Tag: M.W=100-200

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. 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(1H-Imidazol-1-yl)acetonitrile

A mixture of potassium hydroxide (0.17 g, 3.1 mmol) in 3 ml of dimethylsulfoxide was purged with argon and cooled to 10C. A solution of 2-imidazol-1-ylacetonitrile (13, 0.15 g, 1.5 mmol) and carbon disulfide (0.2 g, 3.0mmol) in 2 ml of dimethylsulfoxide was then slowly added. The cooling bath was removed and the resulting orange mixture was stirred for 20 min at room temperature. A solution of (2-bromo-4,6-dichloroindan-1-yl) methanesulfonate(11, 0.35 g, 1.0 mmol) in 2 ml of dimethylsulfoxide was then added dropwise.The reaction mixture was stirred for 1 h at room temperature and then poured on water. The phases were separated, the aqueous phase was extracted with dichloromethane, the combined organic layer was washed with water and brine,dried over sodium sulfate and evaporated under reduced pressure. The remainder was purified by chromatography on silica gel, using ethyl acetate / heptane 1 : 1 as eluent system to deliver 2-(5,7-dichloro-4,8b-dihydro-3aH-indeno[1,2-d][1,3]dithiol-2-ylidene)-2-imidazol-1-yl-acetonitrile (5, 0.16 g, 0.44 mmol, 44%) as an inseparable 1.25 : 1 mixture of the E- and Z-isomer. 1H-NMR (400 MHz,CDCl3): delta = 3.20 – 3.28 (m, 1H), 3.31 – 3.51 (m, 2.6 H), 4.92 – 4.99 (m, 1H), 5.00- 5.07 (m, 0.4H), 5.35 (d, 0.6H, J = 3.7 Hz), 5.42 (d, 0.4H, J = 4.8 Hz), 6.98 (s,1H), 7.00 (s, 0.4H), 7.13 (bs, 1.6H), 7.17 (s, 0.4H), 7.31 (s, 1H), 7.38 (s, 1.6H),7.56 (s, 1H), 7.58 (s, 0.4H). LC-MS: Rt = 0.94 min; MS: m/z = 365 [M+1]+.

According to the analysis of related databases, 98873-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gagnepain, Julien; Jeanmart, Stephane; Bonvalot, Damien; Jacob, Olivier; Lamberth, Clemens; Synlett; vol. 30; 1; (2019); p. 59 – 62;,
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. 71759-89-2, name is 5-Iodo-1H-imidazole, A new synthetic method of this compound is introduced below., name: 5-Iodo-1H-imidazole

Step 1. 4-Iodo-l-methyl-lH-imidazole and 5-iodo-l-methyl-lH-imidazole (1205) [00394] Under an atmosphere of nitrogen at 0 C, a solution of 4-iodo-lH-imidazole (5.82 g, 30.00 mmol) in THF (50 mL) was treated with portionwise addition of sodium hydride (60% dispersion in mineral oil, 1.44 g, 36.00 mmol). After stirring for 30 min at 0 C, iodomethane was added (2.8 mL, 45.00 mmol) and the mixture was stirred for 1 h at 0 C. The reaction mixture was poured into water (100 mL) and was extracted with EtOAc (2 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 6.24 g (90%) of a -3 : 1 mixture of 4-iodo-l-methyl-lH-imidazole and 5- iodo-1 -methyl- lH-imidazole as a light yellow solid. MS (ESI) m/z 209 [M+H]+. Step 2. terf-Butyl 4-(l-methyl-lH-imidazol-4-yl)-3,6-dihydropyridine-l(2H)-carboxylate and terf-butyl 4-(l-methyl-lH-imidazol-5-yl)-3,6-dihydropyridine-l(2H)-carboxylate (1207) [00395] A -3 : 1 mixture of 4-iodo-l -methyl- lH-imidazole and 5-iodo-l-methyl-lH-imidazole (6.24 g, 30.00 mmol), fert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-5,6- dihydropyridine-l(2H)-carboxylate (1 1.1 g, 36.00 mmol), Pd(dppf)Cl2 CH2Cl2 (2.45 g, 3.00 mmol) and sodium carbonate (6.36 g, 60.00 mmol) in water (60 mL) and 1,4-dioxane (300 mL) was stirred under an atmosphere of nitrogen for 3 h at 80 C. After cooling to ambient temperature, the reaction mixture was poured into EtOAc (100 mL) and was washed with water (2 x 100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (eluting with a gradient of 1-5% DCM/MeOH) to afford 5 g (57%) of a -3 : 1 mixture of tert-butyl 4-(l-methyl-lH-imidazol-4-yl)- 3,6-dihydropyridine-l(2H)-carboxylate and tert-butyl 4-(l-methyl-lH-imidazol-5-yl)-3,6- dihydropyridine-l(2H)-carboxylate as a yellow oil. MS (ESI) m/z 264 [M+H]+.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); 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. 10394-38-4, name is 1-Methylbenzoimidazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Methylbenzoimidazol-5-amine

To 6-(4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-1-yl)pyridazine-3-carbonitrile (285.8 mg, 0.82 mmol)And 1-methyl-1H-benzo[d]imidazol-5-amine (149.1 mg, 1.01 mmol)Add in 1,4-dioxane (20mL) solutionPd(OAc) 2 (38.3 mg, 0.17 mmol),BINAP (98%, 106.0 mg, 0.17 mmol)Cs2CO3 (98%, 554.2 mg, 1.67 mmol). The resulting reaction system was stirred at 100 C overnight.After the reaction is completed, concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/40).The title compound was obtained as a beige solid (233.3mg, yield 62%).

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 10394-38-4.

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: 583-39-1, name is 2-Mercaptobenzimidazole, 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 583-39-1, Formula: C7H6N2S

General method: Benzimidazole-2-thiol (7) (1 eq) and pertinent acid chloride or acid anhydride (1.1 eq) were dissolved in pyridine (4.4 eq) under a nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature. After quenching with water (10-25 ml), ethyl acetate (30-45 ml) was added. The organic phase was extracted with 3M hydrochloric acid (3 ¡Á 25 ml), dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified as stated below.

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-Mercaptobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Braun, Stephan; Botzki, Alexander; Salmen, Sunnhild; Textor, Christian; Bernhardt, Guenther; Dove, Stefan; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4419 – 4429;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 106429-59-8, These common heterocyclic compound, 106429-59-8, name is 2-Oxo-2,3-dihydro-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.

Step 5: 5-((7-(5-(4-fluoro-2-(3-fluoro-3-methylbutyl)phenoxy)pyrimidin-4-yl)-2,7- diazaspiro[4.4]nonan-2-yl)methyl)-1H-benzo[d]200midazole-2(3H)-one and 5-((7-(5-(4- fluoro-2-(3-hydroxy-3-methylbutyl)phenoxy)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2- yl)methyl)-1H-benzo[d]imidazol-2(3H)-one (0953) To a solution of 2-(5-(4-fluoro-2-(3-fluoro-3-methylbutyl)phenoxy)pyrimidin-4- yl)-2,7-diazaspiro[4.4]nonane (50 mg, 0.12 mmmol) in anhydrous MeOH (2 mL) was added 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde (Intermediate 40, 22 mg, 0.14 mmol) and NaBH3CN (23 mg, 0.37 mmol) and the solution was stirred at 50 C for 16 h. LCMS showed the desired compound and that the 2-(5-(4-fluoro-2-(3-fluoro-3- methylbutyl)phenoxy)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonane was consumed. The mixture was purified by basic preparative RP-HPLC method D to give 5-((7-(5-(4-fluoro- 2-(3-fluoro-3-methylbutyl)phenoxy) pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2- yl)methyl)-1H-benzo[d]imidazol-2(3H)-one and 5-((7-(5-(4-fluoro-2-(3-hydroxy-3- methylbutyl)phenoxy) pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2-yl)methyl)-1H- benzo[d]imidazol-2(3H)-one, both products as a white solid. (0954) Example 35. LCMS method E: Rt = 0.618 min; (M+H)+ = 610.3.1H NMR (CD3OD): delta 8.23 (d, J = 5.6 Hz, 1H), 7.55 (s, 1H), 7.05-7.12 (m, 1H), 7.03 (s, 1H), 6.95- 7.01 (m, 2H), 6.85-6.95 (m, 1H), 6.70-6.75 (m, 1H), 3.63-3.83 (m, 4H), 3.61 (s, 2H), 2.72-2.78 (m, 2H), 2.60-2.70 (m, 2H), 2.48-2.59 (m, 2H), 1.78-1.98 (m, 6H), 1.33 (d, J = 21.6 Hz, 6H).19F NMR (CD3OD): delta -120.97, -140.72. (0955) Example 36. LCMS method C: Rt = 0.586 min; (M+H)+ = 547.3.1H NMR (CD3OD): delta 8.23 (s, 1H), 7.56 (s, 1H), 7.09 (dd, J = 9.22.8 Hz, 1H), 7.05 (s, 1H), 6.95- 7.00 (m, 2H), 6.85-6.95 (m, 1H), 6.72 (dd, J = 8.84.8 Hz, 1H), 3.69-3.83 (m, 4H), 3.65 (s, 2H), 2.49-2.75 (m, 6H), 1.90-2.00 (m, 2H), 1.84 (t, J = 6.8 Hz, 2H), 1.67-1.76 (m, 2H), 1.20 (s, 6H).19F NMR (MeOD): delta -121.18.

The synthetic route of 106429-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 75370-65-9, A common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H7N3O, 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.

To a solution of 29a (0.42g, 1.8 mmol) in THF (25 mL) was added CDI (2.1 mol eq, 0.61 g) and the mixture was heated at 70C overnight. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×20 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (pale yellow oil, 0.52 g, quantitative yield). The oil obtained (0.25g) was dissolved in DMF (15 mL) and the bicyclic amine la was added (0.8 mol eq, 0.09g), then the mixture obtained was heated at 100C overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (100% EtOAc) to obtain the product as a pale yellow solid (0.08g, 0.4 mmol, 27% Yield). 1HNMR (DMSO, 400 MHz) delta 1.33 (s, 3H), 1.36 (s, 3H), 4.28 (d, 2H, J=6), 5.28 (m, 1H), 6.64 (m, 2H), 6.87-6.93 (m, 2H), 7.46 (d, 1H, J=8), 7.78 (d, 1H), 8.41 (s, 1H), 9.99 (bs, 1H), 10.62 (bs, 1H). [M+1] 409.7 (C18H18F3N5O3 requires 409.36).

The synthetic route of 75370-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 36947-68-9, A common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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.

2-Isopropyl-1H-imidazole (600 mg, 5.45 mmol) was dissolved in 1,4-dioxane (6 mL)-2-methoxyethanol (6 mL), N-chlorosuccinimide (1.0 g, 7.51 mmol) was added, and the mixture was heated at room temperature for 30 min. N-chlorosuccinimide (450 mg, 3.38 mmol) was further added, and the mixture was stirred at room temperature for 1 hr. Water was added to the mixture, and the precipitated crystals were collected by suction filtration to give 4,5-dichloro-2-isopropyl-1H-imidazole (477 mg, 49%). ESIMS m/z: 179 (M + H)+; 1H NMR (270 MHz, CDCl3, delta): 1.32 (d, J = 7.2 Hz, 6H), 2.89-3.11 (m, 1H)

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; Kyowa Hakko Kirin Co., Ltd.; YAMAMOTO, Keisuke; TAMURA, Tomohiro; NAKAMURA, Rina; UENO, Kimihisa; HOSOE, Shintaro; EP2740730; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-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 39070-14-9, Recommanded Product: 39070-14-9

EXAMPLE 1 78.5 g of 1-methyl-2-nitroimidazole-5-methanol were suspended in 1.5 l of anhydrous tetrahydrofuran. After the addition of 102 g of p-chloroacetylaminophenol and 144 g of triphenylphosphane, the mixture was cooled to 10 C. and a solution of 111 g of diisopropyl azodicarboxylate in 750 ml of anhydrous tetrahydrofuran was added thereto with vigorous stirring within 20 minutes, the temperature being held at 10-12 C. by means of an ice-bath. The mixture was stored in a refrigerator overnight and the crystalline precipitate was filtered off under suction. Recrystallization from 2 l of acetonitrile, yielded 90.9 g (56.6%) of pure 2-chloro-alpha-(1-methyl-2-nitroimidazol-5-yl)-p-acetanisidide, m.p. 192-194 C. (decomposition).

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; Hoffmann-La Roche Inc.; US4515790; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, molecular formula is C5H6N2O2, 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. Formula: C5H6N2O2

To a solution of methyl 1H-imidazole-4-carboxylate (3.78 g, 30 mmol) in anhydrous THF (60 mL) was added sodium hydride (0.72 g, 30 mmol). The solution was then stirred at room temperature for 1 h before addition of 2-bromoacetonitrile (4.2 g, 35 mmol). The reaction was stirred at room temperature for 2 h before being concentrated in vacuo. The crude residue was purified on silica gel (petroleum ether:ethyl acetate=3:1) to afford the desired product (2.48 g, 50% yield). MS m/z: 166 [M+H+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17325-26-7, its application will become more common.

Reference:
Patent; Albrecht, Brian K.; Bellon, Steven F.; Gehling, Victor S.; Harmange, Jean-Christophe; LeBlanc, Yves; Liang, Jun; Magnuson, Steven; Tsui, Vicki; Zhang, Birong; US2015/65522; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 45676-04-8,Some common heterocyclic compound, 45676-04-8, name is 1-tert-Butylimidazole, molecular formula is C7H12N2, 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.

E) 1,1′-Di-tert-butyl-3,3′-methylenedimidazolium dibromide 12 0.008 mol of dibromomethane (1.391 g; 0.56 ml) and 5 ml of tetrahydrofuran are added to 0.016 mol of tertbutylimidazole 2 (2.000 g) in an ACE pressure tube. The reaction mixture is stirred at 80 C. for 20 hours. The solid which precipitates is washed repeatedly with a little tetrahydrofuran. A white solid 12 is obtained. Empirical formula: C15H26N4Br2 M=422.206 g/mol Yield: 1.449 g (42.9% of theory) Melting point: decomposition at >230 C. 1H (ppm, d6-DMSO, 300.13 MHz): delta=9.85 (s, 2H, NCN); 8.21 (s, 2H, NCCHN); 8.17 (s, 2H, NCHCN); 6.67 (s, 2H, NC2N); 1.62 (s, 18H, C3 group)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-tert-Butylimidazole, its application will become more common.

Reference:
Patent; BASF SE; TECHNISCHE UNIVERSITAET DRESDEN; US2009/326237; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem