Category: imidazoles-derivatives

Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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. Application In Synthesis of 1H-Imidazole

Step 1. Synthesis of 4-chloro-1H-imidazole (C33) To a solution of 1H-imidazole (22.1 g, 324 mmol) in N,N-dimethylformamide at 0 C. was added drop-wise (over 4 hours) a solution of N-chlorosuccinimide (25 g, 190 mmol) in N,N-dimethylformamide (total solvent, 160 mL). The reaction was stirred at 0 C. for 1 hour, whereupon water (200 mL) was added at 0 C. The mixture was extracted with ethyl acetate (3*50 mL), and the combined organic layers were concentrated in vacuo. Purification was carried out using supercritical fluid chromatography (Column: Princeton Cyano, 5 mum; Eluant: 15:85 methanol/carbon dioxide). The resulting material was purified again, using silica gel chromatography (Mobile phase A: ethyl acetate; Mobile phase B: [20% (2 M ammonia in methanol) in dichloromethane]; Gradient: 0% to 10% B) to afford the title compound as a white solid. Yield: 2.45 g, 23.9 mmol, 12%. GCMS m/z 102, 104 (M+). 1H NMR (400 MHz, CDCl3) delta 7.00 (d, J=1.2 Hz, 1H), 7.57 (br s, 1H), 11.3 (v br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Patent; Pettersson, Martin Youngjin; Johnson, Douglas Scott; Subramanyam, Chakrapani; O’Donnell, Christopher John; Ende, Christopher William Am; Fish, Benjamin Adam; Green, Michael Eric; Mullins, Patrick Bradley; Stiff, Cory Michael; Tran, Tuan Phong; Navaratnam, Thayalan; US2012/252758; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A 20 mL vial was charged with a 1.5 mL of ammonium acetate/acetic acid buffer solution (pH 4) in methanol. To this Example 87D (35.24 mg, 0.109 mmol) was added to form a suspension. lH-benzo[d]imidazole-2-carbaldehyde (23.89 mg, 1.5 eq, 0.164 mmol) and Si-BH3CN (from Silicycle, 0.88mmol/g loading, 371.49 mg) were then added. The vial was capped and placed to stir at 40°C overnight. Upon completion, the crude mixture was filtered, concentrated, and purified by HPLC (see Example 360 for protocols) to provide the title compound as a trifluoroacetic acid salt. lH NMR (400 MHz, pyridine-d5) delta ppm 2.57 (q, J = 4.1, 3.2 Hz, 2H), 2.83 (t, J = 5.7 Hz, 2H), 3.39 (q, J = 2.8 Hz, 2H), 3.71 (s, 3H), 4.17 (s, 2H), 6.61 (s, 1H), 6.64 – 6.67 (m, 1H), 7.09 (dd, J = 9.1, 4.5 Hz, 1H), 7.26 (ddd, J = 9.1, 7.9, 3.2 Hz, 1H), 7.32 (d, J = 4.9 Hz, 1H), 7.34 – 7.39 (m, 2H), 7.49 (dd, J = 8.9, 3.2 Hz, 1H), 7.89 (dd, J = 6.0, 3.2 Hz, 2H), 8.58 (d, J = 5.0 Hz, 1H). MS (ESI+) m/z 454.2 (M+H)+.

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, 1H-Benzo[d]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); 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 78581-99-4 as follows. Recommanded Product: 78581-99-4

Step 3: To a stirred mixture of sodium hydride (60% dispersion in mineral oil, 0.144 g, 3.0 mmol) in anhydrousDMF (10 mL) at 0 C under a nitrogen atmosphere was added portionwise 6-difluoro-1H-benzo[d]imidazole (0.475 g,2.0 mmol) from the previous step. The mixture was stirred at 0 C for 5 min. To the mixture was added dropwise asolution of 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole (0.32 g, 2.0 mmol) from Step 4 of Example 36 in anhydrousDMF (2 mL). The reaction mixture was allowed to warm to rt and stir for 1 h. The mixture was poured into ice-water andextracted with EtOAc (100 mL 3 2). The combined organic layers were further washed with water (20 mL) then brine(20 mL). The organic layer was separated and dried over Na2SO4, filtered, and concentrated under reduced pressureto afford 6-((5,6-difluoro-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (0.55 g, 76%) as a yellow solid,which was not purified further. 1H NMR (300 MHz, CDCl3) delta 7.97 (s, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.59 (m, 1H), 7.50(s, 1H), 7.24 (m, 1H), 7.02 (m, 1H), 5.40 (s, 2H), 2.78 (s, 3H); LCMS (ESI) m/z 348 (M + H)+.

According to the analysis of related databases, 78581-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6160-65-2, A common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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.

Step A: N-(thiazol-2-yl)-1H-imidazole-1-carbothioamide To thiazol-2-amine (2.12 g, 21.17 mmol) in acetonitrile (30 mL) and tetrahydrofuran (5 mL) was added di(lH-imidazol-l-yl)methanethione (4.90 g, 27.5 mmol). The reaction was stirred at 60 C for 5 hours. The reaction was cooled to room temperature and the precipitate was filtered and washed with cold acetonitrile (2 x 15 mL) to afford an orange-brown powder. The product, N-(thiazol-2-yl)-lH- imidazole- l-carbothioamide (3.70 g, 17.60 mmol, 83 % yield), was taken directly to the next step without any further characterization.

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; MCDONALD, Ivar, M.; KING, Dalton; OLSON, Richard, E.; WANG, Nenghui; IWUAGWU, Christiana, I.; ZUSI, Christopher, F.; MACOR, John, E.; WO2011/53292; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 alcohol18(1.0 g, 6.36 mmol) in chloroform (70 mL) was added MnO2(2.76 g, 31.8 mmol) and the mixture was heated to reflux overnight. After cooling, the resulting slurry was filtered through diatomaceous earth and solvent removed in vacuo to yield19(1.5 g, 76%) as a pale yellow solid, mp 112-114 C (lit. [62] mp 114-115 C). deltaH(CDCl3) 9.93 (1H, s, CHO), 7.81 (1H, s, H-4), 4.36 (3H, s, CH3). deltaC(CDCl3) 180.4 (C = O), 148.3 (C-NO2), 139.4 (CH), 132.4 (CH), 35.6 (CH3). LRMS 188.1 (100%, M + CH3OH). These data are in good agreement with literature values [35].

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; Dickson, Benjamin D.; Wong, Way Wua; Wilson, William R.; Hay, Michael P.; Molecules; vol. 24; 8; (2019);,
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. 1457-58-5, name is 2-Methyl-1H-imidazole-5-carboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 1457-58-5

WSC (4.0 g), HOBt (3.2 g) and triethylamine (3.8 mL) were added to a solution of benzyl 4-aminopiperidine-1-carboxylate (3.3 g) and 2-methyl-1H-imidazole-4-carboxylic acid (2.0 g) in acetonitrile (50 mL) and stirred for 12 hours. The reaction solution was concentrated and the residue was dissolved in chloroform and an aqueous saturated sodium bicarbonate solution. A chloroform layer was separated, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography to obtain the title compound (2.4 g, 49%) as colorless powder. NMR (300 MHz, CDCl3) delta: 1.41-1.56 (2H, m), 1.93-2.06 (3H, m), 2.40 (3H, s), 2.92-3.07 (2H, m), 4.06-4.21 (2H, m), 5.14 (2H, s), 7.07 (1H, d, J = 8.3), 7.30-7.42 (5H, m), 10.92 (1H, br)

The synthetic route of 1457-58-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1564213; (2005); 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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

Step A: Ethyl 2,3-dihydro-3-(1-methyl-ethenyl)-2-oxo-1H-benzimidazol-1-butanoate A solution of 19 g of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one [described in J. Chem. Soc. Perkins, 1982, p. 261] in 150 ml of dimethylformamide was added with stirring at 20 C.+-2 C. to 5.75 g of sodium hydride as a 50% suspension in oil and 10 ml of dimethylformamide and the mixture was stirred for another 30 minutes. 23.4 g of ethyl 4-bromo-butyrate were added to the mixture over 15 minutes and the mixture was stirred at room temperature for 4 hours and was poured into 800 ml of iced water. The mixture was extracted with ether and the organic phase was washed with water, dried and evaporated to dryness under reduced pressure to obtain 33 g of ethyl 2,3-dihydro-3-(1-methyl-ethenyl)-2-oxo-1H-benzimidazol-1-butanoate.

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; Roussel Uclaf; US4585770; (1986); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 144690-33-5, These common heterocyclic compound, 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, 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.

Formula 1Of ethyl 4- (2-hydroxypropan-2-yl)-2-Propyl-1-((2 ‘- (1-trityl-1H-tetrazol-5-yl) biphenyl-4-yl) methyl) -1H- imidazole-5-carboxylate was added a mixed solvent of purified water and dioxane Lithium hydroxide was added and reacted at room temperature for 2 hours. After confirming the termination of the reaction by thin-layer chromatography, the organic solvent was removed by concentration under reduced pressure, methylene chloride was added and neutralized with 1 N hydrochloric acid solution. The organic layer was separated, dried and concentrated, 2 4-(2-hydroxypropan-2-yl)-2-propyl-1 – ((2 ‘- (1-trityl-1H-tetrazol-5-yl)Biphenyl-4-yl) methyl)-1H-imidazole-5-carboxylate was synthesized

Statistics shows that Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1’-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 144690-33-5.

Reference:
Patent; DAEBONG LS, LTD; PARK, JIN-HO; KIM, YONG-GIL; KWON, JI-WONG; KIM, EUN-MI; LEE, JI-EUN; PARK, SEOK-YONG; (7 pag.)KR101696851; (2017); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2302-25-2,Some common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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.

-Bromo- lH-imidazole(3.2 g, 21.8 mmol) was weighed into a 500 mL round bottomed flask equipped with a magnetic stir bar under a nitrogen atmosphere. Anhydrous DMF, (12 mL) was added and the mixture was placed on ice. After 10 min the mixture was treated with NaH (0.840 g, 21.0 mmol. 60% dispersion in oil). After 5 min, the ice bath was removed and the reaction was warmed to room temperature. After 15 min of vigorous stirring the ice bath was replaced and 3-(4-cyanophenyl)oxaziridine-2-carboxylic acid tert-butyl ester (1.92 g, 7.80 mmol) was added. The reaction was vigorously stirred for 5 min and the ice bath was removed. After 5 min the mixture was diluted with saturated NaHCC>3 and extracted with EtOAc. The organics were washed with dilute sodium carbonate, dried over Na2SC>4, filtered, and concentrated. The residue was purified using silica gel chromatography (0-5% MeOH / DCM) to afford the title compound (1.16 g, 4.43 mmol, 57 %) as a yellow oil: ]H NMR (400 MHz, CDCI3) delta 9.22 (s, 1H), 7.36 (d, / = 1.5 Hz, 1H), 6.97 (d, / = 1.5 Hz, 1H), 1.48 (s, 9H); ESIMS m/z 262 ([M]+), 260 ([M-2]”).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1H-imidazole, its application will become more common.

Reference:
Patent; DOW AGROSCIENCES LLC; GARIZI, Negar; TRULLINGER, Tony K.; HUNTER, Ricky; ZHANG, Yu; NIYAZ, Noormohamed M.; KNUEPPEL, Daniel; LOWE, Christian T.; BUYSSE, Ann M.; WO2013/62980; (2013); 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 33468-67-6 as follows. Recommanded Product: 33468-67-6

Example 40 Synthesis of l-[l-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]-3-[2-methyl-4- (trifluoromethyl)imidazol-l-yl]pyrrolidin-2-one [0200] A mixture of 3-bromo-l-[l-(4-chlorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2- one (0.110 g, 0.29 mmol), 2-methyl-4-(trifluoromethyl)-lH-imidazole (0.080 g, 0.53 mmol) and K2C03 (0.080 g, 0.58 mmol) in DMF (1.8 mL) was stirred at 65 C for 2 hrs. The mixture was then cooled to room temperature, quenched with water (30 mL), extracted with EtOAc (50 mL), and purified by reverse phase HPLC (CI 8 column, acetonitrile-H20 with 0.1% TFA as eluent) to yield the title compound (0.035 g, TFA salt, 21%). XH NMR (TFA salt) (400 MHz, CDC13) delta 7.58 (s, 1 H), 7.49 (m, 2 H), 7.35 (m, 2 H), 7.27 (s, 1 H), 5.03 (dd, J= 10.4, 8.8 Hz, 1 H), 3.89 (m, 1 H), 3.81 (m, 1 H), 3.04 (heptet, J= 6.8 Hz, 1 H), 2.88 (m, 1 H), 2.58 (s, 3 H), 2.40 (m, 1 H), 1.23 (m, 6 H); MS: (ES) m/z calculated for C2iH21ClF3 50 [M + H]+ 452.1, found 452.1.

According to the analysis of related databases, 33468-67-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; FAN, Pingchen; LI, Yandong; POWERS, Jay P.; MALATHONG, Viengkham; PUNNA, Sreenivas; TANAKA, Hiroko; ZHANG, Penglie; WO2014/89495; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem