Month: July 2021

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. 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 3304-70-9

(1) Dimethyl 1H-imidazole-4,5-dicarboxylate (9.6 g, 52 mmol) was dissolved in acetonitrile (200 mE), and N-bromosuccinimide (13.92 g, 78 mmol) was added thereto, and then the mixture was stirred at 50 C. for 4 hours. After the reaction, water was added and the mixture was extracted twice with ethyl acetate. After being washed with saturated aqueous sodium thiosulfate and saturated aqueous sodium chloride, the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated to obtain dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate (8.3 g). This material was used as is in the next reaction without further purification:10217] ?H-NMR (CDC13) oe: 10.56 (1H, s), 3.96 (6H, s);10218] ESI-MS mlz=263 (M+H).

The synthetic route of 3304-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 219814-29-6,Some common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, molecular formula is C4H4Br2N2, 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.

Step A : (5-Bromo-6-methyl-3 H- 1 ‘ -azaspiro [imidazo [2, 1 -b] oxazole-2,3 ‘ – bicyclo[2.2.2]octan]-l ‘-yl-8-ium)trihydroborate and (6-bromo-5-methyl-3H-l ‘- azaspiro[imidazo[2, l-b]oxazole-2,3 ‘-bicyclo[2.2.2]octan]- -yl-8-ium)trihydroborate To 2,4-dibromo-5-methyl-lH-imidazole (0.8 g, 3.3 mmol) in THF (25 niL) was added N-butyllithium (1.3 niL, 3.3 mmol) dropwise at -78C. After 45 minutes, a solution of racemic r-azaspiro[oxirane-2,3′-bicyclo[2.2.2]octan]-l’-yl-4- ium)trihydroborate (0.56 g, 3.7 mmol) from the reference example, in THF (20 mL) was added dropwise at -78C. The cooling bath was removed and the reaction mixture warmed to room temperature. After 15 minutes, the mixture was heated to 75C for 2 hours and then cooled to room temperature. The reaction was quenched with water and the product was extracted with ethyl acetate (100 mL). The organics were dried with MgS04, filtered and the solvent was removed to yield the crude product. The crude material was purified by chromatography (Biotage) to yield the regioisomeric products. These regioisomers were separated by reverse phase chromatography using a Sunfire column with gradients of acetonitrile-water containing 0.1% of trifluoroacetic acid (TFA), and at 40 mL/min flow rate. The pure fractions for peak 1 and peak 2 were then neutralized with 1 N NaOH (pH ~8-9) and the products were extracted with ethyl acetate. The organic layers were dried with MgS04, filtered and the solvent was removed to yield racemic (5-bromo-6-methyl-3H-l’-azaspiro[imidazo[2,l-b]oxazole-2,3′- bicyclo[2.2.2]octan]-l’-yl-8-ium)trihydroborate (0.32 g, 1.0 mmol, 30.8 % yield) XH NMR (500MHz, DMSO-d6) delta 4.23 (d, J=9.8 Hz, IH), 4.12 (d, J=9.9 Hz, IH), 3.36 (dd, J=15.2, 2.5 Hz, IH), 3.19 (dd, J=15.3, 2.1 Hz, IH), 3.04 – 2.95 (m, IH), 2.91 – 2.73 (m, 3H), 2.35 (br. s., IH), 2.03 – 1.88 (m, 4H), 1.84 – 1.67 (m, 3H), 1.64 – 1.11 (m, 3H). MS (LC/MS) R.T. = 2.09; [M+2]+ = 300.04 and racemic (6-bromo-5-methyl-3H-l’- azaspiro[imidazo[2,l-b]oxazole-2,3′-bicyclo[2.2.2]octan]-r-yl-8-ium)trihydroborate (0.33 g, 1.1 mmol, 31.7 % yield) as powders. NMR (500MHz, DMSO-de) delta 4.32 (d, J=10.1 Hz, IH), 4.12 (d, J=10.2 Hz, IH), 3.36 (d, J=2.4 Hz, IH), 3.18 (dd, J=15.2, 2.2 Hz, IH), 2.99 (d, J=2.9 Hz, IH), 2.93 – 2.78 (m, 3H), 2.31 (d, J=2.0 Hz, IH), 2.06 – 1.94 (m, 4H), 1.84 – 1.69 (m, 3H), 1.62 – 1.22 (m, 3H). MS (LC/MS) R.T. = 2.64; [M+2]+ = 300.04.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dibromo-4-methylimidazole, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; ZUSI, F. Christopher; HILL, Matthew D.; (87 pag.)WO2016/73407; (2016); 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. 147403-65-4, name is Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, A new synthetic method of this compound is introduced below., Formula: C25H24N4O4

Methyl 2-ethoxy- l -((2′-(5-oxo-4,5-dihydro- l ,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)- l H- benzo[< ]imidazole-7-carboxyiate of formula la - reproduction of the procedure (J. Med. Chem. 1996, 39(26), 5228-5235)2-ethylhexyl chloroformate (0.25 g, 2.6 mmol) was added to a stirred mixture of methyl 2- ethoxy- l -((2'-((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)- l H-benzo[i/]imidazole-7- carboxylate (of formula Va; 1.16 g, 2.6 mmol), dry DMF (5 ml) and pyridine (0.22 g) under cooling in a water-ice mixture and the mixture was stirred at the temperature of 0C for 30 minutes. After dilution with water (20 ml) the mixture was extracted with ethyl acetate (4 x 10 ml), the extract was washed with water (4 x 5 ml) and dried with MgS04. The obtained evaporation residue ( 1.7 g) contained 92.2 % of the intermediate (of formula VI; R' = 2- ethylhexyl) according to HPLC. 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; ZENTIVA, K.S.; RADL, Stanislav; STACH, Jan; WO2012/139535; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39513-26-3, A common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, molecular formula is C7H5BrN2O, 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.

Example 1095 Step 1 A solution of Compound 1095A in DMF (2 ml) was treated sequentially with sodium hydride (28 mg, 60% dispersion in oil, 0.70 mmol) and iodomethane (0.04 ml, 80 mg, 0.56 mmol). The reaction mixture was stirred overnight at rt. The reaction was quenched with water, diluted with EtOAc, and washed sequentially with water and brine. The organic phase was dried over anhydrous MgSO4, filtered and concentrated to give crude Compound 1095B (37 mg, 68%), which was used without further purification.

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2007/84451; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-88-1, name is 5-Bromo-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. Safety of 5-Bromo-1H-benzo[d]imidazole

To a solution of 3-[1-(triphenylmethyl)-1H-benzimidazol-5-yl]benzaldehyde and 3-[1-(triphenylmethyl)-1H-benzimidazol-6-yl]benzaldehyde (0.22 g, 0.47 mmol) in dichloromethane (5 mL) was added 1 drop of acetic acid, followed by 4,4-dimethylcyclohexylamine hydrochloride (78 mg, 0.47 mmol) and triethylamine (66 muL, 0.47 mmol). NOTE: If a free amine was used, triethylamine was not added. After stirring 60 min at room temperature, sodium triacetoxyborohydride (0.40 g, 1.9 mmol) was added and the reaction was stirred an additional 3 h. The reaction mixture was diluted with H2O and CH2Cl2. The layers were separated and the aqueous layer was extracted 2× CH2Cl2. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo. Chromatography provided the reductive amination product as a mixture of trityl regioisomers, (4,4-dimethylcyclohexyl)({3-[1-(triphenylmethyl)-1H-benzimidazol-6-yl]phenyl}methyl)amine and (4,4-dimethylcyclohexyl)({3-[1-(triphenylmethyl)-1H-benzimidazol-5-yl]phenyl}methyl)amine. (M+1) 576.4 ES, 2.40 min and 2.51 min (LC/MS Method A).

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 496-46-8, 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 496-46-8 as follows.

Into a suitable reaction vessel equipped with a stirrer, thermometer and reflux condenser, there was introduced 688 parts (10 mol) of aqueous formaldehyde (44%), and the pH was adjusted to 8.7 with 22 parts of 0.5 N NaOH solution. To this solution, there was added 284 parts (2 mol) of acetylene carbamide at 40 C. During the resulting reaction, the temperature was allowed to rise up to 55 C. At this stage, most of the acetylene carbamide entered into solution. After about 15 minutes, the pH was adjusted to 8.0 with five parts of 0.5 N NaOH. A clear, pale yellow colored solution was obtained. The clear solution was distilled at 50 C, under reduced pressure, to remove water until the reaction vessel content was about 640 parts. The resulting syrup in the vessel was poured into 800 parts of methanol. The resulting white crystalline precipitate was filtered and dried. The total yield of the tetramethylol acetylene carbamide was 483 parts (92%) and had a melting point of 132 – 136 C.

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ROTAM AGROCHEM INTERNATIONAL COMPANY LIMITED; BRISTOW, James Timothy; WO2014/166347; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2302-25-2,Some common heterocyclic compound, 2302-25-2, name is 4-Bromo-1H-imidazole, molecular formula is C3H3BrN2, 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-bromo-lH-imidazole (100 mg) in anhydrous THF (3.5 mL) was added di-tert-butyl dicarbonate (149 mg) and DMAP (125 mg). The reaction mixture was stirred at rt for 30 min and partitioned between 9: 1 DCM/MeOH and a sat. aq. NaHC03 solution. The layers were separated and the aq. layer was extracted with 9: 1 DCM/MeOH (3x). The combined org. layers were washed with water and brine, dried over MgS04, filtered and concentrated under reduced pressure. The title compound was obtained, after purification by CC (DCM/MeOH 100:0 to 98:2), as a white solid (143 mg; 85% yield).

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 4856-97-7,Some common heterocyclic compound, 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, molecular formula is C8H8N2O, 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: One of compounds 4a?4f (5 mmol) was dissolved in THF (25 mL) and DCC (1.24 g, 6 mmol), and DMAP (0.12 g, 1 mmol) was slowly added and the mixture was stirred for 30 min. Compounds 2a?2c (5 mmol) was added and the mixture was stirred for 7?9 h. The by-product, N,N’-dicyclohexylurea, was removed by filtration. The filtrate was concentrated in vacuum to give a solid which was dissolved in CH2Cl2 and the product 5a?5n was filtered off.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1H-Benzoimidazol-2-yl)methanol, its application will become more common.

Reference:
Letter; Zhang; Xu; Wang; Kang; Russian Journal of General Chemistry; vol. 87; 12; (2017); p. 3006 – 3016;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 705-09-9, These common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]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: 2-(Difluoromethyl)-1H-benzo[d]imidazole (1 mol),chloro derivative (1 mol) and K2CO3 (2 mol) were taken inDMSO (10 v). The reaction mixture was heated to 130 C,stirred for 4 h. Then the reaction mixture was cooled to roomtemperature, diluted with water (50 v) extracted with EtOAC(2 x 50 v), evaporated the solvent under reduced pressure toget the crude compound. Crude products were purified bycolumn chromatography.

Statistics shows that 2-(Difluoromethyl)-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 705-09-9.

Reference:
Article; Kasturi, Sivaprasad; Surarapu, Sujatha; Uppalanchi, Srinivas; Anantaraju, Hasitha Shilpa; Dwivedi, Shubham; Yogeeswari, Perumal; Ethiraj, Krishna S.; Anireddy, Jaya Shree; Letters in drug design and discovery; vol. 15; 2; (2018); p. 181 – 192;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

[00611] Intermediate 64a: benzyl 2-[4-(trifluoromethyl)imidazol-1 -yI]acetate[00612] Benzyl bromoacetate (0.l4mL, 0.88mmol) was added to a flask containing potassiumcarbonate (305mg, 2.2mmol) and 4-(trifluoromethyl)-1H-imidazole (1 00mg, 0.73mmol) in MeCN(3mL). The reaction mixture was heated to 60 C and left to stir overnight. The reaction was then quenched by the addition of water (2OmL) and extracted with EtOAc(3x2OmL). The combined organic layers were dried over Na2504, filtered and reduced in vacuo to afford the product benzyl 2- [4-(trifluoromethyl)imidazol-1-yl]acetate (1 94mg, 0.68mmol, 93% yield) as a yellow oil.1H NMR (CDCI3,400MHZ) O/ppm: 7.55 (1H, 5), 7.41 -7.30 (6H, m), 5.23 (2H, 5), 4.75 (2H, 5).

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

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem