Tag: M.W=100-200

24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-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: C5H7BrN2

General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%.

The synthetic route of 24134-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, A common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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 125 mL round-bottomed flask equipped with N2 inlet were added 302 mg (730 umol) N-t-butoxycarbonyl-(2-aza- bicyclo[3.3.1]non-6-yl)-(3-trifluoromethoxy-benzyl)-amine, 197 mg (1.09 mmol) N- methylimidazole-4-carbonyl chloride hydrochloride, 141 mg (1.09 mmol) diisopropylethylamine, and 10 mL dry acetonitrile. The reaction was heated at 800C for 72 hours, cooled, diluted with ethyl acetate, washed with aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, and evaporated to an oil. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluant to afford 198 mg (49%) of a mixture of isomers as an oil.13C-NMR (delta, CDCI3): 21.45, 24.04, 24.23, 24.31 , 24.58, 25.45, 27.24, 28.08, 28.60, 28.63, 30.59, 31.09, 31.22, 31.58, 32.63, 32.89, 33.72, 34.11 , 37.87, 39.38, 40.31, 42.85, 44.96, 46.02, 48.71, 48.98, 57.49, 61.47, 61.90, 79.51, 119.35, 119.58, 119.68, 119.80, 120.00, 120.16, 121.91 , 124.14, 125.56, 125.80, 126.02, 129.81 , 139.19, 141.11 , 142.03, 149.48, 155.55, 155.78 (a mixture of isomers).MS: 559 (parent+1 for MW = 558, C25H33N4O5SF3).HRMS Calc’d. for C25H34N4O5SF3: 559.2202. Found: 559.2178 (-4.3 ppm).

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65500; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 36947-68-9,Some common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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.

Add 2-isopropyl imidazole (0.22 g, 2.04 mmol) to a 150 mL round bottom flask.After stirring potassium carbonate as a base (0.30 g, 2.20 mmol) and acetonitrile as a solvent at 50 C for 40 minutes,After cooling to room temperature, intermediate V (0.43 g, 1.70 mmol) was added and the mixture was warmed to 75 C and the mixture was traced to the end of the reaction.After concentration, extraction, column chromatography separation, drying and the like, the intermediate VII-5 (0.53 g) is obtained, the yield is 85.3%; the white solid

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

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei¡¤lamohan¡¤laao¡¤yadafu; Wang Juan; (39 pag.)CN110305064; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 23328-88-3, 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. 23328-88-3 name is 2-Bromo-4-methyl-1H-imidazole, 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.

2-bromo-1-(5-fluoro-3-methoxy-2-nitrophenyl)-4-methyl-1H-imidazole (B) A mixture of 1,5-difluoro-3-methoxy-2-nitrobenzene (9 g, 47.6 mmol), 2-bromo-4-methylimidazole (7.7 g, 47.6 mmol) and potassium carbonate (14.5 g, 104.7 mmol) in 240 mL DMF was stirred at room temperature overnight. The majority of solvent was removed by rotavap and the residue was diluted with ethyl acetate and washed with water. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with water, brined, dried over magnesium sulfate. Condensation and purification using 5-10% ethyl acetate in dichloromethane as eluent provided 4.8 g (31% yield) of 2-bromo-1-(5-fluoro-3-methoxy-2-nitrophenyl)-4-methyl-1H-imidazole as a yellow solid. 1H NMR (400 MHz, DMSO) delta ppm 7.60 (dd, 1H), 7.38 (dd, 1H), 7.21 (s, 1H), 3.98 (s, 3H), 2.09 (s, 3H). EIMS 330.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; ELBION GMBH; WYETH; US2009/143367; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 111851-98-0, These common heterocyclic compound, 111851-98-0, name is 1-Ethyl-1H-imidazole-2-carbaldehyde, 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.

[00453] (¡ê)-3-(l-ethyl-lH-imidazol-2-yl)-l-(thiazol-2-yl)prop-2-en-l-one was prepared from l-(4-methylthiazol-2-yl)-2-(triphenyl- 5-phosphanylidene)ethan-l-one (1.0 equiv.) and 1 -ethyl- lH-imidazole-2-carbaldehyde5 via Wittig reaction (24 h) in 56 % isolated yield, using synthetic procedures described for the preparation of the analog SW209415. H NMR (400 MHz, CDCI3) delta 8.26 (d, / = 15.4 Hz, 1H), 8.03 (d, / = 3.0 Hz, 1H), 7.82 (d, / = 15.4 Hz, 1H), 7.67 (d, 7 = 3.0 Hz, 1H), 7.22 (s, 1H), 7.07 (d, 7 = 1.2 Hz, 1H), 4.15 (q, 7 = 7.4 Hz, 2H), 1.45 t, / = 7.3 Hz, 3H). ESI-MS (m/z): 234.1 [M+H]+.

Statistics shows that 1-Ethyl-1H-imidazole-2-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 111851-98-0.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford D.; READY, Joseph; ZHANG, Yongyou; ANTCZAK, Monika; WILLSON, James K.V.; POSNER, Bruce A.; GREENLEE, William; (254 pag.)WO2016/168472; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 41716-18-1, These common heterocyclic compound, 41716-18-1, name is 1-Methyl-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.

To a solution of intermediate 30-d (2.0 g, 3.73 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (564 mg, 4.47 mmol), HATU (1.70 g, 4.47 mmol) and DIPEA (2.60 mL, 14.91 mmol) and the reaction mixture was stirred at 0¡ã C. for 2 hours. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 31-a as a white foam

Statistics shows that 1-Methyl-1H-imidazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 41716-18-1.

Reference:
Patent; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89830-98-8, 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 89830-98-8 as follows.

J-1 a (4.84 g; 44.8 mmol) in TH F (60 mL) was added dropwise to a suspension of NaH (1 .97 g; 49.2 mmol) in TH F (200 mL) at 0¡ãC under N2. The mixture was stirred at RT for 30 min and SEM-CI (9.9 mL; 55.9 mmol) in THF(20 mL) was added dropwise at 0¡ãC. The mixture was stirred at RT under N2 for 16 h. Water was added and the product was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude was purified by preparative LC (Irregular SiOH 20-45 [Jim , 150g Merck, Mobile phase Gradient from 50percent DCM, 50percent heptane to 100percent DCM). The fractions containing pure compound were combined and the solvent was removed under reduced pressure to give 6.6 g of J-1 b as a yellow oil (62percent).Mixture of 2 regioisomers : 70/30Minoritory regioisomer : 1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.64 (s, 1 H), 6.56 (s, 1 H), 5.34 (s, 1 H), 3.45 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.52-0.57 (m, 2H), -0.04 (s, 9H).Majoritory regioisomer :1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.56 (s, 1 H), 6.94 (s, 1 H), 5.20 (s, 1 H), 3.43 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.56-0.62 (m, 2H), -0.04 (s, 9H).

According to the analysis of related databases, 89830-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; BONFANTI, Jean-Francois; DOUBLET, Frederic Marc Maurice; EMBRECHTS, Werner; FORTIN, Jerome Michel Claude; MC GOWAN, David Craig; MULLER, Philippe; RABOISSON, Pierre Jean-Marie Bernard; WO2013/68438; (2013); 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 360-97-4 as follows. Application In Synthesis of 4-Amino-1H-imidazole-5-carboxamide

EXAMPLE 3 Preparation of 1-(m-cyanobenzyl)-5-aminoimidazole-4-carboxamide A mixture of 5-aminoimidazole-4-carboxamide (5.00 g), potassium carbonate (12.0 g), and alpha-bromo-m-tolunitrile (9.80 g) were refluxed in acetone (300 ml) for 24 hours under a nitrogen atmosphere. The mixture was cooled to room temperature and filtered. The solid residue was washed with acetone and the combined filtrates were evaporated to dryness. The residual solid was dissolved in acetone (50 ml), concentrated to a volume of 20 ml in vacuo, and diluted with diethyl ether (100 ml) to provide a gum. The solvent was decanted from the residue and deposited crystals of crude product on standing. The gum was triturated twice with acetone, and the acetone layers were combined with the above crystals, and evaporated to provide 5.9 g of a dark gum. The gum was dissolved in methanol (100 ml), filtered, added to 100 ml. E. Merck 7734 silica gel, and evaporated to dryness in vacuo. The product on silica gel was placed on top of a column of 1200 ml E. Merck 7734 silica gel and eluted with 9:1 v/v methylene chloride/methanol. After a forerun of 1.0 l, 400 ml fractions were collected and fractions 8-11 and 12-15 were combined separately and evaporated to dryness. The solid product from fractions 8-11 was triturated with a small volume of acetone and filtered. The filtrate was combined separately with the product from fractions 12-15 and evaporated to dryness. The product was recrystallized from methanol to provide 320 mg of 1-(m-cyanobenzyl)-5-aminoimidazole-4-carboxamide, m.p. 246-247 C.

According to the analysis of related databases, 360-97-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US4659720; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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. category: imidazoles-derivatives

To a solution of compound 82-1 (0.04 g, 0.10 mmol, 1.0 eq) and compound 82-2 (1104) (16.3 mg, 0.10 mmol, 1.0 eq) in dioxane (5.0 mL) was added H20 (0.5 mL) Pd(dppf)Cl2 (7.4 mg, 10.14 umol, 0.1 eq) and Na2C03 (21.5 mg, 0.20 mmol, 2.0 eq). The mixture was stirred at 80 C for 16 hour under N2 atmosphere. LCMS showed desired compound was found. The reaction was filtered through Celite and concentrated under reduced pressure to give a residue. The crude product was purified by prep-HPLC to give Compound 82 (6.64 mg, 18.86 umol, 18.60% yield). LCMS (ESI): RT = 0.634 min, mass calc. for Ci7H24N402S 348.16, m/z found 348.9 [M+H]+; 1HNMR (400 MHz, CDC13) delta 8.55 (s, 1H), 7.81 (d, J = 2.0 Hz, 1H), 7.54 (dd, J = 2.3, 8.8 Hz, 1H), 7.47 (s, 1H), 7.24 (s, 1H), 6.69 (d, J = 9.0 Hz, 1H), 4.24 (q, J= 5.4 Hz, 1H), 3.75 (s, 3H), 3.44 (s, 1H), 2.62 (d, J = 5.5 Hz, 3H), 2.12 – 2.00 (m, 2H), 1.86 – 1.75 (m, 2H), 1.69 – 1.64 (m, 1H), 1.48 – 1.25 (m, 5H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25676-75-9, its application will become more common.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 16681-56-4, name is 2-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. HPLC of Formula: C3H3BrN2

In a 10 mL vial was combined N-(4-fluoro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(pyridin-2-ylmethoxy)benzamide (0.30 g, 0.65 mmol), 2-bromo-1H-imidazole (0.143 g, 0.97 mmol), and KOAc (0.159 g, 1.62 mmol) in dioxane (3 mL) to give a black suspension. Nitrogen gas was bubbled in for 20 min before Pd(PPh3)4 (0.075 g,0.06 mmol) was added. The reaction was heated under microwave at 130 C for 4h. After concentration under reduced pressure the residue was dissolved with DMSO (0.5 mL) and MeOH (1.5 mL), filtered and purified by Gilson HPLC (MeCN/0.1% TFA in water) to give the title compound (2 M HCl in Et2O was added) as the HCl salt (0.050 g, 19% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-56-4, its application will become more common.

Reference:
Article; Yang, Bin; Hird, Alexander W.; Bodnarchuk, Michael S.; Zheng, Xiaolan; Dakin, Les; Su, Qibin; Daly, Kevin; Godin, Robert; Hattersley, Maureen M.; Brassil, Patrick; Redmond, Sean; John Russell, Daniel; Janetka, James W.; Bioorganic and Medicinal Chemistry; vol. 28; 2; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem