Tag: M.W=100-200

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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H6N2O2

c) 3-{[(2-Bromo-benzyl)-methyl-carbamoyl]-methyl}-3H-imidazole-4-carboxylic acid methyl ester; To a solution of N-(2-bromo-benzyl)-2-hydroxy-N-methyl-acetamide (1.02 g, 3.95 mmol) in THF (40 mL) at 0 0C is added triphenylphosphine (1.15 g, 4.36 mmol), methyl 4- imidazolecarboxylate (CASNo. 17325-26-7, 0.50 g, 3.96 mmol) and diisopropyl azodicarboxylate ( 0.85 mL, 4.36 mmol). The reaction is permitted to warm to room temperature and allowed to stir 18 hours. The reaction is then adsorbed directly onto silica gel and submitted to silica gel flash chromatography (diethylamine-methanol- dichloromethane, 1 :3:96) to provide 3-{[(2-bomo-benzyl)-methyl-carbamoyl]-methyl}-3H- imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 366.2, 368.2 (M+H)+.

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
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. 3752-24-7, name is 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole

EXAMPLE 7 1-[1-(3,4-Dichloro-phenyl)-1H-imidazol-4-yl-methyl]-4,5,6,7-tetrahydro-1H-benzoimidazole-, Hydrochloride (1:2) Reaction of 4,5,6,7-tetrahydrobenzimidazole with sodium hydride followed by treatment with 4-chloromethyl-1-(3,4-dichloro-phenyl)-1H-imidazole led after extractive workup and chromatography to the free base of the title compound which was converted into its white hydrochloride salt. Mp.>250 C. (MeOH/Et2O), MS: m/e=346 (M+).

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; Alanine, Alexander; Buettelmann, Bernd; Heitz Neidhart, Marie-Paule; Jaeschke, Georg; Pinard, Emmanuel; Wyler, Rene; US2002/151715; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 60-56-0,Some common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, molecular formula is C4H6N2S, 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.

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-N-[4-(hydroxymethyl)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide (500 mg) in THF (10 ml) was added 1 droplet of pyridine, and thionyl chloride (0.09 ml) was added to the mixture at 0C. The mixture was allowed to be at room temperature under nitrogen atmosphere, and stirred for 1 hour. The solvent and excess thionyl chloride were distilled off under reduced pressure, and the residue was dissolved in THF (10 ml). This solution was added to a solution of 2-mercapto-1-methylimidazole (137 mg) and triethylamine (1.67 ml) in THF (10 ml) at 0C, and the mixture was heated overnight under nitrogen atmosphere at 50C. The mixture was allowed to be cooled, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate = 1:2), to give 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[(1-methylimidazol-2-yl)sulfanyl]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (437 mg) (Compound 358) as yellow amorphous. 1H-NMR (200 MHz, CDCl3) delta 0.90 to 0.99 (9H, m), 1.30 to 1.45 (2H, m), 1.50 to 1.70 (2H, m), 1.95 to 2.20 (1H, m), 2.90 to 2.97 (2H, m), 3.19 (2H, d, J = 7.4 Hz), 3.28 (3H, s), 3.30 to 3.40 (2H, m), 3.55 (2H, t, J = 6.6 Hz), 3.80 (2H, t, J = 4.6 Hz), 4.13 to 4.18 (4H, m), 6.87 to 7.11 (7H, m), 7.37 to 7.56 (8H, m). Elemental Analysis for C38H46N4O3S·0.3H2O Calcd. C, 70.84; H, 7.29; N, 8.70; Found. C, 70.62; H, 7.49; N, 8.91.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1422228; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, 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. Recommanded Product: (1-Methyl-1H-imidazol-4-yl)methanol

190b) 1 -Methyl-1 H-imidazole-4-carbal A solution of (1 -methyl-1 H-imidazol-4-yl)methanol (5 g, 44.6 mmol) in acetone (50 mL) was added manganese(IV) oxide (19.38 g, 223 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 60 C for 12 h. The solid was filtered and the liquid was concentrated to obtain the title compound 1 -methyl-1 H-imidazole-4- carbaldehyde (4.12 g, 34.4 mmol, 77 % yield) which was used in next step without further purification. LC-MS m/z 1 1 1 .2 (M+H)+, 0.49 min (ret. time).

The synthetic route of 17289-25-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89830-98-8, A common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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: A mixture of 9-(2-methyloxazol- 4-yl)-3,4,7,8-tetrahydro-[1 ,4]diazepino[7,1-a]isoquinoline-2,5-dione (140 mg, 0.45 mmol) in DCE (10 mL) was treated with POCI3 (84 mu, 0.91 mmol) and heated to 100 °C for 1 h. The mixture was then allowed to cool to RT, poured onto cold H20 and extracted with DCM. The org. phases were dried over Na2SO,, filtered and concentrated in vacuo. The brown residue obtained was taken up in DCE (5 mL) and 4-cyclopropyl-1H-imidazole (59 mg, 0.54 mmol) and pyridine (110 mu, 1.36 mmol) were then added. The mixture was heated to 100 DC for 1 h, and then allowed to cool to RT, poured onto H20 and extracted with DCM. The org. layers were then dried over Na2S04. filtered and concentrated in vacuo. Purification by SFC (column: 2-Ethylpyridine 5 muetaiota, 250 x 30 mm, 60A, Princeton; eluent: 10percent MeOH/C02 for 1 min, then from 10percent MeOH/C02 to 15percent MeOH/C02 in 6 min; then from 15percent MeOH/C02 to 50percent MeOH/C02 in 1 min; flow 100 mL/min; UV detection at 220 nm) afforded the title compound (42 mg) as beige powder. UPLC-MS: MS 400.2 (M+H+); UPLC rt 0.86 min. 1H NMR (400 MHz, CHLOROFORM- : delta ppm 0.61 – 0.82 (m, 2 H); 0.82 – 0.91 (mr 2 H); 1.78 – 1.96 (m, 1 H); 2.56 (s, 3 H); 3.16 (t, J=6.02 Hz, 2 H); 3.89 (t, J=6.15 Hz, 2 H); 4.37 (br. s., 2 H); 6.62 (s, 1 H); 7.19 (d, J=1.25 Hz, 1 H); 7.38 – 7.48 (m, 1 H); 7.63 – 7.70 (m, 2 H); 7.78 (dd, J=7.65, .13 Hz, 1 H); 7.89 (d, J=1.26 Hz, 1 H).

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; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; WO2014/30128; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-53-1, 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 68282-53-1 as follows.

COMPOUND 12.1. 53: NN-DIETHYL-4- {6-METHOXY-2- [4-METHYL-lH- IMIDAZOL-5-YL)METHYL]-7-NITRO-1,2,3,4-TETRAHYDROISOQUINOLIN-1- YLdBENZAMIDE; To a solution of INTERMEDIATE 9.2. 2 (1.16 g, 3.00 mmole) and 4-methyl-5- imidazolecarboxaldehyde (0.31 g, 2.8 mmole) in 1,2-dichloromethane (25 mL) was added sodium triacetoxyborohydride (1.65 g, 7.8 mmole) and the resulting solution was stirred at room temperature for 18 h. Sodium hydroxide (1M, 100 mL) was added and the mixture extracted with ethyl acetate (3 x 100 mL). The organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (ethyl acetate/10% methanol in chloroform, 2/8) to give COMPOUND 12.1. 53 (1.12 g, 78%) as a yellow amorphous solid. 1H NMR (500 MHz, CDC13) : 5 1.12, 1.23 (2 br s, 6H), 2.05 (s, 3H), 2.55 (m, 1H), 2.82 (dd, J3. 5,13 Hz, 1H), 3.02 (m, 1H), 3.12 (m, 1H), 3. 26 (br s, 2H), 3.30 (d, J 13.5 Hz, 1H), 3.54 (br s, 2H), 3.56 (d, J 13.5 Hz, 1H), 3.91 (s, 3H), 4.56 (s, 1H), 6.73 (br s, 2H), 6. 80 (s, 1H), 7.20 (s, 1H), 7.30 (m, 5H); 13C NMR (125 MHz, CDC13) : 8 10.76, 12.82, 14.13, 29.35, 39.39, 43.45, 46.11, 49.33, 56.46, 67.12, 113. 00, 126.13, 126.59, 127.03, 129.45, 129.50, 130.33, 133.05, 136.52, 137.67, 142.46, 144.01, 151.23, 171.07 ; (+) LRESIMS m/z 478 [M+H] +.

According to the analysis of related databases, 68282-53-1, the application of this compound in the production field has become more and more popular.

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

Reference of 496-46-8, 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 496-46-8 as follows.

Synthesis of cucurbit[n]urils in methanesulphonic acid using Diethoxymethane(Ethylal)Unsubstituted glycoluril (19.94 g) and methane sulphonic acid (neat, 82 mL) were placed in a reaction flask and heated to 80 C. Ethylal (35.21 mL) was added in drop-wise and the reaction mixture was then heated to 100 C (internal temp) for 18 hours. The reaction mixture was cooled and added to acetone (410 ml) to produce a brown powder which was analysed by1H NMR.Approximate Yields b1H NMR (% of recovered product) cucurbii[5]urii 8%, cucurbit[6]uri 42%, cucurbit[7]uril 43%, cucurbit[8]uril 7%, cucurbit[9]uril 0%, cucurbit[10]uril 0%, cucurbit[ 13uril 0%.Residual formaldehyde by HPLC method was 34 ppm.

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; DIEC, David; NOGUEIRA, Guilherme; GERARDUS DE ROOIJ, Johannes; (23 pag.)WO2018/115822; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, 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 4856-97-7, Product Details of 4856-97-7

To a solution of 1 (5.0 g, 34 mmol) in DCM was added MnO2(1.3 g, 6.8 mmol). The resulting solution was stirred at 40 C for 2 h and monitored by TLC. Aftercomplete conversion of starting material, reaction mixture was cooled to room temperature, filteredand concentrated in vacuo to obtain 2 as white solid in 85.0% yield. LC-MS m/z: 147.1 [M + H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1H-Benzoimidazol-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Wang, Shuxiang; Guan, Lihong; Zang, Jie; Xing, Kun; Zhang, Jian; Liu, Dan; Zhao, Linxiang; Molecules; vol. 24; 7; (2019);,
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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methyl-1H-imidazole-4-carbaldehyde

Synthesis of 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride To a suspension of 4-((1R,5S,9r)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride (100 mg, 0.32 mmol), 1-methyl-1H-imidazole-4-carboxaldehyde (70 mg, 0.64 mmol) and acetic acid (37 muL, 0.64 mmol) in dichloromethane (5 mL) was added sodium triacetoxyborohydride (203 mg, 0.96 mmol) at ambient temperature. After stirring for 16 hours, the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (*3). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica column chromatography, eluting with 2-10% methanol in dichloromethane to yield 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide (84 mg, 71% yield). To 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide (125 mg, 0.34 mmol) in ethyl acetate (10 mL) and dichloromethane (2 mL), was added 2M HCl in diethyl ether (0.17 mL, 0.34 mmol). The solvent was removed under reduced pressure. The resulting solid was triturated with diethyl ether and the liquors decanted. The solid was dried, dissolved in water and freeze-dried to yield 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride (83 mg, 60% yield). [M+H]+ 370.15. 1H NMR (400 MHz, D2O): 8.60 (d, 1H), 8.21 (s, 1H), 7.98 (s, 1H), 7.60 (d, 1H), 7.54 (s, 1H), 4.33 (s, 2H), 3.74 (s, 3H), 3.61 (d, 2H), 3.48 (d, 2H), 2.92 (s, 2H), 2.67 (s, 3H), 1.85-1.68 (m, 2H), 1.56-1.42 (m, 4H).

According to the analysis of related databases, 17289-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alkermes, Inc.; Wynn, Thomas Andrew; Alvarez, Juan C.; Moustakas, Demetri Theodore; Haeberlein, Markus; Pennington, Lewis D.; US2019/241524; (2019); A1;,
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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem