Category: imidazoles-derivatives

Reference of 401567-00-8, 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. 401567-00-8 name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, 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: 4.1.6. General procedure E: removal of SEM group To a solution of SEM-protected compound (1.0 equiv) in THFwas added TBAF (3.0 equiv, 1 M in THF). The mixture was reuxedfor 11-20 h, then cooled to room temperature, and concentratedunder reduced pressure. The residue was puried by silica gel col-umn chromatography or PTLC to afford the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Okazaki, Shogo; Noguchi-Yachide, Tomomi; Sakai, Taki; Ishikawa, Minoru; Makishima, Makoto; Hashimoto, Yuichi; Yamaguchi, Takao; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5258 – 5269;,
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. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., Formula: C3H3BrN2

CS2CO3 (568 mg, 1.74 mmol) was added to a solution of Cul (16.2 mg, 85.1 pmol) and l,l,l-tris(hydroxymethyl)ethane (10.2 mg, 85.1 iimol) in anhydrous l,4-dioxane (45 mL) and anhydrous DMF (5 mL) in a sealed tube while N2 was bubbling. After 10 min, 4-chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (130 mg, 0.85 mmol) and 2-bromo- lH-imidazole [16681-56-4] (150 mg, 1.02 mmol) were added. The reaction mixture was stirred at room temperature for 10 min, and at 110 C for 4 days. The mixture was filtered through Celite and the solvents were evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 60:40) to afford 1-151 (36 mg, 18%, 35% purity).

The synthetic route of 16681-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1792-40-1, The chemical industry reduces the impact on the environment during synthesis 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

In 100mL round bottom flask, 2-methyl-5-nitrobenzimidazole (0. 46g, 0. 0026mol), potassium carbonate (0 · 72g, 0 · 0052mol) and the amount of acetonitrile, temperature control The reaction was stirred 50 C 0 · 5h, cooled to room temperature, was added II-2 (1. 00g, 0. 0026mol) was heated to 80 C and stirring continued, until thin layer chromatography the reaction was completed track, and then by concentration, extraction, column chromatographic separation, recrystallization, and dried to give square 0. 49g Compound 1-30, yield 33.4%.

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-Methyl-5-nitro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Southwest University; Zhou, Chenghe; Zhang, Ling; (39 pag.)CN104086534; (2016); B;,
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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-imidazole-4-carbaldehyde

N-Boc-piperazine (0.470 g, 2.50 mmol, 1.1 eq) was dissolved in DCM (6.2 mL). To this solution, 1-methyl-1H-imidazole-4-carboxaldehyde (0.250 g, 2.27 mmol, 1 eq) was added followed by chlorotitanium triisopropoxide (1.19 mL, 5.0 mmol, 2.2 eq). The resulting solution was stirred at room temperature for 10 min before the addition of sodium triacetoxyborohydride (2.40 g, 11.3 mmol, 5 eq). The mixture was stirred at room temperature for 17 h and was diluted with EtOAc (12 mL). It was then poured into ammonia (35% sol. in H2O, 6 mL) and the resulting mixture filtered and washed with EtOAc. The organic phase was washed with H2O dried (MgSO4) and the solvent removed in vacuo. The crude material was purified by column chromatography on a Biotage SP1 system eluting with methanol (1-8%) in dichloromethane to give the title compound as a clear oil (0.390 g, 62%); 1H-NMR (500 MHz, CDCl3): delta 1.46 (s, 9H, C(CH3)3), 2.48 (t, J=5.0 Hz, 4H, piperazine N(CH2)2), 3.45 (t, J=5.0 Hz, 4H, piperazine N(CH2)2), 3.52 (s, 2H, NCH2), 3.66 (s, 3H, imidazole Me), 6.80 (s, 1H, imidazole 5-H), 7.38 (s, 1H, imidazole 2-H); LC (Method B)-MS (ESI, m/z): 281 [(M+H+)].

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 17289-26-8.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 40197-20-4, 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. 40197-20-4, name is 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

5-bromo-1H-benzo[d]imidazole-2-carboxylic acid (1 eq) was dissolved in DMF, to which morpholine (1.01 eq),1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 1.1 eq), 1-hydroxybenzotriazole (HOBT, 1.1 eq), and TEA (3 eq)were added stepwise, followed by stirring at room temperature for overnight. The reaction was terminated with a smallamount of water, followed by extraction using water and EtOAc. The small amount of water remaining in the organiclayer was dried over anhydrous MgSO4. The solvent was eliminated by vacuum distillation, followed by vacuum drying.Then, a target compound was obtained by column separation with the yield of 29%. 1H NMR (300MHz, CDCl3) delta 7.77-7.65 (m. 1H), 7.43-7.41 (m, 2H), 3.85-3.82 (m, 8H).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); KIM, Eunhee; YOO, Sung-Eun; KANG, Nam Sook; KOO, Tae-Sung; PARK, Min-Young; KIM, Young-Hoon; BAE, Hyun-Ju; KIM, Jin-Woo; IN, Tae-Kyu; JOO, Choun-Ki; (101 pag.)EP3176163; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 57090-88-7,Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (3.2 g, 11.98 mmol), 1 H-imidazole-4-carbonitrile (2.017g, 14.37 mmol) and ethyl-diisopropyl-amine (8.4 ml, 47.9 mmol) in 10 ml of dioxane is heated to reflux for 24 hours. The solution is allowed to cool to room temperature and evaporated. The residue is chromatographed on silica gel using gradients of dichloromethane and methanol to give 0.36 g (1.05 mmol, 8.8percent) of amorphous 5-(4-cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoicacid methyl ester, ES-MS: m/z 341 [M+Hf.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole-4-carbonitrile, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/10591; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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: C6H6N4O2S

(I) 1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose (3)(1.0 g; 4.0 mmol) was dissolved in DMF (20 ml), cooledat 0 C and under N2-atmosphere NaH (0.14 g; 6.0 mmol)was added to the solution. The suspension was stirred for30 min and cooled to -35 to -40 C. After N?,N-sulfonyldiimidazole(1.2 g; 6.0 mmol) in DMF (12 ml) was droppedto the reaction mixture and stirred for 30 min again at-40 C. MeOH was added (0.8 ml) to the solution andstirred for 30 min at -40 C. The solution was poured intoice-water (200 ml). The precipitate was filtered, washedwith cold water to get the white crystalline product 11(1.2 g; 80%). M.p.: 97-98 C; lit. m.p. (Vatle and Hanessian1996): 98-99 C; Rf = 0.70 (EtOAc-hexane 1:1).(II) From 3 (25.0 g; 96.0 mmol) the yield was 84% (31.5 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7189-69-7, its application will become more common.

Reference:
Article; Nagy, Adrienn; Csordas, Barbara; Zsoldos-Mady, Virag; Pinter, Istvan; Farkas, Viktor; Perczel, Andras; Amino Acids; vol. 49; 2; (2017); p. 223 – 240;,
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. 1072-63-5, name is 1-Vinyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H6N2

1-vinyl imidazole (5.18 g, 55 mmol) and 1,6-dibromohexane (2.79 g, 22 mmol) were dissolved in methanol (50 mL) in a round-bottom flask fitted with a condenser and N2 bubbler. Subsequently, the mixture was stirred at 80 C for 48 h under a nitrogen atmosphere. After then, the reaction mixture was precipitated from diethyl ether (150 mL), and recrystallized twice from diethyl ether. The products were dried under vacuum for 24 h at R.T. [C6VIm]Br was obtained as white solid. Yield: 71%. [C6VIm]Br: 1H-NMR (D2O, 400 MHz, ppm):7.57 (1H, s); 7.37 (1H, s); 6.93 (1H, m); 5.60 (1H, d); 5.22 (1H, d); 4.04 (2H, t); 1.70 (2H, s); 1.17 (2H, s).1H-NMR (DMSO, 400 MHz, ppm): 9.66 (1H, s); 8.24 (1H, t); 7.99 (1H, t); 7.33 (1H, m); 5.99 (1H, m);5.43 (1H, m); 4.22 (2H, t); 1.83 (2H, d); 1.31 (2H, s). 13C-NMR (DMSO, 100 MHz, ppm): 135.36,128.88, 123.31, 119.23, 109.04, 49.02, 28.80, 24.77. ESI-MS (m/z): calcd. for C16H24N4Br2: 432.2,found: 432.2. Elemental analysis (%): Calculated: C, 44.46; H, 5.60; N, 12.96; Br, 36.98. Found: C,42.94; H, 5.36; N, 12.50; Br, 39.20. M.P.: 219 C.

The synthetic route of 1072-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jing; Liu, Jingjiang; Zuo, Yong; Wang, Rongmin; Xiong, Yubing; Molecules; vol. 20; 9; (2015); p. 17378 – 17392;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 36947-68-9, These common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-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.

General procedure: A solution of imidazole 4-13, benzimidazole 40, 41, pyridoimidazole 42 or benzotriazole 43 (23 mmol) in dry DMF (15 mL) and K2CO3 (11.5 mmol) was stirred for 10 min at 0-5 C, under nitrogen atmosphere. After this time, appropriate 1-aryl-2-bromo-ethanone 18-21 (23 mmol) was added and the mixture was stirred for 1.5 h then poured into ice water. The resulting crude material was extracted with dichloromethane (3 × 50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure; the obtained residue were purified by means of flash chromatography performed using silica gel 60 (230-400 mesh) and a mixture of ethyl acetate/methanol 8:2 v/v or dichloromethane/methanol 9.5/0.5 v/v (only for purification of 25 and 26, 49 and 51, 50 and 52, respectively) as eluent.

Statistics shows that 2-Isopropyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 36947-68-9.

Reference:
Article; Salerno, Loredana; Modica, Maria N.; Romeo, Giuseppe; Pittala, Valeria; Siracusa, Maria A.; Amato, Maria E.; Acquaviva, Rosaria; Di Giacomo, Claudia; Sorrenti, Valeria; European Journal of Medicinal Chemistry; vol. 49; (2012); p. 118 – 126;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, 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 1-Methyl-1H-imidazole-2-carboxylic acid

A mixture of 5-methyl-2- (2-pyridyl)-5 ,6,7 ,8-tetrahydropyrido [4,3 d]pyrimidine trifluoroacetic acid salt (100 mg, 442 imol, the product of step 2 in Example 34), 1- methylimidazole-2-carboxylic acid (83.6 mg, 663 j.imol), HATU (336 mg, 884 imol) and DIPEA (171 mg, 1.33 mmol) in DMF (5 mL) was stuffed overnight at rt. The resulting mixturewas poured into water and extracted with DCM (30 mL) twice. The combined organic layer was concentrated in vacuo and the residue was purified by prep-HPLC to give (1-methylimidazol-2- yl)- [5-methyl-2- (2-pyridyl)-7 ,8 -dihydro-5H-pyrido [4,3-d]pyrimidin-6-yl] methanone (69 mg) as a light yellow solid. ?H NMR (400 MHz, Methanol-d4) oe: 8.5 1-8.80 (m, 2H), 8.33-8.43 (m, 1H), 7.80-7.92 (m, 1H), 7.34-7.47 (m, 1H), 7.07-7.18 (m, 1H), 6.97 (d, 1H), 5.66-5.86 (m, 1H), 4.66-4.75 (m, 0.4H), 4.49-4.60 (m, 0.6H), 3.74 (s, 3H), 3.48-3.63 (m, 0.7H), 3.23-3.41 (m, 1H), 2.88-3.15 (m, 1.3H), 1.56 (brd, 3H). MS obsd. (ESI)[(M+H)]: 335.

The synthetic route of 20485-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (84 pag.)WO2018/83106; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem