Tag: M.W=100-200

17228-38-5, These common heterocyclic compound, 17228-38-5, name is N-Methyl-1H-benzo[d]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.

A mixture of 5- (6-formyl-pyridin-2-yl)-thiophene-2-carboxylic acid [88mg, 0. [38MMOL,] Reference Example 14 (e)], [(LH-BENZOIMIDAZOL-2-YL)-METHYLAMINE] (60mg, 0.38mmol) and anhydrous ethanol (4ml) was stirred at room temperature for 2 hours, before sodium borohydride (30mg, 0.76mmol) was added. After stirring overnight the reaction mixture was concentrated, to provide 5-(6-{[(1H-benzoimidazol-2-ylmethyl)-amino]-methyl}- [PYRIDIN-2-YL)-THIOPHENE-2-CARBOXYLIC] acid as an off-white solid, which was used directly without further purification. LCMS (Method C): [RT] = 1.89 minutes; 365 (M+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 17228-38-5.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2004/13130; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 17228-38-5, name is N-Methyl-1H-benzo[d]imidazol-2-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 17228-38-5. 17228-38-5

EXAMPLE 4.01 AND EXAMPLE 4.02 N-Methyl-1-{4-[(3R)-3-methylmorpholin-4-yl]-6-[4-((S)-S-methylsulfonimidoyl)tetrahydro-2H-pyran-4-yl]pyrimidin-2-yl}-1H-benzimidazol-2-amine and N-methyl-1-{4-[(3R)-3-methylmorpholin-4-yl]-6-[4-((R)-S-methylsulfonimidoyl)tetrahydro-2H-pyran-4-yl]pyrimidin-2-yl}-1H-benzimidazol-2-amine; Cesium carbonate (2.076 g, 6.37 mmol) was added to N-[(4-{2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidin-4-yl}tetrahydro-2H-pyran-4-yl)(methyl)oxido-lambda6-sulfanylidene]-2,2,2-trifluoroacetamide (1.00 g, 2.12 mmol), sodium methanesulfinate (0.217 g, 2.12 mmol) and N-methyl-1H-benzo[d]imidazol-2-amine (0.313 g, 2.12 mmol) in DMA (20 ml). The resulting suspension was stirred at 80 C. for 18 hours. The reaction mixture was filtered and then evaporated. The residue was dissolved in EtOAc (100 mL) and washed sequentially with water (100 mL) and then with saturated brine (10 mL). The aqueous layer was washed with EtOAc (2¡Á100 mL). The organic layers were combined, dried over MgSO4, filtered and then evaporated. The residue was purified by flash chromatography on silica, eluting with a gradient of 0 to 7% MeOH in DCM. Fractions containing product were evaporated and the residue was purified by preparative chiral HPLC on a ChiralCel OD column, eluting isocratically with 50% hexane in EtOH (modified with Et3N) as eluent. Fractions containing isomer 1, eluted first, were evaporated and the residue dissolved in DCM (10 ml) and then evaporated onto silica (0.5 g). The resulting powder was purified by flash chromatography on silica, eluting with a gradient of 0 to 7% MeOH in DCM. Pure fractions were evaporated to dryness to afford isomer 1 (58.0 mg, 36%); 1H NMR (400 MHz, DMSO-d6) 1.31 (3H, d), 2.19-2.35 (2H, m), 2.65-2.75 (5H, m), 3.02 (2H, d), 3.24 (2H, dd), 3.33-3.39 (1H, m), 3.56 (1H, td), 3.71 (1H, dd), 3.81 (1H, d), 3.87-3.97 (2H, m), 4.03 (1H, dd), 4.06 (1H, s), 4.16 (1H, d), 4.53 (1H, s), 6.90 (1H, s), 6.99 (1H, td), 7.09 (1H, td), 7.26 (1H, dd), 8.06 (1H, d), 8.39 (1H, q); m/z: (ES+) MH-, 486.53. Chiral HPLC: (HP1100 System 4, 20 mum Chiralpak OJ (250 mm¡Á4.6 mm) column eluting with Hexane/EtOH/TEA 50/50/0.1) Rf, 8.874 >99%.Fractions containing isomer 2, eluted second, were evaporated and the residue dissolved in DCM (10 mL) and then evaporated onto silica gel (0.5 g). The resulting powder was purified by flash chromatography on silica, eluting with a gradient of 0 to 7% MeOH in DCM. Pure fractions were evaporated to afford isomer 2 (71.8 mg, 44%); 1H NMR (400 MHz, DMSO-d6) 1.30 (3H, d), 2.19-2.36 (2H, m), 2.61-2.76 (5H, m), 3.02 (3H, d), 3.18-3.27 (2H, m), 3.36 (1H, dd), 3.56 (1H, td), 3.71 (1H, dd), 3.81 (1H, d), 3.93 (2H, dd), 4.00-4.08 (2H, m), 4.17 (1H, d), 4.52 (1H, s), 6.91 (1H, s), 6.99 (1H, td), 7.09 (1H, td), 7.26 (1H, d), 8.06 (1H, d), 8.39 (1H, q); m/z: (ES+) MH+, 486.57. Chiral HPLC: (HP1100 System 4, 20 mum Chiralpak OJ (250 mm¡Á4.6 mm) column eluting with Hexane/EtOH/TEA 50/50/0.1) Rf, 12.742 >99%.

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 N-Methyl-1H-benzo[d]imidazol-2-amine.

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

These common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, 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. 2849-93-6

A mixture of 1H-benzimidazole-2-carboxylic acid (4.0g, 24.6mmol), aminoethanol (1.48mL, 24.6mmol), 1-hydroxybenzotriazole (4.14g, 27.1mmol) and N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (5.19g, 27.1mmol) in 80mL dimethylformamide was stirred for 12hat room temperature then concentrated in vacuo. The residue could be crystallized from ethanol (35mL). Yield: 3.13g (62%), EI-LRMS m/z 206.1= (M+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 2849-93-6.

Reference:
Article; Szabo, Gyoergy; Kolok, Sandor; Orgovan, Zoltan; Vastag, Monika; Beni, Zoltan; Koti, Janos; Saghy, Katalin; Levay, Gyoergy I.; Greiner, Istvan; Keser?, Gyoergy M.; European Journal of Medicinal Chemistry; vol. 186; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4238-71-5, 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 4238-71-5 as follows.

To a cold (-50 0C) suspension of 1 -benzyl -IH- imidazole (1.58 g, 10.0 ramol) in anhydrous diethyl ether (50 mL) under nitrogen was added ?-butyl lithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) dropwise. After being stirred for 20 min at -50 0C, dry carbon dioxide (passed through Drierite) was bubbled into the reaction mixture for 10 min before it was allowed to warm up to 25 0C. The heavy precipitate which formed on addition of carbon dioxide to the reaction mixture was filtered to yield a hygroscopic, white solid which was taken up in water (7 mL) , acidified to pH = 3, cooled, and induced to crystallize with scratching. Filtration of the precipitate gave a white solid which was suspended in methanol, treated with IN HCl/diethyl ether (4 mL) and concentrated in vacuo. Lyophilization of the residue from water (5 mL) afforded Cap-136 as a white solid (817 mg, 40%) . 1H NMR (300 MHz, DMSO~d6) 6 7.94 (d, J = 1.5 Hz, IH), 7.71 (d, J = 1.5 Hz, IH) , 7.50-7.31 (m, 5H),5.77 (s, 2H} ; Rt = 0.51 min (Cond. -MS-W5) ; 95% homogenity index; LRMS: Anal. CaIc. for [M+H] + CnH12N2O2: 203.08; found: 203.11.

According to the analysis of related databases, 1-Benzyl-1H-imidazole, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAVOIE, Rico; BENDER, John A.; BACHAND, Carol; RUEDIGER, Edward H.; KADOW, John F.; WO2010/120621; (2010); 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. 54624-57-6, name is 2-Bromobenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., 54624-57-6

Step 1. l-allyl-2-bromo-lH-benzo[d]imidazole [0724] A mixture of 2-bromo-lH-benzo[d] imidazole (0.400 g, 2.04 mmol), allyl bromide (0.35 mL, 4.08 mmol), 1,4-dioxane (15 mL), and 2 M aqueous sodium hydroxide solution (15 mL, 3.00 mmol) stirred for 2 h at 100 ¡ãC. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (50 mL). The organic phase was separated and washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via preparative thin layer chromatography (eluting with 20percent ethyl acetate/petroleum ether) to afford 1- allyl-2-bromo-lH-benzo[d]imidazole (0.251 g, 52percent) as a yellow oil. MS (ESI, pos. ion) m/z 237, 239 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C8H8N2O, 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. 1849-01-0.

To a solution of 1,3-dihydro-1,N-methyl-2-oxobenzimidazole (3.185 g, 21.5 mmol) in DMF (60 mL) is added NaH (60% in mineral oil,1.03 g, 25.78 mmol) portionwise at 0 C. After stirring at 0 C for 30 min.2,4-dichloropyrimidine (3.20 g, 21.5 mmol) is added, and the mixture is allowed to stir at 15 C for 12 hrs. The resulting mixture is quenched with water (200 mL) and the mixture is extracted with EtOAc (100 mL x 3), and washed with water (100 mL x 4), dried with Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (petroleum ether: EtOAc =10:1), to give 2-chloro-4-(1,3-dihydro-3,N-methyl-2-oxobenzimimidazol-1-yl)pyrimidine.

The synthetic route of 1-Methyl-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

256519-10-5, 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. 256519-10-5 name is 4-Fluoro-1H-benzo[d]imidazol-2(3H)-one, 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.

Preparation 47 2-Chloro 4-fluoro-1H-1,3-benzimidazole STR92 The title compound was prepared by the method of Preparation 25 from 4-fluoro-1,3-dihydro-2H-1,3-benzimidazole-2-one [see Preparation 46]. 1 H-NMR (d4-MeOH) delta: 7.32 (1H, d), 7.28 (1H, m), 7.00 (1H, t).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US6166011; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 10394-38-4, name is 1-Methylbenzoimidazol-5-amine, molecular formula is C8H9N3, 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. 10394-38-4.

1-methyl-1H-benzo[d]imidazol-5-amine (100 mg, 0.67944 mmol),6-(4-((2,5-Dichloropyrimidin-4-yl)amino)piperidin-1-yl)nicotinonitrile (182 mg, 0.5212 mmol),Cs2CO3 (508.7 mg, 1.561 mmol),BINAP (34.6mg, 0.0556mmol) andPd(OAc) 2 (12.8 mg, 0.0570 mmol)The mixture was dissolved in 1,4-dioxane (10 mL). The reaction mixture is at 100 C,Stir for 4 hours in a nitrogen atmosphere.After the reaction was completed, it was concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (DCM / MeOH (v/v) = 50/1)The title compound was obtained as a white solid (54.4mg, yield: 22.7%).

The synthetic route of 1-Methylbenzoimidazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5955-72-6, 5955-72-6

To a suspension of 3.952 g (20 mmole) of 19 in 100 mL of 1,2-dichloroethane, was added 5 mL (20 mmole) of BSA. The reaction mixture was stirred at 75 C. for 15 min to give a clear solution. This solution was cooled to ~ 20 C. and treated with 7.0 g (22 mmole) of 1,2,3,5-tetra-O-acetyl-b-D-ribofuranose and 4.638 mL (24 mmole) of TMSOTf at room temperature for 2 h. The reaction mixture was diluted with 200 mL of CHCl3. The CHCl3 solution was washed with sat. NaHCO3 solution (200 mL*2), sat. NaCl solution (200 mL), dried (Na2 SO4), and evaporated. The residue was chromatographed on a silica column (5*35 cm, eluted with CHCl3 and 0.5% MeOH/CHCl3). Evaporation of the appropriate fractions gave 6.50 g (71% one spot on TLC) of 74 and 75 as a white foam. Fractional recrystallization of this foam (5 times from MeOH) give 1.59 g (17%) of the pure 6-nitro isomer 75. MP 127-129 C. MS (EI) m/e 455.0750 (2%, M+ =455.0732). 1 H NMR (DMSO-d6): d 8.68 (d, 1, 7-H, J7-5 =2.0 Hz), 8.21 (dd, 1, 5-H, J5-4 =9.0 Hz), 7.88 (d, 1, 4-H), 6.41 (d, 1, 1′-H, J1′-2′ =7.0 Hz), 5.58 (t, 1, 2′-H, J2′-3′ =7.0 Hz), 5.45 (dd, 1, 3′-H, J3′-4′ =4.0 Hz), 4.50, 4.40 (2*m, 3, 4′-H and 5′-H), 2.15, 2.12, 2.03 (3*s,9, 3*Ac). 13 C NMR (DMSO-d6): d 170.12, 169.49, 169.25 (3*OCOCH3), 145.60 (C3a), 143.96 (C2), 143.65 (C6), 132.46 (C7a), 119.65 (C4), 118.92 (C5), 108.47 (C7), 86.96 (C1′), 79.67 (C4′). 71.12 (C2′), 68.75 (C3′), 62.56 (C5′), 20.39, 20.31, 20.03 (3*OCOCH3).

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-6-nitro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Regents of the University of Michigan; US5574058; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, molecular formula is C5H7BrN2, 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. 24134-09-6.

Preparation 95: 4-(1 ,2-Dimethyl-1 H-imidazol-5-yl)-2-methoxyaniline; [00265] To a microwave vial was added 5-bromo-1 ,2-dimethyl-1 /-/-imidazole (230mg, 1 .31 mmol), 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (393mg, 1 .58mmol), Pd(PPh3)4 (152mg, 0.13mmol), CsF (599mg, 3.94mmol) and DME/MeOH 3/1 (4ml_). The mixture was heated in a microwave at 150C for 1 hour. The reaction mixture was then filtered and concentrated onto silica gel and purified by Biotage silica gel column chromatography eluting with (EtOAc/MeOH 100/0 to 96/4) to give the title product as a light brown oil (120mg, 42 %). 1 H NMR (500 MHz, CDCI3): delta 2.43 (s, 3H), 3.48 (s, 3H), 3.87 (s, 3H), 6.73-6.78 (m, 3H), 6.87 (s, 1 H). LC (Method A)-MS (ESI, m/z) tR 0.49 min, 218 [(M+H+), 100%].

The synthetic route of 5-Bromo-1,2-dimethyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem