Tag: M.W=100-200

1615-14-1, Adding some certain compound to certain chemical reactions, such as: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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.

Diethyl azodicarboxylate (174 mg, 1 mmol) was added to a solution of 4-(4-chloro-5-diphenyl-t-butylsilyloxy-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (288 mg, 0.5 mmol), triphenylphosphine (262 mg, 1 mmol) and 2-(imidazol-1-yl)ethanol (62 mg, 0.55 mmol), (J. Med. Chem. 1993, 25, 4052-4060), in methylene chloride (5 ml) and the mixture stirred for 1 hour at ambient temperature. Acetic acid (30 mg, 0.5 mmol) was added and the volatiles were removed by evaporation. The residue was triturated with ether, the solid collected by filtration and dried under vacuum to give 4-(4-chloro-5-diphenyl-t-butylsilyloxy-2-fluoroanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (186 mg, 55%). MS – ESI: 668 [MH]+

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 1615-14-1.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-54-5, A common heterocyclic compound, 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, molecular formula is C8H7ClN2O, 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.

Example 33 2-Chloro-5-methoxy-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole 2-Chloro-5-methoxy-1H-benzimidazole (0.661 g, 3.6 mmol) was coupled to 1,2,3-tri-O-acetyl-5deoxy-D-ribofuranose according to General Procedure II. The crude product was purified by flash chromatography (9:1 methylene chloride/ether) to yield the title compound (0.900 g, 65%) as a ~1:1 mix of regioisomers (1H NMR); MS (AP): m/z 405 (M+Na); 1H NMR (DMSO-d6) delta: 7.65-7.54 (two d, 1H), 7.21 (s, 1H), 6.97 (m, 1H), 6.18-6.11 (two d, 1H), 5.70-5.59 (m, 1H), 5.21 (q, 1H), 4.27 (m, 1H), 3.83 (two s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 1.51 (t, 3H).

The synthetic route of 15965-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of Michigan; Glaxo Wellcome Inc.; US6413938; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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. 71759-89-2.

Step 1 Following a procedure similar to that outlined in Chem. Comm. 2004, 188-189: A solution of 2,5-difluorophenylboronic acid (47 mg, 0.30 mmol), 4-iodo-1H-imidazole (46 mg, 0.24 mmol), copper(I) chloride (1.8 mg, 0.018 mmol), and 1 mL of methanol was stirred under air at 60 C. for 3 h, then concentrated. Column chromatography (0-33% EtOAc/hexanes) afforded 14.5 mg (20%) of 1-(2,5-difluorophenyl)-4-iodo-1H-imidazole as a white solid.

The synthetic route of 5-Iodo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); 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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., 46006-36-4

A mixture of l-(3-((5-aminopyridin-3-yl)amino)-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (60 mg, 0.14 mmol, HC1 salt), lH-benzo[d]imidazole-4- carboxylic acid (57 mg, 0.35 mmol) and EDCI.HC1 (30 mg, 0.16 mmol) in pyridine (2 mL) was heated at 30 C for 12 h. A yellow suspension was formed. LCMS (Rt = 0.586 min; MS Calcd: 531.2; MS Found: 532.2 [M+H]+). The mixture was concentrated and the residue was poured into water (20 mL) and stirred for 2 minutes. The aqueous layer was extracted with ethyl acetate (20 mL x3). The combined organic layer was washed with water (20 mL x2) and brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by prep-HPLC (0.225% FA as an additive) and lyophilized to give N-(5-((5-methyl- 8-(2-oxopyrrolidin-l-yl)-5H-chromeno[4,3-c]pyridin-3-yl)amino)pyridin-3-yl)-lH- benzo[d]imidazole-4-carboxamide (41.7 mg, yield: 55%) as a yellow solid. (1559) NMR (400 MHz DMSO-rie) d 1.56 (3H, d, J= 6.5 Hz), 2.01-2.10 (2H, m), 2.52-2.54 (2H, m, overlapped with the peak of DMSO), 3.84 (2H, t, J= 7.9 Hz), 5.30 (1H, q , J= 6.7 Hz), 6.79 (1H, s), 7.32 (1H, dd, J= 8.7, 2.1 Hz), 7.40 (1H, d, J= 2.3 Hz), 7.47 (1H, t , J= 7.8 Hz), 7.88-7.92 (2H, m), 8.03 (1H, d, J= 7.5 Hz), 8.62 (1H, d, J= 2.0 Hz), 8.66 (1H, s), 8.72 (1H, s), 8.75 (1H, t, J= 2.0 Hz), 8.81 (1H, d, J= 2.0 Hz), 9.72 (1H, brs), 12.06 (1H, brs).

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; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
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 2849-93-6 as follows. 2849-93-6

General procedure: A reaction mixture of H2BIC (0.0162 g,0.1mmol), Gd(NO3)3¡¤6H2O (0.0451 g, 0.1 mmol), Na2C2O4 (0.0134 g, 0.1 mmol), CH3CN(5 mL) and EtOH (5 mL) was stirred for 20 min, then transferred and sealed in a 20mLTeflon-lined autoclave. The system was heated in an oven at 393K for 72 h and cooled toroom temperature at 5Kh1. The resulting colorless flaky crystals were collected, washedwith ethanol and dried in air. Yield: ca. 71% (based on Gd). Anal. Calcd forC24H15N6O6Gd (%): C, 44.99; H, 2.36; N, 13.12. Found (%): C, 45.21; H, 2.88; N, 12.92.IR (KBr)/cm1: 3131(br, m), 1659(s), 1616(s), 1528(m), 1498(m), 1460(s), 1394(s),1319(s), 1307(m), 1230(w), 1029(w), 989(w), 850(m), 821(m), 773(w), 741(s), 657(m),592(m).

According to the analysis of related databases, 2849-93-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Qiao, Chengfang; Xia, Zhengqiang; Wei, Qing; Zhou, Chunsheng; Zhang, Guochun; Chen, Sanping; Gao, Shengli; Journal of Coordination Chemistry; vol. 66; 7; (2013); p. 1202 – 1210;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

17334-08-6, These common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-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.

To 2-hydroxymethyl-1-methylimidazole (874 mg) was added thionyl chloride (10 ml) at 0C, and the mixture was heated for 30 minutes under nitrogen atmosphere at 90C. The mixture was allowed to be at room temperature. The solvent was distilled off under reduced pressure and the obtained residue was recrystallized from ethyl acetate, to give 2-chloromethyl-1-methylimidazole hydrochloride (1.15 g) as brown crystals. 1H-NMR (200 MHz, DMSO-d6) delta 3.88 (3H, s), 5.19 (2H, s), 7.72 (1H, d, J = 1.8 Hz), 7.78 (1H, d, J = 1.8 Hz). Elemental Analysis C5H8N2Cl2 Calcd. C, 35.95; H, 4.83; N, 16.77; Found. C, 35.74; H, 5.03; N, 16.45.

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 17334-08-6.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1422228; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 15788-16-6, name is 1H-Benzo[d]imidazole-5-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 15788-16-6

8.1. PREPARATION OF 5-BENZIMIDAZOLE-CARBOXYLIC ACID, METHYL ESTER A 500 ml round bottom flask equipped with a heating mantle, reflux condenser, and a DrieriteR filled drying tube was charged with 16.22 g (0.10 mol) of 5-benzimidazolecarboxylic acid (Aldrich), 400 ml of anhydrous methanol and then (Caution)) 20 ml of concentrated sulfuric acid (Fisher). The reaction mixture was heated to reflux for 18 h and then cooled to ambient temperature. Approximately 75% of the solvents were removed under vacuum and then the remaining liquid residue was slowly poured into 500 ml of saturated sodium bicarbonate solution. The resultant two phase system was then extracted with three 250 ml portions of ethyl acetate. The organic layers were combined and washed with three 250 ml portions of 5% sodium bicarbonate solution followed by one 250 ml portion of brine. The ethyl acetate layer was dried over MgSO4, filtered and the solvents were then removed under reduced pressure to give 15.68 g (0,089 mol, 89% yield) of 5-benzimidazolecarboxylic acid, methyl ester, as a tan solid. 1 H NMR (CDCl3) delta7.3-7.9 (m, 3H), 3.70 (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, 15788-16-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cytogen Corporation; US5326856; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 2849-93-6

A mixture of 3-nitro-N-(piperidin-4-yl)pyridin-2-amine hydrochloride (intermediate 58, 580 mg, 2.3 mmol), 1H-benzo[d]imidazole-2-carboxylic acid (365 mg, 2.3 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (365 mg, 2.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (516 mg, 2.7 mmol) and N-methylmorpholine (455 mg, 4.6 mmol) in dry dimethylformamide (15 mL) was stirred at room temperature overnight. The mixture was diluted with water (60 mL), and extracted with ethyl acetate (2*50 mL). The organic layer was washed with brine, dried over sodium sulfate and concentrated to give the crude compound which was purified by silica chromatography to afford (1H-benzo[d]imidazol-2-yl)(4-((3-nitro-pyridin-2-yl)amino)piperidin-1-yl)methanone (600 mg, 1.64 mmol, 72.8% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2849-93-6, its application will become more common.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4331-29-7, Adding some certain compound to certain chemical reactions, such as: 4331-29-7, name is 1H-Benzo[d]imidazol-7-amine, 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 4331-29-7.

[00153] IC491791: 2-[l-(4-Amino-benzoimidazol-l-yl)-ethyl]-3-phenyl-3H- thieno[3,2-d]pyrimidin-4-one.; To a solution of 2-(l-Amino-ethyl)-3-phenyl-3H- thieno[3,2-d]pyrimidin-4-one (47 mg, 0.162 mmol) in DMF was added adenine (26 mg, 0.194), followed by the addition of potassium carbonate (22 mg, 0.162 mmol). The resulting mixture was then heated to 125¡ãC in an oil bath for 5 min. The reaction mixture was then cooled to room temperature, then treated with H2O (10 mL) to afford a precipitate. The precipitate was collected and dried in a vacuum oven to afford the crude product. Purification by HPLC (C- 18 Luna column 250 x 21.20 mm, 10-20percent CH3CN/H20 containing 0.05percent CF3CO2H) product was obtained as a fluffy white solid after lyophilizing: 1H NMR (400 MHz, DMSO-d6) delta 8.37 (s, IH), 8.25 (d, / = 5.2 Hz, IH), 8.16 (s, IH), 7.67 (d, / = 8.0 Hz, IH), 7.58 (m, IH), 7.44 (m, 2H), 7.36 (m, IH), 7.17 (d, / = 8.0 Hz, IH), 5.49 (q, / = 6.8 Hz, IH), 1.75 (d, J = 6.4 Hz, 3H). LC/MS (AP-ESI, CH3CO2H 0.05percent) m/z 390 (MH+).

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 4331-29-7.

Reference:
Patent; ELI LILLY & CO.; WO2008/64018; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, 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. 934-22-5, name is 6-Aminobenzimidazole, A new synthetic method of this compound is introduced below.

Compound 216; 1 -(1 H-Benzoimidazol-5-yl)-4-benzylimino-5-(4-bromo-phenyl)- imidazolidin-2-one; 1 H-Benzoimidazol-5-ylamine (1 mmol) and 4-Bromobenzaldehyde (1 mmol) were combined in methanol (2 ml, dry). After 2 hours 2ml of a solution of KOCN (KSCN) (2mmol) and Pyridinehydrochloride (2mmol) in MeOH is added was added. Finally 3- Benzylisocyanide (1 mmol) is added. The reaction was stirred at room temperature for 48h. After evaporation of the solvent the residue was purified with chromatographic methods. Yield: 0.230 g (50 %); mp: 244C, 1H-NMR (500 MHz, DMSO-D6): 4.46 (t, 3J=5.1 Hz, 2 H, CH2), 6.18 (s, 1 H, CH-N), 7.17 (m, 8 H, Ar), 7.39 (d, 3J=8.7 Hz, 1 H, Benzimid), 7.48 (dd, 3J=6.6 Hz, 4J=1.9 Hz, 2 H, Ar), 7.67 (s, br., 1 H, NH), 8.08 (s, 1 H, Benzimid), 8.67 (t, 1 H, Ar), 12.36 (s, br., 1 H, NH). . MS m/z 460.3 (M+H)+, HPLC (254 nm): rt 2.86 min (100 %)molecular weight (g/mol): 460.34 IC50 hQC (nM): 22

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; PROBIODRUG AG; WO2008/55947; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem