Tag: M.W=100-200

Electric Literature of 26663-77-4, These common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, 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: To a stirred solution of copper(I) acetate (2.4 mg, 0.020 mmol, 0.10 equiv.), benzimidazole 1a (23.6 mg, 0.20 mmol), and TMP iodonium(III) salt 2a (124.8 mg, 0.24 mmol, 1.2 equiv) in toluene (2 mL), triethylamine (56 mL, 0.4 mmol, 2 equiv) was added under a nitrogen atmosphere. The mixture was stirred for 5 min at room temperature, and the resulting solution was then heated to 50 C for 6 h (the reaction progress was monitored by TLC). After cooling to room temperature, the reaction was quenched by adding 5% aqueous ammonia solution (4 mL). The aqueous layer was extracted thrice with 20 mL of dichloromethane and the combined organic extracts were dried with anhydrous sodium sulfate. The organic solvents were then evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 1/1) to obtain pure N-phenyl benzimidazole 3aa (38.5 mg, 0.198 mmol) in 99% yield

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

Reference:
Article; Koseki, Daichi; Aoto, Erika; Shoji, Toshitaka; Watanabe, Kazuma; In, Yasuko; Kita, Yasuyuki; Dohi, Toshifumi; Tetrahedron Letters; vol. 60; 18; (2019); p. 1281 – 1286;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, 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. 4857-06-1 name is 2-Chloro-1H-benzo[d]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.

2-chloro- 1 -methyl- 1 H-benzo [d] imidazole[670] To a solution of 2-chloro- lH-benzo[d]imidazole (2.0 g, 13.1 mmol) in DMF(10 mL) was added NaH (0.63 g, 15.7 mmol) at 0 C under N2. After stirring for 30 min at 0 C, iodomethane (5.58 g, 39.3 mmol) was added and the mixture was stirred at room temperature for additional 1 hour. The reaction mixture was quenched with water (100 mL). The aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic layers were dried over a2S04, filtered, and concentrated to give the title compound (1.9 mg, 8.9 mmol, 67.9 % yield) as a white solid. MS: MS (M+H)+; XH NMR (400 MHz, CDC13): ? 7.71-7.68 (m, 1H), 7.31-7.27 (m, 3H), 3.79 (s, 3H).

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

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 256519-10-5, name is 4-Fluoro-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5FN2O, 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. category: imidazoles-derivatives

b) A solution of 4-fluoro-1H-benzo[d]imidazol-2(3H)-one (0.7 g, 4.60 mmol) in phosphorus oxychloride (14.11 ml, 151.39 mmol) was heated at 100 C. for 18 hours. The reaction mixture was cooled to RT and excess phosphorus oxychloride was evaporated in vacuo. The residue was neutralized slowly (Care: exotherm) with saturated sodium bicarbonate solution (10 ml), and the mixture was then extracted with EtOAc (3×20 ml). The combined organic layers were washed with saturated brine and then dried over Na2SO4, filtered and evaporated to afford 2-chloro-7-fluoro-1H-benzo[d]imidazole (0.740 g, 94%) which was used in the next step without further purification; 1H NMR (400 MHz, DMSO-d6) 7.01-7.11 (1H, m), 7.23 (1H, td), 7.32 (1H, s), 13.59 (1H, s); m/z: (ES+) MH+, 171.20.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 256519-10-5, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2011/306613; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4278-08-4, 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. 4278-08-4, name is 2-(4-Fluorophenyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate CC (1 10 mg, 0.363 mmol), 2-(4-fluorophenyl)-lH-imidazole (70 mg, 0.435 mmol), Pd2(dba)3 CHCl3 (166 mg, 0.182 mmol), BINAP (226 mg, 0.3638 mmol), and CS2CO3 (354 mg, 1.08 mmol) were dissolved in 1 mL of toluene in a microwave vial and a stream of nitrogen was bubbled through the mixture for 2 minutes. The resulting solution was heated at 140 C for 1 h in a microwave. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic extracts were dried with Na2S04, filtered and evaporated, and the residue was purified by preparative HPLC to give the title compound (48 mg). LCMS: 429.1 m/z (M+H)+; ret. Time 3.23 min (Analytical Method A).

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-(4-Fluorophenyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; GALEMMO, Robert, A., Jr.; ARTIS, Dean, Richard; YE, Xiaocong, Michael; AUBELE, Danielle, L.; TRUONG, Anh, P.; BOWERS, Simeon; HOM, Roy, K.; ZHU, Yong-Liang; NEITZ, R., Jeffrey; SEALY, Jennifer; ADLER, Marc; BEROZA, Paul; ANDERSON, John, P.; WO2011/79114; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 60-56-0, The chemical industry reduces the impact on the environment during synthesis 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, I believe this compound will play a more active role in future production and life.

Bleach (12% w/w aq, 110 ml) was cautiously added dropwise to a solution of 2-mercapto-1-methylimidazole (2.0 g) in conc. [H2SO4] (50 ml) cooled to [0C.] After stirring 30 minutes at [0C] the mixture was diluted with [H20] (30 ml) and dichloromethane (30 ml). The aqueous layer was re-extracted with dichloromethane and the combined organic layers dried [(MGS04)] and evaporated to give the product as an oil (730 mg).

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-Methyl-1H-imidazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/31139; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17289-26-8, 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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(f) Synthetic Example; N-(1-((1-methyl-1H-imidazol-4-yl)methyl)piperidin-4-yl)-2-(4-(trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamide. (Compound 53); To a solution of the dihydrochloride salt prepared in step 1 of Synthetic Example 1 (e) (65 mg, 0.12 mmol) was dissolved in DCM (2.0 mL), 1-methyl-1H-imidazole-4-carbaldehyde (2×16 mg, 2×0.15 mmol) and sodium triacetoxyborohydride (2×55 mg, 3×260 mumol) were added. The resulting reaction mixture was allowed to stir at room temperature overnight, and upon reaction completion, was poured into saturated sodium bicarbonate solution (30 mL). The layers were separated, extracted aqueous layer with EtOAc (3×20 mL), washed combined organic layer with brine (2×10 mL), dried (MgSO4), filtered and concentrated. Trituration of the residue with ethyl ether provided N-(1-((1-methyl-1H-imidazol-4-yl)methyl)piperidin-4-yl)-2-(4-(trifluoromethyl)benzyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxamide as a white solid (Compound 53, 31 mg, 46%). 1H NMR (DMSO-d6, 300 MHZ) 11.02 (s, 1H), 7.98 (d, J=7.4 Hz, 1H), 7.82 (s, 1H), 7.71 (d, J=8.0 Hz, 2H), 7.62 (d, J=7.7 Hz, 2H), 7.54 (d, J=8.5 Hz, 1H), 7.44 (s, 1H), 7.25 (d, J=8.5 Hz, 1H), 6.92 (s, 1H), 3.86 (s, 2H), 3.78-3.66 (m, 1H), 3.63 (s, 2H), 3.60 (s, 3H), 3.30 (s, 2H), 2.92-2.78 (m, 6H), 1.98 (t, J=11.3 Hz, 2H), 1.73 (d, J=11.0 Hz, 2H), 1.52 (q, J=10.8 Hz, 2H) ppm; MS (ES) 551 (M+H).

The synthetic route of 1-Methyl-1H-imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; US2009/163511; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 46006-36-4,Some common heterocyclic compound, 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, molecular formula is C8H6N2O2, 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.

Example 94N-CCls^sJ^-Cl-CS’-CCCSS^RJ-S^-dimethylpiperazin-l-yOmethyO^’-hydroxybiphenyl-S- yloxy)-5-fluoronicotinamido)cyclohexyl)-lH-benzo[d]imidazole-4-carboxamide To a solution of N-((ls,4s)-4-aminocyclohexyl)-2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l- yl)methyl)-4′-hydroxybiphenyl-3-yloxy)-5-fluoronicotinamide (100 mg, 0.17 mmol) in dry DMF (5 mL) under nitrogen was added DIPEA (0.057 mL, 0.34 mmol) at RT. The solution was stirred until homogeneous. To this solution was added dropwise a solution of IH- benzo[d]imidazole-4-carboxylic acid (27.8 mg, 0.17 mmol) and l,l’-carbonyldiimidazole (27.8 mg, 0.17 mmol) in dry DMF (5 mL) under nitrogen which had been allowed to stir at 40 0C for 1 h. The reaction mixture was allowed to stir at 50 0C overnight. The mixture was evaporated to dryness and the residue dissolved in chloroform (15 mL) and washed with saturated NaHCO3 (aq), water, dried (MgSO4) and evaporated to give a yellow oil. This was purified by preparative HPLC to afford the title compound. Yield: 36.5 mg 1H NMR (400 MHz, CD3OD) delta 8.69 (s, IH), 8.49 (d, J= 6.9 Hz, IH), 8.12 – 8.07 (m, 2H), 7.91 (d, J= 7.7 Hz, IH), 7.84 (d, J= 8.2 Hz, IH), 7.52 – 7.41 (m, 6H), 7.38 (s, IH), 7.16 – 7.10 (m, IH), 6.87 (d, J= 8.5 Hz, IH), 4.21 – 4.09 (m, 2H), 4.07 (s, 2H), 3.62 – 3.49 (m, 2H), 3.41 (d, J= 12.8 Hz, 2H), 2.65 (t, J= 12.4 Hz, 2H), 1.99 – 1.74 (m, 8H), 1.30 (d, J= 6.7 Hz, 6H). MS: [M+H]+=692.3 (calc=692.336) (MultiMode+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Benzimidazole-7-carboxylic acid, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 401567-00-8, The chemical industry reduces the impact on the environment during synthesis 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, I believe this compound will play a more active role in future production and life.

4.1.18. 2-Chloro-5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)benzimidazole and 2-chloro-6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)benzimidazole (17) To a solution of 2-chloro-5-cyanobenzimidazole (1.4 g,8.1 mmol) and triethylamine (3.4 mL, 24 mmol) in anhydrousDMF (30 mL) was added 2-(trimethylsilyl)ethoxymethyl chloride(2.2 mL, 12 mmol), and the mixture was stirred at room tempera-ture for 2.5 h. Triethylamine (1.7 mL, 16 mmol) was further added,and stirring was continued overnight. The reaction was thenquenched by addition of water, and the resulting mixture wasextracted with AcOEt. The combined organic layer was washedwith 2 N aq HCl and brine, dried over Na2SO4, and concentratedunder reduced pressure. The residue was puried by silica gel col-umn chromatography (n-hexane/AcOEt = 3:1) to afford the product17 (2.2 g, 87%, 1:1 regioisomeric mixture) as a white solid.1H NMR (500 MHz, CDCl3) d 8.03 (s, 1/2H), 7.81 (d, J = 1.1 Hz,1/2H), 7.77 (d, J = 8.6 Hz, 1/2H), 7.61-7.55 (m, 3/2H), 5.59 (s, 2H),3.60-3.55 (m, 2H), 0.95-0.89 (m, 2H), 0.03 (s, 9H); 13C NMR(125 MHz, CDCl3) d 144.6, 144.1, 143.3, 141.3, 137.6, 134.5,127.2, 126.9, 124.3, 120.5, 119.2, 115.0, 111.3, 73.6, 73.5, 67.2,17.7, 1.5; MS (FAB) m/z 308 (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-Chloro-1H-benzo[d]imidazole-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Okazaki, Shogo; Noguchi-Yachide, Tomomi; Sakai, Taki; Ishikawa, Minoru; Makishima, Makoto; Hashimoto, Yuichi; Yamaguchi, Takao; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5258 – 5269;,
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. 934-22-5, name is 6-Aminobenzimidazole, A new synthetic method of this compound is introduced below., COA of Formula: C7H7N3

Compound 467: 1 -(1 H-benzo[d]imidazol-6-yl)-5-(2,3-difluorophenyl)-3-hydroxy-4- methyl-1 H-pyrrol-2(5H)-one; 1 H-Benzoimidazol-5-ylamine (1 mmol) was dissolved in 5ml_ of dry EtOH and 2,3- difluorobenzaldehyd (1 mmol) were added. The solution was stirred overnight and after that 2- oxal-propionsaure diethylester (1 mmol) was added and the solution was stirred for 2Oh at 500C. After that the solvent was evaporated and remaining oil was subjected to a flash chromatography device and purified by means of a CHC^/MeOH gradient. The purified carboxylic acid ethyl ester derivative was suspended in 1OmL of a 10% aqueous solution of HCI and kept for 3h at reflux. The resulting precipitate was filtered off and dried. Yield: 0.15Og (46 %);1H-NMR (400 MHz, CD3OD), 1.78 (s, 3H, CH3), 6.06 (s, 1 H, CH-N), 6.94 – 7.17 (m, 3H, aro), 7.74 (s, 2H, benzimid), 8.08 (s, 1 H, benzimid), 9.27 (s, 1 H, benzimid), MS m/z 342.1 (M+H)+, HPLC (254 nm): purity 100 %molecular weight (g/mol): 341.3 Ki hQC (nM): 1 1.6

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; PROBIODRUG AG; WO2008/55945; (2008); 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. 583-42-6, name is 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione, A new synthetic method of this compound is introduced below., Quality Control of 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione

A suspension of 5-fluoro-lJ./-benzoimidazole-2-thiol (168 mg, 1 mmol), 5-bromo-pentanoic acid ethyl ester (188 mg, 0.9 mmol, 145 ILL.) and K2CO3 (276 mg, 2 mmol) inacetone (2 ml) is refluxed for 3 h. It is cooled down and filtered over a short plug ofsilica gel and rinsed with AcOEt. The solvent is removed in vacua. The crude ispurified by flash chromatography on silica-gel (AcOEt / heptane, 1 :2), yielding the titlecompound (190 mg) in 64% as a brown oil: fo = 1.87 min (LC-2), ESI-MS (pos.): m/z297.28 [M+H]+, ESI-MS (neg.): m/z 295.30 [M-H]+; .H-NMR (CDC13): 5 (ppm) 1.25(t, 3H, CH3), 1.79 (br. t, 4H), 2.36 (br. t, 2H, CH2CO), 3.28 (br. t, 2H, SCH2), 4.14 (q,2H, CHaO), 6.93 (dt, lHarom), 7.20 (dd, lHarom), 7.41 (dd, lHarom).

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; ACTELION PHARMACEUTICALS LTD; WO2006/21418; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem