Category: imidazoles-derivatives

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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Example 2[69] Synthesis of 4-methyl-N-[3-(4-methylimidazole-l-yl)-5-trifluoromethyl-phenyl] -3-(4-pyrazine-2-yl-pyrimidine-2-yl amino)benzamide[70][71] Method A[72] A pale yellow solid final compound (18.7g, yield 85%) was obtained by reacting3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) with 4-methyl -3-(4-pyrazine-2-yl-pyrimidine-2-yl amino)-benzoic acid ethyl ester in a similar manner as described in Method A of Example 1, except that 4-methyl-3-(4-pyrazine-2-yl-pyrimidine-2-yl amino) -benzoic acid ethyl ester (15.3g, 45.60mmol) was used, instead of 4-methyl-3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzoic acid ethyl ester.[73] 1H-NMR(DMSOd , delta= 2.21(s,3H), 2.38(s,3H), 7.35(s,lH), 7.39(s,lH), 7.54(s,lH),7.63(d,lH), 7.75(d,lH), 8.14(d,2H), 8.38(d,2H), 8.54(d,2H), 8.68(s,lH), 9.06(s,lH), 9.45(s, IH), 10.56(s,lH)

According to the analysis of related databases, 641571-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IL-YANG PHARM. CO., LTD.; KIM, Dong Yeon; CHO, Dae Jin; LEE, Gong Yeal; KIM, Hong Youb; WOO, Seok Hun; WO2010/18895; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-17-6,Some common heterocyclic compound, 53484-17-6, name is 1-Methyl-1H-benzo[d]imidazole-5-carboxylic acid, molecular formula is C9H8N2O2, 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.

(4aR,9aS)-2,3,4,4a,9,9a-hexahydro-1Hindeno[2,1-b]pyridine-6-carbonitrile (0.91 g, 4.59 mmol) and 1-methyl-1Hbenzimidazole-5-carboxylic acid (1.02 g, 95.0%, 5.51 mmol, 1.2 Eq) were addedinto a 100-ml round-bottom flask. Anhydrous acetonitrile (5 ml) was added, andstirring was started to obtain a slurry. Triethylamine (2.56 ml, 18.38 mmol, 4.0Eq) was added at room temperature. The reaction mixture was cooled toapproximately 3C and propane phosphonic acid anhydride [3.05 g, 50 wt.% intetrahydrofuran (THF), 4.80 mmol, 1.05 Eq] was added dropwise, keeping theinternal temperature below 11C. The resulting slurry was stirred at roomtemperature and monitored by HPLC and LC-MS for conversion. After 20 hoursat room temperature, the reaction reached approximately 98% conversion. Water(5 ml) was added dropwise, keeping the internal temperature below 35C.Subsequently, a 50% sodium hydroxide aqueous solution (1.84 g, 22.97 mmol,5.0 Eq) was added. The resulting mixture was stirred at room temperature for2 hours. The mixture was extracted with 2-methyl-THF (2 50 ml), and thelayers were separated. The combined organic layers were dried over anhydrousmagnesium sulfate (MgSO4), filtered and concentrated to give a crude oil, which was purified by flash chromatography (100 g silica gel 230-400 mesh) by elutionwith pure ethyl acetate first, and then a solution of 5%-20% methanol in ethylacetate. The fractions containing the desired product were pooled togetherand concentrated under vacuum to give (4aR,9aS)-1-(1-methyl-1H-benzo[d]-imidazole-5-carbonyl)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine-6-carbonitrile (N-methylbenzimidazole regioisomer 1, M1) as an off-white solid(1.50 g, 91.6% yield). The identity of M1 was confirmed by NMR analysis (1H,13C, correlation spectroscopy, rotating-frame nuclear Overhauser effect correlationspectroscopy, heteronuclear multiple quantum coherence, and heteronuclearmultiple bond coherence) in DMSO-d6 at 80C (Supplemental Figs. 1-6). 1HNMR (CD3SOCD3, 600 MHz, 353 K) d 8.18 (s, 1H), 7.67 (d, J = 1.2 Hz, 1H),7.63 (s, 1H), 7.58 (d, J = 8.4 Hz, 1H), 7.55 (dd, J = 7.8 and 1.8 Hz, 1H), 7.41 (d, J= 7.8 Hz, 1H), 7.32 (dd, J = 7.8 and 1.8 Hz, 1H), 4.80 (br, 1H), 4.05 (br, 1H), 3.84(s, 3H), 3.24 (dd, J = 16.2 and 10.8 Hz, 1H), 3.14 (dt, J = 11.4 and 6.6 Hz, 1H),2.95-3.05 (m, 2H), 1.98-2.04 (m, 1H), 1.59-1.65 (m, 1H), 1.47-1.56 (m, 1H),1.28-1.36 (m, 1H). 13C NMR (CD3SOCD3, 150 MHz) d 170.45, 147.16, 145.40,145.29, 142.53, 134.81, 130.34, 129.72, 126.61, 125.67, 120.63, 118.50, 117.31,109.65, 109.05, 54.80, 41.00, 39.50 (br), 32.16, 30.20, 27.24, 22.44. LC-MScalculated for C22H20N4O [M+ H]+: 357.17, Found: 357.20.

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-1H-benzo[d]imidazole-5-carboxylic acid, its application will become more common.

Reference:
Article; Maw, Hlaing H; Zeng, Xingzhong; Campbell, Scot; Taub, Mitchell E; Teitelbaum, Aaron M; Drug Metabolism and Disposition; vol. 46; 6; (2018); p. 770 – 778;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 23328-88-3, These common heterocyclic compound, 23328-88-3, name is 2-Bromo-4-methyl-1H-imidazole, 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 1: 2-(2-bromo-4-methyl-1H-imidazol-1-yl)-6-methoxy-3-nitropyridine To a mixture of 2-chloro-3-nitro-6-methoxypyridine (9.43 g, 50 mmol) and 2-bromo-4-methylimidazole (9.66 g, 60 mmol) in 300 mL of DMF was added freshly powdered KOH (3.36 g, 60 mmol) at 0 C. The resulting mixture was stirred at RT for 4 h. Solvent was removed by rotavap and the residue was washed with water and extracted with ethyl acetate (3*). Standard work-up followed by column chromatography using 30-50% ethyl acetate in hexane as eluent provided the product (13.82 g, 88% yield). MS (ESI) 313.0 [M+H]+

Statistics shows that 2-Bromo-4-methyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 23328-88-3.

Reference:
Patent; WYETH; US2010/120762; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33016-47-6, 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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 500 ml, three-necked flask fitted with a magnetic stirrer and a reflux condenser under inert atmosphere, ethyl 4-amino-3-phenylbutanoate hydrochloride x42 (synthesized as described in patent application EP1265862, 6.2 g, 38 mmol), 1-trityl-1 H- imidazole-4-carbaldehyde x43 (Dolensky B., Kirk K.L., Collect. Czech. Chem. Commun. (2002), 67, 1335-1344; 8.2 g, 36.1 mmol) and MeOH (150 ml) are stirred at room temperature. Triethylamine (3.9 ml, 41.85 mmol) and NaBH4 (1.06 g, 41.8 mmol) are added by portions. The mixture is stirred at 45 0C for 3 h, then at room temperature overnight. CH2CI2 (300 ml) and water (300 ml) are added, the aqueous phase is extracted with CH2CI2 (2 x 200 ml). The combined organic phases are washed with a saturated solution of NH4CI (2 x 150 ml), dried, filtered and concentrated in vacuo. The crude product is recrystallized from AcOEt to afford 4-phenyl-1 -[(1 -trityl-1 H-imidazol-4- yl)methyl]pyrrolidin-2-one x44.Yield: 36 %.LC-MS (MH+): 484.

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-Trityl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB S.A.; WO2006/128692; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

A suspension of sodium hydride (2mmol, 2eq) in THF (5mL) was treated with a solution of 2-(1H-imidazol-1-yl)ethanol (1mmol, 1eq) in THF (3mL) at 0C. The resulting mixture was stirred under a nitrogen atmosphere at room temperature for 1h. The mixture was cooled to 0C before addition of 2,4-dichlorobenzyl bromide (1, 1.5mmol, 1.5eq). The resulting mixture was stirred under reflux for 3h. The reaction was quenched by addition of a saturated aqueous solution of NH4Cl (5mL). The aqueous phase was extracted with ethyl acetate (15mL, three times), the organic phase was washed with water (10mL), dried over Na2SO4 and the solvent was removed in vacuo. Purification by column chromatography (SiO2, MeOH/ethyl acetate) afforded 2 as an oil in 65% yield. IR (film): numax: 3109, 2868, 1898, 1589, 1505, 1469, 1075, 813, 737cm-1. 1H NMR (400MHz, CDCl3): delta 7.55 (bs, 1H), 7.37 (s, 1H), 7.24-7.23 (m, 2H), 7.07 (bs, 1H), 6.98 (s, 1H), 4.56 (s, 2H), 4.17 (t, 2H, J=5.1Hz), 3.79 (t, 2H, J=5.1Hz) ppm. 13C NMR (100MHz, CDCl3): delta 137.5, 133.9, 133.88, 133.3, 129.6, 129.4, 129.1, 127.0, 119.4, 70.0, 69.6, 47.0ppm. ESI-TOF-HRMS: m/z calcd for (M+H) C12H12N2Cl2O 271.0405 found 271.0416.

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

Reference:
Article; Roehrig, Ute F.; Majjigapu, Somi Reddy; Chambon, Marc; Bron, Sylvian; Pilotte, Luc; Colau, Didier; Van Den Eynde, Benoit J.; Turcatti, Gerardo; Vogel, Pierre; Zoete, Vincent; Michielin, Olivier; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 284 – 301;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1,Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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 1; [240] Preparation of N-r3-f4-methylimidazol- l-ylV5-trifluoromethyl-phenyll-4-(4-pyridin-3-yl-Pyrimidin-2-ylaminos)-benzamide; EPO [241] 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid prepared in Preparation 19(242mg, 0.83mmol) and 3-(4-methyl-imidazol- l-yl)-5-trifluoromethyl-phenylamine prepared in Preparation 30 (200mg, 0.83mmol), N,N-dimethyl formamide (10ml), and diethylcyano phosphate ( 0.245ml, 1.658mmol) were added to a reaction vessel, and cooled to 100C. Triethylamine (0.231ml, 1.658mmol) was added thereto. After 30 min, the mixture was mixed at 600C for 15 hr. The mixture was cooled to RT, and an organic layer was obtained with the solution of ethyl acetate and sodium bi carbonate, concentrated under vacuum, and subjected to column chromatography (5: 1/CHC1 :MeOH) to give the titled compound as pale yellow solid.[242] 1H-NMR (DMSO-d , delta)= 2.20 (s,3H), 7.39 (s,lH), 7.56 (d,2H), 8.03 (m,5H), 8.17(s,lH), 8.21 (d,lH), 8.32 (s,lH), 8.49 (d,2H), 8.63 (d,lH), 8.72 (d,lH), 9.36 (s,lH), 10.15 (s, IH); 10.48 (s,lH)

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IL-YANG PHARM. CO., LTD.; WO2007/18325; (2007); 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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, A new synthetic method of this compound is introduced below., Computed Properties of C8H6N2O2

Example 180N-((ls,4s)-4-(5-Fluoro-2-(4′-((4-(2-hydroxyethyl)-l,4-diazepan-l-yl)methyl)-2′-(((S)-3- methylmorpholinoJmethylJbiphenyl-S-yloxyJnicotinamidoJcyclohexylJ-lH- benzo [d] imidazole-4-carboxamide To a solution of N-((ls,4s)-4-aminocyclohexyl)-5-fluoro-2-(4′-((4-(2-hydroxyethyl)-l,4- diazepan- 1 -yl)methyl)-2′-(((S)-3 -methylmorpholino)methyl)biphenyl-3 -yloxy Nicotinamide (200 mg, 0.24 mmol) in dry DMF (5 mL) under nitrogen was added DIPEA (0.161 mL, 0.97 mmol) at RT. The solution was stirred until homogeneous. To this solution was added dropwise a solution of lH-benzo[d]imidazole-4-carboxylic acid (39.5 mg, 0.24 mmol) and l,l’-carbonyldiimidazole (39.5 mg, 0.24 mmol) in dry DMF (5 mL) under nitrogen which had been allowed to stir at 40 0C for 1 hour. The reaction mixture was allowed to stir at 50 0C overnight. The mixture was evaporated to dryness and the residue dissolved in DCM (100 ml) and washed with saturated NaHCC^aq), brine, dried (MgSC^) and evaporated to give a yellow oil. The crude product was purified by preparative HPLC using a 95-5% gradient of aqueous 0.2% ammonia in methanol as eluent to give the the title compound as a white solid. Yield: 22 mg1H NMR (W MHz, CDCl3) delta 8.12 – 8.06 (m, 2H), 7.94 – 7.82 (m, 2H), 7.70 (d, J= 7.9 Hz, IH), 7.43 (d, J= 7.9 Hz, IH), 7.38 – 7.31 (m, 2H), 7.24 – 7.10 (m, 5H), 7.07 (d, J= 7.9 Hz, IH), 4.25 – 4.18 (m, IH), 4.16 – 4.09 (m, IH), 3.82 (d, J= 13.9 Hz, IH), 3.64 – 3.58 (m, 5H), 3.49 – 3.43 (m, IH), 3.40 – 3.31 (m, IH) 3.03 – 2.93 (m, 2H), 2.81 – 2.73 (m, 5H) 2.72 – 2.62 (m, 7H), 2.39 – 2.31 (m, IH), 2.12 – 2.03 (m, IH), 1.98 – 1.74 (m, 10H), 0.66 (d, J= 6.2 Hz, 3H). MS: [M+H]+=819 (calc=819) (MultiMode+)

The synthetic route of 46006-36-4 has been constantly updated, and we look forward to future research findings.

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

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. 623577-60-6, name is 4-Bromo-1-isopropyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H9BrN2

To the solution of compound 113-la (50 mg, 0.26 mmol, 1 eq) in dioxane (2 mL) was added compound 113-1 (125 mg, 0.32 mmol, 1.2 eq), Pd(PPh3)4 (31 mg, 26.5 umol, 0.1 eq), Cs2C03 (172 mg, 0.53mol, 2 eq) and H20 (0.4 mL). The mixture was stirred at 100 C for 16 hr. The reaction was monitored by LCMS. LCMS showed that the starting material was consumed and the desired MS was observed. The reaction solution was filtered. The residue was purified by HPLC to give Compound 113 (9.07 mg, 23.61 umol, 8.9% yield). LCMS (ESI): RT = 0.649 min, mass calcd. for C19H23N9O 376.19, m/z found 377.0 [M+H]+, Ti NMR (400MHz, CDCI3) delta 8.71 (br , 1H), 7.89 (d, J= 2.5 Hz, 1H), 7.57 – 7.51 (m, 2H), 7.36 (d, J = 1.0 Hz, 1H), 6.68 (d, J = 8.8 Hz, 1H), 4.52 (q, J = 5.4 Hz, 1H), 4.41 – 4.30 (m, 1H), 3.44 (br , 1H), 2.61 (d, J=5.5 Hz, 3H), 2.10 – 2.02 (m, 2H), 1.84 – 1.75 (m, 2H), 1.69 – 1.60 (m, 1H), 1.51 (d, J = 6.8 Hz, 6H), 1.46 – 1.27 (m, 5H).

The synthetic route of 623577-60-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1739-84-0, name is 1,2-Dimethyl-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 1739-84-0, SDS of cas: 1739-84-0

General procedure: Quaternization of 1,2-dimethylimidazole withalkyl halides was performed in acetonitrile (50% solution)at the boiling point of the solvent and an equimolarratio of the starting reagents for 48 h. The solvent was then removed, and lithium bis(trifluoromethylsulfonyl)imide (10% excess) in water (30% solution) was added to the solid residue, and the reaction mixture was stirred for 30 min. The desired product precipitated from water into the lower liquid phase. The upper aqueous layer was decanted, methylene chloride (equal volume) was added to the lower layer, and the resulting solution was washed again with distilled water till negative reaction to Cl- with AgNO3. The ionic liquids were dried by azeotropic distillation of absolute methylene chloride, then the traces of the organic solvent were removed in vacuum by heating (3 h at 100C).

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

Reference:
Article; Krasovskiy; Chernikova; Glukhov; Kapustin; Koroteev; Russian Journal of Physical Chemistry; vol. 92; 12; (2018); p. 2379 – 2385; Zh. Fiz. Khim.; vol. 92; 12; (2018); p. 1851 – 1858,8;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 35203-44-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 35203-44-2 name is 1-Propyl-1H-imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: All of the imidazolium salts were synthesized with good yields (>85percent, see Supporting Information online) by thequaternization of N-substituted imidazole with corresponding iodide alkane, according to Scheme 1. Take 1-hexadecyl-3-methylimidazolium iodide (1a) for example: the mixture of 1-methylimidazole and 1-iodohexadecane was dissolved in acetone. Then the solution was placed into a 58 mL Teflon-lined, stainless-steel autoclave and heated at 100 ¡ãC for 12 h. The final product was obtained by multiple crystallizations from diethyl ether. The purity of all the imidazolium salts was confirmed by 1H NMR and elemental analysis (see Supporting Information online).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Propyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Article; Wang, Meng; Pan, Xu; Chen, Jian; Dai, Songyuan; Science China Chemistry; vol. 58; 12; (2015); p. 1884 – 1890;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem