Tag: M.W=100-200

2625-49-2, A common heterocyclic compound, 2625-49-2, name is 2-(1-Methyl-1H-imidazol-4-yl)acetic acid, molecular formula is C6H8N2O2, 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 mixture of 2-amino-5-(4-methylphenyl) thiophene-3-carboxamide 1a (0.25 g, 0.107 mol) and 4-benzyloxy benzoic acid 4a (0.319 g, 0.140 mol) in anhydrous chloroform (4 ml) was added triethylamine (0.32 g, 0.323 mol) and phosphonic acid cyclic anhydride (1.02 g, 0.323 mol). The reaction mixture was irradiated at 120 C in a microwave initiator for a given period of time (Table 1, entry 1). Once the substrate was completely consumed as monitored by TLC, the brown reaction mixture was cooled and poured into ice-cold water (10 ml). The product was extracted with ethyl acetate (2 ¡Á 25 ml) and the combined organic phase was washed with water, brine solution and dried over anhydrous sodium sulfite. The solvent was removed under vacuum and the brown residue was passed through a small plug of silica gel using petroleum ether/ethyl acetate (9/1) to afford 429 mg (94%) of 2a as a yellow solid.

The synthetic route of 2625-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Poojari, Subba; Parameswar Naik; Krishnamurthy; Tetrahedron Letters; vol. 53; 35; (2012); p. 4639 – 4643;,
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29043-48-9,Some common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, molecular formula is C8H9N3, 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: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2¡¤2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 ¡Á 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3¡Á10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

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

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
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104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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.

Di(imidazole-1-yl)methanimine (17.59 mmol, 2.83 g) was added to a solution of 2-amino-6-chlorophenol (7.03 mmol, 1.01 g) in acetonitrile (40 mL) with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for ten hours. The reaction was then concentrated under reduced pressure and silica gel column chromatography (2:1 hexanes/ethyl acetate) provided a crystalline white solid in a 92% yield.

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

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
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Imidazole | C3H4N2 – PubChem

6775-40-2, These common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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 ofaldehyde (1 mmol), amine (1 mmol), CCl3CN (2 mmol) in PEG-400 (5mL) at 0 oC, a solution of H2O2 (30%) (3mmol)was added drop wise. Then the reaction mixture was stirred at room temperature for 8-12 h. After completion ofthe reaction (monitored by TLC), the reaction mixture was poured into ice water (50 mL). The solid obtained wasfiltered, washed with water and crude product was purified by column chromatography (silica gel, 60-120 mesh)using hexane/ethylacetate (6:4) as eluent.

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 6775-40-2.

Reference:
Article; Gaddam, Lakshmi Teja; Thata, Sreenivasulu; Adivireddy, Padmaja; Venkatapuram, Padmavathi; Arkivoc; vol. 2019; 6; (2019);,
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10394-38-4, A common compound: 10394-38-4, name is 1-Methylbenzoimidazol-5-amine, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 4 1-(3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)-3-(4-((2-((1-methyl-1H-benzo[d]imidazol-5-yl)amino)pyrimidin-4-yl)oxy)naphthalen-1-yl)urea To a solution of Intermediate C1 (155 mg, 80% purity, 0.236 mmol) in DMF (2.0 mL) was added p-TSA.H2O (90 mg, 0.47 mmol) and 1-methyl-1H-benzo[d]imidazol-5-amine (49 mg, 0.33 mmol). The resulting mixture was heated at 60 C. for 16 hr and was then cooled to RT and partitioned between saturated aq. NaHCO3 (40 mL) and EtOAc (25 mL). The organic layer was separated and washed with water (2*50 mL) and brine (50 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 0-30% MeOH in DCM, gradient elution) and by preparative HPLC to afford the title compound, Example 4, as a pale pink solid (15 mg, 9%); Rt 1.96 min (Method 2, acidic); m/z 638 (M+H)+, (ES+); 1H NMR delta: 1.30 (9H, s), 2.39 (3H, s), 3.74 (3H, s), 6.42 (1H, s), 6.46 (1H, d), 7.23-7.31 (2H, over-lapping m), 7.37 (2H, d), 7.40 (1H, d), 7.47 (2H, d), 7.55 (1H, dd), 7.61 (1H, dd), 7.77 (1H, br s), 7.83 (1H, d), 7.88 (1H, d), 8.00 (1H, s), 8.07 (1H, d), 8.36 (1H, d), 8.86 (1H, s), 9.18 (1H, s), 9.42 (1H, s).

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-Methylbenzoimidazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOPIVERT PHARMA LIMITED; Duffy, Lorna Anne; King-Underwood, John; Longshaw, Alistair Ian; Murray, Peter John; Onions, Stuart Thomas; Taddei, David Michael Adrien; Williams, Jonathan Gareth; Ito, Kazuhiro; Charron, Catherine Elisabeth; US2015/203475; (2015); A1;,
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4887-83-6, 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. 4887-83-6, name is 7-Methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below.

B. 4-Methylbenzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester A solution of 4-methylbenzimidazole (810 mg, 6.1 mmol), N,N-dimethylaminopyridine (75 mg, 0.6 mmol) and di-tert-butyl dicarbonate (1.54 g, 7.1 mmol) in acetonitrile (20 mL) was stirred at room temperature for 15 min. The solvent was evaporated and the residue was chromatographed (10% ethyl acetate/hexanes) to give 4-methylbenzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (1.35 g, 95%).

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; Hoffmann-La Roche Inc.; US6331640; (2001); B1;,
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Imidazole | C3H4N2 – PubChem

104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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. 104619-51-4

To a solution of 2-((dimethylamino)methyl)-6-nitrophenol (KR-400103) (5.74 mmol, 1.13 g) in methanol (120 mL), PtO2 (0.29 mmol, 0.07 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then stirred under hydrogen atmosphere at ordinary pressure (balloon) for ten hours. Argon wasagain flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (50 mL). The filtrate was concentrated in vacuo yielding a brown solid. The solid was quickly re-dissolved in acetonitrile (120 mL) and di(imidazole-1-yl)methanimine (14.35 mmol, 2.31 g) was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (10:1 chloroform/methanol) provided a colorless oil in an 81% yield. The product of the reduction (2-amino-6-((dimethylamino)methyl)phenol) is air unstable and appropriate measures should be taken to minimize air exposure. An analytical sample of the title compound was isolated by reverse-phase HPLC utilizing a gradient from 0.5-7% acetonitrile in water.

Statistics shows that 104619-51-4 is playing an increasingly important role. we look forward to future research findings about Di(1H-imidazol-1-yl)methanimine.

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

137049-00-4, Name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 137049-00-4, 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.

To a solution of intermediate 2.103 (20. mg, 0.078 mmol) and triethylamine (30 muL, 0.2 mmol) in dichloromethane (0.5 mL) at 0 C was added 1-methyl-1H-imidazole-4- sulfonyl chloride (21 mg, 0.12 mmol). The resulting mixture was stirred for 18 h, then diluted with wet DMSO (1 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (18 mg, 57% yield).1H NMR (500 MHz, (0494) Acetonitrile-d3) d 8.61 (s, 1H), 7.73 (s, 1H), 7.69 (dd, J = 11.8, 2.4 Hz, 1H), 7.57 (d, J = 1.4 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.26- 7.18 (m, 1H), 3.85- 3.77 (m, 1H), 3.73 (s, 3H), 3.64 (d, J = 12.0 Hz, 1H), 2.67 (t, J = 11.2 Hz, 1H), 2.62- 2.47 (m, 2H), 1.85- 1.76 (m, 1H), 1.59 (qt, J = 12.5, 4.0 Hz, 1H), 1.53- 1.41 (m, 1H); AMM 423.0678 (ESI) m/z [calc for (0495) C16H18ClFN4O3SNa (M+Na)+ 423.0670].

Statistics shows that 1-Methyl-1H-imidazole-4-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 137049-00-4.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); A1;,
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Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life. 705-09-9

A mixture of 2-difluoromethyl-lH-benzimidazole (0.168 g), 4,6-dichloro-2-morpholinopyrimidine (0.233 g), sodium bicarbonate (0.168 g) and DMA (5 ml) was stirred under nitrogen and heated to 9O0C for 20 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate in methylene chloride as eluent. The solid so obtained was washed with a 1 : 1 mixture of isohexane and diethyl ether. There was thus obtained 6-chloro-4-(2-difluoromethylbenzimidazol- 1 -yl)-2-morpholinopyrimidine (0.075 g); NMR Spectrum: (DMSOd6) 3.7 (m, 4H), 3.78 (m, 4H), 7.2 (s, IH), 7.39-7.72 (m, 3H), 7.84 (d, IH), 7.9 (d, IH); Mass Spectrum: M+H+ 366.

The chemical industry reduces the impact on the environment during synthesis 705-09-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; HILL, George, Beresford; PASS, Martin; WO2008/32033; (2008); A1;,
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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 492-98-8 as follows. 492-98-8

A mixture of CdCl2¡¤2.5H2O (0.1mmol, 30mg), H2biim (0.1mmol, 10mg) and H2ip-OH (0.1mmol, 20mg) and H2O (8mL) was adjusted to pH 5.0 with 0.05 mol L-1 NaOH solution. It was then sealed in a 25mL Teflon reactor and heated at 150 C for 72 h. The mixture was cooled to room temperature after 40 h. Slightly purple crystals were obtained. Yield: 42 % based on the Cd(II) salt. Anal. Calc. for C11H7N2O5Cd: C, 36.70; H, 1.95; N, 7.79. Found: C, 36.76; H, 1.95; N, 7.80%. IR (KBr, cm-1): 3461 (m), 3058 (w), 2930 (w), 2866 (w), 1630 (s), 1583 (s), 1508 (m), 1397 (s), 1333 (s), 1291 (s), 1208 (m), 1165 (w), 1098 (w), 1014 (w), 859 (s), 750 (s), 661 (m), 428 (w).

According to the analysis of related databases, 492-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Fei-Fei; Wang, Xiao-Fang; Yu, Xiao-Yang; Luo, Yu-Hui; Zhang, Hong; Polyhedron; vol. 98; (2015); p. 40 – 46;,
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Imidazole | C3H4N2 – PubChem