Month: March 2021

Related Products of 2849-93-6,Some common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-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.

Compound 42-a (250.52 mg, 1.55 mmol, 1.03 eq) and HATU (1.14 g, 3.00 mmol, 2.00 eq) were dissolved in dichloromethane (20 mL), and stirred at room temperature for 15 min. Compound 7-a (235.82 mg, 1.50 mmol, 231.19 mL, 1.00 eq) and N,N-diisopropylethylamine (581.58 mg, 4.50 mmol, 785.92 mL, 3.00 eq) were then added, and stirred at room temperature for 18 hours. After the reaction was completed, the reaction solution was added with 150 mL of water, and extracted with dichloromethane (80 mL 3 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was subjected to column chromatography (petroleum ether : ethyl acetate = 1:0?5:2) to give the product of compound 42-b (288.00 mg, yield: 50%) as a yellow oil. LCMS m/z = 302.0 [M+H]+.

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; HE, Haiying; WU, Songliang; LUO, Zhi; MOU, Jianfeng; GUO, Fengying; WANG, Chuan; LI, Guoqing; ZENG, Minggao; CHEN, Shuhui; (199 pag.)EP3456711; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 93-84-5, These common heterocyclic compound, 93-84-5, name is 5-Nitro-1H-benzo[d]imidazol-2(3H)-one, 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 2) Preparation of 2-Chloro-5-nitro-1H-benzimidazole According to the procedure of A. T. James, et al., J. Chem. Soc., 1515 (1950), a mixture of 2-hydroxy-5-nitro-1H-benzimidazole (10.0 g, 0.0558 mol) and phosphoryl chloride (100 mL) was heated under reflux for 3 hours. The mixture was cooled, concentrated, and ice water was added. The resulting precipitate was collected by filtration. NMR analysis showed the material to be a 1:1 mixture of starting material and product. (Note: Longer heating does not improve the conversion.) Purification by flash chromatography (material preadsorbed onto silica; eluent 40% EtOAc/hexane) gave 4.4 g (40%) of the off-white solid product m.p. 215-217 C. NMR (DMSO-d6, 300 MHz): delta7.68 (d, J=8.9, 1H), 8.12 (dd, J=8.9, 2.3, 1H), 8.39 (d, J=2.3, 1H), 14.00 (brs, 1H).

The synthetic route of 93-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US5149700; (1992); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 90871-47-9, A common heterocyclic compound, 90871-47-9, name is 2-Amino-1-isopropylbenzimidazole, molecular formula is C10H13N3, 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.

200 mg (0.64 mmol) of compound 2-[(2,5-dichloropyridin-4-yl)amino]-N-methoxybenzamide, 168 mg (0.96 mmol) was added to a 20 ml microwave tube.1-isopropyl-1H-benzo[d]imidazol-2-amine, 417 mg (1.28 mmol) cesium carbonate, 93 mg (0.16 mol) XantPhos, 117 mg (0.128 mmol) Pd2 (dba) 3 and 10 ml of 1,4 – Dioxane, under nitrogen protection, use the oil pump to remove the air in the system, replace it with nitrogen, repeat three times, seal the microwave tube, at 150 C microThe reaction was carried out in a wave reactor for 50 min.After the TLC detection reaction was completed, the catalyst was filtered off with celite, eluted with ethyl acetate, and the solvent was evaporated to dryness, and silica gel column chromatography (gradient elution polarity: PE: EA=100:1 to EA) to collect the crude product 109 mg , the yield is 37.7%,

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; Guangzhou Anyanren Pharmaceutical Technology Co., Ltd.; Xie Dexun; Li Quanwei; Xue Weicai; Liu Hui; (27 pag.)CN108912095; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1003-21-0, 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 1003-21-0 as follows.

Intermediate 2: step c (1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanone To a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo- 1 -methyl- lH-imidazole (47.96 g, 297.9 mmol), followed by THF (537 mL). To this room temperature solution was added isopropyimagnesium chloride/lithium chloride complex [1.3 M in THF] (246.8 mL, 320.8 mmol) (addition temperature maintained between 16.6 and 25 C) to afford a milky suspension and the reaction was stirred for 60 minutes and then cooled to 5.3 C in an ice bath. To this mixture was added a solution of N-methoxy-N-methyl-6- (trifluoromethyi)nicotinamide (53,66 g, 229.14 mmol, Intermediate 2: step b) in THF (268.3 mL) (addition temperature between 5.3 and 5.6 C) to afford an orange mixture. After addition, the reaction was warmed to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C with an ice bath and carefully quenched with 2 N aqueous HC1 to pH = 7 (quenching temperature reached 12 C). The mixture was diluted with ethyl acetate (500 mL), phase split and the organic layer was washed with brine (2 x 200 mL) and dried over sodium sulfate, filtered, and the solvent was removed. Hot, ether was added and the mixture was filtered to give the title compound as a solid.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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 4-methyl-lH-imidazole-5-carbaldehyde (5.0 g, 45.4 mmol) in anhydrous THF (50 mL) was added diaza(l,3)bicyclo[5.4.0]undecane (DBU, 6.8 mL, 45.4 mmol), and iodoethane (3.4 mL, 45.4 mmol). The mixture was stirred at room temperature overnight. Water (50 mL) was added before the THF was evaporated. The mixture was extracted with EtOAc (1 x 50 mL) and 2-butanol (2 x 50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-1% MeOH/DCM), affording l-ethyl-4-methyl-lH-imidazole-5-carbaldehyde (806 mg, 13% yield).

The synthetic route of 68282-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
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. 111851-98-0, name is 1-Ethyl-1H-imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Ethyl-1H-imidazole-2-carbaldehyde

(Reference Example 23) Synthesis of (E)-methyl 3-(1-ethyl-1H-imidazol-2-yl)acrylate: Methyl (triphenylphosphoranylidene)acetate (3.15 g, 9.42 mmol) was added to a solution of 1-ethyl-1H-imidazole-2-carbaldehyde (1.17 g, 9.42 mmol) in dichloromethane (28.3 mL) at room temperature. The reaction liquid was stirred for 16 hours and concentrated under reduced pressure. The residue was washed with a mixed solvent of hexane/dichloromethane = 20/1 and the washing solution was concentrated. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate) to obtain (E)-methyl 3-(1-ethyl-1H-imidazol-2-yl)acrylate (0.670 g, 3.72 mmol, 39%) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 1.45 (3H, t, J=7.6 Hz), 3.81(3H, s), 4.10 (2H, dd, J=7.6, 14.8 Hz), 6.85 (1H, d, J=15.2 Hz), 7.03 (1H, brs), 7.17 (1H, brs), 7.52 (1H, d, J=15.2 Hz). ESI-MS: m/z= 181 (M+H)+.

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 111851-98-0.

Reference:
Patent; Toray Industries, Inc.; ARAI Tadamasa; MORITA Yasuhiro; UDAGAWA Shuji; ISEKI Katsuhiko; IZUMIMOTO Naoki; (95 pag.)EP3263565; (2018); A1;,
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. 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows., name: 1H-Benzo[d]imidazol-2-amine

In a 50 mL single-mouth pear-shaped flask, 0.55 g (4.1 mmol) of 1H-benzo[d]imidazol-2-amine was dissolved in 15 mL of acetone, 0.46 g (8.2 mmol) of potassium hydroxide powder was added, and stirred at room temperature for 10 min, and moved to In an ice water bath, 0.28 mL of methyl iodide (4.5 mmol) was added dropwise, stirred for 10 min, and the reaction was complete by TLC. After moving to room temperature, 15 mL of H2O was added, the solvent was removed, and the mixture was extracted with EA (10 mL*3). The organic phase was combined, concentrated, and purified on silica gel column (eluent: PE: EA=PE~50:1) Fluorescent brown viscous liquid 550 mg, yield 90%

According to the analysis of related databases, 934-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Anyanren Pharmaceutical Technology Co., Ltd.; Xie Dexun; Li Quanwei; Xue Weicai; Liu Hui; (27 pag.)CN108912095; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53484-16-5, 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 53484-16-5 as follows.

3.3.1. Step i. 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrilej00319j A mixture containing 6-bromo-1-methyl-benzimidazole (2.38 mmol), 4-amino-3-fluoro- benzonitrile (3.57 mmol), XPhos (0.95 mmol), Cs2CO3 (7.14 mmol) and Pd(OAc)2 (0.71 mmol) in dry toluene (8 mL) was stirred at 110¡ãC for approximately 16 h. The mixture was diluted (EtOAc), washed (H20), dried (Na2SO4) and concentrated to yield the desired product 3-fluoro-4-[(3-methylbenzimidazol- 5-yl)amino]benzonitrile.

According to the analysis of related databases, 53484-16-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; BLANC, Javier; OR?ULIC, Mislav; RO?CIC, Maja; WO2015/110378; (2015); 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. 33468-67-6, name is 2-Methyl-4-(trifluoromethyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 2-Methyl-4-(trifluoromethyl)-1H-imidazole

Compound 218.1. 5-Iodo-2-methyl-4-(trifluoromethyl)-lH-imidazole. Into a 50- mL round-bottom flask, was placed a solution of 2-methyl-4-(trifluoromethyl)-lH-imidazole (compound 16.2, 1.72 g, 1 1.46 mmol) in CH3CN (25 mL). S (3.87 g, 17.20 mmol) was added to the reaction. The reaction mixture was stirred overnight at 85 C . The reaction mixture diluted with 50 mL of Iota0 and extracted with 3 x 30 mL of ethyl acetate . The combined organic layers were washed with 2 x 20 mL of a2S203(sat.) and 2 x 20 mL of brine , dried over anhydrous sodium sulfate and concentrated under reduced pressure. This resulted in 4.32 g (crude) of the title compound as a brown oil.

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; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4856-97-7,Some common heterocyclic compound, 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, molecular formula is C8H8N2O, 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 procedure for gram scale oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehydewas as follows: (1H-benzo[d]imidazol-2-yl)methanol (0.1 mol,14.8 g) and [Ru(bpbp)(pydic)] (0.001 mmol, 7.32 ¡Á 10-3 g) wereadded into a reactor. The reactor containing this mixture was heatedto 50 C in an oil bath under vigorous stirring and then 30% H2O2(30 mL, 0.3 mol) was slowly dropwise over a period of 30 min. The mixture was stirred for 5 h. After filtering, the solution wasevaporation under reduced pressure at 50 C. Pure 1H-benzo[d]imidazole-2-carbaldehyde (0.07 mmol, 10.2 g) was obtained with ayield of 70% after recrystallisation from 30% H2SO4 solution. Theproduct, 1H-benzo[d]imidazole-2-carbaldehyde, was identified byits 1H NMR spectrum.

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

Reference:
Article; Liu, Shenggui; Pan, Rongkai; Su, Wenyi; Li, Guobi; Ni, Chunlin; Journal of Chemical Research; vol. 41; 2; (2017); p. 88 – 92;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem