Tag: M.W=100-200

Adding some certain compound to certain chemical reactions, such as: 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, 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 1792-40-1. 1792-40-1

To a solution of 2-methyl-5-nitro-1H-benzimidazole (2) (9.0 g,0.05 mol) in ethanol (50 mL), K2CO3 (6.98 g, 0.075 mol) and benzylchloride (9.63 g, 0.075 mol) were refluxed for 8 h. After the completionof the reaction (monitored by TLC), the reaction mixturewas filtered and concentrated to give yellow solid. The residualmass was crystallized from ethanol to give mixture of 1-benzyl-2-methyl-5-nitro-1H-benzimidazole and 3-benzyl-2-methyl-5-nitro-3H-benzimidazole (3) in 75% yield. To a suspension of SnCl2 2H2O (15.45 g, 0.067 mol) in 2 N HCl (47.6 mL), 1/3-benzyl-2-methyl-5-nitro-1H/3H-benzimidazole (3) (4.25 g, 0.019 mol)was heated at 110 C for 7 h. After completion of the reaction,the suspension was neutralized with 2 N NaOH and diluted withethanol. Filtered the solid product and extracted the filtrate with chloroform, dried over Na2SO4, filtered and concentrated to getmixture of products which were separated through column chromatographyusing ethyl acetate/methanol (19:1) as eluent to getsolid compounds 4a and 4b.

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 2-Methyl-5-nitro-1H-benzo[d]imidazole.

Reference:
Article; Singla, Prinka; Luxami, Vijay; Paul, Kamaldeep; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1691 – 1700;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. 1849-01-0

Preparation of l-(3-iodopropyl)-3-methyl-l -benzor< |imidazol-2(3H)-one; [0176] A mixture of l-methyl-lH-benzo[i ]imidazol-2(3H)-one (2 g, 13.5 mmol, 1 equiv), 1- bromo-3-chloropropane (3.98 ml, 40.5 mmol, 3 equiv), and potassium carbonate (2.79 g, 20.25 mmol, 1.5 equiv) in NN-dimethylformamide was heated at 65C for 16 h. The reaction was cooled to ambient temperature and diluted with ethyl acetate. After being washed with water and brine, the organic layer was dried over MgS04, filtered, and concentrated in vacuo. The resulting residue was purified using the Biotage chromatography system (SNAP lOOg cartridge, Rf = 0.6, gradient - 10%- 50%) ethyl acetate/hexanes) to afford l-(3-chloropropyl)-3-methyl-lH-benzo[i ]imidazol-2(3H)-one as a clear oil (2.57 g, 85%); 'ffNMR (400 MHz, DMSO-i/6): delta 2.05-2.12 (m, 1H); 2.14-2.21 (m, 1H); 3.32 (s, 3H); 3.53 (t, 1H, J= 6.8 and 6.4 Hz); 3.66 (t, 1H, J= 6.4 Hz); 3.92-3.97 (m, 2H); 7.05- 7.09 (m, 2H); 7.12-7.16 (m, 1H); 7.17-7.21 (m, 1H); MS for CiiH13ClN20 m/z 226.07 (M+H)+. Statistics shows that 1849-01-0 is playing an increasingly important role. we look forward to future research findings about 1-Methyl-1H-benzo[d]imidazol-2(3H)-one. Reference:
Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1792-40-1, A common compound: 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, 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.

General procedure: 1/3-Butyl-2-methyl-5-nitro-1H/3H-benzimidazole was synthesized by previous reported method by the alkylation of 2-methyl-5-nitro-benzimidazole (0.05 mol) with butyl bromide (0.075 mol) in the presence of NaH (0.126 mol) in THF at room temperature for 8h. To a suspension of SnCl2.2H2O (135 mmol) in 2 N HCl (95.2 ml), 1/3-butyl-2-methyl-5-nitro-1H/3H-benzimidazole (36.4 mmol) was heated at 110 C for 7 h. After the completion of the reaction (monitored by TLC), the suspension was neutralized with 2 N NaOH and diluted with ethanol. Filtered the solid product and extracted the filtrate with chloroform, dried over Na2SO4, filtered and concentrated to get mixture of products which were separated through column chromatography using ethylacetate:methanol (9.5:0.5) to get pure solid compounds 2b and 2d.

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-Methyl-5-nitro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sharma, Alka; Luxami, Vijay; Paul, Kamaldeep; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 414 – 422;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

68282-53-1, Adding some certain compound to certain chemical reactions, such as: 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, 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 68282-53-1.

COMPOUND 12.1. 20: 4- {5. 8-DIMETHOXY-2-rf4-METHYL-l-IMIDAZOL-5- YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1-YL}-N,N- DIETHYLBENZAMIDE; INTERMEDIATE 5.1. 10 (115 mg, 0.31 mmol) and 4-methyl-5- imidazolecarbaldehyde (108 mg, 0.62 mmol) were dissolved in DCE (5.0 mL). After stirring for 10 min at room temperature, sodium triacetoxyborohydride (197 mg, 0.93 mmol) was added and the mixture was stirred for 18 h at room temperature. DCM and 1 M sodium hydroxide solution were added and the mixture was passed through a Whatman 1PS silicon-treated filter paper. The organic phase was evaporated and the crude product was purified by flash chromatography to yield the product (103 mg, 0. 20 mmol, 65%).’H NMR (500 MHz, CDC13) : 8 0. 99, 1.18 (2 brs, 6H), 2.58-2. 74, 3.17-3. 50 (2 m, 8H), 3.32, 3.35 (2 s, 6H), 3.44, 3.65 (2 d, J 12.0 Hz, 2H), 5.05 (s, 1H), 6.51, 6.63 (2 d, J 9. 0 Hz, 2H), 6.87 (s, 1H), 7.00, 7.14 (m, 4H), 7. 21 (m, 5H), 7.80 (d, J 3. 5 Hz, 2H).

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 68282-53-1.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4597-21-1, These common heterocyclic compound, 4597-21-1, name is 1,2-Dimethyl-1H-benzo[d]imidazole-5-carbaldehyde, 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.

Grignard reagent was prepared in an oven-dried three necked flask outfitted with a reflux condenser, dropping funnel, and magnetic stirrer. 3,5-dimethoxy-bromobenzene (2.0 g, 9.0 mmol) in THF (10 mL) was added to a mixture of magnesium turning (0.2 g, 9.0 mmol) in THF (5 mL) with a small piece of iodine. The resulting mixture was refluxed for about 3 h then cooled to room temperature for about 30 min. The (3,5-dimethoxyphenyl)magnesium bromide was then added slowly to a stirred solution of 1,2-dimethoxy-1H-benzoimidazole-5-carbaldehyde (1.3 g, 7.5 mmol) in THF (10 mL) at 0 C. After complete addition, the solution was allowed to stir at room temperature for about 1 h. The mixture was cooled to 0 C. and quenched with saturated NH4Cl solution (40 mL). The aqueous layer was extracted with EtOAc (3¡Á20 mL). The combined organic layers were washed with water (2¡Á30 mL), brine (30 mL) and dried (MgSO4). Solvent was removed and the crude product was slurried in hexane to afford (3,5-dimethoxy-phenyl)-(1,2-dimethyl-1H-benzoimidazlo-5-yl)-methanol (2.1 g, 91%) as a off white solid: 1H NMR (CDCl3) delta 7.66 (s, 1H), 7.24-7.20 (dd, J=1, 8 Hz, 1H), 7.17 (d, J=8 Hz, 1H), 6.56 (d, J=2 Hz, 2H), 6.31 (t, J=2 Hz, 1H), 5.84 (s, 1H), 3.72 (s, 6H), 3.63 (s, 3H), 3.55 (b, 1H), 2.52 (s, 3H). A suspension of (3,5-dimethoxy-phenyl)-(1,2-dimethyl-1H-benzoimidazol-5-yl)-methanol (2.1 g, 6.7 mmol) and MnO2 (2.9 g, 33.6 mmol) in CH2Cl2 (300 mL) was stirred at room temperature for 17 h. The mixture was filtered through celite and solvent was removed. The crude product was slurried with ether to afford (3,5-dimethoxy-phenyl)-(1,2-dimethyl-1H-benzoimidazol-5-yl)-methanone (2.0 g, 99%) as an off white solid: 1H NMR (DMSO-d6) delta 7.90 (s, 1H), 7.71-7.62 (m, 2H), 6.80 (s, 3H), 3.80 (s, 3H), 3.35 (s, 3H), 2.58 (s, 3H); 13C NMR (DMSO-d6) delta 195.28, 160.17, 154.83, 141.54, 140.27, 139.15, 130.15, 123.50, 120.73, 109.70, 107.19, 103.62, 55.47, 29.96, 13.52. 3-(3,5-Dimethoxy-phenyl)-3-(1,2-dimethyl-1H-benzoimidazol-5-yl)-acrylonitrile (E and Z isomers) were prepared analogously to 3-(3-amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile (E and Z isomers) using (3,5-dimethoxy-phenyl)-(1,2-dimethyl-1H-benzoimidazol-5-yl)-methanone (2.0 g, 6.4 mmol), lithium bis (trimethylsilyl)amide (7.7 mL, 7.7 mmol) and diethyl cyanomethylphosphate (1.4 g, 7.7 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2:CH3OH 95:5) to afford mixture of isomers of 3-(3,5-dimethoxy-phenyl)-3-(1,2-dimethyl-1H-benzoimidazol-5-yl)-acrylonitrile (1.1 g, 50%) as a white solid: mp 199-201 C.; 1H NMR (CDCl3) delta 7.69 (m, 3H), 6.56-6.42 (m, 3H), 5.70 (5.74) (s, 1H), 3.77 (s, 3H), 3.73 (3.74) (s, 6H), 2.61 (s, 3H); 13C NMR (CDCl3) delta 163.76 160.63 (160.60), 153.22 (153.54), 142.35 (142.57), 141.69 (139.43), 137.04 (137.38), 130.69 (132.54), 123.74 (122.64), 120.81 (119.54), 118.23 (118.09), 108.84 (108.80), 107.02 (107.72), 102.08 (102.02), 94.32 (93.47), 55.42 (55.41), 30.05 (30.00), 13.88; Anal Calcd for C20H19N3O2+0.2H2O: C, 71.28; H, 5.80; N, 12.47. Found: C, 71.18; H, 5.86; N, 12.42.

