Category: imidazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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 1615-14-1, HPLC of Formula: C5H8N2O

Example 10: 2-Imidazol-l-ylethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)- quinoIine-3-carboxyIate. To a suspension of 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)-quinoline-3- carboxylic acid (1.0 g, 2.8 mmol) in dry tetrahydrofuran (15 mL) at 0 0C under nitrogen atmosphere was added l-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (2.0 g, 11.2 mmol), hydroxybenzotriazole (HOBt, 0.64 g, 4.84 mmol), triethylamine (3.2 mL, 2.3 mmol) and 2-hydroxyethylimidazole (0.65 g, 3.4 mmol). The reaction mixture was slowly brought to room temperature and stirred for 12 hours. The reaction mixture was concentrated in vacuo and after aqueous work up, extracted with dichloromethane, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified on column (flash chromatography on alumina gel, chloroform/methanol 99.8 : 0.2) to give 0.25 g (23 % yield) of 2-imidazol-l-ylethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate as a pale yellow solid. LC-MS (m/z) 446.2 (M+l). 1H NMR delta (CDCl3) 10.65 (s, IH), 9.16 (s, IH), 8.05 (dd, IH, J1 = 8.7 Hz, J2 = 1.8 Hz), 7.97 (d, IH, J= 8.7 Hz), 7.84 (s, IH), 7.76 (s, IH), 7.22-7.10 (m, 3H), 7.08 (s, IH), 6.97 (d, 2H, J= 9.0 Hz), 5.67 (broad s, IH), 4.75 – 4.60 (m, 2H), 4.50-4.35 (m, 2H), 3.87 (s, 3H), 2.88 (s, 3H).

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-(1H-Imidazol-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CLANOTECH AB; MALM, Johan; RINGOM, Rune; CALDIROLA, Patrizia; WESTMAN, Jacob; WO2010/133669; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4856-97-7, These common heterocyclic compound, 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, 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.

The resulting solid (1H-benzimidazol-2-yl) methanol (34 mmol) was dissolved in 250 mL of dichloromethane and stirredFollowed by addition of manganese dioxide (0.68 mmol). The temperature was raised to 40 C and stirring was continued for 2 hours to monitor the reaction. After the reaction is complete, the product is evaporated to drynessDichloromethane, 150 mL of tetrahydrofuran was added. Directly to the next step

Statistics shows that (1H-Benzoimidazol-2-yl)methanol is playing an increasingly important role. we look forward to future research findings about 4856-97-7.

Reference:
Patent; Shenyang Pharmaceutical University; Zhao Linxiang; Liu Dan; Li Kun; Ma Tianyi; Jing Yongkui; (13 pag.)CN107118249; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3034-50-2, A common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, molecular formula is C4H4N2O, 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.

To a 1L three-necked round-bottomed flask with an addition funnel was added 3H-imidazole-4-carbaldehyde (4, 12 g, 0.125 mol) trityl chloride (38.3 g, 0.137 mol) and acetonitrile (400 mL). The mixture was stirred at rt to give a slurry. Triethylamine (30 mL, 0.215 mol) was added drop wise over 20 min. After the addition was complete, the reaction mixture was stirred at rt for 20 h. Hexane (40 mL) and water (400mL) were added. The slurry was stirred for 30 min and filtered. The cake was washed with water (3 × 100 mL) and dried in a vacuum oven at 50 C for 20 h to give 5 as a white solid (39.8 g, 94%).

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:
Article; Suryadevara, Praveen Kumar; Racherla, Kishore Kumar; Olepu, Srinivas; Norcross, Neil R.; Tatipaka, Hari Babu; Arif, Jennifer A.; Planer, Joseph D.; Lepesheva, Galina I.; Verlinde, Christophe L.M.J.; Buckner, Frederick S.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 23; (2013); p. 6492 – 6499;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1072-62-4,Some common heterocyclic compound, 1072-62-4, name is 2-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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: (bromomethyl)-5-fluorophenyl)(2-fluoro-4,5-dimethoxyphenyl)methanone 4 (0.25 g, 0.68 mmol, 1.0 equiv) and 4-hydroxyl piperidine (150 muL, 1.35 mmol, 2.0 equiv) weredissolved in anhydrous dichloromethane (10 mL) and dryK2CO3 (100 mg, 0.72 mmol, 1.1 equiv) was added, and thenthe mixture was stirred at room temperature for 12 h. Thesolvent was removed by rotary evaporation and the residuewas purified by flash column chromatography over silica gelwith the system (14% ethyl acetate/petroleum ether, adding1.4% ammonia water) to obtain compound (5-fluoro-2-((4-hydroxypiperidin-1-yl)methyl)phenyl) 2-fluoro-4,5-dimethoxyphenyl)methanone 5a (0.2 g, 77%) as a yellow solid.The intermediates 5b-5g, 7a-7k, 9a-9g, 11a-11b wereprepared in a similar manner

The synthetic route of 1072-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Xiu E; Kong, De Peng; Ban, Shu Rong; Ge, Rui; Li, Qing Shan; Medicinal Chemistry Research; vol. 28; 8; (2019); p. 1319 – 1337;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 57531-37-0, 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. 57531-37-0, name is 2-Chloro-5-nitroimidazole, This compound has unique chemical properties. The synthetic route is as follows.

Example 1 Preparation of 2-chloro-1-(3-chloro-2-hydroxypropyl)-4-nitroimidazole Sodium hydrogencarbonate (1.25 g, 14.91 mmol) 5 was added to a solution of 2-chloro-4-nitro-1H-imidazole (2 g, 13.56 mmol) and epichlorohydrin (1.38 g, 14.91 mmol) in acetonitrile (60 ml), and the resulting mixture was stirred under reflux for 4 hours. The reaction mixture was allowed to return to room 10 temperature, and concentrated under reduced pressure. To the residue, water (20 ml) was added, the resulting mixture was extracted with methylene chloride (15 ml) twice, and the extracts were dried over sodium sulfate, and then filtrated. The filtrate was concentrated 15 under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-hexane = 1/1) to afford 2-chloro-1-(3-chloro-2-hydroxypropyl)-4-nitroimidazole (2.04 g, yield 63percent) as a light yellow oil. 20 1H-NMR (CDCl3) deltappm: 3.51 – 3.70 (2H, m), 4.02 – 4.35 (4H, m), 7.92 (1H, s).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-5-nitroimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP1555267; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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 39070-14-9, Safety of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

To a suspension of N,N’-bis(2-bromoethyl)phosphorodiamidic acid (50mg, 0.16mmol), 1-methyl-2-nitroimidazole-5-methanol (50mg, 0.32mmol), and PPh3 (84mg, 0.32mmol) in THF (15mL) was added DIAD (0.13mL, 0.32mmol) at 0C. After the addition of DIAD, the reaction mixture was warmed to room temperature and stirred overnight. The solvent was removed, and the residue was purified by column chromatography on silica gel (DCM: MeOH=50:1) to afford compound 14 (37mg, 51%) as yellow gum. 1H NMR (400MHz, DMSO) delta 7.25 (s, 1H), 5.05-4.99 (m, 2H), 4.98 (d, J=7.6Hz, 2H), 3.94 (s, 3H), 3.42 (t, J=6.9Hz, 4H), 3.17-3.05 (m, 4H). 13C NMR (101MHz, DMSO) delta 146.1, 134.1(d, J=8.0Hz), 128.2, 55.7 (d, J=4.3Hz), 42.7, 34.3, 34.1 (d, J=5.0Hz). HRMS (ESI): m/z Calcd for C9H17Br2N5O4P, [M+H]+: 469.9204, found: 469.9186.

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-2-nitro-1H-imidazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Chen; Zhang, Qiumeng; Lu, Wei; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 135 – 141;,
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. 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1964-77-8

1. To a solution of 5-bromo-2-methyl-lH-benzo[d]imidazole (422 mg, 2.00 mmol) in 20 mL of THF, was added 4.1 mL of t-BuLi solution in hexanes (1.6 M) at -78 C. After 1 hr, a solution of 5-methoxy-l-(phenylsulfonyl)-lH-indole-2-carbaldehyde (693 mg, 2.20 mmol) in 10 mL of THF was added slowly. After 2hr, the reaction mixture was allowed to warm up to RT slowly, quenched with saturated ammonium chloride solution, and extracted with EtOAc. The organic layer was washed with brine, dried (MgS04), and concentrated to give impure (5- methoxy-l-(phenylsulfonyl)-lH-indol-2-yl)(2-methyl-lH-benzo[d]imidazol-5-yl)methanol, which was dissolved in 20 mL of dichloromethane and 20 mL of THF, and reacted with Mn02(3.50 g, 40.0 mmol) overnight at RT. The reaction mixture was diluted with EtOAc, filtered through a pad of Celite, and concentrated to give crude product, which was used for the next step without any further purification.

According to the analysis of related databases, 1964-77-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SRI INTERNATIONAL; JONG, Ling; CHANG, Chih-Tsung; PARK, Jaehyeon; (71 pag.)WO2016/114816; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-11-1, These common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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.

To a solutionof amine 3-(4-methyl-1H-imidazol-1-yl)-5-(triuoromethyl)aniline (a) (one equivalent) and Et3N(1.5 equivalents) in dry CHCl3 cooled to 0 C was added dropwise to a solution of4-(chloromethyl)benzoyl chloride (4) (one equivalent) in dry CHCl3. The reaction mixture wasstirred at room temperature. The progress was monitored by TLC. Cold water was added to thereaction mixture. The organic layer was separated, and the water layer was extracted by CHCl3 threetimes. The combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum.The product was purified by column chromatography on silica gel. The white solid 5 was given with 60% yield; m.p. 80-82 C; 1H-NMR (DMSO-d6, 500 MHz) : 10.74 (s, 1H), 8.32 (s, 1H), 8.26 (d,J = 1.0 Hz, 1H), 8.17 (s, 1H), 8.03 (d, J = 8.3 Hz, 2H), 7.77 (s, 1H), 7.66 (d, J = 8.0 Hz, 2H), 7.52 (s, 1H),4.89 (s, 2H), 2.21 (s, 3H); 13C-NMR (DMSO-d6, 125 MHz) : 166.1, 142.2, 141.7, 139.4, 138.4, 135.5, 134.4,129.4, 128.6, 115.4, 114.7, 112.2, 45.8, 14.0; HRMS (ESI+) m/z calculated for C19H16ClF3N3O [M + H]+394.0929, found 394.0927; purity: 97.93% (by HPLC).

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 641571-11-1.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 177843-26-4, name is 4-Bromo-1H-benzo[d]imidazol-5-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 177843-26-4, SDS of cas: 177843-26-4

5-(methylthio)-3,4-dihydro-2H-pyrrole (238mg) was combined with of 1 H-benzimidazol- 6-amine, 7-bromo (430 mg) (CAS 177843-26-4) in 10 mL of isopropyl alcohol. The reaction was stirred at reflux for 4 days. The refluxed mixture was then cooled to room temperature and concentrated. Flash column chromatography (4-6% 7N NH3 in MeOH/DCM) yielded the title compound 1 H NMR (300 MHz, CD3OD) delta 2.08 (m, 2H), 2.55 (t, J=7.92Hz, 2H), 3.39 (t, J=6.74Hz, 2H), 6.93 (d, J=8.50Hz, 1 H), 7.50 (d, J=8.50Hz, 1 H), 8.1 1 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1H-benzo[d]imidazol-5-amine, and friends who are interested can also refer to it.

Reference:
Patent; ALLERGAN, INC.; CHOW, Ken; GIL, Daniel W.; DONELLO, John E.; WANG, Liming; CORPUZ, Evelyn G.; FANG, Wenkui K.; SINHA, Santosh C.; DIBAS, Mohammed I.; WO2011/44229; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-13-3, 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 641571-13-3 as follows.

To a solution of 4-methyl-N3-[l-(7Eta-rhoyrrolo[2,3-J]pyrimidin-4-yl)-lEta- imidazol-2-yl] -benzene- 1,3 -diamine (15.0 mg, 0.049 mmol), 3-(4-methyl-imidazol-l-yl)-5- trifluoromethyl-benzoic acid (16.0 mg, 0.059 mmol), and DIEA (35yL, 0.20 mmol) in DMF (2mL) is added HATU (21 mg, 0.055 mmol). After stirring for 1 hour at room temperature, the solvent is removed under vacuum. The residue is dissolved in DMSO (ImL). The resulting solution is subjected to purification by reverse-phase HPLC to give 3-(4-methyl- EPO imidazol-l-yl)-N-{4-methyl-3-[l-(7H-pyrrolo[2,3-cT]pyrimidm-4-yl)-lH-imidazol-2- ylamino]-phenyl}-5-trifluoromethyI-benzamide: 1H NuMR 600 MHz (DMSO-J6) delta 12.73 (s, IH), 11.32 0, IH), 10.67 (s, 1 H), 9.60 (s, 1 H), 8.82 0,1 H), 8.64-8.56 (m, 2H), 8.46 (s, IH), 8.43 (s, IH), 8.17 (s, IH), 7.93 (d, IH, J= 2.8 Hz), 7.79 (t, IH, J= 3.2 Hz), 7.52 (d, IH, J= 8.0 Hz), 7.30 (J, IH, J= 8.0 Hz), 7.11 (s, IH), 7.07 (m, IH), 2.39 (s, 3H), 2.36 (5, 3H); MS m/z 558.2 (M + 1).

According to the analysis of related databases, 641571-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; WO2006/101783; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem