Tag: M.W=100-200

Synthetic Route of 614-97-1, 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 614-97-1 as follows.

a 4-Iodo-5-methyl-1H-benzoimidazole A solution of 5-methyl-1H-benzoimidazole (132 mg, 1.0 mmol) and NIS (248 mg, 1.10 mmol) in 1 mL of TFA was reflux for 1 hr and then cooled to RT. Treated with 30 mL of EtOAc, the mixture was neutralized with sat. NaHCO3 solution. The organic layer was washed with H2O (10 mL), brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (5% MeOH/CH2Cl2) gave 78 (30%) of product as a white solid: 1H-NMR (CDCl3; 400 MHz) delta 8.07 (d, 1H), 7.57 (br s, 1H), 7.22 (d, 1H, J=8.4 Hz), 2.59 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C8H7IN2, 259.0 (M+H), found 259.2.

According to the analysis of related databases, 614-97-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US2004/9995; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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. Computed Properties of C4H4N2O2

Example 130 (3.2 mg, 5.4 imol), 1H-imidazole-2-carboxylic acid (9.1 mg, 0.082 mmol) and DIEA (4.8 pi, 0.027 mmol) were dissolved in DMF (0.5 mL). HATU (2.07 mg, 5.44 imol) was added, and the reaction mixture was allowed to stir at rt for 2 h.The reaction mixture was concentrated, and the residue was purified by RP HPLC to provide the product (2.2 mg, 58%) as a clear glass (bis TFA salt). MS(ESI) m/z 455.3 (M+H)t ?HNMR(SOOMHz, CD3CN) oe 7.92(s, 1H), 7.87 (s, 1H), 7.57 (s, 2H), 7.17 (m, 3H), 6.80 (t, J=0.96 Hz, 1H), 5.45 (s, 2H), 4.65-4.92 (m, 2H), 4.29 (s, 2H), 3.65-3.99 (m,2H), 2.96 (t, J=5.91 Hz, 2H). Analytical HPLC: RT = 3.34 mm (Method A).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16042-25-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2403-66-9, 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. 2403-66-9, name is 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Methyl Iodide (839muL, 13.48 mmol) was added to a mixture of the 3-(lH-benzimidazol- 2-yl)propan-l-ol (2.5g, 14.19 mmol) and Et3N (2.16mL, 15.6 mmol) in DCM (100 mL) at O0C. The reaction stirred for 40 minutes, was warmed to room temperature and stirred 1 hour. DMF (50 mL) was added and continued stirring for 1 hour. Cesium carbonate (4.62g, 14.19 mmol) and methyl iodide (839muL, 13.48 mmol) were added and the reaction stirred overnight. The reaction was diluted with EtOAc, washed with water, saturated sodium bicarbonate and brine. The combined organics were dried over Na2SO4 and concentrated in vacuo. The crude solids were triturated with ethyl ether/hexane (1 :2) to give the title compound (1-21: step 1) as a solid. Data for 1-21: step 1: ESI+ MS: 191.1[MH]+.

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, 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2006/127550; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 21252-69-7, 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. 21252-69-7, name is 1-Octyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 3-tert-butyl-5-bromomethyl-2-hydroxybenzaldehyde [46,47] in toluene (5.0 mL) was addeddropwise to a solution of N-alkylimidazole (10.0 mmol) in toluene(20.0 mL) over 10 min at room temperature. The mixture was thenheated to reflux for 5 h. After cooling to room temperature, the pre-cipitate product was filtered, washed with toluene (3 × 5 mL) anddried under reduced pressure.

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-Octyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Duan, Shuhui; Jing, Xinyao; Li, Dandan; Jing, Huanwang; Journal of Molecular Catalysis A: Chemical; vol. 411; (2016); p. 34 – 39;,
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. 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, A new synthetic method of this compound is introduced below., Recommanded Product: 2466-76-4

Add 1-acetylimidazole (0.035 g, 0.315 mmol) and triethylamine (0.04 mL, 0.286 mmol) to solution of 2-(R)-[2-(S)-amino-3-(3,5-difluorophenyl)-1-(S)-hydroxypropyl]- piperidine-1-carboxylic acid tert-butyl ester (0.106 mg, 0.286 mmol) in dichloromethane (10 mL) and stir 18 h at room temperature. Dilute with ethyl acetate and wash with 1 N hydrochloric acid (3x), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with dichloromethane and ethyl acetate) to give the title compound as a white solid (0.089 g, 76percent). MS (ES): m/z = 411.2 [M-H].

The synthetic route of 2466-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/108358; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, 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 705-09-9, SDS of cas: 705-09-9

Compound 2 (425 muetaetaomicronIota, 1.0 eq.) is dissolved in DMF (2 ml) and cooled to -5C, treated with anhydrous potassium carbonate (1 .44 eq.) and 2-(difluoromethyl)-1 H-benzo[c/]- imidazole (1 .4 eq.), stirred for 30 min and further stirred at room temperature for 4 h. The reaction mixture is diluted with water and the precipitate is filtered and washed with small amounts of water. Purification is done by silica gel flash column chromatography. Rf: 0.72 (methylene chloride/methanol, 95:5 v/v); 1H NMR (CDCI3, 400 MHz) delta 8.43 (d, J = 7.8 Hz, 1 H), 7.90 (d, J = 7.6 Hz, 1 H), 7.71 -7.43 (m, 3H), 4.00-3.95 (m, 4H), 3.86-3.80 (m, 4H); 19F NMR (CDCI3, 400 MHz) delta -1 19.20 (d, J = 53.9 Hz, 2F).

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-(Difluoromethyl)-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF BASEL; CMILJANOVIC, Vladimir; CMILJANOVIC, Natasa; GIESE, Bernd; WYMANN, Matthias; WO2011/135520; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4857-06-1 name is 2-Chloro-1H-benzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-Chloro-5,6-dibromobenzimidazole (17) To a suspension of 0.763 g (5 mmole) of 2-chlorobenzimidazole in 50 mL of 1:1 MeOH/H2 O, was added dropwise a solution of 1 mL of Br2 in 10 mL of MeOH over a period of 30 min. The reaction mixture was stirred at room temperature overnight and was then filtered. The solid was washed with portions of H2 O until the washings were neutral. This solid was air dried and recrystallized from MeOH to give 1.115 g (3 crops, 72%) of 17. mp 228 C.; 1 H NMR (DMSO-d6) d 13-14 (br. s, 1,1-NH), 7.93 (s, 2,4-H, 7-H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; The Regents of the University of Michigan; US5360795; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33468-69-8, 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 33468-69-8 as follows.

Sodium hydride (7.91 mg, 0.198 mmol, 60% in mineral oil) was added to a solution of 4- (trifluoromethyl)-I H-imidazole (24.46 mg, 0.180 mmol) in dry N,N-dimethylformamide (0.4 ml). The reaction was stirred at room temperature for 30 minutes until gas evolution ceased. A solution of 2-(5- bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfanyl-5-(trifluoromethyl)pyridine (66.0 mg, 0.180 mmol) in N,N-dimethylformamide (2.0 ml) was slowly added and the reaction mixture stirred at room (0511) temperature for 30 minutes. Two more equivalents of the previously described solution consisting of sodium hydride and 4-(trifluoromethyl)-1 H-imidazole were then added and stirring continued overnight at 60C. The mixture was quenched over water and ethyl acetate, the layers separated, the aqueous phase extracted twice with ethyl acetate, the combined organic phases dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (cyclohexane/ethyl acetate) to afford 3-ethylsulfanyl-2-[4-methyl-5-[4-(trifluoromethyl)imidazol-1-yl]-1 ,2,4-triazol-3-yl]-5- (trifluoromethyl)pyridine (compound P2) as a solid (55 mg). LCMS (method 4): 423 (M+H)+, retention time 0.97 min. H-NMR (CDCb, ppm) 8.70 (t, 1 H), 8.00 (d, 1 H), 7.94 (d, 1 H), 7.71 (m, 1 H), 3.81 (s, 3H), 3.06 (q, 2H), 1.42 (t, 3H).

According to the analysis of related databases, 33468-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; MUEHLEBACH, Michel; EDMUNDS, Andrew; RENOLD, Peter; BUCHHOLZ, Anke; (96 pag.)WO2018/41729; (2018); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 106429-59-8,Some common heterocyclic compound, 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, 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.

Step 3.5-((7-(5-(4-fluoro-2-(3-hydroxypentan-3-yl)phenoxy)pyrimidin-4-yl)-2,7- diazaspiro[4.4]nonan-2-yl)methyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one (0942) To a solution of crude 3-(2-((4-(2,7-diazaspiro[4.4]nonan-2-yl)pyrimidin-5- yl)oxy)-5-fluorophenyl)pentan-3-ol from above and 2-oxo-2,3-dihydro-1H- benzo[d]imidazole-5-carbaldehyde (Intermediate 40, 20 mg, 0.12 mmol) in MeOH (3 mL) was added NaBH3CN (10 mg, 0.16 mmol) at RT and the reaction mixture stirred for 4 h. Evaporation of the solvent followed by RP-HPLC method A afforded 5-((7-(5-(4- fluoro-2-(3-hydroxypentan-3-yl)phenoxy)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2- yl)methyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one. LCMS method G: Rt = 3.197 min; (M+H)+ = 547.61.1H NMR (CD3OD): delta 8.52 (bs, 1H), 7.60 (m, 1H), 7.45 (dd, J = 2.8, 10.6 Hz, 1H), 7.21-7.18 (m, 2H), 7.11 (d, J = 8.4 Hz, 2H), 7.05-6.96 (m, 1H), 4.43 (s, 2H), 4.20-3.90 (m, 4H), 3.70-3.50 (m, 2H), 3.48-3.33 (m, 2H), 2.34-1.90 (m, 6H), 1.89- 1.80 (m, 2H), 0.78 (t, J = 7.2 Hz, 6H).

The synthetic route of 106429-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); 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. 583-39-1, name is 2-Mercaptobenzimidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Mercaptobenzimidazole

a. A mixture of 0.46 g (0.0016 mol) of benzyl acetate 6, 0.25 g (0.0016 mol) of 1,3-dihydrobenzimidazole-2-thione, 3 mL of acetone, and 3 mL of formic acid was heated at 40C for 6 h. The reaction mixture was cooled down to ambient temperature and poured into aqueous NaCl. The precipitate that formed was filtered off, washed with water, and dried in air. Yield 0.56 g (92%), mp 168-170C (benzene). 1H NMR spectrum (CDCl3), delta,ppm: 1.34 s (18H, CMe3), 4.73 s (2H, CH2N), 5.23 s(1H, OH), 7.17 s (2H, ArH), 7.23-7.30 m (2H, H5,6),7.71-7.78 m (2H, H4,7). Found, %: C 71.45; H 7.83; N 7.27. C22H28N2OS. Calculated, %: C 71.70; H 7.66; N 7.60. b. A solution of benzyl acetate 6 and 1,3-dihydrobenzimidazole-2-thione in a 1 : 1 mixture of acetone and formic acid at ambient temperature for 2 days to obtain 98% of compound 12.

The synthetic route of 583-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tagasheva; Gataullina; Zaripova; Bukharov; Nugumanova; Deberdeev; Voronina, Yu. K.; Russian Journal of General Chemistry; vol. 87; 1; (2017); p. 22 – 28; Zh. Obshch. Khim.; vol. 87; 1; (2017); p. 26 – 32,7;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem