Tag: M.W=100-200

These common heterocyclic compound, 18075-64-4, name is 1-Phenyl-1H-imidazole-4-carboxylic acid, 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. Recommanded Product: 18075-64-4

DMSO (0.5 mL) was added to a mixture of 1-phenyl-1H-imidazole-4-carboxylic acid (34 mg, 0.18 mmol) and 1-pyrrolo[1,2-c]pyrazin-1-yl-pyrrolidin-3-ylamine dihydrochloride salt (50 mg, 0.18 mmol). To this was added triethylamine (0.100 mL, 0.72 mmol) followed by HATU (76 mg, 0.20 mmol). The mixture was allowed to stir for 30 min after which time it was diluted with dichloromethane (1.0 mL), washed with water (3*1.0 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by reverse phase HPLC (10:90-95:5 MeCN:H2O+0.1% TFA). The combined product fractions were lyophilized to give the TFA salt of the product as a pale yellow solid (49 mg, 0.10 mmol, 56% yield).

The synthetic route of 1-Phenyl-1H-imidazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, 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 934-32-7, Product Details of 934-32-7

General procedure: A mixture of -Fe2O3starch-n-butyl SO3H (10 mg),aromatic aldehyde (1.0 mmol), dimedone (1.0 mmol),2-aminobenzimidazole (1.0 mmol) was heated in an oilbath (100 C) for the appropriate reaction time until thecompletion. The progress of the reaction was monitoredby TLC (n-hexane:ethyl acetate, 8:4). After completion ofthe reaction water (10 mL) was added and the catalyst wassegregated using an external magnet, washed with chloroform,dried out, and used directly without an appreciableloss of its activity for the next run. The product was purifiedby recrystallization from EtOH and dried in air.

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; Shamsi-Sani, Mahnaz; Shirini, Farhad; Mohammadi-Zeydi, Masoud; Journal of Nanoscience and Nanotechnology; vol. 19; 8; (2019); p. 4503 – 4511;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(0044) The original patent for structure 1, FIG. 1 was granted in 1984 to J. Boileau. His synthetic methodology for successfully achieving 1 was the direct nitration of glycoluril using a mixture of N2O5 and 100% HNO3. The yields on his process are claimed to be greater than 85%. It has since been discovered it is possible to successfully synthesize structure 1 using a mixture of acetic anhydride and 100% HNO3 in similar yields without necessitating the making N2O5 directly. Both of these methods yield structure 1 that is highly sensitive to impact and friction (approximately twice more sensitive on both accounts than standard military explosives RDX and HMX) making handling of the material from these processes inherently more dangerous.

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, Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; U.S. Army Research Laboratory ATTN: RDRL-LOC-I; Sherrill, William Matthew; Banning, Joseph Erik; (7 pag.)US2016/90388; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 41806-40-0, 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. 41806-40-0 name is 1-Methylimidazole-5-carboxylic Acid, 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.

EXAMPLE 72 (METHOD T); N-r4-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahvdrori.31thiazolor5.4-clpyridin-2-yl)-3,4- dihvdro-2H- 1 ,4-benzoxazin-6-yl]- 1 -methyl-lH-imidazole-5-carboxamide; To a stirred solution of Example 42 (0.025 g, 0.08 mmol) in DCM (1 mL) were added l-methylimidazol-5-ylcarboxylic acid (0.013 g, 0.10 mmol), DIPEA (0.02 mL, 0.10 mmol), EDC (0.030 g, 0.16 mmol) and HOBT (0.05 g, 0.04 mmol). The reaction mixture was stirred at r.t. for 18 h, then concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.01 g, 29%) as a yellow oil. 6H (CDCl3) 9.25 (IH, s), 8.46-8.43 (IH, m), 7.33 (IH, dd, J8.9 and 2.4 Hz), 7.07 (IH, d, J 0.9 Hz), 7.02 (IH, d, J0.8 Hz), 6.94 (IH, d, J 8.9 Hz), 5.56 (IH, br. s), 4.36-4.29 (2H, m), 4.16-4.09 (2H, m), 4.11 (3H, s), 2.90 (2H, s), 1.40 (6H, s). LCMS (ES+) 439.4 (M+H)+, RT 2.69 minutes (Method 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methylimidazole-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; UCB PHARMA S.A.; WO2008/1076; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3314-30-5, 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 3314-30-5 as follows.

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0°C, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3- thiazole-4-carboxamide dihydrochloride (192) (143 mg, 0.37 mmol), 1 H-1 ,3-benzodiazole-2-carbaldehyde (70.1 mg, 0.48 mmol), MgS04 (200 mg) in MeOH (10 ml) at room temperature for 3 d, followed by addition of NaBH4 (28 mg, 0.74 mmol) gave the title compound (94 mg, 56percent) as a white solid after purification by prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.19 (s, 1 H), 8.71 (t, J = 5.6 Hz, 1 H), 8.37 (dt, J = 4.6, 1.3 Hz, 1 H), 7.70 (ddd, J = 10.0, 8.4, 1.1 Hz, 1 H), 7.54 (d, J = 7.2 Hz, 1 H), 7.45 (d, J = 7.0 Hz, 1 H), 7.40 (dt, J = 8.6, 4.4 Hz, 1 H), 7.14 (t, J = 7.5 Hz, 2H), 4.66 – 4.58 (m, 2H), 3.97 (s, 2H), 3.12 (t, J = 6.3 Hz, 2H), 2.94 (t, J = 6.3 Hz, 2H) HPLCMS (Method A): [m/z]: 445.1 [M+H]+

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

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

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 16681-56-4 as follows. Computed Properties of C3H3BrN2

Obtained in Example 50 (a) (S) -1-tert- butoxycarbonylamino-4- (5-chloro-7- (4,4,5,5-dioxa -1,3,2- borane-2-yl)benzoxazol-2-yl) -3-methyl piperazine (48 mg, 0.1mmol), 2- bromo -1H- imidazole (29 mg, 2.0 eq.), Tetrakis(triphenylphosphine) palladium (0) (11.6 mg, 0.1 eq), potassium carbonate (55 mg, 4.0 equiv) 1, 4-dioxane (800muL) and water (200muL) for dissolution, and under an argon atmosphere in an oil bath from 110 4 hours with stirring did. Water was added to the reaction mixture, the product extracted with ethyl acetate, an organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by preparative TLC (developing solvent, methanol: chloroform = 1: 19) to give the title compound 21.3 mg.

According to the analysis of related databases, 16681-56-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MeijiSeika Pharma Corporation; Kikuchi, Jika; Tabata, Yuji; Yamakawa, Takeru; Matsuhira, Takashi; Watanabe, Naoko; Kuboda, Natsuki; Kaneda, Kaoru; (143 pag.)KR2016/30503; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 615-16-7, These common heterocyclic compound, 615-16-7, name is 2-Hydroxybenzimidazole, 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.

To a stirred solution of compound 114 (1 g, 7.46 mmol) in CH2C12 (10 mL) under argon atmosphere was added chlorosulfonic acid (1 mL, 14.92 mmol) at 0 C; heated to reflux and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo and the residue diluted with water (10 mL); neutralized with aqueous NaOH solution and extracted with EtOAc (3 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford compound 115 (980 mg, 58%) as an off-white solid. TLC: 10% MeOH/ CH2C12 (Rf. 0.5); 1H-NMR (DMSO-i/tf, 400 MHz): delta 10.66 (s, 1H), 10.61 (s, 1H), 7.24 (d, J= 6.4 Hz, 1H), 7.18 (s, 1H), 6.85 (d, J = 8.4 Hz, 1H).

The synthetic route of 615-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ARNOLD, Lee Daniel; MAAG, Hans; TURNER, JR., William W.; (274 pag.)WO2016/168619; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 36947-68-9, 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. 36947-68-9, name is 2-Isopropyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of corresponding 2-chloro-N-phenylacetamide (1 mmol), imidazole (1.5 mmol), N,N-diisopropylethylamine (0.35 ml, 2 mmol) in dimethylformamide (7mL) was stirred for 16 hours at 60C. Then the reaction mixture was cooled to roomtemperature and treated with water (35 ml). The crude product was filtered andpurified by recrystallization from acetonitrile or by HPLC chromatography (methanol/water). Yield: 15-70 % depending on the structures of the starting materials.

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-Isopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH; SPRINGER, Wolfdieter; FIESEL, Fabienne C.; CAULFIELD, Thomas R.; (172 pag.)WO2018/23029; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1632-83-3, name is 1-Methylbenzimidazole, 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 1632-83-3, Formula: C8H8N2

1-methylbenzimidazole (1 mmol, 132.1 mg)Perfluoroiodobutane (1.1 mmol, 380.5 mg) was placed in a 10 mL round bottom flask.Potassium tert-butoxide (1.2 mmol, 134.7 mg) is addedAnd 5mL of toluene,Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction.After the toluene was removed by rotary evaporation, the mixture was washed with water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give a crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (ratio by volume = 15:1).2-Iodo-1-methylbenzimidazole was obtained (white solid, 208.9 mg, yield 81%).

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:
Patent; Liaoning University; Liang Fushun; Liu Xia; Han Zhengbo; Su Zhongmin; (10 pag.)CN107501023; (2017); A;,
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. 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