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 4597-21-1.

Reference:
Patent; Muller, George W.; Man, Hon-Wah; US2006/52596; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-80-3, 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. 4887-80-3, name is 5-Methoxy-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of NaH (972 mg, 40.5 mmol) in DMF (20 mL) was added 5- methoxy-lH-benzo[d] imidazole (2.0 g, 13.5 mmol) at 27C. After stirring for 5 minutes, Mel (2.3 g, 16.2 mmol) was added and the resulting mixture was stirred for 16 h. The mixture was then diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the crude product (1.2 g, 54.5%) as a grown solid. This crude was used in next step without further purification. LCMS (m/z): 163.1 (M+l).

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; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; BORIACK-SJODIN, Paula, Ann; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100730; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 583-39-1, name is 2-Mercaptobenzimidazole, molecular formula is C7H6N2S, 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. 583-39-1.

Acetic anhydride (30 mL, 0.033 mol) was added to 1H-benzo[d]imidazole-2(3H)-thione 1 (5 g,0.033 mol) and the stirred mixture was heated to 110-115 C for 30 min. The solution was cooledthen water (150 mL) was added, and finally kept for 30 min at room temperature. Colorless crystalswere filtered off (6.21 g, 97% Yield); TLC, Rf = 0.773 (1:1, n-hexane:ethyl acetate). The product wasrecrystallized from benzene to give white crystals. m.p. 201-202 C, (lit. [21] m.p., 195 C); IR (KBr) nu 1716 (C=O), 1368 (CH3), 2996 (CH aliphatic), and 3146 (CH aromatic), 1591 cm-1 (C=C). 1H-NMR(CDCl3/D2O) delta: 1.92 (s, 3H, CH3), 7.19 (m, 2H, Ar-H), and 7.26 ppm (m, 2H, Ar-H). 13C-NMR(DMSO-d6) delta: 27.1 (CH3), 108.5 (CH), 114.3 (CH), 122.3 (CH), 124.3 (CH), 129.8 (C), 130.1 (C), 168.9(C=S), and 171.1 ppm (C=O).

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

Reference:
Article; El Ashry, El Sayed H.; Kilany, Yeldez El; Nahas, Nariman M.; Barakat, Assem; Al-Qurashi, Nadia; Ghabbour, Hazem A.; Fun, Hoong-Kun; Molecules; vol. 21; 1; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C4H6N4O2, 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. 496-46-8.

3a-Methylglycoluril 1 (0.26 g, 1.67 mmol), glycoluril 2 (1.42 g, 10 mmol) and paraformaldehyde (0.9 g, 30 mmol) were added to concentrated hydrochloric acid (5 ml), and the resultant mixture was heated at 95 C for 24 h. After evaporation of the solvent, the residue was added to water (300 ml) and heated under stirring. The white solid was filtered, and then added to a mixed solvent (30 ml) consisting of formic acid and acetic acid in a ratio of 2:1 (v/v). After thorough stirring, the insoluble material (CB[6]) was removed by filtration, and acetone was added to the acidic filtrate. The precipitates generated therein were collected to afford the desired product 4 in a yield of 14%. TOF mass: m/z 1033 (M+Na+). 1H NMR (500 MHz, in D2O with Na2SO4): delta 5.66 (d, Jin,out = 15.8 Hz, 11H, methylene Hout), 5.59 (d, Jin,out = 16 Hz, 1H, methylene Hout), 5.55 (s, 10H, methine H), 5.29 (s, 1H, methine H), 4.35 (d, Jin,out = 16 Hz, 1H, methylene Hin), 4.28 (d, Jin,out = 15.8 Hz, 11H, methylene Hin) and 1.75 ppm (s, 3H, methyl H). 13C NMR (125 MHz, in D2O with Na2SO4): delta 157.7 (C’O), 157.2 (CO), 77.1 (CH), 74.8 (C-CH3), 71.0 (CH), 52.1 (CH2), 48.1 (CH2) and 20.2 ppm (CH3).

The synthetic route of Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ahmed, Mostafa M.; Koga, Kazutaka; Fukudome, Makoto; Sasaki, Hideaki; Yuan, De-Qi; Tetrahedron Letters; vol. 52; 36; (2011); p. 4646 – 4649;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1467-16-9, 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. 1467-16-9 name is 1H-Imidazole hydrochloride, 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 6 17-(5-cyanopyridin-3-yl)oestra-1,3,5(10),16-tetraene-3-carboxamide 17 mg (0.044 mmol) of 17-(5-cyanopyridin-3-yl)oestra-1,3,5(10),16-tetraene-3-carboxylic acid were initially charged in 0.4 ml of 2-methyltetrahydrofuran. Then 11 mg of 1,1′-carbonyldiimidazole and 2 mg of 1H-imidazole hydrochloride were added thereto and the mixture was stirred at room temp. for 18 h. Then 79 mul of 33% ammonia solution were added and the mixture was stirred at room temp. for 72 h, admixed with 10 ml of 1M hydrochloric acid solution, extracted with ethyl acetate and concentrated, and the crude product was purified by preparative HPLC (acetonitrile/water/formic acid). Yield: 9 mg of the title compound. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.00 (s, 3H), 1.35-1.50 (m, 1H), 1.50-1.68 (m, 3H), 1.73 (td, 1H), 1.85-1.98 (m, 1H), 2.07-2.23 (m, 2H), 2.25-2.36 (m, 2H), 2.36-2.44 (m, partly concealed by DMSO signal), 2.83-2.95 (m, 2H), 6.33-6.36 (m, 1H), 7.19 (br. s., 1H), 7.31 (d, 1H), 7.55-7.61 (m, 2H), 7.82 (br. s., 1H), 8.28 (t, 1H), 8.87 (dd, 2H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BOTHE, Ulrich; BUSEMANN, Matthias; BARAK, Naomi; ROTGERI, Andrea; FISCHER, Oliver Martin; MARQUARDT, Tobias; (41 pag.)US2016/24142; (2016); 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., 41716-18-1

To a solution of intermediate 36-h.HCl (2.0 g, 2.96 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (448 mg, 3.55 mmol), HATU (1.23 g, 3.25 mmol) and DIPEA (2.06 mL, 11.83 mmol) and the reaction mixture was stirred at room temperature for 3 hours. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 39-a as a white foam.

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; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem