Month: May 2021

Synthetic Route of 46006-36-4,Some common heterocyclic compound, 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, molecular formula is C8H6N2O2, 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 94N-CCls^sJ^-Cl-CS’-CCCSS^RJ-S^-dimethylpiperazin-l-yOmethyO^’-hydroxybiphenyl-S- yloxy)-5-fluoronicotinamido)cyclohexyl)-lH-benzo[d]imidazole-4-carboxamide To a solution of N-((ls,4s)-4-aminocyclohexyl)-2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l- yl)methyl)-4′-hydroxybiphenyl-3-yloxy)-5-fluoronicotinamide (100 mg, 0.17 mmol) in dry DMF (5 mL) under nitrogen was added DIPEA (0.057 mL, 0.34 mmol) at RT. The solution was stirred until homogeneous. To this solution was added dropwise a solution of IH- benzo[d]imidazole-4-carboxylic acid (27.8 mg, 0.17 mmol) and l,l’-carbonyldiimidazole (27.8 mg, 0.17 mmol) in dry DMF (5 mL) under nitrogen which had been allowed to stir at 40 0C for 1 h. The reaction mixture was allowed to stir at 50 0C overnight. The mixture was evaporated to dryness and the residue dissolved in chloroform (15 mL) and washed with saturated NaHCO3 (aq), water, dried (MgSO4) and evaporated to give a yellow oil. This was purified by preparative HPLC to afford the title compound. Yield: 36.5 mg 1H NMR (400 MHz, CD3OD) delta 8.69 (s, IH), 8.49 (d, J= 6.9 Hz, IH), 8.12 – 8.07 (m, 2H), 7.91 (d, J= 7.7 Hz, IH), 7.84 (d, J= 8.2 Hz, IH), 7.52 – 7.41 (m, 6H), 7.38 (s, IH), 7.16 – 7.10 (m, IH), 6.87 (d, J= 8.5 Hz, IH), 4.21 – 4.09 (m, 2H), 4.07 (s, 2H), 3.62 – 3.49 (m, 2H), 3.41 (d, J= 12.8 Hz, 2H), 2.65 (t, J= 12.4 Hz, 2H), 1.99 – 1.74 (m, 8H), 1.30 (d, J= 6.7 Hz, 6H). MS: [M+H]+=692.3 (calc=692.336) (MultiMode+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Benzimidazole-7-carboxylic acid, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17289-26-8, 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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(f) Synthetic Example; N-(1-((1-methyl-1H-imidazol-4-yl)methyl)piperidin-4-yl)-2-(4-(trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamide. (Compound 53); To a solution of the dihydrochloride salt prepared in step 1 of Synthetic Example 1 (e) (65 mg, 0.12 mmol) was dissolved in DCM (2.0 mL), 1-methyl-1H-imidazole-4-carbaldehyde (2×16 mg, 2×0.15 mmol) and sodium triacetoxyborohydride (2×55 mg, 3×260 mumol) were added. The resulting reaction mixture was allowed to stir at room temperature overnight, and upon reaction completion, was poured into saturated sodium bicarbonate solution (30 mL). The layers were separated, extracted aqueous layer with EtOAc (3×20 mL), washed combined organic layer with brine (2×10 mL), dried (MgSO4), filtered and concentrated. Trituration of the residue with ethyl ether provided N-(1-((1-methyl-1H-imidazol-4-yl)methyl)piperidin-4-yl)-2-(4-(trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamide as a white solid (Compound 53, 31 mg, 46%). 1H NMR (DMSO-d6, 300 MHZ) 11.02 (s, 1H), 7.98 (d, J=7.4 Hz, 1H), 7.82 (s, 1H), 7.71 (d, J=8.0 Hz, 2H), 7.62 (d, J=7.7 Hz, 2H), 7.54 (d, J=8.5 Hz, 1H), 7.44 (s, 1H), 7.25 (d, J=8.5 Hz, 1H), 6.92 (s, 1H), 3.86 (s, 2H), 3.78-3.66 (m, 1H), 3.63 (s, 2H), 3.60 (s, 3H), 3.30 (s, 2H), 2.92-2.78 (m, 6H), 1.98 (t, J=11.3 Hz, 2H), 1.73 (d, J=11.0 Hz, 2H), 1.52 (q, J=10.8 Hz, 2H) ppm; MS (ES) 551 (M+H).

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; US2009/163511; (2009); 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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., Safety of 1H-Imidazole

The starting material was prepared as follows : 1-Methoxymethyl-imidazole To a solution of imidazole (1. 00 g, 14. 7 MMOL) in anhydrous THF (30 ML) AT-78 C was added in portions sodium hydride (0. 88 g of a 60% dispersion in oil, 22. 0 MMOL). The mixture was avowed to warm to room temperature, stirred for 30 minutes, then cooled to- 78 C, and chloromethyl methyl ether (1. 06 ML, 14. 0 MMOL) SLOWLY added. After 2 hours at- 78 C, sat. NAHC03 was added to quench the reaction. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with sat. NAHC03, dried over MgS04, filtered, and concentrated to give 1. 3 G OF an oil, which contained the NaH dispersion oil, displayed AN 1H NMR that matched previous (Zhao, et AL., J. Med. CHEM., VOL. 40, pp. 216-225 (1997)), and was used without further purification

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; PFIZER INC.; WO2004/74283; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 60-56-0, The chemical industry reduces the impact on the environment during synthesis 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, I believe this compound will play a more active role in future production and life.

Bleach (12% w/w aq, 110 ml) was cautiously added dropwise to a solution of 2-mercapto-1-methylimidazole (2.0 g) in conc. [H2SO4] (50 ml) cooled to [0C.] After stirring 30 minutes at [0C] the mixture was diluted with [H20] (30 ml) and dichloromethane (30 ml). The aqueous layer was re-extracted with dichloromethane and the combined organic layers dried [(MGS04)] and evaporated to give the product as an oil (730 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-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/31139; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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: C12H12N2O2

General Procedure 2 (PG 2):3-Methoxy-4-(4-methyl-imidazol-l-yl)-benzaldehyde, phosphonium salt, and lithium hydroxide hydrate were placed in a flask under nitrogen. Solvents were added and the reaction mixture stirred for 16h at room temperature. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The combined organic layers were washed with brine and dried over magnesium sulfate. After solvent evaporation the crude material was purified by chromatography on silica gel.; Example 4 2-{(E)-2-[3-Methoxy-4-(4-methyl-imidazol-l-yl)-phenyl]-vinyl}-lH-benzimidazole Aldehyde (150 mg, 0.69 mmol), phosphonium salt (357 mg, 0.83 mmol), LiOH H2O (87 mg, 2.08 mmol), THF (4.5 mL), and ethanol (1.5 mL) according the GP 2 gave the title compound (178 mg) as a colorless solid after recrystallization from ethyl acetate.1H (600 MHz, dmso-d6): 2.14 (s, 3H), 3.90 (s, 3H), 7.15T7.17 (m, 3H), 7.29-7.34 (m, 3H), 7.39-7.41 (m, 3H), 7.66 (d, J= 16.4 Hz, IH), 7.80 (s, IH).LCMS (ESI): calcd for C20H19N4O [M+H]+ 331.1, found 331.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 870837-18-6, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2008/97538; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, 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 95470-42-1, Safety of Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate

Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate (2.75 g, 11.8 mmol) was dissolved in DMF (20 mL), potassiumcarbonate (3.26 g, 23.6 mmol) and 2,5-dichloronbenzyl bromide (3.4 g, 14.2 mmol) were added thereto, and thereaction mixture was stirred at 90°C for 3 hours. Water (50 mL) was added after the reaction was complete, andthe reaction mixture was extracted twice with ethyl acetate (50 mL). After washing with a saturated aqueous sodiumchloride solution, the organic phase was dried over sodium sulfate. After concentration under reduced pressure,the residue was purified by silica gel column chromatography to obtain ethyl 2-bromo-1-(2,5-dichlorobenzyl)-4-methyl-1H-imidazole-5-carboxylate (1.72 g) : 1H-NMR (CDCl3) delta: 7.34 (1H, d, J=8.8 Hz), 7.20 (1H, dd, J=8.8, 2.4Hz), 6.40 (1H, d, J=2.4 Hz), 5.60 (2H, s), 4.25 (2H, q, J=7.2 Hz), 2.56 (3H, s), 1.27 (3H, t, J=7.1 Hz); ESI-MS m/z=391(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Teijin Pharma Limited; MARUYAMA, Akinobu; TAKEUCHI, Susumu; TAKAHASHI, Yoshimasa; (30 pag.)EP3144306; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4278-08-4, 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. 4278-08-4, name is 2-(4-Fluorophenyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate CC (1 10 mg, 0.363 mmol), 2-(4-fluorophenyl)-lH-imidazole (70 mg, 0.435 mmol), Pd2(dba)3 CHCl3 (166 mg, 0.182 mmol), BINAP (226 mg, 0.3638 mmol), and CS2CO3 (354 mg, 1.08 mmol) were dissolved in 1 mL of toluene in a microwave vial and a stream of nitrogen was bubbled through the mixture for 2 minutes. The resulting solution was heated at 140 C for 1 h in a microwave. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic extracts were dried with Na2S04, filtered and evaporated, and the residue was purified by preparative HPLC to give the title compound (48 mg). LCMS: 429.1 m/z (M+H)+; ret. Time 3.23 min (Analytical Method A).

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, 2-(4-Fluorophenyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; GALEMMO, Robert, A., Jr.; ARTIS, Dean, Richard; YE, Xiaocong, Michael; AUBELE, Danielle, L.; TRUONG, Anh, P.; BOWERS, Simeon; HOM, Roy, K.; ZHU, Yong-Liang; NEITZ, R., Jeffrey; SEALY, Jennifer; ADLER, Marc; BEROZA, Paul; ANDERSON, John, P.; WO2011/79114; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6154-30-9, name is 2,5-Dibromo-4-nitro-1H-imidazole, 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 6154-30-9, SDS of cas: 6154-30-9

Reference example 2 Preparation of 2,5-dibromo-1-methoxymethyl-4-nitroimidazole Under an ice-cooling condition, sodium hydride (3.56 g) was added to a N,N-dimethylformamide (100 ml) solution of 2,5-dibromo-4-nitroimidazole (20.08 g). 10 minutes later, being added dropwise chloromethylmethyl ether (6.75 ml) thereto at 10 to 15C, then the reaction mixture was turned back to a room temperature. After being stirred this reaction mixture for 5 hours, under an ice-cooling condition, sodium hydride (0.30 g) and chloromethylmethyl ether (0.56 ml) were added, further stirred at a room temperature for 1 hour. Then the reaction mixture was ice-cooled, water was added and extracted with ethyl acetate. The organic layer was washed with an aqueous solution being saturated with sodium chloride, dried over anhydrous sodium sulfate, then concentrated under a reduced pressure. Thus obtained crude crystals were washed with diisopropyl ether, and dried at 50C for 24 hours, there was obtained 2,5-dibromo-1-methoxymethyl-4-nitroimidazole (19.68 g, yield: 84.3%) as yellow powder product.

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, 2,5-Dibromo-4-nitro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Otsuka Pharmaceutical Company, Limited; EP1553088; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 256519-10-5, name is 4-Fluoro-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5FN2O, 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

b) A solution of 4-fluoro-1H-benzo[d]imidazol-2(3H)-one (0.7 g, 4.60 mmol) in phosphorus oxychloride (14.11 ml, 151.39 mmol) was heated at 100 C. for 18 hours. The reaction mixture was cooled to RT and excess phosphorus oxychloride was evaporated in vacuo. The residue was neutralized slowly (Care: exotherm) with saturated sodium bicarbonate solution (10 ml), and the mixture was then extracted with EtOAc (3×20 ml). The combined organic layers were washed with saturated brine and then dried over Na2SO4, filtered and evaporated to afford 2-chloro-7-fluoro-1H-benzo[d]imidazole (0.740 g, 94%) which was used in the next step without further purification; 1H NMR (400 MHz, DMSO-d6) 7.01-7.11 (1H, m), 7.23 (1H, td), 7.32 (1H, s), 13.59 (1H, s); m/z: (ES+) MH+, 171.20.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 256519-10-5, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2011/306613; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 5395-50-6,Some common heterocyclic compound, 5395-50-6, name is 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C8H14N4O6, 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 ,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo [4,5-d]imidazole-2,5(1H,3H)-dione (1.88 g, 7.2 mmol) in 1.5 ml of DMSO was dissolved. Then, 0.15 ml nitric acid (65%) and n-l3uOH (13.12 ml, 143 mmol) were added to the solution and the mixture was heated at 60 C. for 16 hours. After the reaction was over, the reaction liquid was cooled and iN NaOH was added around pH 7. Around 100 ml ethyl acetate was used to extract with mixture and the organic phase was washed by saturated NaC1(aq) solution for 2 times. After being dried by Na2504, the solvent was removed. The crude compound was purified by flash chromatography (Heptane/EtOAc). The product was obtained colorless viscous oil in 0.38 g, yield (11%) ?H NMR (600 MHz, DMSO-d6): oe (ppm) 5.52 (s, 2H), 4.73 (m, 8H), 3.35 (m, 8H), 1.46 (m, 8H), 1.29 (m, 8H), 0.85 (t, 12H)

The synthetic route of 5395-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Electronic Materials LLC; Rohm and Haas Electronic Materials Korea Ltd.; Grandbois, Matthew; Kim, Myung Yeol; Ryu, Eui Hyun; Sim, Jae Hwan; Jang, Min Kyung; Lee, Jung-June; (17 pag.)US2017/59991; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem