Month: March 2021

1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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: 1849-01-0

Example 37; Preparation of Intermediate Compound 37A; To a solution of 2-bromo-4-carbomethoxythiazole (1.5 g, 6.78 mmol) in dioxane (80 mL) at room temperature was added 1 -methyl-2-benzimidazolone (1.0 g, 6.78 mmol) followed by CuI (0.13 g, 0.68 mmol), K2CO3 (1.0 g, 7.47 mmol), trans- N, lambda/-dimethylcyclohexane (0.21 mL, 1.35 mmol). The mixture was degassed under house vacuum and filled with N2 six times and heated to 90 C. The mixture was stirred for 12 hours, cooled to rt, and concentrated under reduced pressure. The EPO crude product was purified using flash chromatography using a 20:1 mixture of CH2CVMeOH to provide 1.8 g (92% yield) of the title compound as an off-white solid. LC-MS [M+H] = 290.2; 98% purity.

The synthetic route of 1849-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2008/54749; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, 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. Recommanded Product: 5-Methyl-1H-imidazole-4-carbaldehyde

To a solution of 4-methyl-lH-imidazole-5-carbaldehyde (5.0 g, 45.4 mmol) in anhydrous THF (5OmL) was added diaza(l,3)bicyclo[5.4.0]undecane (DBU, 6.8 mL, 45.4 mmol) and 2-iodopropane (4.5 mL, 45.4 mmol). The reaction mixture was stirred at room temperature overnight. Water (50 mL) was added. The mixture was extracted with EtOAc (1 x 50 mL) and 2-butanol (2 x 50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-2% MeOH/DCM), affording 4-methyl-l-(propan-2-yl)-lH-imidazole-5-carbaldehyde (691 mg, 10% yield).

The synthetic route of 68282-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 124312-73-8, These common heterocyclic compound, 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, 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 13 To a solution of ester (750 mg, 1.83 mmol), (1-methyl-1H-imidazol-2-yl)methanamine (0.50 mL, 4.50 mmol) and DBU (0.80 mL, 5.35 mmol) in DCM (50 mL) was added AlCl3 (750 mg, 5.62 mmol). The reaction mixture was stirred at rt for 3 h. The reaction was diluted with DCM (200 mL) and 3N NaOH (100 mL) and stirred for 10 min. The layers were separated and the organic layer was washed with H2O (2¡Á100 mL), brine (100 mL), and dried over Na2SO4. The solvent was removed under reduced pressure and the reaction crude was purified on silica column (0-5% MeOH/DCM) to yield the desired product as a white solid (275 mg, 32%). 1H NMR (CDCl3) delta: 11.0 (t, 1H), 9.45 (d, 1H), 8.61 (d, 1H), 7.76 (dd, 1H), 7.50 (m, 1H), 7.45 (m, 1H), 6.99 (d, 1H), 6.90 (d, 1H), 6.83 (d, 1H), 4.82 (d, 2H), 3.93 (t, 4H), 3.81 (t, 4H), 3.70 (s, 3H). LCMS (ES): m/z 475 [M+1]+.

The synthetic route of 124312-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NAGASAWA, Johnny Yasuo; PIERRE, Fabrice; HADDACH, Mustapha; SCHWAEBE, Michael; DARJANIA, Levan; WHITTEN, Jeffrey P.; US2009/93455; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3543-72-4, 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. 3543-72-4, name is Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 3 Synthesis of ethyl 4-(5-amino-1-methyl-1H-benzimidazol-2-ylbutanoate (6) 163 g (559.5 mmol) of compound (5) were dissolved in 1875 g ethanol. 14 g of palladium catalyst on activated carbon doped with iron (5% Pd, 1% Fe) and an additional 0.8 g of iron (II) sulfate 7-hydrate or 0.8 g of iron (III) nitrate 9-hydrate were added. Compound (5) was 10 then hydrogenated at a hydrogen pressure of up to 4 bar until complete conversion of the starting compound (5). The catalyst was removed by filtration, and the ethanolic solution concentrated until a dry product remained. This residue was crystallized from propan-2-ol or ethyl acetate. The yield of compound (6) was 128 g (489.8 mmol) with a content of >99% (87.5% of theory). The overall yield of compound ( 6) was 80.4% of theory in relation to 2-fluoro-5-nitroaniline. In comparison, the synthesis according to DD34727 starting from N-1-methyl-4-nitrobenzene-1,2-diamine (CAS 41939-61-1) is characterized by a yield of 39.0%.

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, Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG; Frey, Michael; Walther, Dirk-Detlef; US2014/31560; (2014); 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. 176721-01-0, name is (2,3-Dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., Safety of (2,3-Dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanol

The compound of formula IV (50 g, 0.11 mol) was added to 1,4-dioxane (750 mL).Add MnO2 (100g,1.15mol),Warming up to reflux,Reaction for 3h,The reaction is complete,Hot filtered,The filtrate is concentrated and dried.Obtained a crude white solid,Add methanol (350mL) at room temperature (25 C) for 1-2h,filter,Vacuum drying to give a white solid compound of formula V (45 g).Yield: 90.0%.

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; Shanghai Tianci International Pharmaceutical Co., Ltd.; Chi Wangzhou; Sha Fei; (11 pag.)CN109912508; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 167487-83-4, 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. 167487-83-4, name is Ethyl 1H-benzo[d]imidazole-7-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Into a 100-mL round-bottom flask was placed a suspension of sodium hydride (1.24 g, 31.00 mmol, 1.20 equiv) in DMF (10 mL). Ethyl 1H-1,3-benzodiazole-4-carboxylate (4.9 g, 25.76 mmol, 1.00 equiv) was added to the reaction solution at 0 C. The resulting solution was stirred for 1 h at 0 C. Next, iodomethane (3.66 g, 25.79 mmol, 1.00 equiv) was added to the reaction mixture at 0 C. The resulting solution was allowed to react, with stirring, for an additional 2 h while the reaction mixture temperature was maintained 0 C in an ice bath. Then, the reaction was quenched by the addition of 100 mL of water. The resulting solution was extracted with 3×200 mL of dichloromethane. The combined organic layers were washed with 3×200 mL of H2O. The resulting mixture was concentrated under vacuum and the resulting residue was purified by silica gel column with dichloromethane/methanol (97:3) as eluent to furnish 2.4 g (46%) of ethyl 1-methyl-1H-1,3-benzodiazole-4-carboxylate as a red solid.

The synthetic route of Ethyl 1H-benzo[d]imidazole-7-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); 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. 6154-30-9, name is 2,5-Dibromo-4-nitro-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2,5-Dibromo-4-nitro-1H-imidazole

Reference Example 1Synthesis of l-ethoxymethyl-2, 5-dibromo-4- nitroimidazoleA mixture of 2, 5-dibromo-4-nitroimidazole (20.0 g, 73.8 mmol) , ethylal (100 ml), and methanesulfonic acid (1.42 g, 14.8 mmol) was stirred under heating (bath temperature: 65 to 70C, internal temperature: 60C, 1.5 hours) . Further, the reaction mixture was evaporated under reduced pressure for two hours (fractional distillation column was used) . The residue was allowed to cool to room temperature, and EPO then ice water (200 g) was added, and the mixture was stirred for 10 minutes. The filtered crystals were washed with cold water and then air-dried (room temperature, 3 days) . Thus, l-ethoxymethyl-2, 5- dibromo-4-nitroimidazole was produced. Yield: 23.5g (96.8%) IR spectrum (KBr) :1532, 1491, 1464, 1397, 1365, 1344, 1315, 1273, 1248, 1127, 1106, 1054, 1020, 830, 740cm”1 1H-NMR spectrum (CDCl3) deltappm:1.25 (t, J=7.0Hz, 3H), 3.64 (q, J=7.0Hz, 2H), 5.50 (s, 2H) .

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; OTSUKA PHARMACEUTICAL CO., LTD.; WO2006/35960; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 31722-49-3, 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 31722-49-3 as follows.

A mixture of (2R ,5R)-5-chloromethyl-4-{2-[6-(4-fluoro-benzyl)-3, 3-dimethyl-2, 3-dihydro-pyrrolo[3,2-b]pyridin- 1 -yl]-2-oxo-ethyl}-2-methyl-piperazine- 1 -carboxylic acid tert-butyl ester(0.10 g, 0.18 mmol), 2-cyanoimidazole (0.025 g, 0.27 mmol), potassium carbonate (0.10 g, 0.72 mmol) and potassium iodide (0.09 g, 0.54 mmol) in acetonitrile (5 mL) was heated at 90 O for 18 h, cooled, then partitioned between water (30 mL) and DCM (3 x 20 mL). Thecombined organic extracts were dried and evaporated to give an oil. Chromatography (Si02,0 – 100% EtOAC in petrol gradient) gave the title compound (0.102 g) as an oil. MS: [M+H]= 602.

According to the analysis of related databases, 31722-49-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CHESSARI, Gianni; JOHNSON, Christopher Norbert; PAGE, Lee William; MILLEMAGGI, Alessia; HOWARD, Steven; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; WO2014/60768; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4532-96-1, The chemical industry reduces the impact on the environment during synthesis 4532-96-1, name is 1-Isopropyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

A) 1,1′-Diisopropyl-3,3′-methylenediimidazolium dibromide 8 0.009 mol of dibromomethane (1.564 g; 0.63 ml) and 5 ml of tetrahydrofuran are added to 0.018 mol of isopropylimidazole 1 (2.000 g) in an ACE pressure tube. The reaction mixture is stirred at 80 C. for 20 hours. The solid which precipitates is washed repeatedly with a little tetrahydrofuran. A white solid 8 is obtained. Empirical formula: C13H22N4Br2 M=394.154 g/mol Yield: 1.032 g (36.7% of theory) Melting point: decomposition at >172 C. 1H (ppm, d6-DMSO, 300.13 MHz): delta=9.68 (s, 2H, NCN); 8.11 (t, 2H, J=1.75 Hz, NCCHN); 8.04 (t, 2H, J=1.75 Hz, NCHCN); 6.66 (s, 2H, NC2N); 4.70 (sept, 2H, J=6.6 Hz (CH3)2CN); 1.50 (d, 12H, J=6.6 Hz, C3 group)

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-Isopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; TECHNISCHE UNIVERSITAET DRESDEN; US2009/326237; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 68282-53-1, A common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

COMPOUND 12.1. 31: 4-({6,7-DIMETHOXY-2-[(4-METHYL-1H-IMIDAZOL-5- YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1-YL}METHOXY)-N,N- DIETHYLBENZAMIDE; To a solution of INTERMEDIATE 5. 1. 1 (0.2 mg, 0.5 mmole) and 4-methyl-5- imidazolecarboxaldehyde (0.06 g, 0.6 mmole) in 1,2-dichloromethane (5 mL) was added sodium triacetoxyborohydriden (0.32 g, 1.5 mmole) and the resulting solution was stirred at room temperature for 18 h. Sodium hydroxide (1M, 20 mL) and chloroform (60 mL) was added and the mixture filtered through a Whatman IPS filter paper. The solvent was removed from the organic phase in vacuo and the residue purified by flash chromatography (2/98 Methanol/Chloroform) to give COMPOUND 12.1. 31 (0.06 g, 25%) as a yellow amorphous solid. 1H NMR (500 MHz, CDC13) : No. 1.17 (br s, 6 H), 2.14 (s, 3H), 2.56 (dd, J4,14. 5 Hz, 1H), 3.83 (m, 2H), 3.84 (s, 3H), 3.86 (s, 3H), 4.03 (app q, J 5 Hz, 2H), 4.27 (app t, J 10 Hz, 1H), 5.95 (br s, 1H), 6.62 (s, 1H), 6.67 (s, 1H), 6.87 (d, J 9 Hz, 2H), 7.31 (d, J9 Hz, 2H), 7.49 (s, 1H). 13C NMR (125 MHz, CDC13) : i5ll. 28,24. 22,44. 38,48. 34,55. 86,56. 01,59. 20,71. 59, 111. 14, 111. 56, 114. 30, 125.38, 125.64, 127.12, 128. 18, 129.78, 130.76, 132.99, 147.53, 148. 17,159. 27,171. 15. (+) LRESIMS mlz 493 [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:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem