Month: June 2021

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. 1122-28-7, name is 4,5-Dicyanoimidazole, A new synthetic method of this compound is introduced below., Safety of 4,5-Dicyanoimidazole

Example 19 2-Bromo-4,5-dicyanoimidazole (21) STR70 To 1.18 g (10 mmol) 4,5-dicyanoimidazole and 25 ml 0.1 M NaOH was added 1.8 ml Br2 (35 mmol). The mixture was stirred overnight at room temperature and then acidified with dilute HCl. The solid was filtered, rinsed with water and recrystallized from water to give 1.5 g of dicyanobromoimidazole 21 (yield 76.4%).: m.p. 147-149 C. (lit. 141-143 C.); Rf=0.65 (ethyl acetate_methanol=4:1); MS(EI): 198([M+2], 96%), 196 ([M+ ], 100%), 171 (28.5), 169 (29.2), 117 (27.4), 91 (19.0), 64 (20.6), 53 (22.4), 38 (18.8).

The synthetic route of 1122-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Isis Pharmaceuticals, Inc.; McGill University; US6160109; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5805-57-2, 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. 5805-57-2 name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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: The 4-chloro-6-methylpyrimidin-2-amine (1) (1 mmol)was dissolved in dry ethanol (5 ml). To this, (benzoxazol-2-yl)methanamine (3a)/(benzothiazol-2-yl)methanamine (3b)/(1H-benzimidazol-2-yl)methanamine (3c) (1.1 mmol) and acatalytic amount of methanesulfonic acid (0.2 ml) wereadded and refluxed for 4-6 h. After completion of thereaction, the reaction mixture was cooled and diluted withwater (15 ml). The separated solid was filtered, washed withwater, dried and recrystallized from 2-propanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1H-Benzo[d]imidazol-2-yl)methanamine, and friends who are interested can also refer to it.

Reference:
Article; Seenaiah, Dandu; Rekha, Tamatam; Padmaja, Adivireddy; Padmavathi, Venkatapuram; Medicinal Chemistry Research; vol. 26; 2; (2017); p. 431 – 441;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2301-25-9, 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 2301-25-9 as follows.

YB112 (162mg) was dissolved in THF solvent. After the reaction system was deaerated,10% Pd / C 20mg was added.A hydrogen balloon was added to the reaction system, and the reaction was allowed to proceed overnight.The reaction was filtered and washed with ethyl acetate, concentrated, and the target product YB126 (154 mg) was purified on a silica gel column.

According to the analysis of related databases, 2301-25-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Jia; Wang Zengtao; Zhang Shiyan; Zang Yi; Wang Peipei; Sun Dandan; Zhang Hanyan; (155 pag.)CN110818683; (2020); A;,
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. 116568-17-3, name is 1H-Benzo[d]imidazole-6-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H7N3O

EXAMPLE 3 1-(6-Chloropyrazin-2-yl)-1H-benzimidazole-5-carboxamide and and A mixture of 2, 6-dichloropyraz’rne (2.0 g, 13. 4 mmol), 1H-benzimidazole-5-carboxamide (2. 0 g, 12.3 mmol) and cesium carbonate (5. 6, 17. 2 mmol) in DMF (10 mL) was heated at 90C for 3h. The solution was cooled to RT and diluted with ethyl acetate (20 mL) and filtered. The solid material was washed with chloroform-methanol (20mL, 4:1) and the combined flitrates (at) concentrated in vacuo. The residue thus obtained (3. 02 g) was used without further purification. m/z (EI) 273/275 (M+1)

According to the analysis of related databases, 116568-17-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2005/54230; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 15813-09-9, These common heterocyclic compound, 15813-09-9, name is 4,5-Diiodo-1H-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.

To a solution of 4,5-diiodo-1H-imidazole (2.0 g, 5.9 mmol) in DMF (45 mL) was added NaH (60% in mineral oil, 356 mg, 8.91 mmol). The mixture was stirred at RT for 30 min, then treated with 2-(2-bromoethyl)isoindoline-1,3-dione (2.33 g, 8.91 mmol). The mixture was stirred at 60 C. overnight, then allowed to cool to RT and poured into water (30 mL). The precipitated solid was collected and dried to give the title compound as a white solid (1.72 g, 59%). MS (ES+): C13H9I2N3O2 requires: 493, found: 434 [M+H]+.

The synthetic route of 15813-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Board of Regents, The University of Texas System; LE, Kang; SOTH, Michael J.; JONES, Philip; CROSS, Jason Bryant; CARROLL, Christopher L.; MCAFOOS, Timothy Joseph; MANDAL, Pijus Kumar; US2019/298729; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic 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 641571-13-3, Application In Synthesis of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid

(E)-7-(5-amino-2-methylstyryl)thieno[3,2-d]pyrimidine-4-amine (100 mg, 0.354 mmol) and 3-(4-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl)benzoic acid (96 mg, 0.354 mmol) were dissolved in DMF (1.5 mL), HATU (404 mg, 1.063 mmol) and TEA (0.248 mL, 1.7728 mmol) were added thereto and stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried with MgSO4, filtered and concentrated. The resulting mixture was purified by silica gel chromatography to obtain the title compound (142 mg, 75% yield). MS m/z [M+1] 535.15.

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; HANMI SCIENCE CO., LTD.; CATHOLIC UNIVERSITY INDUSTRY ACADEMIC COOPERATION FOUNDATION; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; Son, Jung Beom; Jung, Seung Hyun; Choi, Wha ll; Jung, Young Hee; Choi, Jae Yul; Song, Ji Yeon; Lee, Kyu Hang; Lee, Jae Chul; Kim, Eun Young; Ahn, Young Gil; Kim, Maeng Sup; Choi, Hwan Geun; Sim, Tae Bo; Ham, Young Jin; Park, Dong-sik; Kim, Hwan; Kim, Dong-Wook; US2013/53370; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 25676-75-9, A common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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.

A solution of (4-(aminomethyl)phenyl)boronic acid hydrochloride (0.85 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.37 g), 4-bromo-1-methyl-1H-imidazole (0.80 g) and sodium carbonate (1.20 g) in DME (12 mL)-water (3 mL) was stirred under an argon atmosphere at 120C for 6 hr under microwave irradiation. To the reaction mixture was added 6N hydrochloric acid, and the mixture was washed with ethyl acetate. The aqueous layer was separated, neutralized with 8N aqueous sodium hydroxide solution, and concentrated under reduced pressure. The residue was washed with THF, and the obtained organic layer was concentrated. The residue was crudely purified by NH silica gel chromatography (hexane-ethyl acetate). The obtained crudely purified product was diluted with ethyl acetate, 4N hydrogen chloride ethyl acetate solution (1 mL) was added, and the resulting precipitate was collected by filtration, and dried to give the title compound (0.12 g). 1H NMR (300 MHz, DMSO-d6) delta 3.90 (3H, s), 4.05-4.10 (2H, m), 7.63 (2H, d, J = 8.3 Hz), 7.90 (2H, d, J = 8.3 Hz), 8.20 (1H, d, J = 1.1 Hz), 8.42 (3H, brs), 9.19 (1H, s), 1H not detected.

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); 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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,1′-Thiocarbonyldiimidazole

A solution of (2R)-3-PHENYL-1-PIVALOYLOXY-2-PROPYL amine (19-1, LMMOL) and ET3N (1 mmol) in DMF (1 mL) was added dropwise into the pre-dissolved solution of 1,1- thiocarbonyl diimidazole (1.2 mmol) in DMF (2 mL) at 50 C over 1 min. The mixture was stirred for 1 min. at 50 C and then for 10 min. at room temperature. The mixture was directly purified by column chromatography using EtOAc: hexanes (1: 5) as eluant to afford (2R)-3-phenyl-1-pivaloyloxy-2-propyl isothiocyanate (19-3, SU-684). 89% yield, colorless oil. H NMR (CDC13) 5 7.15-7. 35 (M, 5 H), 4.22 (dd, 1 H, J= 2. 7,10 Hz), 4.02-4. 12 (m, 2 H), 2.94 (d, 2 H, J= 6. 3 HZ), 1.25 (s, 9 H)

According to the analysis of related databases, 6160-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIGITALBIOTECH CO., LTD.; WO2005/3084; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2851-13-0, name is N,N-Dimethyl-1H-benzo[d]imidazol-2-amine, molecular formula is C9H11N3, 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. Recommanded Product: 2851-13-0

Scheme 3 exemplifies a method of forming compounds of Formula I. Chloro purines (4) (1 mmol) can be coupled with R3-H (for example, wherein R3 is benzimidazol-1-yl) (1.03-1.30 mmol), under Buchwald conditions, for example tris(dibenzylideneacetone)-dipalladium(0) (0.02-0.05 mmol), XPhos (0.10-0.20 mmol), cesium carbonate (2 mmol) in DMF (7-10 mL) with heating under microwave at 140-150 C. for 30 minutes to form purines of Formula I. Formula I purines can be further purified by diluting with EtOAc, filtering the contents of the reaction, concentrating and purifying with flash chromatography or reverse phase HPLC. Formula I purines can be further derivatized in subsequent transformations to functionalize R1, for example by deprotecting any protected functional groups (for example deprotecting BOC-protected amine groups followed by additional steps, such as reductive amination, amide coupling or acylation to form additional compounds of Formula I.Example 131 1-(3-(2-(2-(dimethylamino)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yloxy)azetidin-1-yl)-2-methylpropan-1-one 131 The compound was prepared from 1-(3-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yloxy)azetidin-1-yl)-2-methylpropan-1-one and N,N-dimethyl-1H-benzo[d]imidazol-2-amine following General Procedure of Buchwald coupling shown in Scheme 3. 1H NMR (400 MHz, CDCl3) delta 8.29 (s, OH), 7.58 (d, J=7.5 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.15 (dd, J=11.0, 4.3 Hz, 1H), 7.01 (dd, J=10.1, 4.2 Hz, 1H), 5.58-5.45 (m, 1H), 4.60 (d, J=7.2 Hz, 2H), 4.53-4.39 (m, 2H), 4.31 (d, J=9.6 Hz, 1H), 4.19 (s, 5H), 3.88-3.74 (m, 4H), 3.65 (s, 2H), 3.60 (s, 1H), 3.17 (s, 1H), 2.98 (s, 4H), 2.56-2.42 (m, 1H), 1.14 (d, J=6.8 Hz, 5H). LCMS: M+H+=520.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2851-13-0, its application will become more common.

Reference:
Patent; Li, Jun; Safina, Brian; Sutherlin, Daniel P.; Sweeney, Zachary; US2012/15931; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 147403-65-4, name is Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, 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 147403-65-4, Recommanded Product: Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

Example 4Methyl 2-ethoxy- 1 -((2′-(5-oxo-4,5-dihydro- 1 (2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)- 1H- benzo[< ]imidazole-7-carboxylate of formula la l ,8-Diazabicyclo[5.4.0.]undec-7-ene (DBU; 0.1 g, 0.65 mmol) was added dropwise to a mixture of methyl 2-methoxy- l -((2'-((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)- lH- benzo[i ]imidazole-7-carboxylate (of formula Va; 0.22 g, 0.5 mmol), the corresponding solvent (3 ml) and carbonyldiimidazole (0.1 g, 0.6 mmol) in a reaction vial under stirring and the mixture was stirred at the room temperature for 3 hours. Then, the content of the vial was poured into water ( 10 ml) and, after acidification with acetic acid, the separated solids were aspirated and washed with water. The yields and purity of the products are summarized in Table I. Table I - Yield and purity of the product of Example 4* - Also contains 40.4 % of the starting compound of formula Va; ** - Carbonyl-di- 1 ,2,4- triazole was used instead of carbonyldiimidazole. 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, Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, other downstream synthetic routes, hurry up and to see. Reference:
Patent; ZENTIVA, K.S.; RADL, Stanislav; WO2012/139536; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem