Tag: M.W=100-200

Related Products of 104619-51-4, A common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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 I: 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide, and 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide (0386) Into a 10000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-bromo-2-(1H-1,2,3,4-tetrazol-5-yl)-6-(trifluoromethyl)benzene-1-sulfonamide (230 g, 618.08 mmol, 1.00 equiv), potassium carbonate (276 g, 2.00 mol, 3.23 equiv), NaI (18.4 g), Bu4NCl (34.0 g, 122 mmol, 0.20 equiv), chloroform (3800 mL, 1.00 equiv), 1-(chloromethyl)-4-methoxybenzene (380 g, 2.43 mol, 3.93 equiv), water (2550 mL). The resulting solution was stirred for 12 hr at 55 C. The aqueous phase was extracted with 2×1000 mL of DCM. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/ hexane (1:10). Purification afforded 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide, and 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide. (0387) LC-MS: (ES, m/z): 732 [M+H]+. (0388) H-NMR: (CDCl3, 300 Hz, ppm): delta 3.763 (9H, s), 3.820-3.872 (2H, d, J=15.6), 4.402-4.454 (2H, d, J=15.6), 5.154-5.203 (1H, d, J=14.7), 5.560-5.609 (1H, d, J=14.7), 6.702-6.763 (6H, m), 6.912-6.941 (4H, m), 7.109-7.138 (2H, m), 7.839-7.854 (2H, m). Reference Example 25 (3-[bis[(4-methoxyphenyl)methyl]sulfamoyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-4-(trifluoromethyl)phenyl)boronic acid and (3-[bis[(4-methoxyphenyl)methyl]sulfamoyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-4-(trifluoromethyl)phenyl)boronic acid Into a 1 L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide and 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide (REFERENCE EXAMPLE 24, 120 g, 163.81 mmol, 1.00 equiv), 1,4-dioxane (360 mL), 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (111 g, 491 mmol, 3.00 equiv), KOAc (80.3 g, 818 mmol, 5.00 equiv), 2-2-[chloro(triphenyl-5-phosphanylidene)palladio]phenylaniline (9.4 g, 16.42 mmol, 0.10 equiv). The resulting solution was stirred for 6 hr at 60 C. The resulting solution was diluted with 500 mL of CH3CN. The solids were filtered out. The filtrate was concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, CH3CN/H2O=1:2 increasing to CH3CN/H2O=2:1 within 25 min, and then CH3CN/H2O=2:1 within 25 min, and then CH3CN/H2O=1:0 within 10 min; Detector, UV 210 nm. This afforded (3-[bis[(4-methoxyphenyl)methyl]sulfamoyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-4-(trifluoromethyl)phenyl)boronic acid and (3-[bis[(4-methoxyphenyl)methyl]sulfamoyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-4-(trifluoromethyl)phenyl)boronic acid. (0391) LC-MS: (ES, m/z): 698 [M+H]+ (0392) H-NMR: (300 MHz, DMSO, ppm): delta 3.616-3.860 (11H, m), 3.860 (0.855H, s), 4.459-4.511 (1.492H, m), 5.172 (1.335H, s), 5.877 (0.403H, s), 6.733-6.827 (10H, m), 7.199-7.306 (2H, m), 8.456 (1.2H, m). Step A: 3-(2,3-diaminopyridin-4-yl)-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide and 3-(2,3-diaminopyridin-4-yl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide (1111) To a 10 mL RBF was added cesium carbonate (280 mg, 0.860 mmol), 2-bromopyridine-3,4-diamine (53.9 mg, 0.287 mmol), (3-(N,N-bis(4-methoxybenzyl)sulfamoyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acid (200 mg, 0.287 mmol) and Xphos Pd G2 (22.56 mg, 0.029 mmol). The vial was sealed, degassed, and filled with dioxane (2.4 ml) and water (0.6 ml). The resulting mixture was heated at 80 C. for 2 hr. The reaction mixture was filtered through a celite pad. The filtrate was diluted with EtOAc and washed with water. The organic layer was dried over anhydrous MgSO4, filtered, concentrated and purified by silica gel column chromatography (ISCO RediSep gold column, 24 g) using 0-10% MeOH/DCM as mobile phase (3% and 6% isostatic) to afford the title compound. LC/MS (M+H)+: 761.37. Step B: 3-(2-amino-1H-imidazo[4,5-b]pyridin-7-yl)-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide and 3-(2-amino-1H-imidazo[4,5-b]pyridin-7-yl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2…

The synthetic route of 104619-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Mandal, Mihir; Tang, Haifeng; Xiao, Li; Su, Jing; Li, Guoqing; Yang, Shu-Wei; Pan, Weidong; Tang, Haiqun; DeJesus, Reynalda; Hicks, Jacqueline; Lombardo, Matthew; Chu, Hong; Hagmann, William; Pasternak, Alex; Gu, Xin; Jiang, Jinlong; Dong, Shuzhi; Ding, Fa-Xiang; London, Clare; Biswas, Dipshikha; Young, Katherine; Hunter, David N.; Zhao, Zhiqiang; Yang, Dexi; (405 pag.)US2016/333021; (2016); A1;,
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Imidazole | C3H4N2 – PubChem

Application of 93-84-5, 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. 93-84-5, name is 5-Nitro-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a 1,3-dimethyl-5-nitro-1,3-dihydrobenzimidazol-2-one 90 parts of 5-nitro-1,3-dihydrobenzimidazol-2-one are suspended in 500 parts of aqueous sodium hydroxide solution (30%) and the suspension is heated to 53 C.; 161 parts of dimethyl sulphate are added dropwise over 12 hours during which the temperature rises to 70 C. The mixture is cooled to room temperature and filtered and the solid product is washed to neutrality. Drying under reduced pressure at 80 C. gives 99 parts of a beige powder of a compound of the following formula Yield: 96% Melting point: 206.3 C. 1H-NMR (DMSO): delta: 3.35 (s, CH3)-3.37 (s,CH3)-7.28 (d, 3J=9 Hz, H-C7)-7.98 (d, 4J=2 Hz, H-C4)-8.00 (dd, 3J=9 Hz, 4J=2Hz, H-C6)

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, 5-Nitro-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Clariant Finance (BVI) Limited; US6255482; (2001); B1;,
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. HPLC of Formula: C5H5F3N2

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

Synthetic Route of 124312-73-8, A common heterocyclic compound, 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, molecular formula is C5H9N3, 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.

General procedure: To a solution of K2PtCl4 (0.208 g, 0.500 mmol) in 16 mL of H2O/HCl 4 M (ratio 15/1), the diamine (0.500 mmol) was added. The mixture was stirred for 6 h and heated under reflux, then it was warmed to room temperature and stirred overnight. The complex was filtered off and washed with water, methanol and diethyl ether. The solid was dried under vacuum at room temperature.

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

Reference:
Article; Ferri, Nicola; Cazzaniga, Stefano; Mazzarella, Luca; Curigliano, Giuseppe; Lucchini, Giorgio; Zerla, Daniele; Gandolfi, Raffaella; Facchetti, Giorgio; Pellizzoni, Michela; Rimoldi, Isabella; Bioorganic and Medicinal Chemistry; vol. 21; 8; (2013); p. 2379 – 2386;,
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. name: 5,6-Difluorobenzimidazole

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

Synthetic Route of 1792-40-1, 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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 150 mL round-bottomed flask, the benzimidazole compound represented by Formula III (R1 is methyl, R2 is H, R3 is nitro) (0.361 g, 2.04 mmol) was added, and potassium carbonate was used as a base (0.324 g, 2.35 mmol) of acetonitrile as solvent. After stirring at 70C for 30 minutes, the mixture was cooled to room temperature and Compound II (0.400 g, 1.57 mmol) was added to continue the reaction and the temperature was raised to 70C. TLC followed the reaction to completion. After concentration, extraction, column chromatography, drying and other post-treatments, compound IV-3 (0.449 g) was obtained with a yield of 66.1%.

The synthetic route of 2-Methyl-5-nitro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei·lamohan·laao·yadafu; Ge Pala·lawaya; Wang Yanan; Fang Xuejie; (27 pag.)CN107721933; (2018); A;,
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Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 36947-69-0, name is 2-(tert-Butyl)-1H-imidazole, molecular formula is C7H12N2, 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. Safety of 2-(tert-Butyl)-1H-imidazole

Step c: 2-tert-butyl-N,N-dimethyl- 1H- imidazole- 1 -sulfonamide[0465] 2-tert-Butyl-lH- imidazole (0.5 g, 4.03 mmol) was added to a suspension of 60% sodium hydride (0.5 g, 12.1 mmol) in DMF (6.0 mL) at 0C and the mixture was stirred for 0.5 h. Then N,N-dimethylsulfamoyl chloride (0.7 g, 4.84 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 2 h. Saturated NH4CI solution was added and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (DCM/MeOH = 20: 1 to 5: 1) to afford 0.8 g of the title compound as a white solid (86%> yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36947-69-0, its application will become more common.

Reference:
Patent; ZENOBIA THERAPEUTICS, INC.; BOUNAUD, Pierre-Yves; NIENABER, Vicki; STEENSMA, Ruo, W.; LOWE, John, A., III; WO2012/178015; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1074-59-5, name is 3-(1H-Imidazol-4-yl)propanoic acid, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H8N2O2

3-(1-Triphenylmethyl-4-imidazolyl)propionic acid 3-(4-Imidazolyl)propionic acid (1.0 g, 7.1 mmol) was suspended in a mixture of dichloro-methane (5 ml) and acetonitrile (25 ml). Trimethylsilyl chloride (781 mg, 7.2 mmol) was added and the mixture refluxed for 4 hours. Triethylamine (1 ml) was added, and refluxing continued for 15 minutes. Cooled, triethylamine (1 ml) added followed by chlorotriphenylmethane (1.99 g, 7.1 mmol) in dichloromethane (10 ml), and the mixture stirred at ambient temperature for 2 hours. MeOH (20 ml) was added, the mixture stirred for 30 minutes, then evaporated to dryness. Water (50 ml) was added to the residue, and the pH adjusted to 8-8.5 with triethylamine. The precipitate was filtered off, washed with diethyl ether, and dried to give the desired product (2.25 g). MS (ESP): 383 (MH+) for C25H22N2O2 NMR (DMSO-d6) delta: 2.48 (t, 2H); 2.77 (t, 2H); 6.65 (s, 1H); 7.08 (d, 6H); 7.29 (s, 1H); 7.36 (m, 9H); 12.10 (br, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1074-59-5.

Reference:
Patent; Syngenta Limited; US2003/144263; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, Quality Control of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

General procedure: Benzimidazole 1 or 2 (1 mmol)was added to the mixture of TfOH (1 mL) or H2SO4 (2 mL) and arene (2-18 mmol). Reactionmixture was stirred at room temperature for the time as indicated in Table 3 or Scheme 2. Themixture was poured into ice water (30 mL). After extraction with CH2Cl2 (3 × 30 mL), thecombined extracts were consequently washed with water (50 mL), saturated aqueous solution ofNa2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporated in vacuo to givecrude products, which was subjected to chromatographic separation on silica gel using petroleumether/diethyl ether as an eluent.

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

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1632-83-3, name is 1-Methylbenzimidazole, 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: 1-Methylbenzimidazole

In an oven dried nitrogen purged 3 neck 100 mL round bottom flask, 1.00 g (7.57 mmol) of 1 -methylbenzimidazole in 20 mL of dry tetrahydrofuran is cooled to -78C. 10.69 mL (18.17 mmol) of 1.7 M t-butyllithium in hexanes is added and the reaction mixture is stirred at -780C. for 1 h. 2.55 g (11.36 mmol) of NIS in 20 mL of dry tetrahydrofuran is added. Reaction is removed from bath and stirred at room temperature for 1 hour, quenched with saturated aqueous solution of ammonium chloride, and diluted with dichloromethane. The layers are separated, the aqueous is extracted 3X100 mL dichloromethane, dried (MgSO4), and concentrated. The crude mixture is purified by EPO chromatography using hexanes:ethyl acetate as a solvent system. The product containing fractions are combined to obtain 0.400 g of the title compound, 21% yield. MS, ES+ = 259.0 (M+l); 1H NMR (DMSO-d6) 57.580-7.552 (m, 2H); 7.228-7.129 (m, 2H); 3.750 (s, 3H) ppm.

The synthetic route of 1632-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/107784; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem