Month: March 2021

Application of 17325-26-7, A common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, molecular formula is C5H6N2O2, 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.

lambda/-bromosuccinimide (0.900 g, 5.0 mmol) was added to a stirred solution of methyl 1 H-imidazole-4-carboxylate (0.630 g, 5.0 mmol) in CH3CN (50 mL). The reaction mixture was stirred for 12 h in the dark and then concentrated in the presence of silica gel. The absorbed crude material was purified by column chromatography (20- 100% EtOAc/hexanes) to afford the title compound (0.708 g, 70%) as a white solid. 1H NMR (400 MHz, DMSOd6) delta ppm 1 1.00 (br. s., 1 H), 7.81 (s, 1 H), 3.81 (s, 3 H). ES-LCMS: m/z 204.9, 206.9 (M+1 ).

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); 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. 10040-96-7, name is 1-(4-Bromophenyl)imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 10040-96-7

Pd(PPh3)4 (112 mg, 96.7 mumol) was added to a mixture of 6 (600 mg, 0.967 mmol) and 1-(4-bromophenyl)-1H-imidazole (863 mg, 3.87 mmol) in aqueous Na2CO3 (2 M, 2.0 mL, 4.0 mmol) and anhydrous THF (18.0 mL), and the solution was stirred at room temperature for 15 min. The resulting two-phase system was refluxed under stirring overnight, and was then allowed to cool to room temperature. To this was added water (50 mL), and the mixture was extracted with CHCl3 (100 mL¡Á3). The organic layer was washed with water (50 mL), dried over anhydrous MgSO4, and filtered. After the solvent was removed by evaporation, the residue was subjected to SEC fractionation to obtain 2 (516 mg, 79%) as a bluish white solid. Mp: 251.8-252.0 C. IR (KBr, cm-1): 1523, 1305, 1273, 1139, 1114, 1055, 989. 1H NMR (500 MHz, CDCl3): delta 7.89 (s, 2H, ArH), 7.65 (d, J=8.6 Hz, 4H, PhH), 7.42 (d, J=8.6 Hz, 4H, PhH), 7.32 (s, 2H, ArH), 7.25 (s, 2H, ArH), 2.01 (s, 6H, CH3). 13C NMR (125 MHz, CDCl3): delta 142.1, 140.9, 136.9, 135.6, 132.7, 130.9, 127.1, 126.2, 123.1, 122.0, 118.2, 14.8. MS (ESI+): m/z=653 [M+H]+. Anal. Calcd for C33H22F6N4S2: C, 60.73; H, 3.40; N, 8.58. Found: C, 60.74; H, 3.48; N, 8.45.

According to the analysis of related databases, 10040-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iida, Hiroki; Umebayashi, Naofumi; Yashima, Eiji; Tetrahedron; vol. 69; 52; (2013); p. 11064 – 11069;,
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 1243204-92-3 as follows. Quality Control of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile

[0428] To a stirred solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl) benzonitrile (450 mg, 2 mmol) in MeOH (23 mL) at room temperature under an argon atmosphere were added hydroxyl amine hydrochloride (230 mg, 2 mmol) and sodium bicarbonate (230 mg, 3 mmol). The reaction mixture was stirred at 85 C for 3 h. After consumption of starting material (by TLC), the volatiles were evaporated in vacuo. The residue was diluted with ice cold water (50 mL), stirred for 10 mm, to obtain the solid. The solid was collected by filtration and dried in vacuo to obtain (Z)-iV-hydroxy-3-methoxy-4-(4-methyl-1H-imidazol-1- yl) benzimidamide (450 mg, 88%) as an off-white solid.?H NMR (DMSO-d6, 500 MHz): 9.73 (s, 1H), 7.79 (s, 1H), 7.47 (s, 1H), 7.37 (s, 2H), 5.92 (s, 2H), 3.82 (s, 3H), 2.15 (s, 3H); LCMS: 92.4%; 247 (M+1); (column; X-select CSH C-18 (50 x 3.0 mm, 2.7 tim); RT 2.06 mm; mobile phase: 2.5mM NH400CH in water+5% ACN:ACN+5% 2.5mM NH400CH in water; T/B%: 0.01/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: 3% MeOH/CH2C12 (R1: 0.3).

According to the analysis of related databases, 1243204-92-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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 41716-18-1, SDS of cas: 41716-18-1

To a solution of intermediate 24-d (580 mg, 1.11 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (168 mg, 1.33 mmol), HATU (591 mg, 1.55 mmol) and DIPEA (581 uL, 3.33 mmol) and the reaction mixture was stirred at 0¡ã C. for 1 hour. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 27-a as a white foam.

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:
Patent; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 213133-77-8, These common heterocyclic compound, 213133-77-8, name is 2-(3,4-Dichlorobenzyl)-1H-benzo[d]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.

General procedure: To a stirred solution of 2-phenyl-1H-benzo[d]imidazole 7a (50 mg, 0.26 mmol) and NaH (7 mg, 0.31 mmol) in DMF (0.5 mL) was added methyl bromoacetate (29 muL, 0.31 mmol) dropwise. After stirring at room temperature for 16 h, the reaction mixture was extracted with EtOAc (3 ~ 20 mL) and washed with H2O (~ 20 mL). The organic layer was dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, n-hexane/EtOAc 2/1) to yield the title product 8a (35 mg, 50%).

The synthetic route of 213133-77-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, TaeHun; Yang, Ha Yun; Park, Beoung Gun; Jung, Seo Yun; Park, Jong-Hyun; Park, Ki Duk; Min, Sun-Joon; Tae, Jinsung; Yang, Hyejin; Cho, Suengmok; Cho, Sung Jin; Song, Hyundong; Mook-Jung, Inhee; Lee, Jiyoun; Pae, Ae Nim; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1172 – 1192;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 68282-53-1, 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 68282-53-1 as follows.

COMPOUND 12.1. 53: NN-DIETHYL-4- {6-METHOXY-2- [4-METHYL-lH- IMIDAZOL-5-YL)METHYL]-7-NITRO-1,2,3,4-TETRAHYDROISOQUINOLIN-1- YLdBENZAMIDE; To a solution of INTERMEDIATE 9.2. 2 (1.16 g, 3.00 mmole) and 4-methyl-5- imidazolecarboxaldehyde (0.31 g, 2.8 mmole) in 1,2-dichloromethane (25 mL) was added sodium triacetoxyborohydride (1.65 g, 7.8 mmole) and the resulting solution was stirred at room temperature for 18 h. Sodium hydroxide (1M, 100 mL) was added and the mixture extracted with ethyl acetate (3 x 100 mL). The organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (ethyl acetate/10% methanol in chloroform, 2/8) to give COMPOUND 12.1. 53 (1.12 g, 78%) as a yellow amorphous solid. 1H NMR (500 MHz, CDC13) : 5 1.12, 1.23 (2 br s, 6H), 2.05 (s, 3H), 2.55 (m, 1H), 2.82 (dd, J3. 5,13 Hz, 1H), 3.02 (m, 1H), 3.12 (m, 1H), 3. 26 (br s, 2H), 3.30 (d, J 13.5 Hz, 1H), 3.54 (br s, 2H), 3.56 (d, J 13.5 Hz, 1H), 3.91 (s, 3H), 4.56 (s, 1H), 6.73 (br s, 2H), 6. 80 (s, 1H), 7.20 (s, 1H), 7.30 (m, 5H); 13C NMR (125 MHz, CDC13) : 8 10.76, 12.82, 14.13, 29.35, 39.39, 43.45, 46.11, 49.33, 56.46, 67.12, 113. 00, 126.13, 126.59, 127.03, 129.45, 129.50, 130.33, 133.05, 136.52, 137.67, 142.46, 144.01, 151.23, 171.07 ; (+) LRESIMS m/z 478 [M+H] +.

According to the analysis of related databases, 68282-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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. Computed Properties of C11H12N2O2

General procedure: To the dry solid of compound 3 (2.04 g, 0.01 mol) ammonium acetate (0.50 g) eithercyclophentanone (0.78 g, 0.01 mol) or cyclohexanone (0.92 g, 0.01 mol) were added. Thereaction mixture was heated in an oil bath at 120 oC for 1 h then left to cool. The product wastriturated with ethanol and the formed solid product was collected by filtration.Ethyl 2-(1H-benzo[d]imidazol-2-yl)-2-cyclopentylideneacetate (15a). Pale yellow crystals fromethanol; yield: 2.53 g (83%); m.p. 155 oC. IR, : 3459-3322 (NH), 3053 (CH aromatic), 2929,2863 (CH3, CH2), 1686 (CO), 1636 (C=N), 1630 (C=C). 1H-NMR: : 1.13 (t, 3H, J = 6.93 Hz,CH3), 1.18-1.24 (m, 4H, 2CH2), 2.19-2.21 (m, 4H, 2CH2), 4.22 (q, 2H, J = 6.93 Hz, CH2), 7.27-7.38 (m, 4H, C6H4), 8.32 (s, 1H, NH, D2O exchangeable). 13C NMR (DMSO): 16.2 (ester CH3),1.89-2.13 (2m 4CH2), 52.6 (ester CH2), 86.4, 90.6 (C=C), 120.3, 121.2, 123.2, 125.6, 128.6(C6H4), 164.8 (CO), 173.2 (C=N); Anal. calcd for C16H18N2O2: C, 71.09; H, 6.71; N, 10.36%.Found: C, 70.93; H, 6.93; N, 10.47%. MS: m/z: (%) 270 (M+, 36%).

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 714273-83-3, A common heterocyclic compound, 714273-83-3, name is 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, molecular formula is C8H12N2O, 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.

In 5000 ml dry three-mouth flask was added magnesium chips (14.4g, 0.60 mol) and dry tetrahydrofuran (1L). Drop 1ml 1,2-dibromoethane and initiate the reaction. Then slowly add dropwise bromoacetaldehyde ethylene acetal (100g, 0.60 mol) in tetrahydrofuran solution (500 ml). After adding dropwise, stir for two hours until magnesium chips disappear. Then 5-tert-butyl-1H-imidazole-4-carbaldehyde (30g, 0.20 mol) in tetrahydrofuran solution (500 ml) was slowly added dropwise to the above solution. Stir overnight. Then use concentrated hydrochloric acid to adjust to acidic (pH=1), and heated to 60 C and stir for 30 minutes. Steaming and remove the tetrahydrofuran, adding the ethyl acetate extraction. The organic phase and water washing twice, a saturated salt water washing, final drying with anhydrous sodium sulfate, concentrated. The crude product is purified by column chromatography (petroleum ether/ethyl acetate of the volume ratio: 2/1) to obtain a yellow solid (17.8g, yield: 50%).

The synthetic route of 714273-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Haiwang Pharmaceutical Technology Research Institute Co., Ltd.; Tang, Tian; Peng, Jianghua; Wu, Jing; Feng, Yidong; Yang, Jingan; She, Qin; Feng, Hanlin; (28 pag.)CN106565685; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4887-88-1,Some common heterocyclic compound, 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, molecular formula is C7H5BrN2, 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 solution of 5-bromo-1H-benzimidazole (1.0 g, 5.1 mmol) in dichloromethane (25 mL) was added triethylamine (3.6 mL, 25.5 mmol) followed by di-t-butyldicarbonate (3.3 g, 15.2 mmol) and 4-(dimethylamino)-pyridine (cat). The reaction was stirred at room temperature for 30 min, then was quenched with H2O. The layers were separated and the aqueous extracted 2¡Á CH2Cl2. The combined organics were dried (Na2SO4), concentrated in vacuo, and chromatographed (10-20% EtOAc/hexanes). This provided the product as the two Boc regioisomers which were separated and characterized but not assigned as to the specific regioisomer. The more polar isomer was used for the subsequent reactions.Isomer a (less polar): 1H NMR (400 MHz, CDCl3): delta-8.40 (s, 1H), 7.92 (s, 1H), 7.86 (d, 1H, J=8.5 Hz), 7.49 (d, 1H, J=8.5 Hz), 1.69 (s, 9H).Isomer b (more polar): 1H NMR (400 MHz, CDCl3): delta-8.38 (s, 1H), 8.18 (s, 1H), 7.63 (d, 1H, J=8.5 Hz), 7.46 (d, 1H, J=8.5 Hz), 1.69 (9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); 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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, A new synthetic method of this compound is introduced below., COA of Formula: C7H6N4S

To a stirred solution of 6.8 g (35.0 mmol) of (5) in 150 mL Of CH2Cl2 at RT was added 6.4g (35mmol) of l,l ‘-thiocarbonyldiimidazole. The mixture was stirred at room temperature for 15 minutes and then evaporated under reduced pressure and the residue was passed through a short pad of silica gel, eluting with a gradient of hexane/EtOAc, which gave (5-Isothiocyanato-2-methoxy-phenyl)-methyl-propyl-amine (6) (7.85g, 95%) as a colorless 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; SYNTA PHARMACEUTICALS CORP.; WO2008/57246; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem