Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 109012-23-9, name is Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, 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 109012-23-9, Application In Synthesis of Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate

Ethyl 1-methyl-4-nitroimidazole-2-carboxylate17 (6, 613 mg, 3.1 mmol) was hydrogenated over 5% palladium on charcoal in ethanol. The resulting amino compound was dried thoroughly under vacuum to remove traces of ethanol. It was then dissolved in dichloromethane (20.0 mL) and the solution was cooled to 0-5 C. To the cold solution was added triethylamine (0.5 mL, 3.7 mmol) followed by benzoyl chloride (0.4 mL, 3.4 mmol). The reaction mixture was allowed to attain room temperature and then stirred for 12 h. Upon completion, the reaction was quenched with water (15.0 mL) and stirred for 15 min. The organic layer was separated and aqueous layer was washed with dichloromethane (2 × 10 mL). Combined organic layers were dried over sodium sulfate and evaporated to obtain a yellow oil. The crude product was purified by column chromatography using silica gel and 2% methanol in chloroform as the eluent system to obtain 7 as a yellow solid (808 mg, 96%).

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; Satam, Vijay; Babu, Balaji; Chavda, Sameer; Savagian, Mia; Sjoholm, Robert; Tzou, Samuel; Liu, Yang; Kiakos, Konstantinos; Lin, Shicai; David Wilson; Hartley, John A.; Lee, Moses; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 693 – 701;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 89088-69-7, A common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36 , 16.39 g, 122.74 mmol) and 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-J]pyrimidine (Intermediate 9, 21 g, 61.37 mmol) and DIPEA (42.9 ml, 245.47 mmol) in ethanol (264 ml) were heated at 88 0C overnight. The reaction mixture was cooled to 0 0C and filtered to provide 2-chloro-N-(l -methyl- lEta-imidazol-4-yl)-7-tosyl-7Eta-pyrrolo[2,3-d]pyrimidin-4-amine contaminated with DIPEA. The solid was dissolved in EtOAc (400 ml) and the solution was washed with water (3×100 ml). During the process, the title product crashed out of solution and collected through filtration. Concentration of the mother liquor provided additional title product (total=18.8 g, 76%). LCMS: 403 [M+H]+.1H NMR (300 MHz, DMSO-J6) deltappm 10.75 (br. s., 1 H), 7.96 (d, 2 H), 7.63 (d, 1 H),7.40 – 7.55 (m, 3 H), 7.35 (s, 1 H), 7.23 (br. s., 1 H), 3.68 (s, 3 H), 2.37 (s, 3 H)

The synthetic route of 89088-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 253453-91-7, 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. 253453-91-7 name is 2-Chloro-1-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.

Example 53[0208] A 1.6 M solution of n-butyllithium in hexanes (2.27 ml, 3.6 mmol) was added dropwise to a solution of 2-chloro-l -methyl- lH-imidazole* (0.4 g, 3.45 mmol) in anhydrous TEtaF (10 ml) at – 78 C. The reaction mixture was maintained below -78 C during the addition. After 15 min, a solution of 2-chloro-6-methylphenyl isocyanate (0.64 g, 3.79 mmol) in TEtaF (5 ml) was added and the solution was stirred at -78 C for further 2h. The solution was quenched by the addition of aq NH4Cl and partitioned between EtOAc and water. The organic layer was separated and washed with brine, dried and concentrated. The crude product was purified on silica gel chromatography by using 30% EtOAc/Hexane, to give compound 53 as white solid (353 mg, 36% yield). 1H NMR (500 Hz, DMSO-d6) delta 9.96(s, IH), 7.82 (s, IH), 7.40 (dd, J= 1.7, 5.74 Hz, IH), 7.27 (m, 2H), 3.83 (s, 3H,), 2.23 (s, 3H); ESI-MS: calcd for (C12H11C12N3O) 282, found 282 (M-H+). HPLC: retention time: 17.83 min.; purity: 96%

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

Reference:
Patent; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; NALLAN, Laxman; POLAT, Tulay; KORONIAK, Lukasz; DESAI, Neil; WO2010/144338; (2010); 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 19213-72-0 as follows. SDS of cas: 19213-72-0

SYNTHESIS EXAMPLE 9 Synthesis of 4(5)-Chloro-5(4)-phenylimidazole-2-carboxylic acid (Compound No. 15) 2.5 g of 4(5)-chloro-2-(ethoxycarbonyl)-5(4)-phenylimidazole (Compound No. 5) was added to 50 ml of a 5% aqueous sodium hydroxide solution, and the mixture was reacted at the reflux temperature for one hour to obtain a reaction mixture including sodium 4(5)-chloro-5(4)-phenylimidazole-2-carboxylate. The reaction mixture was poured into ice water and neutralized with hydrochloric acid. A precipitated crystal was separated by filtration and washed with water to obtain 4(5)-chloro-5(4)-phenylimidazole-2-carboxylic acid (Compound No. 15) having a melting point of 158 to 160 C.

According to the analysis of related databases, 19213-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US5023336; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 67014-36-2, These common heterocyclic compound, 67014-36-2, name is 5-Amino-6-methyl-1H-benzo[d]imidazol-2(3H)-one, 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.

8.1 g of 5-amino-6-methylbenzimidazolone-(2) was stirred with 250 ml of water and 14.5 ml of 31.5% hydrochloric acid for 1 hour and then diazotized at 0 C. after the addition of ice, by adding an aqueous sodium nitrite solution. EXAMPLE 2 8.1 g of 5-amino-6-methylbenzimidazolone-(2) was diazotized with sodium nitrite solution in the same method as described in Example 1.

The synthetic route of 67014-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dominion Colour Corporation; US6706864; (2004); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 38585-62-5, 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. 38585-62-5, name is (4-Methyl-1H-imidazol-5-yl)methanol hydrochloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 7 2,3,4,5-Tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1-one A mixture of 2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (49.97 g), p-toluenesulphonic acid monohydrate (9.50 g) and 4-hydroxymethyl-5-methylimidazole hydrochloride (20.25 g) in N-methylpyrrolidinone (250 ml) was stirred and heated to 125 (over 1 h) The reaction was then heated at 125-130 for 4.5 h, during which time two further portions of 4-hydroxymethyl-5-methylimidazole hydrochloride (17.51 g and 6.88 g) were added. The reaction mixture was cooled, diluted with water (100 ml), and the stirred mixture was treated slowly with 8% aqueous sodium bicarbonate (750 ml). The resultant suspension was stirred in an ice bath for 1 h and then filtered to give a solid (57.64 g). A portion of this solid (11.09 g) was dissolved in dichloromethane (307 ml) and ethanol (166 ml), boiled with decolourising charcoal for 10 min and then filtered. The dichloromethane was distilled off at atmospheric pressure until the temperature of the mixture was at 65. The stirred mixture was cooled and the resulting precipitate was filtered off to give the title compound (9.28 g), t.l.c. (System A, 50:8:1) Rf 0.55.

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, (4-Methyl-1H-imidazol-5-yl)methanol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxo Group Limited; US5196534; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 66247-84-5,Some common heterocyclic compound, 66247-84-5, name is (1H-Imidazol-4-yl)methanamine hydrochloride, molecular formula is C4H8ClN3, 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 solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1H-Imidazol-4-yl)methanamine hydrochloride, its application will become more common.

Reference:
Patent; MASARYKOVA UNIVERZITA; BRYJA, Vitezslav; JANOVSKA, Pavlina; GREGOROVA, Michaela; NEMEC, Vaclav; KHIRSARIYA, Prashant; PARUCH, Kamil; (171 pag.)WO2019/185631; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 582-60-5,Some common heterocyclic compound, 582-60-5, name is 5,6-Dimethyl-1H-benzo[d]imidazole, molecular formula is C9H10N2, 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. Benzimidazole-5,6-dicarboxylic acid The compound was prepared from 5,6-dimethylbenzimidazole as described in J.Org.Chem. 1987, 52, 2934.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dimethyl-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; James Black Foundation Limited; US5795907; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 279226-70-9, name is 1-Methyl-1H-benzimidazole-5-carboxaldehyde, 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. COA of Formula: C9H8N2O

To a solution of 1-methyl-1H-benzoimidazole-5-carbaldehyde (prepared as described in WO0037473) (420 mg, 2.62 mmol) in trimethylsilyl cyanide (2 mL, 15.0 mmol) was added a catalytic amount of zinc iodide. The reaction mixture was stirred at ambient temperature overnight, concentrated under vacuum and the resulting residue dissolved in a 7N solution of ammonia in methanol (10 mL, 70 mmol) in a sealed tube. The mixture was heated for 1.5 hours at 55 C. then cooled to ambient temperature and concentrated under vacuum. The residue was dissolved in 6N aqueous hydrochloric acid (?10 mL) in a sealed tube. The mixture was stirred at 110 C. for 6 hours then cooled and concentrated under vacuum to afford a solid residue. This solid was dissolved in N,N-dimethylformamide (?20 mL). Triethylamine (4 mL, 28.7 mmol) and di-tert-butyl dicarbonate (850 mg,3.93 mmol) were added and the mixture was stirred for 4 hours at ambient temperature. The solvent was then removed, the residue was washed with ether, dried and then dissolved in tetrahydrofuran (55 mL). To this solution was added (S)-2-(2-amino-3-phenylpropinylamino-thiazole-4-carboxylic acid methyl ester (prepared as described in example 3) (800 mg, 2.62 mmol) and the reaction mixture cooled to 0 C. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (500 mg, 2.61 mmol) was added and the reaction mixture was allowed to slowly warm to ambient temperature and then stirred for 48 hours. The reaction mixture was then partitioned between ethyl acetate and water, the ethyl acetate layer was dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography over silica gel gradient eluted between 0 and 50% v/v ethyl acetate in dichloromethane and then gradient eluted between 0 to 4% methanol in dichloromethane. Precipitation of the isolated product from a tetrahydrofuran solution with an excess of hexanes afforded 2-{(S)-2-[2-tert-butoxycarbonylamino-2-(1-methyl-1 H-benzoimidazol-5-yl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester as an amorphous white solid (510 mg, 33%). HRMS: Obs. Mass, 593.2167. Calcd. Mass, 593.2177 (M+H)

The synthetic route of 1-Methyl-1H-benzimidazole-5-carboxaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goodnow,, Robert Alan; Huby, Nicholas J.S.; Kong, Norman; McDermott, Lee Apostle; Moliterni, John Anthony; Zhang, Zhuming; US2006/63814; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 89088-69-7,Some common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazol-4-amine hydrochloride, its application will become more common.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem