Month: March 2021

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5400-75-9, name is 5-Methyl-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H8N2O

A mixture of 5-methyl-1,3-dihydrobenzimidazol-2-one (1.00 g, 6.84 mmol) and phosphorous oxychloride (9.54 mL, 103 mmol) was stirred for 1.5 h at 95 C. After being cooled to ambient temperature, the reaction mixture was carefully added to a mixture of saturated NaHCO3 aq. (60 mL) and ethyl acetate (60 mL). The separated organic layer was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was evaporated in vacuo, The resulting precipitates were collected by filtration, and successfully washed with isopropyl ether to give 2-chloro-5-methyl-benzimidazole (1.74 g, 58.9 %). ESI-HRMS calcd. for C8H8ClN2 ([M+H]+) 167.0371; found m/z 167.039. NMR (DMSO-d6, delta): 2.40 (3 H, s), 7.00-7.06 (1H,m), 7.29 (1 H, s), 7.39 (1H, d, J=8.2 Hz). Other substituted 2-chloro-benzimidazols were prepared in a manner similar.

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:
Article; Nakao, Syuhei; Mabuchi, Miyuki; Shimizu, Tadashi; Itoh, Yoshihiro; Takeuchi, Yuko; Ueda, Masahiro; Mizuno, Hiroaki; Shigi, Naoko; Ohshio, Ikumi; Jinguji, Kentaro; Ueda, Yuko; Yamamoto, Masatatsu; Furukawa, Tatsuhiko; Aoki, Shunji; Tsujikawa, Kazutake; Tanaka, Akito; Bioorganic and Medicinal Chemistry Letters; vol. 24; 4; (2014); p. 1071 – 1074;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 1231930-33-8, These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, 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.

DMSO (100 mL) was added to a 500 mL one-necked flask and the compound of formula XVI-1 (20.0 g,73.80 mmoL), bis (pinacolato) diboron (27.6 g, 108.69 mmol), tricyclohexylphosphine (3.53 g, 12.61 mmol)Potassium acetate (21.3 g, 217.38 mmol). Nitrogen gas was added to the reaction flask after the rapid addition of palladium acetate (1.5g), nitrogen PaulProtect the next open heating to 90C. After 3 hours the reaction flask was cooled to room temperature and the reaction mixture was poured into 700 mL of water, mixed thoroughly and subtractedPressure filtration, the filter cake was washed twice with 100mL of water and dried to give a light brown solid. Crude was added 50mL petroleum ether, 10mL BEthyl acetate beating 10min, vacuum filtration to give a white solid (18.8g, yield 80.3%)

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Liu Yingshuai; Qin Hui; Li Yuan; Zhao Kaidi; Miao Lei; Hu Jie; Liu Haiyan; Wang Xiaojin; (33 pag.)CN107266421; (2017); A;,
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Imidazole | C3H4N2 – PubChem

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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1H-Imidazole-4-carbonitrile

To a solution of lH-Imidazole-4-carbonitrile (300 mg, 3.22 mmol) and 4-Fluoro- 3-methoxynitrobenzene (552 mg, 3.22 mmol) in DMF (Volume: 6446 mul) was added K2CO3 (891 mg, 6.45 mmol). The resulting mixture was brought to 120 0C and stirred overnight. The reaction mixture was diluted with EtOAc (20 mL), washed with water (2 x 10 mL), brine (10 mL), dried over MgSO4, filtered and concentrated in vacuo to give 1- (2-methoxy-4-nitrophenyl)-lH-imidazole-4-carbonitrile (698 mg, 2.86 mmol, 89 percent yield). LC-MS (M+H)+ = 245.0. IH NMR (500 MHz, MeOD) delta ppm 8.30 – 8.34 (1 H), 8.19 – 8.23 (1 H), 8.09 – 8.12 (1 H), 8.00 – 8.05 (1 H), 7.71 – 7.79 (1 H), 4.02 – 4.10 (3 H).

The synthetic route of 57090-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, III, Lorin A.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2011/14535; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 705-09-9, A common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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: 1 : To a solution of 6c (1.92g, 6.98mmol) in DMF (20mL) was added NaH (307mg, 7.68mmol) under ice bath. The resulting mixture was stirred at 0-50C for 30min and was added 3a (1.17g, 6.98mmol). The reaction mixture was stirred at r.t. for 2.5h and evaporated. The residue was dissolved in morpholine (30mL) and heated at 800C for 2h. After cooling to room temperature, the mixture was added IN NaOH (28mL). The resulting mixture was stirred at r.t. for 2h, evaporated. The residue was purified by column chromatography (PE:EA=1:1) to give 6 (660mg, 23% yield from 6c). 1H NMR(300MHz, CDCl3): delta=3.45 (t, 1H), 3.78-3.94 (m, 8H), 4.12-4.17 (m, 2H), 4.52-4.56 (m, 2H), 7.18 (t, 1H), 7.42-7.56 (m, 3H), 7.78 (s, 1H), 7.95-7.98 (m, 1H). LC-MS [M+H]+: 416.0.

The synthetic route of 705-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TYROGENEX, INC.; LIANG, Congxin; LI, Zhigang; WO2010/56320; (2010); A2;,
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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Example No. 289Preparation of 6- (7- ( (2-methyl -lH-benzo [d] imidazol-5- yl)amino) -IH-pyrazolo [4, 3-d] pyrimidin- 5 -yl) -2H- benzo [b] [1 , 4] oxazin-3 (4H) -one6- (7-chloro-2- (4-methoxybenzyl) -2H-pyrazolo [4 , 3 -d] pyrimidin- 5- yl) -2H-benzo [b] [1, 4] oxazin-3 (4H) -one (0.16 mmol) and 2-methyl- lH-benzo [d] imidazol-5-amine (0.3 mmol 2 eq. , ) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140 C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was concentrated and purified by semi- preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 412.1584 g/molHPLC-MS: analytical method Drt: 3.81 min – found mass: 413 (m/z+H)

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 29043-48-9.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; TRAUBE, Nadine; WO2012/143144; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 89830-98-8, A common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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 suspension 4-bromo-N-(5-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamide (63 mg, 0.16 mmol), 4-cyclopropyl imidazole (35 mg, 0.24 mmol), Cu2O (1.2 mg, 0.0081 mmol), 4,7-dimethoxy-1,10-phenanthroline (5.9 mg, 0.024 mmol, (or 8-hydroxy-quinoline may be used as the ligand with comparable results), cesium carbonate (116 mg, 0.36 mmol), and PEG-3350 (32 mg) in butyronitrile (1 mL) was heated at 100¡ã C. for 16 hours. The solvent was removed and the residue was purified by reverse-phase HPLC to 4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamide as a white powder (9.2 mg, 0.377 mmol, 13percent yield). C21H19N7OS. 418.2 (M+1). 1H NMR (DMSO) delta 11.42 (s, 1H), 8.77 (s, 1H), 8.60 (s, 1H), 8.54 (s, 1H), 8.37 (d, J=2 Hz, 1H), 8.33 (d, J=2 Hz, 1H), 8.04 (d, J=1 Hz, 1H), 7.97 (dd, J=2, 5 Hz, 1H), 7.85 (s, 1H), 3.55-3.59 (m, 1H), 1.85-1.88 (m, 1H), 1.22-1.26 (m, 2H), 1.11-1.13 (m, 2H), 0.82-0.86 (m, 2H), 0.72-0.75 (m, 2H).

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; US2012/4267; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 14741-71-0,Some common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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 compound 3 (2.04 g, 0.01 mol) in dimethylformamide (30 mL) either aniline(0.93 g, 0.01 mol) or 4-methylaniline (1.08 g, 0.01 mol) was added. The reaction mixture, ineach case, was heated under reflux for 4 h then poured onto ice/water mixture containing fewdrops of hydrochloric acid and the formed solid product was collected by filtration. 2-(1H-Benzo[d]imidazol-2-yl)-N-phenylacetamide (5a). Light brown crystals from ethanol;yield: 2.08 g (80%); m.p. 220-222 oC. IR, : 3472-3324 (2NH), 3050 (CH aromatic), 1680(C=O), 1648 (C=N), 1629 (C=C). 1H-NMR, : 4.93 (s, 2H, CH2), 7.25-7.41 (m, 9H, C6H5,C6H4), 8.26, 8.32 (2s, 2H, 2NH, D2O exchangeable). 13C NMR (DMSO): 54.8 (CH2), 119.2,120.8, 122.8, 123.6, 124.3, 125.2, 126.1, 127.3, 128.3, 129.2, (C6H5, C6H4), 164.8 (CO), 172.4(C=N); Anal. calcd for C15H13N3O: C, 71.70; H, 5.21; N, 16.72%. Found: C, 71.83; H, 5.08; N,16.82%. MS: m/z: (%) 251 (M+, 24%).

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Cyclopropyl-1H-imidazole

A mixture of 9-iodo-1-methyl-3,4,7,8- tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (30 mg, 81 muGammaetaomicronIota) in DCE (2 mL) is treated with POCI3 (15 mu, 0.16 mmol) and heated to 100 ¡ãC for 3 h. The mixture was then allowed to cool to RT, poured onto H20 and extracted with DCM, The org. phases were dried over Na2S0 , filtered and concentrated in vacuo. The brown residue obtained was taken up in DCE (2 mL) and 4-cyclopropyl-1H-imidazole (31 mg, 0.28 mmol) and pyridine (20 mu, 0.24 mmol) were then added. The mixture was heated to 100 ¡ãC for 4.5 h, and then allowed to cool to RT, poured onto H20 and extracted with DCM. The org. layers were then dried over Na2S04, filtered and concentrated in vacuo. Filtration through a pad of Si02 (AcOEt) afforded a brown solid that was purified by SFC (column: Diol 5 muiotaeta, 250 x 30 mm, 60A, Princeton; euent: 13percent MeOH/C02 for 1 min, then from 13percent MeOH/C02 to 18percent MeOH/C02 in 6 min; then from 18percent MeOH/C02 to 50percent MeOH/C02 in 1 min; flow 100 mL/min; UV detection at 220 nm) to give the title compound (11 mg) as a white powder. UPLC-MS: MS 459.0 (M+hf ); UPLC rt 0.98 min.

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; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; WO2014/30128; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 615-16-7, 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. 615-16-7 name is 2-Hydroxybenzimidazole, 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 23; Preparation of 3-((2-(l,3-dimethyl-2-oxu-2)3-dihydro-l//-benzimidazol-5-yl)-2- oxoethyl)tbio) propanoic acid (23); (i) l,3-Dimethyl-l,3-dihydro-2W-bcn7.iitauiidazol-2-onc; l,3-Dihydro-2H-benziiuida7;ol-2-one (7.522 g, 56.1 mmol) was dissolved in anhydrous DIvIF (125 oil) and anhydrous potassium carbonate (46.581 g, 337 mmol) and iodomethane (21 ml, 337 mmol) were added then the mixture stirred at room temperature overnight. The reaction mixture was poured into chloroform (500 ml), filtered and the filtrate was evaporated to dryness. The resultant residue was dissolved in a mixture of ethyl acetate (150 ml) and water (100 ml). The cthyi acetate phase was washed with water (2 x 100 ml) and brine ( 100 ml), dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to dryness to give the title compound (7,229 g, 79% yield) as a pale yellow solid.1H nmr (400 MHz1 CDCl3) delta 3.43 (s, 6H); 6.95-7.01 (m, 2H); 7.08-7.14 (m, 211).

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

Reference:
Patent; CORTICAL PTY LTD; WO2007/70961; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3012-80-4, 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

The synthetic route of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem