Tag: M.W=100-200

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 16681-59-7 as follows. Computed Properties of C4H5BrN2

Step 3: 7-Chloro-2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridine (7); To a solution of the tin derivative 6 (24.79 g, 54.05 mmol) and 2-bromo-1-methyl-1H-imidazole (10.4 g, 64.86 mmol) [McCallum, P. W.; Weavers, R. T.: Grimmet, M. R.; Blackman, A. G.; Aust. J. Chem.; 52; 3; 1999; 159-166.1 in toluene (180 mL) Pd[PPh3]4 (5 g, 4.32 mmol) was added and the mixture was refluxed under nitrogen for 2 days, cooled to room temperature. A precipitate was formed which was collected by filtration, washed with Et2O and dried, to afford the title compound 7 as a grey solid (12.72 g, 94% yield). MS (m/z): 250.0 (M+H).

According to the analysis of related databases, 16681-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Methylgene, Inc.; US2007/4675; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 716-79-0, name is 2-Phenyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 716-79-0

General procedure: To a solution of TBZ (1.0 equiv) (for TBZ-10, 11, 12, 13, 18) or 2-phenyl-1H-benzo[d]imidazole (1.0 equiv) (for TBZ-20) with sodium hydride (1.2 equiv) in DMF for 15 min, then corresponding iodomethane, benzyl bromide, 4-methoxybenzylchloride, 3-nitrobenzyl bromide, 5-(chloromethyl)-1,2,3-trimethoxybenzene(1.0 equiv) was added slowly at room temperature. On completion of the reaction monitored by TLC, the solvent was evaporated and the residue was purified by silica gel chromatography by DCM/MeOH system to afford the final product.

The synthetic route of 716-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Chao; Zhong, Bo; Yang, Simin; Pan, Liangkun; Yu, Siwang; Li, Zhongjun; Li, Shuchun; Su, Bin; Meng, Xiangbao; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3774 – 3780;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-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 33468-69-8, Safety of 4-(Trifluoromethyl)-1H-imidazole

Reaction Scheme 14 [00180] Referring to Reaction Scheme 14, Stage 1, a solution of 4-chloro-6-(3,4- dichloro-phenyl)-pyrimidine (leq), 4-(trifluoromethyl)-lH-imidazole (2eq) and potassium carbonate (l . leq) in fert-butanol (lOvol) was heated at 150C in a microwave for 25 minutes. Potassium carbonate (l .leq) was added to the reaction mixture, which was heated at 160C in a microwave for 35 minutes. Water was added and the desired material was extracted with EtOAc. The organic phase was dried with MgS04, filtered and evaporated to dryness. Purification by flash column chromatography (eluent: [99.5:0.5] DCM:MeOH) afforded the target compound.

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; CHDI, INC.; DOMINGUEZ, Celia; TOLEDO-SHERMAN, Leticia, M.; WINKLER, Dirk; BROOKFIELD, Frederick; DE AGUIAR PENA, Paula, C.; WO2011/91153; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 85692-37-1, A common heterocyclic compound, 85692-37-1, name is 1-(1-Methyl-1H-imidazol-2-yl)ethanone, molecular formula is C6H8N2O, 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 3-Synthesis of 4-[1-(2-aminopyrimidin-4-yl)-3-methyl-1H-indazol-6-yl]-2-(1-methyl-1H-imidazol-2-yl)but-3-yn-2-ol To a solution of 4-(6-ethynyl-3-methylindazol-1-yl)pyrimidin-2-amine (150 mg, 0.6 mmol) in THF (2 mL) at -78 C. under nitrogen was added 2M LDA in THF (0.75 mL, 1.50 mmol). After 5 minutes, 1-(1-methyl-1H-imidazol-2-yl)ethanone (225 mg, 1.81 mmol) in THF (1.0 mL) was added, and after a further 20 minutes the mixture was allowed to warm to RT and stirred for 1.5 hours. The reaction mixture was then cooled to -78 C. and treated with additional 2M LDA in THF (0.3 mL, 0.6 mmol) and 1-(1-methyl-1H-imidazol-2-yl)ethanone (90 mg, 0.6 mmol). After stirring at RT for 4 hr, the reaction mixture was quenched by addition of saturated aqueous NH4Cl (2 mL). The volatiles were removed in vacuo and the mixture was diluted with DCM (10 ml) and washed with water (2 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Biotage, 3-12% methanol gradient in DCM) to give the title compound: 1H NMR (500 MHz, DMSO) delta 2.00 (3H, s), 2.57 (3H, s), 3.92 (3H, s), 6.32 (1H, s), 6.77 (1H, s), 6.98 (2 H, s), 7.03 (1H, d, J=5.5 Hz), 7.15 (1H, s), 7.36 (1H, d, J=8.2), 7.84 (1H, d, J=8.2 Hz), 8.25 (1H, d, J=5.5 Hz), 8.84 (1H, s); LC-MS: m/z=+374.05 (M+H)+.

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; Genentech, Inc.; US2012/214762; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 334893-99-1, The chemical industry reduces the impact on the environment during synthesis 334893-99-1, name is (5-Chloro-1-methyl-1H-imidazol-2-yl)methanol, I believe this compound will play a more active role in future production and life.

A Dess-Martin reagent (1.04 g, 2.46 mmol) was added to a solution of (5-chloro-1-methyl-1H-imidazol-2-yl)methanol (0.300 g, 2.05 mmol) in dichloromethane (20.0 mL) at 0 C. The reaction liquid was stirred at room temperature for 4 hours. The reaction liquid was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane/ethyl acetate) to obtain 5-chloro-1-methyl-1H-imidazole-2-carbaldehyde (0.289 g, 2.00 mmol, 98%) as a white solid. (0157) 1H-NMR (400 MHz, CDCl3) delta: 3.97 (3H, s), 7.24 (1H, s), 9.70 (1H, s).

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

Reference:
Patent; Toray Industries, Inc.; Osada, Yuji; Izumimoto, Naoki; Morita, Yasuhiro; Udagawa, Shuji; Iseki, Katsuhiko; Miyoshi, Tomoya; Iwano, Shunsuke; (38 pag.)US2018/72701; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 5805-57-2, The chemical industry reduces the impact on the environment during synthesis 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, I believe this compound will play a more active role in future production and life.

The solution of (3-(2,4-dichlorophenylamino)propanoic acid (20 mg , 0.089 mmoL 1.0 equiv), DIPEA ( 3 equiv), EDC HCI ( 1.5 equiv) and DMAP (1 ,0 equiv) in DCM (2.0 mL) was stirred for lOmin, To this reaction mixture (IH- 1 14 benzo[d]imidazol-2-yl)methanamine (1.0 equiv) was added. The reaction mixture was stirred at room temperature overnight. The organic layer was washed with aq NaHC03 and brine. It was then dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by flash column chromatography to afford N-(lH-Benzoimidazol-2-ylmethyl)- 3-(2,4-dichloro-phenylamino)-propionamide (1763). LC/MS: (ESI) (M ¡¤ ) 364.3.

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

Reference:
Patent; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5465-29-2, The chemical industry reduces the impact on the environment during synthesis 5465-29-2, name is 2-Propylbenzimidazole, I believe this compound will play a more active role in future production and life.

2-Propyl-1H-benzo[d]imidazole (Synthetic Communication, 2002, vol. 32, p3703, 246 mg, 1.54 mmol) and (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (550 mg, 1.54 mmol) obtained in Reference Example 1 were dissolved in DMF (7 mL), potassium carbonate (1.06 g, 7.68 mmol) was added and the mixture was stirred overnight. To the mixture was added water (20 mL), and the precipitated crystals were collected by suction filtration to give the title compound (640 mg, 94%). ESIMS m/z: 438 (M + H)+; 1H NMR (300 MHz, CDCl3,delta): 1.02 (t, J = 7.4 Hz, 3H), 1.77-1.97 (m, 2H), 2.23 (s, 3H), 2.80 (t, J = 7.4 Hz, 2H), 4.73 (d, J = 12.6 Hz, 1H), 5.32-5.48 (m, 3H), 6.51-6.58 (m, 1H), 6.59-6.69 (m, 1H), 6.94-7.07 (m, 3H), 7.11-7.29 (m, 3H), 7.43 (d, J = 7.8 Hz, 1H), 7.78 (d, J = 7.5 Hz, 1H)

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-Propylbenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; YAMAMOTO, Keisuke; TAMURA, Tomohiro; NAKAMURA, Rina; UENO, Kimihisa; HOSOE, Shintaro; EP2740730; (2014); 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. 83741-35-9, name is 4-Bromo-1H-benzoimidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Bromo-1H-benzoimidazole

Preparation 47A: 4-Bromo-l- 4-fluorophenyl)-lH-benzo[d]imidazole[00151] A round bottom flask charged with molecular sieves, 4A (189 mg, 1.918 mmol) was flame-dried, then allowed to cool to room temperature. To this vial were added 4-bromo-lH-benzo[d]imidazole (0.378 g, 1.918 mmol), copper (II) acetate (0.523 g, 2.88 mmol), and 4-fluorophenylboronic acid (0.805 g, 5.76 mmol) followed by CH2CI2 (Volume: 9.59 ml) and triethylamine (0.695 ml, 4.99 mmol). The heterogeneous green reaction was stirred at room temperature. After 19 h, the reaction mixture was filtered through a disposable filter funnel and the filter cake rinsed with CH2CI2. The filtrate was concentrated to afford a green residue. The crude material was dissolved in a minimal amount of CH2CI2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (24 g column, 35 mL/min, 0-100% EtOAc in hexanes over 25 min, tr = 13 min) gave 4-bromo-l-(4-fluorophenyl)-lH- benzo[d]imidazole (158 mg, 0.299 mmol, 15.56% yield) as a white solid. LC-MS showed by-product was present. The material was re-dissolved in a minimal amount of CH2CI2 (required a few drops of MeOH). Purification of the crude material by silica gel chromatography using an ISCO machine (12 g column, 30 mL/min, 0-25% EtOAc in hexanes over 13 min, tr = 10 min) gave Preparation 47A (158 mg, 0.299 mmol, 15.56% yield) as a white solid. LC-MS showed the product was 55% pure. The mixture was further purified by MPLC (40 g column, 36 mL/min, 30-60% EtOAc in hexanes) to afford Preparation 47A as a white solid (51 mg, 9.1%). MS (ESI) : m/z = 291.0 [M+H]+. HPLC Peak tr = 1.70 minutes was product. HPLC conditions: Column:Luna CI 8 4.6x30mm 3u A: 10:90 H20:ACN NH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow.

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 83741-35-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HUANG, Audris; WO2012/44537; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, 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. Computed Properties of C7H7N3

Example 38 N-(1H-benzo[d]imidazol-5-yl)-2-(4-(5-chloro-2-propionylphenyl)-5-methoxy-2-oxopyri din-1(2H)-yl)-3-phenylpropanamide 38 Compound 8i (80 mg, 181.86 mumol), 1H-benzo[d]imidazol-5-amine 38a (24.22 mg, 181.86 mumol, prepared by a known method disclosed in “”) and N,N-diisopropylethylamine (70.51 mg, 545.59 mumol) were added to 10 mL of tetrahydrofuran, followed by addition of a solution of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide in ethyl acetate (50%, 231.34 mg, 363.73 mumol). After completion of the addition, the reaction solution was warmed up to 50C, and stirred for 1.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was added with 25 mL of saturated sodium bicarbonate solution, and extracted with ethyl acetate (50 mL*2). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by the silica gel column with elution system A to obtain the title compound 38 (75 mg, yield: 74.3%). MS m/z (ESI): 555.5 [M+1] 1H NMR (400 MHz, DMSO-d6) delta 10.84 (s, 1H), 9.05 (s, 1H), 9.14 (s, 1H), 8.27 (s, 1H), 7.79-7.77 (d, 1H), 7.72-7.69 (d, 1H), 7.59-7.52 (m, 2H), 7.41 (s, 1H), 7.34 (s, 1H), 7.30-7.24 (m, 4H), 7.19-7.17 (m, 1H), 6.30 (s, 1H), 6.03-5.99 (m, 1H), 3.52-3.50 (m, 4H), 3.48-3.44 (m, 1H), 2.85-2.75 (m, 2H), 1.25-1.18 (m, 3H).

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

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; YANG, Fanglong; WANG, Weimin; LI, Xiaodong; CHEN, Gang; HE, Feng; TAO, Weikang; (198 pag.)EP3486242; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 45676-04-8, 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 45676-04-8 as follows.

trans-diiodo(pyridine)(1-benzyl-3-tert-butylimidazol-2-ylidene)platinum(II)Step 1: 1-benzyl-3-tert-butylimidazolium chlorideA solution of 1-tert-butylimidazole, which was obtained according to A. J. Arduengo (2001) U.S. Pat. No. 6,177,575, (0.31 g; 2.5 mmol) in benzyl chloride (0.3 ml; 2.5 mmol) is stirred at room temperature for 48 h. The volatiles are then evaporated under vacuum. The residue obtained is triturated in ethyl ether and then filtered, thus making it possible to obtain 0.54 g (87%) of 1-benzyl-3-tert-butylimidazolium chloride whose characteristics are the following:1H NMR (300 MHz, CDCl3) delta ppm: 1.73 (s, 9H), 5.71 (s, 2H), 7.15 (m, 1H), 7.25 (m, 1H), 7.38 (m, 3H), 7.52 (m, 2H), 11.41 (s, 1H).

According to the analysis of related databases, 45676-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; US2011/172199; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem