Tag: M.W=100-200

Related Products of 2735-62-8,Some common heterocyclic compound, 2735-62-8, name is 2-(1-Methyl-1H-benzo[d]imidazol-2-yl)acetonitrile, molecular formula is C10H9N3, 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.

2-(1-Methyl-1H-benzo[d]imidazol-2-yl)acetonitrile (171 mg, 1.0 mmol), t-BuOK (112 mg, 1.0 mmol), and dry THF (5 mL) were stirred for 30 min at room temperature. To the resulting mixture 3-(phenylethynyl)quinoxaline-2-carbonitrile 1a (128 mg, 0.5 mmol) was added by portions. The reaction mixture was stirred for 48 h at room temperature and then evaporated to dryness without heating. The residue was treated with some drops of acetic acid. After evaporation it was mixed with silica gel and purified by flash column chromatography on silica gel (2.5¡Á40 cm) with CHCl3 as the eluent. The first fraction recovered was 1a (32 mg, 25%). The orange fraction was collected and purified additionally by flash column chromatography on Al2O3 (2.5¡Á20 cm) with CHCl3 as the eluent. The orange red fraction with Rf 0.65 gave 5e (48 mg, 24%).

The synthetic route of 2735-62-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nguyen, Huong T.L.; Gulevskaya, Anna V.; Pozharskii, Alexander F.; Nelina-Nemtseva, Julia I.; Tetrahedron; vol. 70; 31; (2014); p. 4617 – 4625;,
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

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

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

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

Adding a certain compound to certain chemical reactions, such as: 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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 6775-40-2, COA of Formula: C9H9N3

General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH.

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:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 5805-57-2, The chemical industry reduces the impact on the environment during synthesis 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, I believe this compound will play a more active role in future production and life.

A mixture of 241 (97 mg, 0.25 mmol), (1H-benzimidazol-2-yl)methanamine3 (108 mg, 0.737 mmol), NaBH(OAc)3 (58 mg, 0.27 mmol), and MS4A (80 mg) in CH2Cl2 (8.2 mL) was stirred at room temperature for 10 h. After addition of MeOH, the reaction mixture was partitioned between AcOEt and sat. aq. NaHCO3. The organic layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by NH silica gel column chromatography (hexane/CH2Cl2, 1:1-0:1) to give the corresponding amine as pale red oil. To a solution of the amine in EtOH (1.0 mL) was added aq. HCl (2 M, 2.0 mL) and the mixture was heated under reflux for 4 h. The solvent was evaporated, and the residue was partitioned between CH2Cl2 and aq. HCl (1 M). The aqueous layer was basified with aq. NaOH and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (CHCl3/MeOH, 99:1) to give 13 as a free amine. The amine was dissolved in methanolic HCl (2 M) and the solvent was evaporated. The residue was triturated with Et2O to give 13?3HCl (45 mg, 0.12 mmol, 47% for 2 steps) as a pale-brown amorphous solid. 1H NMR (500 MHz, CD3OD) delta 8.76 (1 H, s, imidazole-2), 7.89 (2 H, dd, J = 6.3, 2.9 Hz, aromatic), 7.65 (2 H, dd, J = 6.3, 2.9 Hz, aromatic), 7.32 (1 H, s, imidazole-5), 4.89 (2 H, s, -NCH2Ar), 3.49 (2 H, brs, -CH2CH2N-), 2.04-1.85 (3 H, m, H-1, -CH2CH2N-), 1.34 (1 H, brs, H-2), 1.13 (1 H, brs, H-3a), 1.08 (1 H, brs, H-3b); 13C NMR (125 MHz, CD3OD) delta 144.36, 136.72, 134.40, 133.25, 128.17, 115.99, 115.68, 49.85, 42.96, 30.98, 19.43, 14.37, 13.33; HRMS (EI) calcd for C16H20N5 282.1713, found 282.1715 [(M + H)+]; Anal. Calcd for C16H19N5?3HCl?1H2O: C, 47.02; H, 5.92; N, 17.13. Found: C, 47.15; H, 5.91; N, 17.05.

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]imidazol-2-yl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Watanabe, Mizuki; Kobayashi, Takaaki; Ito, Yoshihiko; Fukuda, Hayato; Yamada, Shizuo; Arisawa, Mitsuhiro; Shuto, Satoshi; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3630 – 3633;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

623577-60-6, name is 4-Bromo-1-isopropyl-1H-imidazole, 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. category: imidazoles-derivatives

A mixture of methyl 5-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2- carboxylate (300 mg, 1.08 mmol), 4-bromo-l -(propan-2 -yl)-lH-imidazole (307.0 mg, 1.62 mmol), Pd(PPh3)4 (250.2 mg, 0.22 mmol), K2CO3 (448.8 mg, 3.25 mmol) in dioxane (5 ml) was stirred at 100 C under nitrogen atmosphere overnight. The resulting mixture was 39 concentrated under vacuum and purified by reverse phase flash chromatography with 0-37% MeCN/fhO to afford compound 23-a (180 mg, 64.12%) as yellow oil.

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

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WANG, Guoqiang; SHEN, Ruichao; GRANGER, Brett; HE, Jing; XING, Xuechao; HE, Yong; LONG, Jiang; MA, Jun; WANG, Bin; OR, Yat, Sun; (99 pag.)WO2019/213244; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem