Tag: M.W=100-200

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

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

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

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 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

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;,
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. 7152-24-1, name is 2-(Methylthio)benzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-(Methylthio)benzimidazole

To a stirred solution of a benzimidazole g (beta.OOmmols) and p- fluoronitrobenzene h (6.00mmols) in 1OmL of anhydrous DMF, was added [potassium t-butoxide (f-BuOK) (7.61 mmols, 1.25eq.), and the reaction mixture was stirred at 80 0C overnight. The reaction mixture was added into 5OmL of water and the product was extracted with ethylacetate (3 x 2OmL). The extracts were washed with brine and concentrated. Column chromatography on silica gel using mixture of hexane:ethylacetate provided compound i in 25-45% yields.To a stirred solution of compound i (1.31 mmols) in 2OmL of 1 :1 CH2CI2IEtOH, was added SnCb (13.06mmols) followed by a few drops of water. The mixture was stirred overnight and concentrated. 2OmL of water was added to the residue, and the solution the brought to pH ~ 8-9 using 2N NaOH. The resulting mixture was extracted with ethylacetate (2OmL x 4), washed with brine (2OmL), dried over Na2SO-I, and concentrated to afforded compound j in 70-97% yields.To a solution of compound j (0.30mmols) in 5mL of CH2CI2, was added an acyl chloride k (0.30mmols), followed by diisopropyl-ethylamine (0.60mmols). The resultant mixture was stirred at room temperature for 30min and eluted through a short pad of silica gel using mixture of hexane:ethylacetate to afford, upon concentration, the product I in 80-96% yields.

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 7152-24-1.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2007/112093; (2007); A2;,
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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Preparation of 1-(4-chloro-2-(3-hydroxypyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea 1-(2-(aminomethyl)-5-chlorophenyl)pyrrolidin-3-ol 2ai (1.18 g, 5.2 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (1.4 g, 5.2 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (674 mg, 4.52 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 8 / MeOH 2). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1 X 40 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 390mg of a pale pink solid. Yield = 21% 1HNMR (DMSO, 200 MHz) delta 2.20 (2H, m), 3.33 (4H, m), 3.69 (2H, s), 4.29 (1H, b), 5.20 (1H, b), 6.62 (2H, m), 6.90 (4H, m), 7.27 (1H, d, J = 8 Hz), 8.29 (1H, s), 9.95 (1H, bs), 10.60 (1H, bs); [M+1] 402.4 (C19H20ClN5O3 requires 401.85).

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; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. Formula: C4H6N2S

Dithiafulvalenyl compound 1 (0.2 mmol), mercapto-thiazole 2 (2 mmol, 10 equiv.), and I2 (0.6 mmol, 3 equiv., 152.4 mg) were dissolved in DMSO (3 mL). The reaction mixture was stirred at 25 C for 12 h under N2 atomsphere. Then quenched with a saturated solution of Na2S2O3 and stirred for half an hour, the solution was extracted with dichloromethane (CH2Cl2). The organic layer was separated, and dried over Na2SO4. Then the organic solvent was removed in vacuo to afford the respective thiadiazole-based dithiafulvalene (DTF) derivatives (3), which were purified by column chromatography (silica gel, PE / CH2Cl2) to afford pure substances.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fu, Huimin; Zhao, Bangtun; Zhu, Weimin; Tetrahedron Letters; vol. 60; 2; (2019); p. 124 – 128;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 583-39-1, name is 2-Mercaptobenzimidazole, 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. Formula: C7H6N2S

General procedure: A mixture of 0.001 mol of chloroethynylphosphonate1a-1c and 0.002 mol of benzimidazole-2-thione 2d in 15 mL of anhydrous acetonitrile was stirred at room temperature for 2-5 h. The precipitate was filtered off. The solvent was removed from the filtrate, the precipitate was combined and recrystallizedfrom ethanol. Yields and melting points of the obtained compounds are given in Table 1.

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

Reference:
Article; Egorov; Piterskaya, Yu. L.; Kartsev; Polukeev; Krivchun; Dogadina; Russian Journal of General Chemistry; vol. 88; 9; (2018); p. 1824 – 1831; Zh. Obshch. Khim.; vol. 88; 9; (2018); p. 1478 – 1485,8;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem