Month: August 2021

Electric Literature of 930-62-1, 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 930-62-1 as follows.

A mixture of 2,4-dimethyl-lH-imidazole (5.00 g, 52.0 mmol),1 ,2-difluoro-4~nitrobenzene (8.27 g, 52.0 mmol), and sodium bicarbonate (4.37 g, 52.0 mmol) in DMSO (100 mL) was heated at 80 0C for 24 h . The reaction mixture was allowed to cool to rt and was poured into water (800 mL). The aqueous mixture was extracted with EtOAc (3 x 200 mL). The combined organic extracts were sequentially washed with water (500 mL) and brine solution (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The dark residue was dissolved in ethyl acetate (200 mL). Hexane (50 mL) was added to the solution. The resulting mixture was allowed to age for 72 h at it. The resulting solid was collected by vacuum filtration. The solid was dried under high vacuum to afford l-(2-fluoro-4-nitrophenyl)-2,4-dimethyl-lH-imidazole (6.68 g, 27.8 mmol., 54 % yield) as a yellow crystalline solid. LC-MS (M+H)+ = 236.1. IH NMR (500 MHz, CHLOROFORM-d) B ppm 8.13 – 8.22 (m, 2 H), 7.51 (dd, J=8.9, 7.3 Hz, 1 H), 6.72 (s, 1 H), 2.28 – 2.36 (m, 3 H), 2.22 – 2.28 (m, 3 H).

According to the analysis of related databases, 930-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Dimethyl sulfoxide (10 mE), 3-(4-methyl-1H-imi- dazole-1 -yl)-5-(trifluoromethyl) aniline (aromatic amine, 4.5 mmol), N-5-bromo-2-methylphenyl(4-(pyridine-3-yl) pyrimidine-2-amine (5.4 mmol), 1, 1?-bis(diphenylphos- phino)ferrocene-palladium (II) dichloride dichioromethane complex (0.135 mmol), triphenylphosphine (0.27 mmol), phenol (0.225 mmol), triethylamine (13.5 mmol) and a 4 A molecular sieve (1 g) are added into an autoclave for uniform stirring. Nitrogen is introduced to displace air, and then a carbon monoxide is introduced to displace the nitrogen to and the pressure in the autoclave is increased to 0.8 MPa. A temperature is increased by heating to 90-105 C. for reaction. Afier 72 h reaction, a product system containing an amination product is obtained. The product system is cooled to be below 50 C., and the carbon monoxide is evacuated and displaced with the nitrogen.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASYMCHEM LABORATORIES (TIANJIN) CO., LTD; ASYMCHEM LIFE SCIENCE (TIANJIN) CO., LTD; TIANJIN ASYMCHEM PHARMACEUTICAL CO., LTD; ASYMCHEM LABORATORIES (FUXIN) CO., LTD; JILIN ASYMCHEM LABORATORIES CO., LTD; HONG, Hao; JAMES, Gage; LI, Jiuyuan; LI, Changfeng; HUANG, Gaochao; (16 pag.)US2018/148430; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3543-73-5, 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. 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE-II Preparation of Ethyl 4-(5-(bis(2-Hydroxyethyl)Amino)-1-Methyl-1H-Benzo[d]-Imidazol-2-yl)Butanoate (Formula-IV) To a clean dry flask were charged compound of formula III (20 g), sodium carbonate (16.24 g), sodium Iodide (10.6 g) and 80 ml of 2-chloroethanol. The mixture was stirred for 5 minutes at room temperature and the reaction mass was heated to 65-70 C. and maintained for 8-12 hours. The mass was cooled to room temperature and pH adjusted to 1.0 using 6N HCl. The aqueous layer was extracted with ethyl acetate and the aqueous layer pH is adjusted to 8 to 9 using sodium carbonate solution. The Aqueous layer is extracted with dichloromethane and is distilled out completely and the solid obtained which is then purified in ethyl acetate to give 10 g of the title compound.

The synthetic route of Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOPHORE INDIA PHARMACEUTICALS PVT. LTD; Pullagurla, Manik Reddy; Rangisetty, Jagadeesh Babu; Presley, S. I. Davis; Nagarapu, Radha; US2013/317234; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, 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) resin swelling: 400 mg of Fmoc-protected phenylhydrazine resin (0.66 mmol / g, 0.264 mmol) and 3 mL of CH2CI2 were added to a 10 mL solid phase reactor, the resin was swollen for 30 min, CH2CI2 was withdrawn, (B) removal of Fmoc protecting group: A solution of 3 mL of 20% piperidine / DMF was added to the swollen resin in step (a) N2 was bubbled and mixed. After lOmin, the solvent was extracted, and then 3 mL of 20% piperidine / DMF solution was added. N2 was bubbled and mixed. After lOmin, the resin was washed with DMF (4X3mL) and the resin was washed with 3 mL of anhydrous DMF ,spare; (C) Amino acid condensation: 4-tert-Butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid (254 mg, 1.056 mmol) and triphosgene (BTC, 128 mg, 0.433 mmol) were dissolved in 2 mL of anhydrous THF, A large amount of white precipitate was immediately added to the reaction, and the reaction was further carried out for 3 min. Then, 2 mL of a solution of DIEA / DMF (5%, nu / nu) The reaction solution was transferred to the phenylhydrazine resin in which the protecting group was removed, N2 was bubbled and mixed, the reaction was carried out for 0.5 to 1 h, the reaction solution was extracted, and the resin was washed with DMF (4 X 3 mL) ,spare;(D) removal of tert-butoxycarbonyl protecting group: The mixture was washed with CH2C12 (2 X 3 mL), the CH2C12 was removed, and the tert-butyl group was removed by the addition of 3. OmL TFA / benzoic acid / Eta2Omicron (nu: nu: nu = 92: 5: 2.5) (2 × 3 3) and DMF (4 X) were added to the reaction mixture for 2 min, and then the solvent was extracted for 2 min, and then the mixture was stirred for 20 min with 3. OmL TFA / phenol / H20 (nu: nu: nu = 92: 5: 2.5) 3 mL) and the resin was washed with 3 mL of anhydrous DMF, The above-mentioned condensation and deprotection steps (c) and (d) were repeated until completion of the synthesis of the peptide on the phenylhydrazine resin represented by the formula (1) (E) condensing amino acids: 4-tert-butoxycarbonylamino-1-methyl -1H- imidazole-2-carboxylic acid (254mg, 1.056mmol) and triphosgene (BTC, 128mg, 0.433mmol) was dissolved in 2mL anhydrous of THF, to this solution was slowly added dropwise trimethyl pyridine (collidine, 488muL, 3.696mmol), the reaction to produce a heavy white precipitate immediately addition was complete the reaction 3min, added 2mLDIEA / DMF solution (5%, v / v), white the precipitate completely disappeared, the reaction solution was transferred to step (b) deprotection of the resin phenylhydrazine, N 2Bubbled mixing, the condensation reaction 0.5 ~ 1h, the reaction solution pumping, with DMF (4 × 3mL) resin was washed, to give formula (2) is supported on the peptide resin represented phenylhydrazine;A(G) solution of R-2-(9-fluorenylmethoxycarbonylamino)-4-tert-butoxycarbonylaminobutyric acid (465 mg, 1.056 mmol) and triphosgene (128 mg, 0.433 mmol) in 2 mL of anhydrous THF was added to the solution (48 mg) was added dropwise to a solution of HOAt (144 mg, 1.056 mmol) followed by addition of 2 mL of DIEA / DMF solution (5%, nu / nu), followed by the addition of trimethylpyrone (488 yL, 3.696 mmol) The reaction solution was transferred to a linear peptide (NH2-Im-Im-Py-Py-phenylhydrazine resin) supported on a phenylhydrazine resin represented by the formula (1), and the N2 pellet was completely removed. And the reaction was carried out with DMF (4 x 3mL) to obtain the peptide supported on the phenylhydrazine resin as shown in formula (3) (H)repeating the condensation and deprotection guard step (d) and (C), wherein the load until the completion of the synthetic peptides of formula (4) in the resin phenylhydrazine;(I)repeating the condensation and deprotection guard step (d) and (E), wherein the load until the completion of the synthetic peptides shown in formula (5) in the resin phenylhydrazine;(J)1-methyl -1H- imidazole-2-carboxylic acid (132mg, 1.056mmol) and PyBOP (550mg, 1.056mmol) was dissolved in dry 3mL of DMF, DIEA (350muL, 2.112mmol ), the reaction 5min, the reaction solution was transferred to a step (h) the load represented by the formula (4) in the resulting peptide resin phenylhydrazine, N2Mix bubbled condensation reaction 2h, the reaction solution pumping, with DMF (4 × 3mL) the resin was washed, and the procedure (b) The method of removing the load represented by the formula (5) phenylhydrazine peptide on the resin Fmoc protecting group, the peptide load of formula (6) in a phenylhydrazine of the resin;(K) Boc2O (243muL, 1.056mmol) was dissolved in dry 3mL of DMF, DIEA (350muL, 2.112mmol), transferring the reaction solution to remove the Fmoc formula (6) is supported on the peptide resin phenylhydrazine, N2Mix bubbled condensation reaction 20min. In addition to pumping load reaction solution with DMF (4 × 3mL) the resin was washed to give Boc protected compound of formula (7) phenylhydrazine peptide on the resin;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2-carboxylic acid, its application will become more common.

Reference:
Patent; Shenzhen Advanced Technology Institute; Su Wu; Wang Wei; Pan Zhengyin; Cheng Zhehong; Wu Chunlei; Fang Lijing; (36 pag.)CN106674209; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 60-56-0, 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-Mercapto-l-methylimidazol (40.8 mg, 0.35 mmol) was neat to a solution of l-bromo-3- (4-chloro-phenyl)-3-methyl-butan-2-one (98.5 mg, 0.35 mmol) in CH3CN (5 mL) at room temperature, then Et3N (0.098 mL, 0.70 mmol) was added neat to the mixture and the reaction was stirred overnight. Thiol residues were trapped by addition of a small spatula of resin 2-chlorotrityl chloride in 30 min then the mixture was filtered and concentrated under vacuum. The crude mixture was purified by flash chromatography (hexane/EtOAc gradient 0-40%) to give the expected compound (108.5 mg, 100%) as brown solid. TLC single spot at R/ 0.47 (MeOH/DCM 1:9); Mp = [43.7-47.3 0C]; 1H NMR (270 MHz, CDCl3): delta 1.46 (s, 6H), 3.59 (s, 3H), 3.86 (s, 2H), 6.84 (d, J = 1.1 Hz, IH), 6.94 (d, J = 1.4 Hz, IH), 7.07-7.15 (m, 2H), 7.23-7.30 (m, 2H); Accurate Mass: calculated (MVH) 309.0823; found 309.0811; HPLC tr = 2.06 min (100%) in 10% water-acetonitrile.

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, 1-Methyl-1H-imidazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; STERIX LIMITED; WO2009/106817; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1615-14-1, These common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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.

Synthesis of 10-(2-(1H-Imidazol-1-yl)ethyl) 2-benzyl (25,4a5,6a5,6bR,8a5, 105, 12a5, l2bR, l4bR)-2,4a,6a,6b,9,9, 12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9, 10, 11, 12, 12a, 1 2b, 13,1 4b-icosahydropicene-2, 1 0-dicarboxylate (7-1). Into a 25 -mL round-bottom flask, wasplaced 1-7 (137 mg, 0.23 mmol, 1.00 equiv.), DCM (10 mL), 2-(1H-imidazol-1-yl)ethan-1-ol (51 mg, 0.45 mmol, 2.00 equiv.), DMAP (3 mg, 0.02 mmol, 0.10 equiv.), TEA (0.047 mL, 1.50 equiv.). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with DCMIMeOH(20:1). This resulted in 140mg (91%) of 7-1 as a white solid.

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; LUEHR, Gary; DRAGOLI, Dean; LEADBETTER, Michael; CHEN, Tao; LEWIS, Jason; (181 pag.)WO2019/60051; (2019); 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. 1072-62-4, name is 2-Ethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1072-62-4

In an argon stream, 2-ethylimidazole (1.92 g, 20 mmol) and sodium hydride (0.84 g, 21 mmol) were suspended in tetrahydrofuran (30 mL) and cooled to 0 C. 1-Iodohexane (4.67 g, 22 mmol) was added to the suspension, and the mixture was stirred at room temperature for 30 minutes and then at 75 C. for 24 hours. After standing to cool, diethyl ether and water were added to the reaction mixture, the organic layer was extracted, and the organic layer was washed with brine. After adding sodium sulfate to the organic layer and stirring, the solid was filtered off and the solvent was distilled off. The resulting oily substance was purified by silica gel column chromatography (chloroform / methanol = 10: 1) to obtain 1-hexyl-2-ethylimidazole as a yellow oily substance (2.93 g, 81%).

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 1072-62-4.

Reference:
Patent; Tosoh Corporation; Sagami Chemical Research Institute; Aihara, Hidenori; Yamagata, Takuya; Hachiya, Hitoshi; Watanabe, Makoto; Fukuda, Takashi; Ueda, Saori; Miyashita, Masato; (64 pag.)JP2018/168149; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 870837-18-6, The chemical industry reduces the impact on the environment during synthesis 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, I believe this compound will play a more active role in future production and life.

Synthesis of (Z)-(S)-4-[(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]-2-[1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]methylidene]-6-methylmorpholin-3-one In nitrogen atmosphere, an acetonitrile solution (4 mL) of (S)-4-[(1R,2R)-2-tert-butyl-diphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-2-hydroxy-6-methyl-morpholin-3-one (92 mg) and triphenylphosphine hydrobromide (68 mg) was heated under reflux for 1 hr. The solvent of the reaction solution was evaporated under reduced pressure. To an ethanol solution (4 mL) of the obtained residue, 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (40 mg) and TEA (0.12 mL) were added. The resulting reaction solution was stirred in nitrogen atmosphere at room temperature overnight and then concentrated under reduced pressure. To the obtained residue, trifluoroacetic acid (1 mL) was added. The resulting reaction solution was stirred at room temperature for 2 hr and then poured into a saturated sodium hydrogencarbonate aqueous solution. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and then with saturated saline and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH, eluding solvent; heptane:ethyl acetate=1:1 to 0:1) to give 61.9 mg of the title compound. The physical property values of this compound were as follows: ESI-MS; m/z 502 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.33 (d, J=6.0 Hz, 3H), 1.42 (d, J=6.0 Hz, 3H), 2.34 (s, 3H), 3.20 (dd, J=9.6, 12.8 Hz, 1H), 3.61 (dd, J=2.4, 12.8 Hz, 1H), 3.85 (s, 3H), 4.42-4.52 (m, 2H), 5.35 (d, J=6.8 Hz, 1H), 6.85 (s, 1H), 6.95 (s, 1H), 7.06-7.15 (m, 2H), 7.22 (d, J=8.0 Hz, 1H), 7.33 (dd, J=1.6, 8.0 Hz, 1H), 7.53 (d, J=1.6 Hz, 1H), 7.86 (s, 1H).

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, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2009/48213; (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. 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, A new synthetic method of this compound is introduced below., Formula: C7H8N2O4

lH-Imidazole-4,5-dicarboxylic acid dimethyl ester (592 mg, 3.21 mmol) is combined with hydrazine (600 mg, 18.8 mmol) and MeOH (10 mL). The reaction mixture is heated to 115C for 30 min. Cool and filter off the resulting precipitate. Wash with additional water. Combine the precipitate with hydrazine (1.38 mL) and reflux for 4 h. Pour the reaction mixture into ice water and adjust the to pH 2 with HCl (12 N). The new precipitate is isolated by filtration to afford the title product (293 mg, 60%) 1H NMR (400 MHz, DMSO-^6) delta 11.41 (br. s., 1.47 H), 8.27 (s, 1 H), 3.37 (br. s., 6.2 2H).

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

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 52099-72-6,Some common heterocyclic compound, 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C10H10N2O, 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.

Compound III-1 (1.74 g, 10 mmol) represented by the following structural formulaPotassium carbonate (2.74 g), 1,4-dibromopropane (6.07 g, 30 mmol) was added to a solution of (20 ml) in DMF for 3 hours,Stir at 60 C. Water was added to the reaction solution, and extracted with ethyl acetate.The organic layer was washed with brine and dried over Na 2 SO 4. Filtration,After evaporation of the solvent, the residue is subjected to silica gel column chromatographyPurification by (AcOEt / n-hexane 1: 4) gave compound III-2 (1.961 g, 66%) as a colorless oil.

The synthetic route of 52099-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokyo Medical and Dental University; Hata, Yutaka; Kagechika, Hiroyuki; Ito, Shigeru; Tsuemoto, Nozomi; kodaka, Manami; Dilihumaer, Ainiwaer; (24 pag.)JP2019/89720; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem