINSON, Andrew, John; FABRITIUS, Charles-Henry; WO2011/77098; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem