Month: May 2021

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. 2735-62-8, name is 2-(1-Methyl-1H-benzo[d]imidazol-2-yl)acetonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H9N3

General procedure: To a solution of substituted acetonitriles (12 mmol) in MeOH (25 mL) was added triethylamine (12 mmol) and aldehydes (12 mmol). The mixture was stirred at 50 C, after the reaction was complete (typically 1-3 h). The reaction mixture was cooled to room temperature, the precipitate was isolated by filtration and washed with cold MeOH (2 * 1 mL) to give the desired products.

The synthetic route of 2735-62-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Huijie; Lv, Kaikai; Ma, Lanping; Zhang, Yongliang; Yu, Ting; Chen, Lin; Wang, Xin; Shen, Jingkang; Meng, Tao; Tetrahedron Letters; vol. 61; 23; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5465-29-2,Some common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, molecular formula is C10H12N2, 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 116] (E)-2-Fluoro-8-(2-propylbenzimidazol-1-yl)methyl-11-[1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)ethylidene]-6,11-dihydrodibenzo[b,e]oxepine(compound 116) [step 1] (E)-2-(2-Fluoro-8-hydroxymethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)propiononitrile (0.115 g, 0.299 mmol) obtained in Reference Example B12 was dissolved in THF (1.5 mL), 2,6-lutidine (0.21 mL, 1.79 mmol), lithium bromide (0.156 g, 1.79 mmol) and methanesulfonic anhydride (0.130 g, 0.747 mmol) were added, and the mixture was stirred at room temperature for 16 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue. 2-Propylbenzimidazole (0.032 g, 0.199 mmol) was dissolved in DMF (1.5 mL), potassium carbonate (0.125 g, 907 mmol) was added and the mixture was stirred for 15 min. To this mixture was added the residue obtained above, and the mixture was stirred at 60C for 2 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give (E)-2-[2-fluoro-8-(2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile (0.063 g, 48%).

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

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2327690; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33468-69-8, 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. 33468-69-8 name is 4-(Trifluoromethyl)-1H-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.

Step A: (+/-)-methyl 4-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenyl)butoxy)benzoate Dimethylsulfoxide (1.5 mL) was added to a screw-top reaction vial charged with Intermediate (34) (128 mg, 0.339 mmol), 4-(trifluoromethyl)imidazole (55 mg, 0.406 mmol), copper (I) iodide (13 mg, 0.068 mmol), quinolin-8-ol (9.9 mg, 0.068 mmol), and potassium carbonate (92 mg, 0.67 mmol). The vial was evacuated and back-filled with nitrogen repeatedly then heated with stirring to 100 C. overnight. After 18 hours the reaction was diluted with saturated ammonium chloride (20 mL) and ethyl acetate (20 mL). The phases were separated and the organic layer was washed with water (2*20 mL) and brine (5 mL). The organics were dried over magnesium sulfate, filtered and concentrated. Purification by column chromatography (0-50% ethyl acetate in heptanes) gave (+/-)-methyl 4-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenyl)butoxy)benzoate (65 mg, 44%) as a clear oil. 1H NMR (400 MHz, CDCl3, delta): 7.94-7.89 (m, 2H), 7.84 (s, 1H), 7.58 (s, 1H), 7.53-7.48 (m, 2H), 7.40-7.36 (m, 2H), 6.89-6.84 (m, 2H), 5.31 (dd, J=9, 4.6 Hz, 1H), 3.86 (s, 3H), 2.04 (m, 1H), 1.96-1.83 (m, 1H), 1.67-1.59 (m, 1H), 1.04 (d, J=6.6 Hz, 3H), 0.99 (d, J=6.6 Hz, 3H). MS (M+1): 433.0.

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

Reference:
Patent; PFIZER INC.; US2012/202834; (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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1H,1’H-2,2′-Biimidazole

A mixture of 14 Na2WO4 (0.329g, 1.00mmol), 15 H3PO4 (0.147g, 1.50mmol), 16 H2C2O4 (0.270g, 1.00mmol), 17 Cu(CH3OO)2 (0.356g, 1.50mmol), biim (0.067g, 0.50mmol), 18 TEA (0.03g, 0.50mmol) and 19 H2O (20ml) were stirred for 30min, then 20 NH3·H2O was added to adjust the pH value to 6.5. Finally, the suspension was transferred to a 30ml Teflon-lined autoclave and heated at 160C for 120h under autogenous pressure. After the system was cooled to room temperature, black block crystals were filtered and dried at room temperature. Yield: 62.5% (based on W). Anal. Calcd. for C48H90Cu4N20O82P2W24: C, 8.25; H, 1.30; N, 4.01; W, 63.13; Cu, 3.64; P, 0.89. Found: C, 8.28; H, 1.25; N, 4.06; W, 63.02; Cu, 3.73; P, 0.87. IR (cm-1): 3447, 3302, 1642, 1566, 1514, 1414, 1090, 1063, 965, 879, 818, 785, 677

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; Shi, Shu-Yun; Chen, Ling-Yu; Zhu, Tong-Hui; Zhang, Jun; Cui, Xiao-Bing; Inorganica Chimica Acta; vol. 477; (2018); p. 292 – 299;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 10111-08-7, These common heterocyclic compound, 10111-08-7, name is Imidazole-2-carboxaldehyde, 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.

Compound 234.1. lH-Imidazole-2-carbonitrile. Into a 1-L round-bottom flask, was placed a solution of lH-imidazole-2-carbaldehyde (5 g, 52.04 mmol) in NN- dimethylformamide (200 mL). Triethylamine (10.8 mL, 77.97 mmol), hydroxylamine hydrochloride (3.95 g, 56.84 mmol, 1.10 equiv), 1-propanephosphonic anhydride solution and 2,4,6-tripropyl-l,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution (T3P) (36.4 g, 114.40 mmol) were added to the reaction. The reaction mixture was stirred for 4h at 100 C, cooled and then quenched with 500 mL of water/ice. The aqueous phase was extracted with 3 x 1L of ethyl acetate, then the combined organic layers was washed with 2 x 1L of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/2) as eluent to furnish 2 g (41%) of the title compound as an off-white solid.

Statistics shows that Imidazole-2-carboxaldehyde is playing an increasingly important role. we look forward to future research findings about 10111-08-7.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 23814-14-4,Some common heterocyclic compound, 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O3, 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 14 N-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide Procedure: A mixture of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (100 mg, 0.245 mmol), 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid (48 mg, 0.27 mmol), EDCI (97 mg, 0.49 mmol) and N-methylimidazole (60 mg, 0.735 mmol) in 10 mL of DCM was stirred at room temperature for 16 hours. The mixture was washed with water (5 mL), The organic layer was dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography on silica gel eluting with a mixture of CH2Cl2 and methanol (100:1: to 20:1, V/V) to give N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide (25 mg, 19%) as white solid. 1H NMR (300 MHz, DMSO): delta 9.57 (s, 1H), 8.81 (s, 1H), 8.475-8.46 (m, 1H), 8.27-8.25 (m, 2H), 7.60-7.25 (m, 2H), 6.92 (d, 1H, J=8.7 Hz), 6.47-6.39 (m, 3H), 4.54-4.52 (m, 1H), 3.76-3.58 (m, 10H), 2.27-2.05 (m, 2H). LC-MS: 247 [M/2+H]+, 493 [M+H]+, 491 [M-H]-, tR=1.22 min. HPLC: 95.20% at 214 nm, 95.06% at 254 nm, tR=5.64 min.

The synthetic route of 23814-14-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 144690-33-5,Some common heterocyclic compound, 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, molecular formula is C45H44N6O3, 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.

79(b) (5-Methyl-2-oxo-1,3-dioxolen-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate Following-procedures similar to those described in Example 78(a) and 78(b), but using ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in step (a) above], the title compound was obtained in a 71% yield. The Nuclear Magnetic Resonance Spectrum of this compound was identical with that of the compound obtained as described in Example 61(b).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, its application will become more common.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 86604-86-6, These common heterocyclic compound, 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, 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.

Example 9: 3-(3,4-Dichlorophenyl)-8-[5-(trifluoromethyl)-1 H-benzimidazol-2-yl1-1 -oxa-3,8- diazaspiro[4.51decan-2-one; 2-Chloro-5-(trifluoromethyl)-1 /-/-benzimidazole (Intermediate 1 , 100 mg, 0.45 mmole) and 3-(3,4-dichlorophenyl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrobromide (Intermediate 16, 190.5 mg, 0.498 mmol) were dissolved in a mixture of 2-pentanol:CH3CN (4:1 , 2 ml) in a vial for microwave reactions, DIPEA was added (235.1 mul, 1.35 mmol) and the mixture was heated at 200 C for 10 minutes. The mixture was concentrated under vacuum; the crude was purified by MDAP, then the fractions were collected and purified by ion- exchange SCX to give the title compound (35.4 mg, 16%). 1 H-NMR (500MHz, CDCI3): delta 1.89-2.04 (4H, m), 3.57-3.66 (2H, m), 3.76-3.87 (2H, m), 3.95 (2H, s), 7.20-7.51 (3H, m), 7.54-7.59 (1 H, m), 7.63-7.69 (1 H, d), 7.84-7.86 (1 H, d), 11.79 (1 H, br s); MS: m/z 485 [M+H]+.

Statistics shows that 2-Chloro-6-(trifluoromethyl)benzimidazole is playing an increasingly important role. we look forward to future research findings about 86604-86-6.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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. Application In Synthesis of 2-(Difluoromethyl)-1H-benzo[d]imidazole

Example 55 1-(2-(2-(difluoromethyl)-1H-benzo[c]imidazol-1-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)ethanone To a 5 mL microwave vial equipped with a magnetic stir-bar were added 1-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)ethanone (300 mg, 1.116 mmol), 2-(difluoromethyl)-1H-benzo[d]imidazole (179 mg, 1.063 mmol), tris(dibenzylideneacetone)dipalladium(0) (38.9 mg, 0.043 mmol) and cesium carbonate (520 mg, 1.595 mmol). The vial was evacuated and filled with nitrogen four times and then sealed. DMF (2.1 mL) was added to give an orange suspension, which was heated to 140 C. for 45 minutes. The reaction mixture was heated for an additional 30 minutes, was subsequently diluted with ACN (3 mL), and was passed through a syringe filter. The filtrate was directly purified by preparatory HPLC using a gradient of 40-60% CH3CN (with 0.035% TFA) in H2O (with 0.05% TFA). Lyophilization of the collected fractions gave a TFA salt of the title compound (135 mg, 31.7%). ESI-MS m/z [M+H]+ calc’d for C19H18F2N6O2, 401.15. found 401.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 705-09-9, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2012/220575; (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. 68892-07-9, name is Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 68892-07-9

A solution of compound 1 (300.0 mg, 1.74 mmol) in a NaOH solution (2.0 M, 4.0 mL, 8.0 mmol) in water (4.0 mL) was stirred at 20 C for 4 h. The solution was adjusted to pH = 2.0with conc. HC1 solution. The precipitate formed was collected by filtration, and dried in vacuo to afford Compound 2 (200 mg, 1.264 mmol, 72.6% yield) as a white solid. ?H NMR (400 MHz, DMSO-d6) 5 12.76 (s, 1H), 7.69 (d, J= 2.4 Hz, 1H), 3.68 (s, 3H). LCMS showed most product was dimer. LCMS (5-95AB/1.5min): RT = 0.807 mi [M+Hjb 158.7, dimer: [M+ljb 314.9.

According to the analysis of related databases, 68892-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; DRAGOVICH, Peter; PEI, Zhonghua; PILLOW, Thomas; SADOWSKY, Jack; CHEN, Jinhua; WAI, John; (237 pag.)WO2017/64675; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem