Tag: M.W=100-200

Synthetic Route of 22884-10-2, These common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic 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.

To a 50 mL flask was added 4-chloro-orthozilidine 1c (1 mmol), alpha-bromo-tert-butyl ketone (1.2 mmol), and potassium carbonate (1.5 mmol), and reacted at 45 C, The reaction solvent was chloroform (20 mL). After reacting for 2 hours, diphenylmethylphosphine (1.5 mmol) was further added, and the reaction was carried out at 30 C. After the reaction was continued for 3 hours, the solvent chloroform was removed under reduced pressure. The residue was transferred to a solution of triphenylphosphine (2.5 mmol) and iodine (2.5 mmol) in chloroform (15 mL). After reacting for 2 hours, after completion of the reaction, the solvent chloroform was removed under reduced pressure. Residue column chromatography gave 0.223 g of the title compound 2c. The yield was 71%.

Statistics shows that 2-(1H-Imidazol-1-yl)acetic acid is playing an increasingly important role. we look forward to future research findings about 22884-10-2.

Reference:
Patent; China Three Gorges University; Wang Long; Yang Qingqing; Li Yongshuang; Li Dejiang; (8 pag.)CN109265448; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

The starting material was prepared as follows: Diethyl azodicarboxylate (160 mg, 1.4 mmol) was added to a solution of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride (261 mg, 0.7 mmol), (prepared as described for the starting material in Example 22), triphenylphosphine (367 mg, 1.4 mmol) and 2-(imidazol-1-yl)ethanol (94 mg, 0.84 mmol), (J. Med. Chem. 1993, 25, 4052-4060), in methylene chloride (5 ml) and the mixture stirred for 1 hour at ambient temperature. Acetic acid (42 mg, 0.7 mmol) was added and the solvent was removed by evaporation. The residue was triturated with ether, the solid collected by filtration, dried under vacuum and purified by chromatography eluding with methylene chloride/methanol (9/1 followed by 8/2) to give 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (250 mg, 76%).

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

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
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. Formula: C7H5BrN2

[00586] A. tert-Buty 5-bromo-lH-benzo[d]imidazole-2-carboxyIate. A solution of 5-bromo-lH-benzimidazole (1.06 g, 5.38 mmol), di-tert-butyl dicarbonate (1.3 g, 5.91 mmol), triethylamine (0.9 mL, 6.45 mmol) and dimethylaminopyridine (few crystals) in anhydrous tetrahydrofuran (15 mL) was allowed to stir at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the crude product was purified by Biotage chromatography (0-55% ethyl acetate in hexanes) to provide the desired product (0.85 g, 54%) as a white solid. MS (ESI) m/z 297.3 [M+l]+.

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

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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: (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).

The synthetic route of 7189-69-7 has been constantly updated, and we look forward to future research findings.

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

Adding a certain compound to certain chemical reactions, such as: 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, 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 3304-70-9, COA of Formula: C7H8N2O4

1H-Imidazole-4,5-dicarboxylic acid dimethyl ester (1.5 g, 8.15 mmol, 1 equiv. ) was dissolved in MeOH (10 mL) and benzyl bromide (1.16 mL, 9.77 mmol, 1.1 equiv.) before sodium hydride (360 mg, 1.1 equiv., 60% dispersion) and sodium iodide (200 mg) was added. The reaction was stirred for 16 hours before being quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (2 x 30 mL) and the organic layer washed several times with water (4 x 30 mL), brine solution (50 mL). It was dried over Na2S04, filtered and concentrated in vacuo. 1-Benzyl-1H- imidazole-4,5-dicarboxylic acid dimethyl ester 254 (2.01 g, 90 %, 7.33 mmol). ¹H NMR (300 MHz) CDC13 No. 7.58 (s, 1 H), 7.33 – 7.42 (m, 3 H), 7.14 – 7.18 (m, 2 H), 5.41 (s, 2 H), 3.92 (s, 3 H), 3.84 (s, 3 H). MS: 275.1 (M+1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl 4,5-imidazoledicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong, R.; CHEN, Xiaowu; FARDIS, Maria; JABRI, Salman, Y.; JIN, Haolun; KIM, Choung, U.; METOBO, Sanuel, E.; MISH, Michael, R.; PASTOR, Richard, M.; WO2005/117904; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2851-13-0, name is N,N-Dimethyl-1H-benzo[d]imidazol-2-amine, molecular formula is C9H11N3, 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: 2851-13-0

Scheme 3 exemplifies a method of forming compounds of Formula I. Chloro purines (4) (1 mmol) can be coupled with R3-H (for example, wherein R3 is benzimidazol-1-yl) (1.03-1.30 mmol), under Buchwald conditions, for example tris(dibenzylideneacetone)-dipalladium(0) (0.02-0.05 mmol), XPhos (0.10-0.20 mmol), cesium carbonate (2 mmol) in DMF (7-10 mL) with heating under microwave at 140-150 C. for 30 minutes to form purines of Formula I. Formula I purines can be further purified by diluting with EtOAc, filtering the contents of the reaction, concentrating and purifying with flash chromatography or reverse phase HPLC. Formula I purines can be further derivatized in subsequent transformations to functionalize R1, for example by deprotecting any protected functional groups (for example deprotecting BOC-protected amine groups followed by additional steps, such as reductive amination, amide coupling or acylation to form additional compounds of Formula I.Example 131 1-(3-(2-(2-(dimethylamino)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yloxy)azetidin-1-yl)-2-methylpropan-1-one 131 The compound was prepared from 1-(3-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yloxy)azetidin-1-yl)-2-methylpropan-1-one and N,N-dimethyl-1H-benzo[d]imidazol-2-amine following General Procedure of Buchwald coupling shown in Scheme 3. 1H NMR (400 MHz, CDCl3) delta 8.29 (s, OH), 7.58 (d, J=7.5 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.15 (dd, J=11.0, 4.3 Hz, 1H), 7.01 (dd, J=10.1, 4.2 Hz, 1H), 5.58-5.45 (m, 1H), 4.60 (d, J=7.2 Hz, 2H), 4.53-4.39 (m, 2H), 4.31 (d, J=9.6 Hz, 1H), 4.19 (s, 5H), 3.88-3.74 (m, 4H), 3.65 (s, 2H), 3.60 (s, 1H), 3.17 (s, 1H), 2.98 (s, 4H), 2.56-2.42 (m, 1H), 1.14 (d, J=6.8 Hz, 5H). LCMS: M+H+=520.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2851-13-0, its application will become more common.

Reference:
Patent; Li, Jun; Safina, Brian; Sutherlin, Daniel P.; Sweeney, Zachary; US2012/15931; (2012); 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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1,1′-Thiocarbonyldiimidazole

A solution of (2R)-3-PHENYL-1-PIVALOYLOXY-2-PROPYL amine (19-1, LMMOL) and ET3N (1 mmol) in DMF (1 mL) was added dropwise into the pre-dissolved solution of 1,1- thiocarbonyl diimidazole (1.2 mmol) in DMF (2 mL) at 50 C over 1 min. The mixture was stirred for 1 min. at 50 C and then for 10 min. at room temperature. The mixture was directly purified by column chromatography using EtOAc: hexanes (1: 5) as eluant to afford (2R)-3-phenyl-1-pivaloyloxy-2-propyl isothiocyanate (19-3, SU-684). 89% yield, colorless oil. H NMR (CDC13) 5 7.15-7. 35 (M, 5 H), 4.22 (dd, 1 H, J= 2. 7,10 Hz), 4.02-4. 12 (m, 2 H), 2.94 (d, 2 H, J= 6. 3 HZ), 1.25 (s, 9 H)

According to the analysis of related databases, 6160-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIGITALBIOTECH CO., LTD.; WO2005/3084; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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: C7H10N2O2

To an oven- dried three-neck reaction flask charged with a magnetic stir bar, an internal thermometer at rt under argon was added ethyl 4-methyl-lH-imidazole-5- carboxylate (2.20 g, 14.3 mmol) and anhydrous DMF (71 mL). The yellow solution was cooled to -20C using a dry ice and EtOAc bath. Lithium hexamethyldisilane (1.0M in TetaF, 15.7 mL, 15.7 mmol) was then added dropwise via an addition funnel while maintaining the internal temperature below -12C. To the solution was then added o-(diphenylphosphinyl)- hydroxylamine (4.00 g, 17.1 mmol) in two portions while maintaining the internal temperature at O0C. The resulting white suspension was diluted by the addition of DMF (15 mL) and stirred at rt overnight. The white suspension was quenched with water (5 mL) and the solvent was removed under vacuum. The resulting yellow solid was extracted with CH2Cl2 (50 mL), EtOAc (100 mL) and then the organic extracts were combined and concentrated by rotary evaporation to a brown solid. It was purified by flash column chromatography (80 g pre-packed silica gel column, gradient elution with CH2Cl2, to CH2Cl2:Me0H, 4:96) to give 1.00 g (41%) of the title compound as a white solid. 1H NMR (CDCl3) 7.59 (s, I H), 5.32 (br s, 2H), 4.36 (q, J= 7.1 Hz, 2H), 2.45 (s, 3H), 1.40 (t, J= 7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51605-32-4, its application will become more common.

Reference:
Patent; CYTOVIA, INC.; WO2008/57402; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 939-70-8, A common heterocyclic compound, 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, molecular formula is C9H8N2O, 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: Various o-substituted anilines (0.05 mol) and lactic acids (3.75 mL, 0.05 mol) were dissolved in 20 mL of HCl (4 M). The mixture was heated under reflux for 1.5 h. After cooling to room temperature, the reaction mixture was poured into water. Next, the pH was adjusted to 10-11 with ammonia. The mixture was filtered, and the residue was recrystallized from water to give intermediates 1b-3b. Next, 1b-3b (0.02 mol) were each dissolved in 15 mL of acetic acid. When the mixture was heated to 90 C, chromium trioxide solution was added. The reaction mixture was stirred at 105C for 30 min. After cooling to room temperature, the reaction mixture was poured into water (1 L) and then extracted by ethyl acetate (EtOAc). The organic layers were combined, dried with MgSO4, filtered and then concentrated under reduced pressure. The residue was recrystallized from toluene to give the intermediates 1c-3c. Last, 1c-3c (0.02 mol) and 8 mL of a 10% NaOH aqueous solution were dissolved in 20 mL of ethanol. The reaction mixture became a clear red solution. Next, various substituted aromatic aldehydes (0.02 mol) were added. After stirring for 5 h, the mixture was filtered, and the residue was purified by column chromatography (EtOAc: hexane = 1:5) to give the target compounds A1-A13, B1-B3 and C1-C3.

The synthetic route of 939-70-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Lin-Tao; Jiang, Zhi; Shen, Jia-Jia; Yi, Hong; Zhan, Yue-Chen; Sha, Ming-Quan; Wang, Zhen; Xue, Si-Tu; Li, Zhuo-Rong; European Journal of Medicinal Chemistry; vol. 114; (2016); p. 328 – 336;,
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. 35203-44-2, name is 1-Propyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Propyl-1H-imidazole

Part of the trans-[RuCl4(DMSO)2]Na 0.10g (0.24mmol) prepared in Example 1 was dissolved in acetone andTo 0.33 ml of dimethyl sulfoxide, 0.14 ml (1.23 mmol) of N-propylimidazole was further added. The ultrasonic reaction was carried out for 2 hours. The reaction liquid was filtered, and a mixture of chloroform and diethyl ether was added to the filtrate to cause crystallization. The crystals were filtered, washed with a mixture of chloroform/diethyl ether (v/v = 1:9) and dried over silica gel to give the desired product G99. Yield: 70percent.

According to the analysis of related databases, 35203-44-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Zhongyi Academy Of Sciences Traditional Chinese Medicine Institute; Beijing Tangshi Traditional Chinese Medicine Research Center; Gu Liwei; Liang Yaohua; Li Canghai; Shen Jianying; Liang Guogang; Jiang Tingliang; Li Xiaodong; (16 pag.)CN104744518; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem