Tag: M.W=100-200

Related Products of 38993-84-9,Some common heterocyclic compound, 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, 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.

DIAD (0. [0195 MOL)] was added dropwise at a temperature between 0 and [5°C] to a mixture of 4-hydroxybenzaldehyde (0.015 mol), [5-HYDROXYMETHYL-1-METHYL-1H-] imidazole (CA No: 38993-84-9) (0.018 mol) and [PPH3] (0.0225 mol) in THF (40ml) under [N2] flow. The mixture was stirred at room temperature overnight, then stirred for a week end, diluted in EtOAc, extracted with [HC1] 3N, washed with EtOAc, alkalinized with [K2CO3] and extracted with EtOAc. The organic layer was separated, dried [(MGS04),] filtered, and the solvent was evaporated. Yielding: 1.6g of intermediate 38 (49percent).

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-5-yl)methanol, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2004/7498; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 5465-29-2, These common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, 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 50 ml of water, 450 ml of concentrated sulfuric acid (i.e., 90% concentration) was added dropwise, 50.0 g of 2-propylbenzimidazole was added, and 300 ml of a 30% aqueous solution of hydrogen peroxide was added dropwise. The reaction was exothermic to reflux and the dropping speed was maintained to keep the reaction solution boiling.After completion, the reaction was continued for 3 hours.Add water 400ml, cold to room temperature.The solid was precipitated and stirred at 0-5 C for 3 hours, filtered, washed with water, washed with 100% of 5% sodium sulfite aqueous solution and dried to constant weight to give 2-propylimidazole-4,5-dicarboxylic acid as a white solid (21.7 g, 35%), HPLC purity 89.4%,

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huanggang LUBAN Pharmaceutical Co.,Ltd. (LUBAN); YANG, XIAOLONG; LIU, XIANGQUN; LI, QIANG; CHEN, QIAN; YANG, TIEBO; (17 pag.)CN104262260; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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. Safety of (1H-Benzo[d]imidazol-2-yl)methanamine

(R/5)-2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)- l,2,4-oxadiazol-3-yl)phenyl)acetic acid (Int-V, 20 mg, 0.046 mmol), (1H- benzo[d]imidazol-2-yl)methanamine (10.24 mg, 0.070 mmol), HATU (22.92 mg, 0.060 mmol), and 4-methylmorpholine (18.76 mg, 0.185 mmol) were added to DMF (1 mL). This was stirred for 1 h before it was purified via preparative LCMS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5-muiotaeta particles; Guard Column: Waters XBridge CI 8, 19 x 10 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 methanohwater with 10-mM ammonium acetate; Mobile Phase B: 95:5 methanol: water with 10-mM ammonium acetate; Gradient: 45-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give (R/5)-N- ((lH-benzo[d]imidazol-2-yl)methyl)-2-hydroxy-2-(4-(5-(3-phenyl-4- (trifluoromethyl)isoxazol-5-yl)-l,2,4-oxadiazol-3-yl)phenyl)acetamide (12.8 mg, 0.023 mmol, 49.3 % yield): LCMS = 561.1 [M+H]+; ‘H NMR (400 MHz, methanol- cU) 5 ppm 8.19 (2 H, d, J=8.58 Hz), 7.51-7.79 (10 H, m), 7.34 (2 H, dd, J=6.05, 3.19 Hz), 5.27 (1 H, s), 4.76-4.94 (2 H, m); HPLC peak RT = 2.6 min (Method E).

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Robert J.; ZHANG, Yanlei; WO2011/133734; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1003-21-0, 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 1003-21-0 as follows.

lntermediate 1: step b (1-Methyl-lH-imidazol-5-yl)(tetrahydro-2H-pyran-4-yl)methanone A clear colorless solution of 5-bromo-l-methyl-lH-imidazole (1.12 g, 6.93 mmol) in THF (10 mL) was placed in an ice bath and ethylmagnesium bromide (3.0 M in Et20, 2.31 mL, 6.93 mmol) was added via syringe. The reaction mixture was stirred for 20 minutes at room temperature. N-Methoxy~N-methyltetrahydro-2H~pyran-4~ca.rboxamide (1.0 g, 5.8 mmol. Intermediate 1 : step a. Procedure A) was added neat by syringe (using 1 mL THF rinse to quantitate transfer), and the resulting white suspension was stirred at room temperature for 2 days. The mixture was diluted with saturated aqueous NH4C1 followed by water, then was extracted with EtOAc (3 x). The organic phase was dried (Na2S04), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography two times (1 -4% MeOH-DCM first column; 40-60% CH CN-DCM second column) to provide the title compound as a white crystalline solid.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

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: 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-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 51605-32-4, Quality Control of Ethyl 5-methyl-1H-imidazole-4-carboxylate

[2757] To a stirred solution of 964 (Ethyl 4-methyl-5-imidazole carboxylate, 7.7 g, 50 mmol) in 100 ml of acetone at room temperature, was added K2CO3 (6.9 g, 50 mmol) portionwise. Stirred at room temperature for 25 minutes, added in MeI (5 ml, 80 mmol) stirred for 21/2 h, (monitored reaction by TLC). Additional K2CO3 (3.09 g, 22 mmol) and MeI (3 ml) were added. Stirred reaction for 16 h, then filtered reaction mixture and rinsed with acetone (80 ml). A clear filtrate obtained. Filtrate was evaporated and the residue was chromatographed (eluent methylene chloride/methanol (60:1) to afford 1.8 g of solid. This solid was purified by Prep Plate chromatography ((20:1) CH2Cl2:MeOH NH3), compound still impure. Another column chromatography ((50:1) CH2Cl2:MeOH.NH3) was done to afford 383 mg of the desired product, compound 965.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-methyl-1H-imidazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US2004/122018; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 68282-47-3, 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. 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

COMPOUND 12.1.58: N,N-DIETHYL-4-{5,6,7-TRIMETHOXY-2-[(2-PHENYL- 1H-IMIDAZOL-5-YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1- YLIBENZAMIDE; 2-Phenyl-imidazole-4-carboxyaldehyde (92.6 mg, 0.54 mmol) was added to a solution of INTERMEDIATE 5.1. 16 (107.7 mg, 0.27 mmol) in 1,2-dichloroethane (5 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (400 mg, 1.89 mmol) was added followed by N-methyl-2- pyrrolidinone (350 pL) and the reaction mixture stirred at RT for 16 h. 1 N NaOH (5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with EtOAc (3 x 20 mL) and the organic layer washed with water (20 mL). The organic layer was concentrated in vacuo and the residue purified by flash chromatography on SiOx column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 58 as an oil (33 mg, 22%). lH NMR (500 MHz, CDC13) : 8 1.10 (br s, 3H), 1.24 (br s, 3H), 2.63 (m, 1H), 2.76 (m, 2H), 3. 10 (m, 1H), 3.26 (br s, 2H), 3.57 (s, 3H), 3.51-3. 62 (m, 4H), 3.84 (s, 3H), 3. 88 (s, 3H), 4.65 (s, 1H), 5.98 (s, 1H), 6.91 (s, 1H), 7.25-7. 35 (m, 7H), 7.87 (d, J 8.5 Hz, 2H) ; 13C NMR (125 MHz, CDCl3) : 6 13.12, 14.45, 22. 51, 39.70, 43.67, 46.18, 49.68, 56.09, 60.70, 61.03, 66. 58, 107.94, 121.56, 125.43, 126.50, 128.46, 128.90, 129.91, 130. 76, 132. 78,136. 08,140. 72,144. 76, 146.76, 147.07, 150. 89, 151. 73, 171.64 ; (+) LRESIMS m/z 555.25 [M+H]+.

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-Phenyl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 6775-40-2,Some common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, molecular formula is C9H9N3, 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: An equimolar mixture (1.0 mmol) of thecorresponding 2-amino-4-arylimidazole 1, aromatic aldehyde 2and Meldrum?s acid 3 was refluxed in iPrOH (3 mL) for3-5 min. After cooling, the solid products 4 were filtered off,washed with iPrOH and dried on air. 4a: colourless solid, 77%;mp 243-245 C; IR (KBr, cm-1) nu: 3404-2800 (NH2, NH, OH),1684 (C=O); 1H NMR (200 MHz, DMSO-d6) delta 12.27 (br s, 2H,NH, OH), 7.61-7.49 (m, 2H, Harom), 7.48-7.31 (m, 5H, Harom),7.27-7.01 (m, 5H, NH2,, Harom), 5.48 (s, 1H, CH), 1.51 (s, 6H,CH3); 13C NMR (125 MHz, CDCl3) delta 166.8 (C=O), 146.6(C-OH), 144.0, 129.4, 128.9, 128.4, 128.3, 127.5, 127.4, 127.2,125.9, 121.1, 100.6, 76.0 (C=COH), 35.1 (CH), 26.4 (CH3),25.9 (CH3); MS (m/z) (%): 289 (76), (391 [M+?] – 44 -58), 247(53), 159 (36), 104 (19), 77 (8), 44 (39), 43 (100); anal. calcdfor C22H21N3O4 (391.5) C, 67.52; H, 5.37; N, 10.74; found: C,68.77; H, 5.93; N, 10.79.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Phenyl-1H-imidazol-2-amine, its application will become more common.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 35203-44-2,Some common heterocyclic compound, 35203-44-2, name is 1-Propyl-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.

Take a 100 mL two-necked flask, add N-propyl imidazole (2.17 g, 19.0 mmol), 35 mL toluene,3-Bromopropyldiphenylphosphine oxide (6.46 g, 20.0 mmol) was added dropwise with heating and stirring; the reaction was carried out at 85°C for 8 h and cooled to room temperature. The upper layer of toluene is poured out, and 100 mL of deionized water is added to dissolve the product to obtain an aqueous phase.The aqueous phase was washed with an EtOAc_PE=3:1 organic phase (30 mL x 4) to separate the aqueous phase two;Di(2-ethylhexyl)phosphate (P204) (6.12 g, 19.0 mmol) was refluxed for 23 h under sodium.The resulting sodium salt was dissolved in dichloromethane and the previously separated aqueous phase was stirred at room temperature for 3 h.Add 50 mL of CH2Cl2 and stir to separate the organic phase. Wash the organic phase with deionized water (20 mL x 5)Separate the organic phase two, add anhydrous Na2SO4 to dry the organic phase two, filter,The majority of CH2Cl2 was evaporated under reduced pressure and vacuum dried at 70°C for 3 hours.The pale yellow viscous liquid was 10.93 g (yield 90percent),

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

Reference:
Patent; Ningbo University; Wang Junping; Liang Hongze; Feng Da; Zhao Jieying; Kang Xinchun; Zhang Xiaozhen; Shen Fei; Huang Feilong; (21 pag.)CN104945435; (2018); B;,
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. 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H9N3

Method B. A solution of 8 (0.247 g, 1.17 mmol) in MeOH (20 mL) was treated sequentially with 2-aminomethyl-1-methylimidazole (0.059 g, 0.53 mmol) and NaBH3CN (0.07 g, 1 mmol). The reaction mixture was stirred at room temperature overnight and the solvent was removed under vacuum yielding L2 a yellow oil. The crude product was purified as described in method A with similar isolated yields. IR (KBr) 3052 cm-1 (amide-NH), 1667 cm-1 (amide-C=O); 1H NMR CD2Cl2 delta 7.81 (s, AmIm(N-H)), 7.09 (s, 2, AmIm(H-5)), 6.80 (s, 1, Im(H-5)), 6.75 (s, 1, Im(H-4)), 3.60 (s, 2, Im(-CH2)), 3.57 (s, 4, AmIm(CH2)), 3.07 (s, 3, Im(-CH3)), 3.02 (s, 6, AmIm(-CH3)), 1.18 (s, 18, AmIm(-C(CH3)3)). 13C NMR delta 174.1, 169.7 (s, AmIm(-C=O)), 145.4 (s,Im(C2)), 141.2 (s, AmIm(C2)), 135.5 (s, AmIm(C4)), 126.4 (s,Im(C5)), 120.8 (s, Im(C4)), 107.9 (s, AmIm(C-5)), 47.8 (s, Im(-CH2-), AmIm(-CH2-)), 38.0 (s, AmIm(C(CH3)3), 31.1 (s, Im(CH3)), 28.9 (s, AmIm(C(CH3)3); HRMS calcd for C25H40N9O2, 498.3305 [M+H+], found 498.3311.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 124312-73-8.

Reference:
Article; Cheruzel, Lionel E.; Cui, Jinlan; Mashuta, Mark S.; Grapperhaus, Craig A.; Buchanan, Robert M.; Tetrahedron Letters; vol. 52; 37; (2011); p. 4771 – 4774;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 26663-77-4,Some common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, molecular formula is C9H8N2O2, 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.

REFERENCE EXAMPLE 8 (+)-4,5,6,7-tetrahydrohenzimidazole-5-carboxylic acid hydrochloride Methyl benzimidazole-5-carboxylate was subjected to catalytic reduction according to the method described in CROATICA CHEMICA ACTA 45, 297-312 (1973), to obtain methyl 4,5,6,7-tetrahydrobenzimidazole-5-carboxylate.

The synthetic route of 26663-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokyo Tanabe Company Limited; US5677326; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem