Tag: M.W=100-200

These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, 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. HPLC of Formula: C7H7N3

Example 38 N-(1H-benzo[d]imidazol-5-yl)-2-(4-(5-chloro-2-propionylphenyl)-5-methoxy-2-oxopyri din-1(2H)-yl)-3-phenylpropanamide 38 Compound 8i (80 mg, 181.86 mumol), 1H-benzo[d]imidazol-5-amine 38a (24.22 mg, 181.86 mumol, prepared by a known method disclosed in “”) and N,N-diisopropylethylamine (70.51 mg, 545.59 mumol) were added to 10 mL of tetrahydrofuran, followed by addition of a solution of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide in ethyl acetate (50%, 231.34 mg, 363.73 mumol). After completion of the addition, the reaction solution was warmed up to 50C, and stirred for 1.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was added with 25 mL of saturated sodium bicarbonate solution, and extracted with ethyl acetate (50 mL*2). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by the silica gel column with elution system A to obtain the title compound 38 (75 mg, yield: 74.3%). MS m/z (ESI): 555.5 [M+1] 1H NMR (400 MHz, DMSO-d6) delta 10.84 (s, 1H), 9.05 (s, 1H), 9.14 (s, 1H), 8.27 (s, 1H), 7.79-7.77 (d, 1H), 7.72-7.69 (d, 1H), 7.59-7.52 (m, 2H), 7.41 (s, 1H), 7.34 (s, 1H), 7.30-7.24 (m, 4H), 7.19-7.17 (m, 1H), 6.30 (s, 1H), 6.03-5.99 (m, 1H), 3.52-3.50 (m, 4H), 3.48-3.44 (m, 1H), 2.85-2.75 (m, 2H), 1.25-1.18 (m, 3H).

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

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; YANG, Fanglong; WANG, Weimin; LI, Xiaodong; CHEN, Gang; HE, Feng; TAO, Weikang; (198 pag.)EP3486242; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic 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 22884-10-2, Computed Properties of C5H6N2O2

A suspension of imidazol-1-ylacetic acid, compound of formula 2 (50g, 0. 396mol) and phosphorous acid (48.7g, 0. 594mol) in sulfolan (180ml) was heated to 75 C for 30 min. The mixture was cooled to 35-40 C and phosphorous trichloride (117ml, 1. 346mol) was gradually introduced while maintaining the temperature between 35-45 C. The mixture was heated to 63-67 C for 3 hours, whereby white solid results. It was then cooled to 0- 5’C and quenched by slow addition of water (500ml) at 0-5 C over a period of 1 hour. The resulting clear solution was heated at 100 C for 3 hours, cooled to ambient temperature and charcoalized. Acetone was added to the charcoalized solution. The mixture was then stirred for 4 hours at 20-25 C and the crystallized product was filtered, washed sequentially with chilled water, acetone and dried to obtain zoledronic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1H-Imidazol-1-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; WO2005/66188; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39021-62-0, These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-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.

A mixture of 3-methyl-3H-imidazole-4-carbaldehyde (1.40 g, 12.7 mmol), (R)-(+)-2- methyl-2-propanesulfinamide (2.36 g, 19.1 mmol) and titanium (IV) isopropoxide (11.2 mL, 38.1 mmol) in TEtaF (10 mL) was warmed at reflux for 18 hours. The mixture was cooled to room temperature, and diluted with ether (100 mL) and water (6 mL). The mixture was stirred for 10 minutes and then dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes, and concentrated to afford 2-methyl-propane-2- sulfinic acid [l-(3-methyl-3H-imidazol-4-yl)-prop-(£)-ylidene] -amide as a yellow solid.

Statistics shows that 1-Methyl-1H-imidazole-5-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 39021-62-0.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; DISALVO, Darren; FANDRICK, Daniel Robert; HARCKEN, Christian; KUZMICH, Daniel; LEE, Thomas Wai-Ho; LIU, Pingrong; LORD, John; MAO, Can; NEU, Jochen; RAUDENBUSH, Brian Christopher; RAZAVI, Hossein; REEVES, Jonathan Timothy; SONG, Jinhua, J.; SWINAMER, Alan, David; TAN, Zhulin; WO2010/36632; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 934-22-5, name is 6-Aminobenzimidazole, 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 934-22-5, Computed Properties of C7H7N3

2,3-Dibromo-6-hydroxy-5-methoxybenzaldehyde (0.1 g, 0.32 mmol), 5-Aminobenzimidazole (0.03 g, 0.21 mmol), and isoamyl alcohol (2 mL) were stirred at room temperature under N2. Acetic acid (0.07 mL) was added drop-wise, and the mixture was refluxed overnight. The reaction mixture was filtered, washed with CH2Cl2, MeOH, and dried to yield 26 (0.06 g, 0.14 mmol, 65.4%) as an orange powder. 1H NMR (DMSO, 300 MHz) delta 15.54 (s, 1H), 9.20 (s, 1H), 8.34 (s, 1H), 7.76-7.68 (m, 2H), 7.43 (s, 1H), 7.38 (s, 1H), 3.86 (s, 3H); 13C NMR (DMSO, 700 MHz) delta 162.30, 154.74, 149.45, 144.27, 140.84, 120.42, 118.82, 118.46, 117.60, 117.43, 117.10, 113.95, 112.87, 56.78. Rf=0.48 (CH2Cl2/MeOH 9:1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Shim, Hyun Jae; Yang, Hye Ran; Kim, Han Ie; Kang, Shin-Ae; No, Kyoung Tai; Jung, Young Hoon; Lee, Seung-Taek; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4659 – 4663;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 614-97-1, A common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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: Equivalent amount of the N-protected amino acid or dipeptide (1.45 mmol) (2a: 300 mg, 2b: 320 mg, 2c: 440 mg, 2d: 480 mg, 2e: 250 mg, 2f: 390 mg, 2g: 300 g, 2h: 440 mg, 2i: 250 mg, 2j: 390 mg, 2k: 300 mg, 2l: 320 mg, 2m: 440mg, 2n: 480 mg, 2o: 390 mg, 2p: 520 mg), benzimidazole (or its derivative) (1.45 mmol), (2a, 2b, 2c, 2d, 2e, 2f: 170mg, 2g, 2h, 2i, 2j: 190 mg, 2k, 2l, 2m, 2n, 2o: 240 mg, 2p:170 mg) and DCC (300 mg, 1.45 mmol) were reacted in dried THF (10 mL) under an atmosphere of argon for 3 h at room temperature and formed dicyclohexzylurea was filtered off. The volatiles were removed with reduced pressure. The residue was crystallized from ethanol/diethyl ether (1:2) (Fig. 1).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bu?day, Nesrin; Kuecuekbay, F. Zehra; Apohan, Elif; Kuecuekbay, Hasan; Serinda?, Ayfer; Ye?ilada, Oezfer; Letters in Organic Chemistry; vol. 14; 3; (2017); p. 198 – 206;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16093-82-6, A common heterocyclic compound, 16093-82-6, name is 1H-Imidazole-2-carboxamide, molecular formula is C4H5N3O, 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.

A solution of lH-imidazole-2-carboxylic acid amide (360 mg, 3.24 mmol) and phenyl dichlorophosphate (2 mL) was heated at 1700C for 8 min, in a microwaves oven. The reaction mixture was cooled at room temperature and poured into water (50 mL). The solution was cooled at 0C and the pH was adjusted to 11 by addition of NaOH 10 M. Ethyl acetate was added and the phases were separated. The organic layer was dried over sodium sulphate and evaporated in vacuo to provide IH- Imidazole-2-carbonitrile. A solution of lH-imidazole-2-carbonitrile and hydroxylamine (50% sol. in water, 794 muL, 13 mmol) in ethanol (15 mL) was refluxed for 4h. The solvent was removed and the crude N-hydroxy-lH-imidazole-2- carboxamidine was used for the next step without further purification. EPO Yield: quantitative; LCMS (RT): 0.62 min (Method D); MS (ES+) gave m/z: 127.0 (MH+).

The synthetic route of 16093-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADDEX PHARMACEUTICALS SA; WO2006/123257; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

872-49-1, 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. 872-49-1, name is 5-Chloro-1-methylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Chloro-1-methyl-imidazole (4.0 g, 34.32 mmol) was dissolved in a mixture of 4.0 g of conc. nitric acid and 14 mL of water, and concentrated in vacuo to give a yellow slurry. To this mixture was added dropwise 12 g of conc. sulfuric acid and heated to 95C for 2 hours. Upon cooling, ice was added to the reaction mixture, which was then left standing 10 hours at 5C. The white precipitation was collected by filtration, washed with water, recrystallized from ethanol and dried in vacuo to give compound 60A.

The synthetic route of 5-Chloro-1-methylimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; EP1066286; (2009); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 85692-37-1, A common heterocyclic compound, 85692-37-1, name is 1-(1-Methyl-1H-imidazol-2-yl)ethanone, molecular formula is C6H8N2O, 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.

Step 3-Synthesis of 4-[1-(2-aminopyrimidin-4-yl)-3-methyl-1H-indazol-6-yl]-2-(1-methyl-1H-imidazol-2-yl)but-3-yn-2-ol To a solution of 4-(6-ethynyl-3-methylindazol-1-yl)pyrimidin-2-amine (150 mg, 0.6 mmol) in THF (2 mL) at -78 C. under nitrogen was added 2M LDA in THF (0.75 mL, 1.50 mmol). After 5 minutes, 1-(1-methyl-1H-imidazol-2-yl)ethanone (225 mg, 1.81 mmol) in THF (1.0 mL) was added, and after a further 20 minutes the mixture was allowed to warm to RT and stirred for 1.5 hours. The reaction mixture was then cooled to -78 C. and treated with additional 2M LDA in THF (0.3 mL, 0.6 mmol) and 1-(1-methyl-1H-imidazol-2-yl)ethanone (90 mg, 0.6 mmol). After stirring at RT for 4 hr, the reaction mixture was quenched by addition of saturated aqueous NH4Cl (2 mL). The volatiles were removed in vacuo and the mixture was diluted with DCM (10 ml) and washed with water (2 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Biotage, 3-12% methanol gradient in DCM) to give the title compound: 1H NMR (500 MHz, DMSO) delta 2.00 (3H, s), 2.57 (3H, s), 3.92 (3H, s), 6.32 (1H, s), 6.77 (1H, s), 6.98 (2 H, s), 7.03 (1H, d, J=5.5 Hz), 7.15 (1H, s), 7.36 (1H, d, J=8.2), 7.84 (1H, d, J=8.2 Hz), 8.25 (1H, d, J=5.5 Hz), 8.84 (1H, s); LC-MS: m/z=+374.05 (M+H)+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 52099-72-6, The chemical industry reduces the impact on the environment during synthesis 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, I believe this compound will play a more active role in future production and life.

To a stirred solution of l-Isopropenyl-l,3-dihydro-benzimidazol-2-one (5g, 28.7mmol) in DMF (20ml) was added methyl acrylate (2.8ml, 31.6mmol) followed by benzyltrimethylammonium hydroxide (Triton B, 40 wt% in MeOH, 3.2ml). The resulting solution was stirred at ambient temperature until the reaction was complete. After this time the reaction was poured into water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic layers were dried (MgSCH), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 30% ethyl acetate/hexanes). The product-containing fractions were combined and concentrated to give 4.8g (64%) of the desired product.

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-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/147697; (2008); 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. 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2O

To a solution of 1,3-dihydro-1,N-methyl-2-oxobenzimidazole (3.185 g, 21.5 mmol) in DMF (60 mL) is added NaH (60% in mineral oil,1.03 g, 25.78 mmol) portionwise at 0 C. After stirring at 0 C for 30 min.2,4-dichloropyrimidine (3.20 g, 21.5 mmol) is added, and the mixture is allowed to stir at 15 C for 12 hrs. The resulting mixture is quenched with water (200 mL) and the mixture is extracted with EtOAc (100 mL x 3), and washed with water (100 mL x 4), dried with Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (petroleum ether: EtOAc =10:1), to give 2-chloro-4-(1,3-dihydro-3,N-methyl-2-oxobenzimimidazol-1-yl)pyrimidine.

According to the analysis of related databases, 1849-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem