Tag: M.W=100-200

Reference of 4857-06-1, The chemical industry reduces the impact on the environment during synthesis 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

Example 32-5 Synthesis of 1-((2-(trimethylsilyl)ethoxy)methyl)-2-chloro-1H-benzo[d]imidazole General Method XE To a solution of 2-chloro-1H-benzo[d]imidazole (1 g, 6.6 mmol.) in dry DMF (10 mL) was added sodium hydride (60%, 0.26 g, 6.5 mmol.) at room temperature under nitrogen atmosphere. 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl, 1.14 g, 6.8 mmol.) was added dropwise after the solution stirred for 1.5 h. The resulting mixture stirred overnight and then quenched with water and extracted with ethyl acetate (30 mL*3). The combined organic layers was washed with water, dried over sodium sulfate and concentrated to give a residue. The residue was purified by column chromatography to give 1-((2-(trimethylsilyl)ethoxy)methyl)-2-chloro-1H-benzo[d]imidazole (1.13 g, 60.8%).

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

Reference:
Patent; InterMune, Inc.; US2009/269305; (2009); 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. 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 614-97-1

To a solution of compound DD2 (24.5 mmol) in CH3CN (65 mL) was added di-tertbutyl dicarbonate (5.89 g, 27.0 mmol), triethylamine (3.76 mL, 27.0 mmol) and 4-dimethylamino pyridine (300 mg, 2.45 mmol) and the resulting reaction was heated to 80 C. and allowed to stir at this temperature for 1.5 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo, and the residue obtained was purified using flash column chromatography (silica gel, EtOAc/Hexanes 5-20%) to provide a mixture of isomeric compounds DD3 and DD4 (5.38 g, 94.3% yield over steps A and B).

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; Schering Corporation; US2010/322901; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89830-98-8, A common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

[0345] A mixture of Example 13a (600 mg, 5.55mmol) and Example 13b (400 mg, 1.65 mmol) Cul (45 mg, 0.24 mmol), K3P04 (1 g, 4.7 mmol), 4,7-Dihydroxy-l,10-phenanthroline (cas: 3922-40-5, 90 mg, 0.42 mmol), TBAB (386 mg, 1.2 mmol) in H20 (10 mL) under N2 was heated at 100 oC overnight. After cooling, filtered and concentrated under reduced pressure to give the crude and further purified by silica gelchromatography to give the product 200 mg as yellow solid. LCMS [M+1] + =271.0

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 128293-62-9, 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. 128293-62-9, name is Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To Im-3 (0. 38 g) in DMF (8 mL) and Hunig’s base (2ML) was added ditert-butyl dicarbonate (0.7 ml) and the mixture stirred at 60 C for 3 hr. It was then cooled to room temperature and brine (6 ML) and ethyl ether (6 ML) were added. The ether layer was extracted with 10% citric acid, brine, saturated sodium bicarbonate, and brine (10 mL each). The ether layer was then dried over sodium sulfate and evaporated under vacuum. NAOH (1M, 5mL) in methanol was then added and solution stirred at 60 C for 1 hr. The mixture was then cooled to 0 C and neutralised with 1M HC1 to pH 2 at which a white gel was formed. The gel was collected by gravity filtration and washed with water pH=6 before it was freeze dried to yield the product as a white powder. Yield (0.41 g, 76%). 1H NMR (DMSO): 6 9.45 (bs, 1H, NH), 7.21 (bs, 1H), 3. 86 (s, 3H), 3.67 (bs, 1H, OH), 1.4 (s, 9H).

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, Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF WESTERN SYDNEY; WO2005/33077; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, name is 5-Iodo-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. Application In Synthesis of 5-Iodo-1H-imidazole

General procedure: Method A: In a20 mL microwave Biotage tube, a mixture of 4-iodo-1H-imidazole(1a) (0.194 g, 1.0 mmol), a boronic acid 2(2.0 mmol), CsF (0.456 g,3.0 mmol), PdCl2(dppf)(0.041 g, 0.05 mmol) and BnEt3NCl(0.011 g, 0.05 mmol) in toluene(7 mL) and water (7 mL)was purged with argon andheated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3a-3i and 3k-3o in yields ranging from 40 to 91%. Time and temperaturereactions were collected in Table 1.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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. Formula: C5H6N2O

General procedure: Into a round-bottom flask, equipped with a condenser and containing a suspension of 6 (2.0 mmol, 1 equiv) in ethanol (15 mL), was introduced the aldehyde (2.2 mmol, 1.1 equiv) and two drops of concentrated HCl. The reaction mixture was stirred and heated at 80 C for approximately 18 h. While cooling down the crude mixture in an ice bath, a precipitate was formed which was subsequently filtered off and washed with both water (2 ¡Á 10 mL) and cold ethanol (3 ¡Á 15 mL). The solid residue was then dried in vacuum at 60 C.

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

Reference:
Article; Pevet, Isabelle; Brule, Cedric; Tizot, Andre; Gohier, Arnaud; Cruzalegui, Francisco; Boutin, Jean A.; Goldstein, Solo; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2517 – 2528;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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. name: 1-Methyl-1H-imidazole-4-sulfonyl chloride

Example 227 1-methyl-N-[3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-phenoxyphenyl]-1H-imidazole-4-sulfonamide [1006] The product from Example 225C (0.044 g, 0.15 mmol), 1-methyl-1H-imidazole-4-sulfonyl chloride (0.033 g, 0.180 mmol) and triethylamine (0.042 mL, 0.30 mmol) were combined in dichloromethane (0.75 mL), heated at 60 C. for 2 hours and concentrated. Purification by chromatography (silica gel, 0-3% methanol in dichloromethane) afforded the title compound (0.038 g, 56%). 1H NMR (300 MHz, DMSO-d6) delta 10.21 (s, 1H) 7.84 (d, J=1.36 Hz, 1H) 7.75-7.78 (m, 2H) 7.48 (dd, J=9.49, 2.71 Hz, 1H) 7.25-7.35 (m, 2H) 7.21 (d, J=2.71 Hz, 1H) 7.09 (dd, J=8.82, 2.71 Hz, 1H) 7.03 (t, J=7.46 Hz, 1H) 6.89 (d, J=8.82 Hz, 1H) 6.83 (d, J=7.80 Hz, 2H) 6.37 (d, J=9.49 Hz, 1H) 3.67 (s, 3H) 3.43 (s, 3H). MS (ESI+) m/z 437 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 137049-00-4, its application will become more common.

Reference:
Patent; HUBBARD, Robert D.; WANG, Le; PARK, Chang H.; SUN, Chaohong; McDANIEL, Keith F.; PRATT, John K.; SOLTWEDEL, Todd N.; WENDT, Michael D.; HOLMS, John H.; LIU, Dachun; SHEPPARD, George S.; US2013/331382; (2013); 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., Computed Properties of C7H6N4S

To a stirred solution of 6.8 g (35.0 mmol) of (5) in 150 mL of CH2Cl2 at RT was added 6.4g(35mmol) of l .l’-thiocarbonyldiimidazole. The mixture was stirred at room temperature for 15 minutes and then evaporated under reduced pressure and the residue was passed through a short pad of silica gel, eluting with a gradient of hexane/EtOAc, which gave (5-Isothiocyanato-2-methoxy- phenyl)-methyl-propyl-amine (6) (7.85g, 95%) as a colorless oil.

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; SYNTA PHARMACEUTICALS CORP.; WO2007/140002; (2007); A2;,
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. 405173-97-9, name is 2-(2-Chloroethyl)-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H9ClN2

General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 – 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 – 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion to general procedure 7, -(pyridin-2-ylmethyl)-4H,5H,6H,7H-thieno[2,3-c]pyridine-3- carboxamide (450) (65 mg, 0.24 mmol), K2C03 (49 mg, 0.36 mmol) and 2-(2-chloroethyl)-1 H- benzimidazole (47 mg, 0.26 mmol) in acetone (3 ml) at room temperature for 24 h, followed by the addition of DMF (5 ml), Nal (39 mg, 0.26 mmol), DIPEA (0.16 ml, 0.95 mmol) and 2-(2-chloroethyl)-1 H- benzimidazole (94 mg, 0.52 mmol) at room temperature for 72 h, gave the title compound (9 mg, 9%) as an orange solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.17 (s, 1 H), 8.75 (t, J = 6.0 Hz, 1 H), 8.50 (d, J = 4.2 Hz, 1 H), 7.94 (s, 1 H), 7.75 (td, J = 7.7, 1.8 Hz, 1 H), 7.46 (s, 2H), 7.31 (d, J = 7.8 Hz, 1 H), 7.28- 7.23 (m, 1 H), 7.10 (dd, J = 6.0, 3.1 Hz, 2H), 4.48 (d, J = 6.0 Hz, 2H), 3.71 (s, 2H), 3.05 (t, J = 7.2 Hz, 2H), 2.96 (t, J = 7.2 Hz, 2H), 2.82 (d, J = 5.3 Hz, 2H), 2.75 (t, J = 5.7 Hz, 2H) HPLCMS (Method B): [m/z]: 418.2 [M+H]+

The synthetic route of 405173-97-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 24134-09-6, These common heterocyclic compound, 24134-09-6, name is 5-Bromo-1,2-dimethyl-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.

A solution of n-BuLi (2.5 M in hexanes, 0.24 mL, 0.6 mmol) was added dropwise by syringe to a solution of 5-bromo-1,2-dimethyl-1H-imidazole (107.8 mg, 0.616 mmol) in dry THF (6 mL) in a dry ice-acetone bath. After 1-2 minutes, (4-chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (0.217 g, 0.512 mmol, Intermediate 46: step b) in dry THF (2 mL) was added to the mixture via syringe. After 5 minutes, the reaction was removed from the cold bath and was allowed to warm to ambient temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride. Water was added and the aqueous mixture was extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM) to provide the title compound. 1H NMR (400 MHz, CDCl3) delta 8.23 (d, J=2.2 Hz, 1H), 7.63 (d, J=8.7 Hz, 1H), 7.37 (dd, J=8.8, 2.1 Hz, 1H), 7.30-7.25 (m, 2H), 6.97-6.92 (m, 2H), 6.19 (s, 1H), 6.12 (s, 2H), 4.22 (s, 2H), 4.07 (s, 3H), 3.37 (s, 6H), 2.24 (s, 6H); MS m/e 520.2 [M+H]+.

Statistics shows that 5-Bromo-1,2-dimethyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 24134-09-6.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem