Category: 39070-14-9

Synthetic Route of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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 solution of Compound i (1 g) in DMF (15 mL) was added N- bromosuccinimide (NBS, 1.25 g) and the reaction mixture stirred at 600C for 3h. Then the reaction mixture was diluted with brine, extracted with EtOAc, dried and concentrated to yield a residue that was separated by column chromatography using 0 – 80% EtOAc/Hexanes to yield Compound ii (1.3 g).

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; CHEN, Tao; WO2008/151253; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39070-14-9, 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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The corresponding hydroxy startingcompound (1a, 2a and 3a) (2 mmol) in tetrahydrofuran (10 mL) was added to phosgene (4 mL,8 mmol) and tetrahydrofuran (THF) (15 mL) at 0 C. The reaction mixture was stirred for 16 h, then the solvent was removed in vacuo. The crude chloroformate was used without further purification.

The chemical industry reduces the impact on the environment during synthesis (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol. I believe this compound will play a more active role in future production and life.

Reference:
Article; Anduran, Emilie; Aspatwar, Ashok; Bua, Silvia; Dubois, Ludwig; Lambin, Philippe; Nocentini, Alessio; Parkkila, Seppo; Parvathaneni, Nanda-Kumar; Supuran, Claudiu T.; Suylen, Dennis; Winum, Jean-Yves; Molecules; vol. 25; 10; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

300 mg of 3 (1 eq., 0.55 mmol), 86 mg of 1 (1 eq., 0.55 mmol),326 mg of Cu(OAc)2·H2O, 18 mg of potassium iodide (0.2 eq.,0.11 mmol) and 6 mg of Pd(OAc)2 were dissolved in 3 mL of dimethylsulfoxide and 12 mL acetonitrile. The reaction vessel was set under anatmospheric pressure of carbon monoxide (CAUTION: highly toxic) andshortly warmed with a hot water bath (40 C). After 1 h the reactionmixture was taken up in EtOAc and washed with sat. NaHCO3 andwater. The combined aqueous solutions were washed with EtOAc andthe combined organic solutions were washed with brine, dried overMgSO4 and the solvent was removed under reduced pressure. The crudeproduct was dried in vacuo overnight. Purification was performed usingcolumn chromatography (EtOAc/petrol ether 9:1). Yield: 160 mg(40%). 1H NMR (500 MHz, DMSO-d6) delta 9.35 (s, 1H), 8.65 (s, 1H), 8.41(s, 1H), 8.23 (s, 2H), 7.84 (s, 1H), 7.54 (dd, J = 8.9, 5.0 Hz, 1H), 7.45(t, J = 8.7 Hz, 1H), 7.38 (s, 1H), 7.28 (s, 1H), 6.15 (d, J = 6.6 Hz, 1H),5.30 – 5.19 (m, 2H), 4.52 (t, J = 10.9 Hz, 1H), 3.96 (s, 3H), 3.10 (dd,J = 23.1, 11.6 Hz, 2H), 2.23 (d, J = 11.4 Hz, 2H), 2.15 – 2.06 (m, 2H),1.73 (d, J = 6.6 Hz, 3H), 1.43 (s, 9H) ppm. ESI-MS (M + Na): calc:755.19 found: 755.39.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Berger, Walter; Bielec, Bjoern; Heffeter, Petra; Keppler, Bernhard K.; Kowol, Christian R.; Schueffl, Hemma; Terenzi, Alessio; Bioorganic Chemistry; vol. 99; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

EXAMPLE 61: 1-Methyl-2-nitro-5-imidazolaldehyde To a solution of 0.15 g. of 1-methyl-2-nitro-5-hydroxymethylimidazole in 20 ml. of benzene, 0.33 g. of MnO2 is added and the reaction mixture is heated on the steambath for 2 hours. After filtration and evaporation to dryness under vacuum, the crude product is crystallized from ethyl acetate and 0.060 g. (40.5%) of 1-methyl-2-nitro-5-imidazolaldehyde is obtained.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruppo Lepetit S.p.A.; US3954789; (1976); A;,
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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., SDS of cas: 39070-14-9

A solution of triphosgene (62 mg, 0.21 mmol) in DCM (4.0 mL) was added to a stirred solution of A13 (prepared as described in: WO 2013/055987; 500 mg, 0.52 mmol) and Et3N (120 mg, 1.18 mmol) in DCM (20 mL) at 22 C. The mixture was stirred at that temperature for 2 h. A solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (112 mg, 0.71 mmol) in DCM (1 mL) was then added, followed by nBu2Sn(OAc)2 (3 drops). The resulting solution was stirred at 22 C for 16 h under N2 then was concentrated under reduced pressure. The residue was purified by prep-TLC (DCM/MeOH = 30/1) to give A14 as a yellow solid (180 mg, 31%). LCMS (condition A): RT = 1.11 min, m/z = 1136.9 [M+H]+.

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; Dragovich, Peter S.; Broccatelli, Fabio; Chen, Jinhua; Fan, Peter; Le, Hoa; Mao, Weiguang; Pillow, Thomas H.; Polson, Andrew G.; Wai, John; Xu, Zijin; Yao, Hui; Zhang, Donglu; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5300 – 5304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

General procedure: To a solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 39070-14-9, name is (1-Methyl-2-nitro-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 39070-14-9, Application In Synthesis of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

To a suspension of N,N’-bis(2-bromoethyl)phosphorodiamidic acid (50mg, 0.16mmol), 1-methyl-2-nitroimidazole-5-methanol (50mg, 0.32mmol), and PPh3 (84mg, 0.32mmol) in THF (15mL) was added DIAD (0.13mL, 0.32mmol) at 0C. After the addition of DIAD, the reaction mixture was warmed to room temperature and stirred overnight. The solvent was removed, and the residue was purified by column chromatography on silica gel (DCM: MeOH=50:1) to afford compound 14 (37mg, 51%) as yellow gum. 1H NMR (400MHz, DMSO) delta 7.25 (s, 1H), 5.05-4.99 (m, 2H), 4.98 (d, J=7.6Hz, 2H), 3.94 (s, 3H), 3.42 (t, J=6.9Hz, 4H), 3.17-3.05 (m, 4H). 13C NMR (101MHz, DMSO) delta 146.1, 134.1(d, J=8.0Hz), 128.2, 55.7 (d, J=4.3Hz), 42.7, 34.3, 34.1 (d, J=5.0Hz). HRMS (ESI): m/z Calcd for C9H17Br2N5O4P, [M+H]+: 469.9204, found: 469.9186.

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-2-nitro-1H-imidazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Chen; Zhang, Qiumeng; Lu, Wei; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 135 – 141;,
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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

EXAMPLE 7 A lithium diisopropylamine solution (prepared from 65 ml of a 2.2 molar solution of butyl lithium in hexane and 14.5 g of diisopropylamine in 150 ml of tetrahydrofuran) was added dropwise at a temperature of -60 C. within 15 minutes to a solution of 22 g of 1-methyl-2-nitroimidazole-5-methanol in 300 ml of tetrahydrofuran and 150 ml of dimethylformamide. The mixture was stirred at -60 C. for 30 minutes and treated with 28 g of p-toluenesulphonyl chloride in 150 ml of tetrahydrofuran. After removing the cooling, warming to room temperature and adding 300 ml of ice/water, the mixture was extracted three times with 300 ml of ethyl acetate each time. The combined extracts were washed with 150 ml of saturated sodium chloride solution and evaporated under reduced pressure. The residue was purified on 800 g of silica gel with ethyl acetate/dichloromethane (1:3, v/v). After a forerun of 1.5 l, the next 1.5 l were collected and evaporated. Recrystallization from 70 ml of toluene yielded 12 g (50%) of 5-(chloromethyl)-1-methyl-2-nitroimidazole, m.p. 100-101 C.

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 39070-14-9.

Reference:
Patent; Hoffmann-La Roche Inc.; US4515790; (1985); A;,
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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

Step 2: To a solution of compound G2 (3.41mmol) in THF cooled to -12C was added dropwise phosphorus oxychloride (5.12 mmol). The reaction mixture was stirred at -12C for 40minutes and then, proton sponge (13.64mmol) was added. The reaction mixture was stirred at -12C overnight. To this stirred reaction mixture was added a solution of benzylamine (3.75mmol) and triethylamine (17.05mmol) in acetonitrile (7mL).The reaction mixture was then allowed to warm to -5C. The reaction mixture was stirred for 5 hours. The reaction was monitored by LC/MS. To the reaction mixture was then added a solution of (3-methyl-2-nitro-3H-imidazol-4-yl)-methanol (10.23mmol) and 4-(dimethylamino)pyridine (10.23 mmol) in acetonitrile (10 mL). The reaction mixture was stirred at room temperature overnight, and then concentrated under reduced pressure. The crude residue was partitioned between a 5% solution of citric acid and ethyl acetate. The organic layer was washed with water and brine, dried over over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (DCM/methanol: 0 to 3%) to afford the expected compound G3.

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.

Adding a certain compound to certain chemical reactions, such as: 39070-14-9, name is (1-Methyl-2-nitro-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 39070-14-9, Recommanded Product: 39070-14-9

EXAMPLE 1 78.5 g of 1-methyl-2-nitroimidazole-5-methanol were suspended in 1.5 l of anhydrous tetrahydrofuran. After the addition of 102 g of p-chloroacetylaminophenol and 144 g of triphenylphosphane, the mixture was cooled to 10 C. and a solution of 111 g of diisopropyl azodicarboxylate in 750 ml of anhydrous tetrahydrofuran was added thereto with vigorous stirring within 20 minutes, the temperature being held at 10-12 C. by means of an ice-bath. The mixture was stored in a refrigerator overnight and the crystalline precipitate was filtered off under suction. Recrystallization from 2 l of acetonitrile, yielded 90.9 g (56.6%) of pure 2-chloro-alpha-(1-methyl-2-nitroimidazol-5-yl)-p-acetanisidide, m.p. 192-194 C. (decomposition).

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; Hoffmann-La Roche Inc.; US4515790; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem