Category: 41716-18-1

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., 41716-18-1

To a solution of intermediate 36-h.HCl (2.0 g, 2.96 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (448 mg, 3.55 mmol), HATU (1.23 g, 3.25 mmol) and DIPEA (2.06 mL, 11.83 mmol) and the reaction mixture was stirred at room temperature for 3 hours. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 39-a as a white foam.

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Reference:
Patent; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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.

190a) (1 -Methyl-1 H-imidazol-4-yl)methanol A solution of 1 -methyl-1 H-imidazole-4-carboxylic acid (25 g, 198 mmol) in tetrahydrofuran (THF) (1000 ml_) was added LiAlhU (15.05 g, 396 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 50 ¡ãC for 12 h. It was added 15 mL of water, 15 mL of 10percent NaOH, 45 mL of water to the reaction mixture at 0 ¡ãC. The solid was filtered and the filtrate was concentrated to obtain the title compound (1 -methyl-1 H- imidazol-4-yl)methanol (13.2 g, 94 mmol, 47.5 percent yield) which was used for next step without further purification. LC-MS m/z 1 13.1 (M+H)+, 0.33 min (ret. time).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
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. 41716-18-1

Preparation of Compound 69aAt 0¡ã C., a suspension of 1-methyl-1H-imidazole-4-carboxylic acid (100.9 mg, 0.8 mmol) in CH2Cl2 (8 mL) was added oxalylchloride (305 mg, 0.21 mL, 2.4 mmol) followed by addition of 1 drop of DMF. The mixture was stirred for 2 days at 25¡ã C. All solvent was removed in vacuo to give a crude 69a.

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; Pfizer Inc.; US2009/318440; (2009); A1;,
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 41716-18-1 as follows. 41716-18-1

A mixture of (+/-)-ferf-butyl ((c/s)-3-aminocyclohexyl)carbamate (5 g, 23.3 mmol) and DMAP (7.1 g, 58.3 mmol) in CH2CI2 (100 mL) was stirred at ambient temperature, then 1 -methyl-1 h-imidazole-4-carboxylic acid (2.9 g, 23.3 mmol) was added. After stirring for 10 minutes at room temperature, EDC (6.7 g, 35 mmol) was added. The mixture stirred for 18h at room temperature. The reaction mixture was washed with citric acid (5percent aq.), the organic layer was removed, dried (MgS04), the solids removed by filtration, and the solvent of the filtrate removed under reduced pressure to give (+/-)-f-butyl ((c/’s)-3-(1 -methyl-1 – -imidazole-4- carboxamido)cyclohexyl)carbamate. LC-MS ES+ m/z = 323.5; Rt: 0.75 min, method A.

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; JANSSEN SCIENCES IRELAND UC; JONCKERS, Tim, Hugo, Maria; RABOISSON, Pierre, Jean-Marie, Bernard; GUILLEMONT, Jerome, Emile, Georges; MC GOWAN, David, Craig; EMBRECHTS, Werner, Constant, Johan; COOYMANS, Ludwig, Paul; MICHAUT, Antoine, Benjamin; (162 pag.)WO2016/20526; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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 41716-18-1. 41716-18-1

1-methyl -1H- imidazole-4-carboxylic Acid (1eq) was dissolved in dimethylformamide (DMF) and, morpholine (1.01 eq) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide imide was added dropwise (EDC, 1.1 eq), 1- hydroxybenzotriazole (HOBT, 1.1 eq) and triethylamine (TEA, 3 eq) in sequence. After stirring overnight at room temperature, then terminate the reaction with a small amount of water, extracted with EtOAc and water and a small amount of water in the organic layer was removed by using anhydrous MgSO4, and evaporated under reduced pressure to remove the solvent and dried in vacuo. Then, separated by column to give the title compound in 45percent yield.

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 1-Methyl-1H-imidazole-4-carboxylic acid.

Reference:
Patent; THE INDUSTRY & ACADEMIC COOPERATION IN CHUNGNAM NATIONAL UNIVERSITY (IAC); KIM, EUN HEE; YOO, SUNG EUN; KANG, NAM SOOK; KOO, TAE SUNG; PARK, MIN YOUNG; KIM, YOUNG HOON; BAE, HYUN JU; KIM, JIN WOO; IN, TAE KYU; JOO, CHOUN KI; (25 pag.)KR101555033; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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.

e) {(S)-3-[4-(5-Amino-6-methoxy-pyridin-3-yl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxy]-pyrrolidin-1-yl}-(1-methyl-1H-imidazol-4-yl)-methanone A solution of 1-methyl-1H-imidazole-4-carboxylic acid (CAS registry 41716-18-1) (36.0 mg, 0.26 mmol) and Et3N (0.11 ml, 0.78 mmol) in DMF (1 ml) was treated with HBTU (CAS registry 94790-37) (107 mg, 0.28 mmol). After stirring at rt for 20 min, the reaction mixture was cooled down to 5¡ã C. and a solution of 2-methoxy-5-[6-((S)-pyrrolidin-3-yloxy)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-pyridin-3-ylamine (88 mg, 0.26 mmol) in DMF (3 ml) was added. The reaction mixture was stirred at rt for 1 h, concentrated and the residue was taken up in DCM (10 ml), washed with a sat. aq. NaHCO3 soln. (5 ml), the organic layer was separated by elution through a separating phase cartridge and concentrated. The residue was purified by flash chromatography on silica gel (heptane/EtOAc 100:0 to 0:100), the combined fractions were concentrated, dissolved in tBuOH/H2O and lyophilized to afford the title compound as a colourless solid (21 mg, 37percent yield). UPLC RtM2=0.85 min; ESIMS: 451 [(M+H)+]. 1H NMR (400 MHz, CD3OD): delta 7.64 (s, 1H), 7.62 (s, 1H), 7.65 m, 1H), 6.93 (m, 1H), 6.70 (m, 1H), 6.20-6.34 (m, 1H), 6.15 (m, 1H), 4.81 (m, 1H), 4.19-4.31 (m, 2H), 3.90-4.05 (m, 4H), 3.55-3.83 (m, 8H), 2.04-2.28 (m, 2H).

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

Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 41716-18-1

Production Example 9 N-(3-Bromo-4-fluorobenzyl)-N-cyclobutyl-1-methyl-1H-imidazole-4-carboxamide A solution of methyl-1H-imidazole-4-carboxylic acid (1.17 g), N-(3-bromo-4-fluorobenzyl)cyclobutanamine (2.40 g) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) (3.09 g) in methanol (25 mL) was stirred at room temperature for 4 hr. After the reaction mixture was concentrated under reduced pressure, the resulting residue 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. The desiccant was filtered off and the solvent was then distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, chloroform_methanol=98:2-92:8) to afford the title compound (469 mg). 1H NMR (600 MHz, CHLOROFORM-d) d ppm 1.50-1.76 (m, 2H), 1.98-2.26 (m, 4H), 3.65-3.80 (m, 3H), 4.47-5.94 (m, 3H), 6.93-7.56 (m, 5H) (ESI pos.) m/z: 366([M+H]+), 368([M+3]+)

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, 41716-18-1, other downstream synthetic routes, hurry up and to see.

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

A common compound: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 41716-18-1

Production Example 9 N-(3-Bromo-4-fluorobenzyl)-N-cyclobutyl-1-methyl-1H-imidazole-4-carboxamide A solution of methyl-1H-imidazole-4-carboxylic acid (1.17 g), N-(3-bromo-4-fluorobenzyl)cyclobutanamine (2.40 g) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) (3.09 g) in methanol (25 mL) was stirred at room temperature for 4 hr. After the reaction mixture was concentrated under reduced pressure, the resulting residue 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. The desiccant was filtered off and the solvent was then distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, chloroform_methanol=98:2-92:8) to afford the title compound (469 mg). 1H NMR (600 MHz, CHLOROFORM-d) d ppm 1.50-1.76 (m, 2H), 1.98-2.26 (m, 4H), 3.65-3.80 (m, 3H), 4.47-5.94 (m, 3H), 6.93-7.56 (m, 5H) (ESI pos.) m/z: 366([M+H]+), 368([M+3]+)

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, 41716-18-1, other downstream synthetic routes, hurry up and to see.

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

41716-18-1, 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.

EXAMPLE 2 1-Methyl-1H-imidazole-4-carboxylic acid 4-[3-hydroxy-4-(3-methyl-butyryl)-2-trifluoromethyl-phenoxymethyl]-benzylamide Mix 1-[4-(4-aminomethyl-benzyloxy)-2-hydroxy-3-trifluoromethyl-phenyl]-3-methyl-butan-1-one hydrochloride (120 mg, 287.2 mumol), 1-methyl-1-H-imidazole-4-carboxylic acid (43.5 mg, 344.6 mumol), 1-hydroxybenzotriazole hydrate (52.8 mg, 344.6 mumol) in anhydrous tetrahydrofuran (4.5 mL). Add triethylamine (72.7 mg, 718 mumol, 100 muL) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66.1 mg, 344.6 mumol) to the mixture. Stir the reaction mixture at room temperature overnight. Dilute the reaction mixture with water. Extract the mixture with ethyl acetate (3*). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate under reduced pressure. Purify the crude residue by flash chromatography (silica gel) eluding with 5percent methanol/ethyl acetate followed by reverse phase chromatography using 90/10 to 20/80 (water/0. 1percent trifluoroacetic acid)/acetonitrile to provide the product as a white solid (75 mg, 153 mumol, 53.4percent yield). MS (m/z): 490 (M+1).

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:
Patent; Khilevich, Albert; Liu, Bin; Mayhugh, Daniel Ray; Schkeryantz, Jeffrey Michael; Zhang, Deyi; US2010/16373; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, A common compound: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 141-Methyl-N-[3-methyl-5-(trifluoromethoxy)benzyl]-N-(tetrahydro-2H-thiopyran-4-yl)-1H-imidiazole-4-carboxamideA mixture of N-[3-methyl-5-(trifluoromethoxy)benzyl]tetrahydro-2H-thiopyran-4-amine (830 mg), 1-methyl-1H-imidazole-4-carboxylic acid (380 mg), EDC.HCl (860 mg), HOBt (460 mg), dimethylformamide (20 mL) and triethylamine (0.94 mL) was stirred overnight at room temperature.The solvents were distilled off under reduced pressure and extraction was conducted with ethyl acetate; the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and dried over anhydrous magnesium sulfate.After filtering off the desiccant, the solvent was concenrated.The residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=90:10 to 10:90) to give the titled compound (810 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