Category: imidazoles-derivatives

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., Quality Control of (1H-Benzo[d]imidazol-2-yl)methanamine

General procedure: To the triazole carbamate ester of MMB (7) (0.167 mmol) indichloromethane (2 mL) was added the appropriate imidazole orbenzimidazole amine (0.167 mmol) at ambient temperature, andthe reaction mixture was stirred for 4-16 h. After completion ofthe reaction (monitored by TLC), water was added and the resultingmixture extracted with dichloromethane. The organic liquorswere separated, washed with water, followed by brine solution,dried over anhydrous Na2SO4, filtered, and the solvent removedto afford the crude reaction product. The crude product was purifiedby column chromatography (silica gel, 2-5% methanol indichloromethane) to afford the appropriate carbamate derivativeof MMB as a white solid (yield: 65-75%).

According to the analysis of related databases, 5805-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Albayati, Zaineb A.F.; Janganati, Venumadhav; Chen, Zheng; Ponder, Jessica; Breen, Philip J.; Jordan, Craig T.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry; vol. 25; 3; (2017); p. 1235 – 1241;,
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. 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Formula: C8H7BrN2

A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1 ,4-dioxane (1 mE) was sonicated and added undernitrogen to a mixture of 6-bromo-1-methyl-benzimidazole (0.45 mmol), 2-(4-aminophenyl)acetonitrile (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mE). The mix-ture was stirred at 1100 C. for 12 h. The mixture was diluted (DCM), washed (H20), dried (phase separator and concentrated. The residue was purified by prep HPEC to yield the desired product (Compound A).MW: 262.3. MS Ms?d: 263.2.NMR: 1H NMR (400 MHz, DMSO-d6): oe=8.13 (1H, s), 7.68 (1H, dd), 7.60 (1H, dd), 7.54 (1H, d), 7.32 (1H, d), 7.24 (1H, t), 6.91 (1H, dd), 3.77 (3H, s), 3.39 (3H, s).

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; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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. Product Details of 28890-99-5

500ml of four bottles,In the atmosphere of nitrogen gas,0.01 mol of 5H-benzimidazol [1,2-a] benzimidazole was added,0.05 mol (6-bromo-9-phenyl-9H-carbazol-3-yl) -di-dibenzofuran-4-yl-0.03 mol of sodium tert-butoxide,1 x 10-4 mol Pd2 (dba) 3,1 x 10-4 mol tri-tert-butylphosphine,250ml toluene,Heated to reflux for 24 hours,Sampling point plate, antiShould be completely, natural cooling, filtration, the filtrate steamed, silica gel column, get the target product,Purity 99.10, yield 36.00%.

The synthetic route of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Sanyue Photoelectric Technology Co., Ltd.; Li, Chong; Xu, Kai; Zhang, Zhaochao; Ye, Zhonghua; Wang, Lichun; (29 pag.)CN106467549; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, Recommanded Product: 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole

A mixture of 1a (0.70 g , 2.0 mmol), bis(pinacolate)diborane (0.53 g, 2.1 mmol), l,l’-bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)Cl2) (0.060g,0.08mmol), andanhydrous potassium acetate (0.393 g, 4.0 mmol) in 1,4-dioxane(20 mL) was heated at 80C under nitrogen for 12 h. After cooling to room temperature, the mixture was extracted with ethyl acetate (30 mL*3). The organic extracts were washed with water, brine, and then dried with anhydrous MgSO4. After filtration, the filtrate was pumped dry in vacuo. The crude residue was subjected to column chromatography by eluting with hexanes/EA (8:1) as the eluent to give a white solid (yield: 81%). 1H NMR (400 MHz, acetone-d6): d (ppm ) 7.79 (d, J 7.6 Hz, 1H), 7.71 (d, J=7.6 Hz, 2H), 7.62-7.56 (m,5H), 7.45 (d, J=7.6 Hz, 2H), 7.37-7.23 (m, 3H) and 1.34 (s, 12H); 13C NMR (125 MHz, acetone-d6): d (ppm) 152.9, 144.3, 138.6, 138.2, 135.2, 134.0, 131.0, 129.7, 129.6, 128.6, 124.3, 123.7, 120.7, 111.4, 84.9, 25.3; Mass (FAB ): m/z: 397.1 [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:
Article; Muangpaisal, Rossatorn; Hung, Wei-I.; Lin, Jiann T.; Ting, San-Yu; Chen, Li-Yin; Tetrahedron; vol. 70; 18; (2014); p. 2992 – 2998;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1402838-08-7,Some common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, molecular formula is C29H22N2O, 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 mixture of 10b (210 mg, 1.180 mmol) , 2-hydroxyisoindoline-1, 3-dione (38 mg, 0.233 mmol) , Bis (acetylacetonato) cobalt (30 mg, 0.117 mmol) in HOAc (5 mL) was stirred under oxygen atmosphere at 75 for 6 h. The reaction mixture was concentrated to dryness under reduced pressure. The residue was diluted with EtOAc (10 mL) and the insoluble solid was filtered off. The filtrate was concentrated in vacuo to afford a crude mixture of 14b and 14c (160 mg) as slight brown oil, which was used for the next step without further purification. To a stirred mixture of compound 10a (150 mg, 0.362 mmol) and compounds 14b and 14c (70 mg, 0.362 mmol) in anhydrous THF (10mL) was added dropwise a solution of EtONa (21in EtOH, 152mg, 0.471mmol) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h. After the mixture was concentrated to dryness under reduced pressure, the residue was diluted with NH4Cl solution (10mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was dissolved in MeOH (8 mL) . To this solution was added HOAc (2 mL) , and the reaction mixture was stirred at 60 for 2 h. The mixture was concentrated in vacuo to give a residue, which was diluted with NaHCO3saturated solution (10 mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was purified by preparative TLC (EtOAc) to afford compound 14d (70 mg, 55yield) , MS 349.2 [M+H]+, and 14e (40 mg, 31yield) as a light yellow solid, MS Found 365.2 [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 2-(1-Trityl-4-imidazolyl)benzaldehyde, its application will become more common.

Reference:
Patent; HANGZHOU INNOGATE PHARMA CO., LTD.; ZHANG, Hancheng; LIU, Shifeng; (53 pag.)WO2016/165613; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 106429-59-8 as follows. Application In Synthesis of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde

A solution of intermediate 2 (100 mg, crude HCI salt, 0.29 mmol) and 2-oxo-2,3-dihydro-1H-benzo[d]jimidazole-5-carbaldehyde (CAS: 106429-59-8) (71 mg, 0.44 mmol) in MeOH (2 mL) was stirred at room temperature for 2 h. NaBH3CN (37 mg, 0.58 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with H2O and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na,SOu, filtered and concentrated. The residue was purified by prep-HPLC (Waters 2767/Qda, Column: Waters Xbridge 19*150 mm 10 um, Mobile Phase A: H20 (0.1% TFA), B: ACN)to give the racemic Compound 14 (49 mg, TFA salt). The obtained racemic Compound 14 was separated by SFC (SFC80, Waters, IC 2.5*25 cm, 10 um, A: Supercritical COQ., B: MeOH/DEA= 100/0.03; A:B = 70/30; Flow rate: 70 mL/min; column temperature (T): 25 C; Backpressure (BPR): 100 bar) to give Compound 108 (12 mg as TFA salt, 6.8% yield) as a white solid and Compound 109 (13 mg as TFA salt, 7.3% yield) as a white solid.

According to the analysis of related databases, 106429-59-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1848-84-6, name is 2-Ethyl-1H-benzo[d]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. SDS of cas: 1848-84-6

A mixture of 4-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8- yl)piperidine-l -carboxylic acid tert-butyl ester (375 mg, 0.858 mmol), 2-ethylbenzimidazole (151 mg, 1.03 mmol), Xphos (43 mg, 0.09 mmol) and Cs2CO3 (421 mg, 1.29 mmol) in dioxane (5 niL) was degassed with nitrogen bubbling for 15 minutes.Tris(dibenzylideneacetone)dipalladium (20 mg, 0.022 mmol) was added and the mixture was heated to 120 0C for 20 hours. The reaction mixture was diluted with EtOAc, filtered, concentrated in vacuo and purified by column chromatography (Si-PCC, EtOAcxyclohexane, 40-90percent) affording 647 (390 mg, 83percent). LCMS: Rx 4.54 min, [M+H]+ 547.24 1H NMR (400 MHz, DMSO): delta 8.00-7.99 (m; 1 H); 7.68-7.60 (m; 1 H); 7.25-7.24 (m; 2 H); 4.45-4.12 (m; 4 H); 4.12-4.01 (d; J = 13.26 Hz, 2 H); 3.85-3.70 (m; 6 H); 3.25- 3.10 (m, 4 H); 3.04-2.82 (m, 2 H); 2.00-1.90 (d; J = 13.26 Hz, 2 H); 1.76-1.59 (m, 2 H); 1.43 (s; 9 H); 1.35 (t, J = 7.44 Hz, 3 H).

The synthetic route of 1848-84-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); 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. 58089-25-1, name is 2-Mercapto-5-benzimidazolecarboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Mercapto-5-benzimidazolecarboxylic Acid

EXAMPLE 48 5-Carboxy-2-[{4-(2-benzyloxy)ethoxy-3-methylpyridine-2-yl}methylthio]-1H-benzimidazole STR110 A mixture comprising 1.26 g of 5-carboxy-2-mercaptobenzimidazole, 1.8 g of 4-(2-benzyloxyethoxy)-2-chloromethyl-3-methylpyridine, 0.57 g of sodium hydroxide and 150 ml of methanol was stirred at 50 C. for 1.5 hours and distilled under a reduced pressure to remove the methanol. The obtained residue was purified by silica gel column chromatography and recrystallized from a methanol/ethyl acetate mixture to obtain 1.52 g of the title compound. 1 H-NMR(DMSO-d6) delta; 2.25(s, 3H), 3.65~3.9(m, 2H), 4.1~4.3(m, 2H), 4.58(s, 2H), 4.74(s, 2H), 6.95(d, J=5.7 Hz, 1H), 7.32(s, 5H), 7.50(d, J=8.3 Hz, 1H), 7.79(dd, J=1.3 Hz, 8.3 Hz, 1H), 8.04(s, 1H), 8.24(d, J=5.7 Hz, 1H).

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 58089-25-1.

Reference:
Patent; Eisai Co., Ltd.; US5045552; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 10111-08-7, name is Imidazole-2-carboxaldehyde, molecular formula is C4H4N2O, 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. HPLC of Formula: C4H4N2O

To a solution of compound 1 H-imidazole-2-carbaldehyde (5g, 52.08 mmol) in MeOH (50 mL) was added sodium borohydride (3.93g, 104.16 mmol) portion-wise, at 5 00, and the reaction mixture was allowed to stir at RT for 3h. The reaction mixture was quenched with brine (25 mL) and concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 10% MeOH/CHCI3) to obtain (1H-imidazol-2-yl)-methanol as a pale yellow solid (4g, 78%).R:0.1 (10% MeOH/CHCI3).1H NMR (400MHz, CD3OD): O 6.97 (5, 2H), 4.61 (5, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10111-08-7, its application will become more common.

Reference:
Patent; INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL (THE); ASHWORTH, Alan; LORD, Christopher, James; ELLIOTT, Richard, James, Rowland; NICULESCU-DUVAZ, Dan; PORTER, Roderick, Alan; AQIL, Rehan; BOFFEY, Raymond, John; BAYFORD, Melanie, Jayne; FIRTH-CLARK, Stuart; HOPKINS, Anna; JARVIS, Ashley, Nicholas; PERRIOR, Trevor, Robert; SKONE, Philip, Alan; KEY, Rebekah, Elisabeth; WO2015/36759; (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. 78581-99-4, name is 5,6-Difluorobenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 78581-99-4

27: Methyi 3-{[(1 /?)-1-(2-chioro-3-hydroxyphenvi)ethv?oxv}-5- (5.6-dif iuoro-1 MbenzimidazoS-1 -yl)-2-thiophenecarboxyiateStep A – Methyl 5-{5,6-dif.uoro-1 Mbe?zimidazoi-1-yl)~3-hydroxy~2- thiophe?ecarboxylate To a mixture of 5,6-dif.upsilonoro-1 Mbenzsmidazoie (0.5 g, 3.2 rnmol) and 2-chioro- 3-oxo-2,3~dihydro~2-thiophenecarboxyiate (0.72 g, 3.7 mrnof) in 10 mL of CHCI3 was added Mmefhyiimidazole (0.4 g, 4.9 mrnol) and NaHCO3 (0.82 g, 5 9.7 mmol). The mixture was heated to 550C for 24 h. Silica gel (2 g) was added and the voiatites were evaporated under reduced pressure and the residue was purified by flash column chromatography (0 to 50% EtOAc: DCIVI) to afford 0.71 g of the tilted compound, MS (ESI): 311 [M+H]*.

According to the analysis of related databases, 78581-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143456; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem