Tag: M.W=100-200

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 4857-06-1 as follows. COA of Formula: C7H5ClN2

[0267] To a solution of 2-chloro-1H-benzo[d]imidazole (916 mg, 6 mmol) in 10 mL of dry DMF, which was cooled to 0 C., was careffilly added NaH (240 mg, 10.8 mmol) in small portions. The mixture was stirred for 15 minutes at this temperature. Then, methyl iodide (0.41 mL, 6.6 mmol) was added under continuous stirring for an additional 15 minutes. When thin layer chromatography (TLC) showed full conversion, the mixture was poured into 60 mL of water and a white solid precipitated. The precipitate was collected by filtration and dried in vacuo to obtain 2a 650 mg (65%) of pure product as a white solid. ?H NMR (400 MHz, DMSOd 5) oe 7.62-7.54 (m, 2H), 7.34-7.27 (m, 1H), 7.27-7.20 (m, 1H), 3.80 (s, 3H)

According to the analysis of related databases, 4857-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYLOR COLLEGE OF MEDICINE; O’Malley, Bert W.; Lonard, David Michael; Wang, Jin; Xu, Jianming; Chen, Jianwei; (47 pag.)US2017/290830; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 583-42-6,Some common heterocyclic compound, 583-42-6, name is 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione, molecular formula is C7H5FN2S, 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 I 9 Preparation of 5-fluoro-2-[[(4-cyclopropylmethoxy-2-pyridinyl)methyl)thio]-1H-benzimidazole To 5-fluoro-2-mercapto-1H-benzimidazole (0.88 g, 0.0051 mol) in methanol (25 ml) NaOH (0.2 g, 0.0051 mol) dissolved in H2 O (1 ml) and 4-cyclopropylmethoxy-2-chloromethylpyridine hydrochloride (0.91 g, 0.0046 mol) dissolved in methanol (10 ml) were added in the given order. The mixture was heated to boiling and NaOH (0.2 g, 0.005 mol) dissolved in H2 O (1 ml) was added and the mixture was refluxed for 1 hour. After evaporation of methanol, CH2 Cl2 (75 ml) and H2 O (50 ml) were added and pH adjusted to 10. The mixture was vigorously stirred, the phases were separated, the organic phase was dried over Na2 SO4 and evaporated giving the desired product (1.25 g, 72%). NMR data for the product is given below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione, its application will become more common.

Reference:
Patent; Aktiebolaget Hassle; US5049674; (1991); A;,
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Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, 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 24134-09-6, Quality Control of 5-Bromo-1,2-dimethyl-1H-imidazole

Example 42a: (4-chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)(2,6-dimethylpyridin-3-yl)methanol A solution of -BuLi (2.5 M in liexanes, 1.2 mL, 3.0 mmol) was added dropwise by syringe to a solution of 5-bromo- 1 ,2-dimethyl- lH-imidazole (570.8 mg, 3.261 mmol) in dry THF (6 mL) in a dry ice-acetone bath. After 1-2 minutes, a solution of (4-chloro~2~methoxy-3-((6- (frifluoromethyl)pyridin-3-yl)m (0.790 g, 1 .626 mmol, Intermediate 47: step b) in dry THF (2 mL) was added dropwise. The reaction was stirred for 5 minutes, then was moved into an ice bath and allowed to warm to ambient temperature. The reactio was quenched with saturated aqueous ammonium chloride. The mixture was partitioned between water and dichloromethane. The separated aqueous phase was further extracted with dichloromethane. The organic phase was dried (Na2S04), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-5% MeOH-DCM) followed by reverse-phase HPLC (acetonitrile/H20 + 0.05% TFA). The product fractions were basified with saturated aqueous sodium bicarbonate and extracted with DCM, before being dried (Na2S04), filtered, and concentrated to dryness to provide the title compound. H NMR. (400 MHz, CDC13) delta 8.76 (d, J = 2.0 Hz, 1H), 8.13 (d, J = 2.2 Hz, 1H), 7.79 – 7.73 (m, 2H), 7.57 (dd, J = 8.1, 0.9 Hz, 1H), 7.41 (dd, J = 8.7, 2.2 Hz, 1H), 7.1 1 (d, J = 8.0 Hz, 1H), 6.94 (d, J = 8.0 Hz, i f }. 6.04 (s, 1H), 4.35 (s, 2H), 4.08 (s, 3H), 3.39 (s, 3H), 2.53 (s, 3H), 2.41 (s, 3H), 2.37 (s, 3H); MS m/e 582.2 [M+H]+.Example 42a was purified by chira SFC (ChiralPak AD-H, 70:30 C02:mixture of MeOH/?PrOH (50:50 + 0.3% PrNH2)) to provide two pure enantiomers. The first eluting enantiomer was Example 42b: H NMR (400 MHz, CDCI3) delta ppm 8.77 (s, 1H), 8.15 – 8.52 (m, I I I). 7.77 (d, ,/ 8.3 Hz, 2H), 7.57 (d, ./ 8.2 Hz, 1 H), 7.45 – 7.40 (rn, 1H), 7.1 1 (d, J = 8.0 Hz, I I I). 6.94 (d, ./ = 8.1 Hz, I I I). 6.06 (s, 1 1 1). 4.36 (s, 2H), 4.09 (s, 3H), 3.40 (s, 3H), 3.30 (s, IH), 2.54 (s, 3H), 2.42 (s, 3H), 2.39 (s, 3H); MS m/e 582.2 [M+H]+. The second eluting enantiomer was Example 42c: 1 I NMR (400 MHz, CDCI3) 6 ppm 8.76 (d, ,/ 2.1 Hz, l i s). 8.56 (d, ./ 2,1 Hz, 1H), 7.79 – 7.74 (rn, 1H), 7.70 (d, J = 8.7 Hz, 5 H), 7.60 – 7.55 (m, I H), 7.37 (dd, J= 8.7, 2.1 Hz, IH), 7.1 1 (d, ./ 8.0 Hz, IH), 6.93 (d, ./ = 8.0 Hz, IH), 5.98 (s, IH), 4.35 is. 21 1). 4.28 – 4.18 (m, IH), 4.07 (s, 3H), 3.37 (s, 3H), 2.53 (s, 3H), 2.40 (s, 3H), 2.33 (s, 3H); MS m/e 582.0 [M+Hf .

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, 5-Bromo-1,2-dimethyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, 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 16681-59-7, Formula: C4H5BrN2

General procedure: To degassed DMF (8.0 mL) was added Pd(dppf)Cl2 (73 mg, 0.10 mmol), bis(pinacolato)diboron (508 mg, 2.0 mmol), potassium acetate (589 mg, 6.0 mmol), and 2,6-dibromobenzene (0.121 mL, 236 mg, 1.0 mmol) in order at room temperature. The mixture was heated to 130 C for 1 hour to complete formation of the boronic ester. Then 3-bromopyridine (0.289 mL, 474 mg, 3.0 mmol) and degassed aqueous sodium hydroxide (2.00 mL, 3.0 M, 6.0 mmol) were sequentially added to the hot reaction, and heating at 130 C was continued for another 3 hours when the reaction was complete (by GCMS). The reaction was cooled and evaporated to a residue in vacuo. The residue was extracted with chloroform, and the combined extracts were concentrated and applied to preparative silica TLC plates. After development by 1:1 THF:EtOAc the product bands were removed and extracted with DME. Evaporation of extract solutions resulted in the yields. The products could be purified by sublimation at 180 C and 10 mmHg if needed.

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

Reference:
Article; Avitia, Bertoldo; MacIntosh, Eric; Muhia, Samuel; Kelson, Eric; Tetrahedron Letters; vol. 52; 14; (2011); p. 1631 – 1634;,
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 53710-78-4 as follows. HPLC of Formula: C6H9ClN2

EXAMPLE 23 A mixture of 4-(3′-chloro-4′-fluoroanilino)-6-hydroxy-7-methoxyquinazoline (1.5 g), 3-(imidazol-1-yl)propyl chloride (0.67 g), potassium carbonate (3 g) and DMF (40 ml) was stirred and heated to 90 C. for 1 hour. A second portion (0.12 g) of the propyl chloride was added and the mixture was heated to 90 C. for a further hour. The mixture was cooled to ambient temperature, filtered and evaporated. The residue was purified by column chromatography using a 9:1 mixture of methylene chloride and methanol as eluent. There was thus obtained 4-(3′-chloro-4′-fluoroanilino)-6-(3-imidazol-1 -ylpropoxy)-7-methoxyquinazoline (0.66 g); NMR Spectrum: 2.5 (m, 2H), 4.12 (s, 3H), 4.25 (t, 2H), 4.35 (t, 2H), 7.08 (s, 1H), 7.4 (d, 2H), 7.6 (t, 1H), 7.8 (s, 1H), 7.95 (m, 2H), 8.25 (m, 1H), 8.65 (s, 1H), 9.7 (broad s, 1H); Elemental Analysis: Found C, 58.2; H, 4.6; N, 16.6; C21 H19 ClFN5 O2 0.2H2 O requires C, 58.5; H, 4.5; N, 16.2%.

According to the analysis of related databases, 53710-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zeneca Limited; US5770599; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16093-82-6, 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 16093-82-6 as follows.

Preparation 19-1) (2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidine (21.5 g) and 2-carbamoylimidazole (7.07 g) were reacted in substantially the same manner as that of Preparation 10-3) to give (2R,4R)-1-allyloxycarbonyl-2-{2-(2-carbamoylimidazol-1-yl) ethyl}-4-methylsulfonyloxypyrrolidine (15.2 g) as a yellow solid. NMR (CDCl3, 200 MHz, delta): 1.9-2.2 (2H, m), 2.4-2.6 (2H, m), 3.04 (3H, s), 3.5-3.7 (1H, m), 3.9-4.1 (2H, m), 4.5-4.6 (4H, m), 5.1-5.3 (3H, m), 5.63 (1H, br), 5.8-6.0 (1H, m), 7.0-7.3 (3H, m)

According to the analysis of related databases, 16093-82-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5608056; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 934-32-7, 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. 934-32-7 name is 1H-Benzo[d]imidazol-2-amine, 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.

General procedure: A mixture of 2-aminobenzimidazole 7 (1.33 g, 10.0 mmol), 10.0 mmol of the proper alkyl halide, 1.0 g of finely powdered KOH mixed with 2.0 g of anhydrous K2CO3 and acetone (50 mL) was heated at reflux for 3 h, with stirring. The solvent was removed in vacuo and the residue was partitioned between water (100 mL) and CH2Cl2 (100 mL), and the aqueous phase was further extracted twice with CH2Cl2. The combined extracts, dried over anhydrous Na2SO4, after removal of solvent afforded an oily or solid residue which was treated with a small amount of ethyl ether to give compounds 8a-e,l-o as whitish solids which were crystallized from the proper solvent. Only in the case of compound 8f, a preliminary purification by column chromatography [SiO2/ethyl acetate-acetone (1:1)] was necessary to obtain a crystalline compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzo[d]imidazol-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Di Braccio, Mario; Grossi, Giancarlo; Signorello, Maria Grazia; Leoncini, Giuliana; Cichero, Elena; Fossa, Paola; Alfei, Silvana; Damonte, Gianluca; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 564 – 578;,
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Imidazole | C3H4N2 – PubChem

Application of 939-70-8,Some common heterocyclic compound, 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, molecular formula is C9H8N2O, 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: To a solution of 1-(1H-benzo [d] imidazol-2-yl)ethanone (2) (0.01 mol) in ethanol (60 ml),benzaldehyde (0.01 mol) and a few drops of glacialacetic acid were added and the mixture refluxed for10 hr. It was then cooled concentrated and pouredinto crushed ice and filtered. The solid thus obtainedwas purified by recrystallizaton from ethanol.

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

Reference:
Article; Bhaskar; Bharahmeswari; Indian Journal of Heterocyclic Chemistry; vol. 23; 2; (2013); p. 207 – 212;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 939-70-8, 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. 939-70-8 name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, 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.

To a solution of 1-(1H-benzo [d] imidazol-2-yl)ethanone (2) (0.01 mol) in ethanol (60 ml),benzaldehyde (0.01 mol) and a few drops of glacialacetic acid were added and the mixture refluxed for10 hr. It was then cooled concentrated and pouredinto crushed ice and filtered. The solid thus obtainedwas purified by recrystallizaton from ethanol.1 H NMR (400 MHz, DMSO-d6): delta 6.81 (d, 1H,J=10.2 Hz), 6.98-7.20 (m, 5H), 7.24 (d, 1H, J=10.2Hz), 7.42 (m, 4H), 10.24 (brs, 1H). Mass [M+H], 249.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(1H-Benzo[d]imidazol-2-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Article; Bhaskar; Bharahmeswari; Indian Journal of Heterocyclic Chemistry; vol. 23; 2; (2013); p. 207 – 212;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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 41716-18-1, Recommanded Product: 41716-18-1

[00393] To a solution of (+/?)-cis-N1-(2-chloro-7-methyl-7H-pyrrolo[2,3 -d]pyrimidin-4-yl)cyclohexane-i,3-diamine (110.5 mg, 9 mmol) in a mixed solvent of tetrahydrofuran (4 mL) and dimethyl sulfoxide (1 mL) was added N,N-diisopropylethylamine (0.16 mL, 1.19 mmol) and i-methyl-1H-imidazole-4-carboxylic acid (99 mg, 0.78 mmol). The mixture was stirred at rt for 10 minitues, and then HATU (300 mg, 0.79 mmol) was added. The resulting mixture was stirred at rt for 3 h. To the reaction mixture was added water (10 mL), and the resulting mixture was extracted with ethyl acetate (10 mL x 3). The combined organic layers were washed with saturated brine (30 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a colorless solid (86 mg, 56percent).MS (ESI, pos.ion) m/z: 388.2 [M+H]+1H NMR (400 MHz, MeOD) (ppm) : 7.65 (d, J 6.1 Hz, 2H), 6.99 (d, J 3.3 Hz, 1H), 6.56 (d,J = 3.4 Hz, 1H), 3.78 (s, 3H), 3.72 (s, 3H), 2.68 (s, 2H), 2.34 (d, J = 11.6 Hz, 1H), 2.06 (s, 2H),1.93 (d, J = 13.6 Hz, 1H), 1.61 (d, J = 13.5 Hz, 1H), 1.44 (d, J = 11.7 Hz, 1H), 1.39 (d, J = 3.6Hz, 2H).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem