Month: August 2021

Related Products of 32673-41-9,Some common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

(iii) (1-trityl-1H-imidazol-4-yl)methanol Trityl chloride (2.1 g) was added to a mixture of 4-hydroxymethyl imidazole hydrochloride (1.0 g) and triethylamine (3.1 ml) in DCM (25 ml) at RT. Further DCM (20 ml) was added and the mixture stirred for 18 h. The precipitate was filtered, washed with water and then ether to give the subtitle compound (2.0 g). 1H NMR DMSO-d6: delta 7.44-7.36 (9H, m), 7.29 (1H, s), 7.10-7.08 (6H, m), 6.72 (1H, s), 4.87 (1H, t), 4.33 (2H, d).

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

Reference:
Patent; ASTRAZENECA AB; US2008/293775; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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.

PREPARATION 321H-imidazole-2-carboxylic acid21.75 mL (43.5 mmol) of a 2M solution of lithium hydroxide in water were added to a solution of 1.22 g (8.71 mmol) of ethyl 1H-imidazole-2-carboxylate (ref) in a mixture of tetrahydrofurane (20 mL) and water (20 mL).The reaction mixture was warmed up to reflux, and stirred for 1.5 hours.The reaction mixture was cooled to room temperature and the solvent was evaporated under vacuum.The crude residue (3.0 g) was used in next step without further purification.LRMS (m/z): 113 (M+1)+.

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Almirall, S.A.; EP2518070; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5805-57-2, 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. 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of C-(1H-benzoimidazol-2-yl)-methylamine (200 mg, 1.0 mmol) and triethylamine (139 muL, 1 mmol) in CH2Cl2 (5 mL) (Boc)2O (420 mg, 2 mmol) is added, and the reaction mixture is stirred at r.t. for 1 h. After solvent evaporation, the crude product is purified by flash chromatography (1:1 EtOAc-Et.petr., Rf=0.5), to give 2-(tert-butoxycarbonylamino-methyl)-benzoimidazole-1-carboxylic acid t-butyl ester as a yellow oil (246 mg, 0.71 mmol) in 71.% yield. 1H NMR (CDCl3, 200 MHz) epsilon 7.96-7.91 (m, 1H), 7.72-7.67 (m, 1H), 7.35-7.26 (m, 2H), 5.85 (br, 1H), 4.80 (d, 2H), 1.71 (s, 9H), 1.48 (s, 9H) ppm. This intermediate (175 mg, 0.5 mmol) is dissolved in anhydrous THF (10 mL) and PPh3 (330 mg, 0.5 mmol) and 4-pentynol (46 muL, 0.5 mmol) are added. Then, after cooling to 0 C., DIAD (100 muL, 0.5 mmol) is slowly added, and after 15 min at 0 C., the mixture is heated under microwave irradiation at 110 C. for 1 h. Following flash chromatography purification (5:1 EtOAc-petr. et.), compound 10 is obtained in 64% yield. 1H NMR (CDCl3, 200 MHz) delta 7.95-7.90 (m, 1H), 7.71-7.67 (m, 1H), 7.34-7.26 (m, 2H), 5.79 (d, 2H), 2.30-2.20 (m, 2H), 2.03 (s, 1H), 1.95-1.92 (m, 2H), 1.80 (t, 2H), 1.71 (s, 9H), 1.47 (s, 9H) ppm.

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

Reference:
Patent; UNIVERSITA’ DEGLI STUDI DI FIRENZE; Guarna, Antonio; Menchi, Gloria; Cini, Nicoletta; Trabocchi, Andrea; Pupi, Alberto; Bottoncetti, Anna; Raspanti, Silvia; Calorini, Lido; US2013/40964; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 693-98-1, 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. 693-98-1 name is 2-Methyl-1H-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.

General procedure: In a typical experiment, imidazole (1.2 mmol), aryl halide (1.0 mmol), catalyst, and base (2.0 mmol) were added to a hydrothermal reactor (20 mL). The mixture was heated to the desired temperature with stirring. After the completion of the reaction and cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate (3 × 15mL). The combined organic extracts were dried with anhydrous Na2SO4 and the obtained product was purified by column chromatography on silica gel using dichloromethane: methanol (100:1, v/v) as the eluent.

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

Reference:
Article; Huang, Qiang; Zhou, Limei; Jiang, Xiaohui; Qi, Xiaolong; Wang, Zhonghua; Lang, Wencheng; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 35; 11; (2014); p. 1818 – 1824;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, 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. Product Details of 33543-78-1

the solution of 5.3 g of ethyl imidazole-2-carboxylate in 20 ml of anhydrous dimethylformamide is added dropwise over 30 minutes at a temperature close to 20° C. to a suspension of 2.43 g of 50percent sodium hydride in 60 ml of anhydrous dimethylformamide kept under a nitrogen atmosphere. After stirring for 15 minutes, a solution of 9.26 g of 2-bromo-4-fluoro-1-indanone in 25 ml of anhydrous dimethylformamide is added dropwise over 30 minutes at a temperature close to 20° C. The mixture is stirred for 18 hours, and then after slowly adding 30 ml of water, poured into 200 ml of distilled water and extracted four times with 100 ml of dichloromethane. The organic phases are pooled, washed with 600 ml of distilled water, dried over anhydrous sodium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 45° C. The residue thus obtained is purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar) with ethyl acetate as eluent. 1.2 g of ethyl 1-(4-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 145° C.

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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.

Synthesis of 1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4-carbonitrile To a stirred solution of 2-chloro-3-methoxy-5-nitropyridine (1.5 g, 79.78 mmol) in DMSO (15 mL) under an argon atmosphere were added potassium carbonate (4.4 g, 31.91 mmol) and 1H-imidazole-4-carbonitrile (890 mg, 9.57 mmol) at room temperature. The reaction mixture was stirred at 50° C. for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL). The obtained solid was filtered and dried in vacuo to obtain 1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4-carbonitrile (1.1 g, 56percent) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.97 (s, 1H), 8.86 (s, 1H), 8.67 (s, 1H), 8.47 (s, 1H), 4.11 (s, 3H); LCMS: 245.8 (M+1); (column; X-Select CSH C-18 (50*3.0 mm, 3.5 m); RT 2.96 min. 0.05percent aq TFA: ACN; 0.80 mL/min); TLC: 40percent EtOAc:hexane (Rf: 0.4).

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 89830-98-8, 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. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Potassium hydroxide (73.9 mg, 1.3 177 mmol%) and tert-butyl N-[(2R)-2-bromopropyl]carbamate (230.1mg, 0.96634 mmol) are added to a solution of 4-cyclopropyl-1H-imidazole (100 mg, 0.087849 mmol) in DMSO (2 mL) at 0 C. The mixture is stirred at room temperature for 65 hours. The reaction is quenched with water and extracted with EtOAc (3x). The organic extracts are washed with saturated NaC1 (3x), dried over Na2SO4, filtered, and concentrated to dryness. The residue is purified bysilica gel flash chromatography with 4% MeOH in DCM to give the title compounds as a mixture of 2 regioisomers (112 mg, 22.82%) and as a yellow oil. ES/MS (m/z): 266 (M+ 1). TFA (2 mL, 26.45 mmol) is added to racemic tert-butyl N-[2-(4-cyclopropylimidazol- i-yl)-i -methyl-ethyl] carbamate and to racemic tert-butyl N- [2-(5 -cyclopropylimidazol-1-yl)-1-methyl-ethyl]carbamate (112 mg, 0.2005 mmol) in DCM(10 mL) at room temperature. The mixture is stirred at room temperature for 1 hour andis concentrated to give the crude title compounds as a mixture of regioisomers (69.8 mg,100%) as a yellow oil. ES/MS (m/z): 166 (M+1). Sodium triacetoxyborohydride (56.9 mg, 0.260 mmol) is added to a solution of racemi c-i -(4-cyclopropylimidazol -1 -yl)propan-2-amine and racemic- 1 -(5- cyclopropylimidazol- 1 -yl)propan-2-amine (69.7 mg, 0.200 mmol) and tert-butyl N-(2- oxoethyl)carbamate (33.6 mg, 0.200 mmol) in DCM (5 mL) and acetic acid (15.6 mg, 0.260 mmol) at room temperature. The mixture is stirred at room temperature for 18 hours. The reaction is quenched by the addition of saturated NaHCO3. The mixture is extracted with DCM (3x), the organic extracts are dried over Na2SO4, filtered, and concentrated to give the crude title compound as a mixture of regioisomers (130 mg, 100%) as a yellow oil. ES/MS (m/z): 309 (M+1).

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

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; LIU, Lian Zhu; WANG, Xiaoqing; WILEY, Michael Robert; (34 pag.)WO2019/50794; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 405173-97-9, name is 2-(2-Chloroethyl)-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 405173-97-9, Quality Control of 2-(2-Chloroethyl)-1H-benzo[d]imidazole

Similarly, using 2-(2-chloroethyl)benzimidazole, the product is N-methyl-N’-[2-(2-(2-benzimidazolyl)ethylamino)-ethyl]thiourea.

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

Reference:
Patent; Smith Kline & French Laboratories Limited; US3950353; (1976); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15469-97-3, name is 1-Trityl-1H-imidazole, 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. Recommanded Product: 15469-97-3

n-butyllithium (1.6M hexane solution, 6.9ml) was added dropwise to a solution of 1-tritylimidazole (3.10g) in THF (80mL) under ice-cooling in the argon atmosphere. After stirred at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52mL) was added. After stirred for 1.5 hours under ice-cooling and at room temperature for 1 hour, water was added to the reaction solution, followed by ethyl acetate. The extract was washed with water and a brine, dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified by subjecting to the silica column gel chromatography (eluent; ethyl acetate_hexane= 1:1) to obtain the title compound (1.402g) as a pale yellow oil. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J = 2.8Hz, 18.0Hz), 3.08 (1H, dd, J = 5.4Hz, 9.8Hz), 3.21 (1H, dd, J = 5.4Hz, 9.8Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J = 1.4Hz), 6.93 (1H, d, J = 1.4Hz), 7.0-7.4 (20H, m).

The synthetic route of 15469-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1350792; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, 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 72-40-2, COA of Formula: C4H7ClN4O

[0161] Synthesis of 2-methyl-N-(naphthalen-2-yl)-9H-purin-6-amine.; [0162] This compound is synthesized according the scheme above and is characterized as follows: melting point: 85 0C. 1H NMR (300 MHz, DMSO-d6): d 10.45 (brs, NH, exchangeable), 8.65 (s, IH), 8.57 (s, IH), 7.91-7.99 (m, 4H), 7.46-7.56 (m, 2H), 2.71 (s, 3H); MS m/z : 276.1 (M + H+).

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; BOARD OF REGENTS, UNIVERSITY OF TEXAS SYSTEM; UNIVERSITY OF WASHINGTON; WO2009/82691; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem