Tag: M.W=100-200

Reference of 1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1,3-cyclohexanedione (561 mg, 5.0 mmol) and imidazole (340 mg, 5.0 mmol) in CH2C12 (50 ml) was added neat N-trifluoroacetyl imidazole (2.27 ml, 20 mmol). The reaction mixture was stirred at room temperature for 45min. The reaction was diluted with 4N aq. HCl and the layers were separated. The aqueous layer was extracted 2x CH2C12. The combined organics were washed with H20 and brine. The organics were dried over MgS04, filtered and concentrated. The crude product was used directly for the next step.

The chemical industry reduces the impact on the environment during synthesis 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GILEAD SCIENCES, INC.; BONDY, Steven S.; CANNIZZARO, Carina E.; CHOU, Chien-hung; HALCOMB, Randall L.; HU, Yunfeng Eric; LINK, John O.; LIU, Qi; SCHROEDER, Scott D.; TSE, Winston C.; ZHANG, Jennifer R.; WO2013/6738; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 60-56-0 as follows. Quality Control of 1-Methyl-1H-imidazole-2(3H)-thione

Dithiafulvalenyl compound 1 (0.2 mmol), mercapto-thiazole 2 (2 mmol, 10 equiv.), and I2 (0.6 mmol, 3 equiv., 152.4 mg) were dissolved in DMSO (3 mL). The reaction mixture was stirred at 25 C for 12 h under N2 atomsphere. Then quenched with a saturated solution of Na2S2O3 and stirred for half an hour, the solution was extracted with dichloromethane (CH2Cl2). The organic layer was separated, and dried over Na2SO4. Then the organic solvent was removed in vacuo to afford the respective thiadiazole-based dithiafulvalene (DTF) derivatives (3), which were purified by column chromatography (silica gel, PE / CH2Cl2) to afford pure substances.

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fu, Huimin; Zhao, Bangtun; Zhu, Weimin; Tetrahedron Letters; vol. 60; 2; (2019); p. 124 – 128;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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. Quality Control of 5-Bromo-1-methyl-1H-imidazole

To a flask containing 5-bromo-1-methyl-1H-imidazole (360 mg, 2.24 mmol) was added THF and the solution was cooled to 0 C. To this clear homogeneous solution was added isopropyl magnesium chloride-LiCl complex (1.3 M, 2.3 mL, 2.98 mmol) which resulted in a white suspension. The reaction mixture was stirred at 0 C. for 30 min, and a THF (2 mL) solution of N-methoxy-N,2,6-trimethylnicotinamide (522 mg, 2.69 mmol, Intermediate 40, step a) was introduced and the mixture was allowed to warm to room temperature for 3 hours and then heated to 50 C. for 20 hours. The contents were cooled to room temperature, poured into a saturated NH4Cl solution and extracted with EtOAc (4×50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography on silica gel (25-50% Acetonitrile-DCM increasing gradient to 5% MeOH-DCM) afforded the title compound as a pale yellowish solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-21-0, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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 39021-62-0, Product Details of 39021-62-0

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (3.0 g, 6.97 mmol, Intermediate 10: step d) was added THF (40 ml) and the solution was cooled to -70 C. n-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was added dropwise. After 2 minutes, 1-methyl-1H-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C. bath. After 35 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc:THF (10:2) 5*50 mL. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Chromatography on silica gel (30% acetone-DCM increasing to 5% MeOH) provided the title compound. 1H NMR (500 MHz, CDCl3) delta ppm 8.21 (s, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.60 (dd, J=8.6, 1.9 Hz, 1H), 7.50 (d, J=8.2 Hz, 2H), 7.39 (d, J=8.1 Hz, 2H), 7.33 (s, 1H), 6.65 (s, 1H), 6.04 (s, 1H), 4.34 (s, 2H), 4.07 (s, 3H), 3.55 (s, 3H). MS (ESI): mass calcd. for C23H19ClF3N3O2, 461.1, m/z found 462.1 [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; JANSSEN PHARMACEUTICA NV; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015/105372; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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. category: imidazoles-derivatives

Triphenylphosphine (47.64 g, 181.64 mmol) and diisopropyl azodicarboxylate (36.73 g, 181.64 mmol) were dissolved in tetrahydrofuran (120.00 mL) at 0 C under a nitrogen atmosphere, followed by sequential addition of compound 1 (10.00 g, 90.82 mmol) and n-propanol (10.91 g, 181.64 mmol). The mixture was warmed to 25 C and stirred for 12 hours under a nitrogen atmosphere. After completion of the reaction, dilute hydrochloric acid (1 M) was added to the mixture to adjust to pH = 1 and extracted with ethyl acetate (50 mL × 3). The aqueous phase was adjusted to pH = 13 with sodium hydroxide (1M) and extracted with ethyl acetate (50 mL × 4). The organic phases were combined, washed with saturated brine (50 mL 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography (petroleum ether: ethyl acetate = 20:1-5:1) to obtain the title compound BB-3H-2 ((12.00 g, pale-yellow oily liquid, yield: 27.60%). 1H NMR (400MHz,CDCl3) delta: 9.81 (s, 1H), 7.50 (s, 1H), 4.19 (t, J = 7.1 Hz, 2H), 2.49 (s, 3H), 1.98- 1.74 (m, 2H), 0.89 (t, J = 7.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 68282-53-1, its application will become more common.

Reference:
Patent; Medshine Discovery Inc.; LUO, Yunfu; BA, Yuyong; CHEN, Shuhui; (135 pag.)EP3567028; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 123470-47-3, 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. 123470-47-3, name is 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (0.075 mmol), 1,10-phenanthroline (0.15 mmol), 1,8-diiodonaphthalene 1a (0.5 mmol), 1H-benzo[d]imidazole-2-thiols or 2-thiouracils b (0.5 mmol) and base (1.0 mmol). The tube was placed under vacuum for twenty minutes and backfilled with N2, then DMF (2.0 mL) was added via syringe. The reaction mixture was stirred at 100 oC for 24 h. The reaction was monitored by TLC. When b consumed completely, the reaction was stopped and cooled to room temperature, EtOAc (40 mL) was added and the mixture was washed with brine (20 mL × 3). The organic phase was dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel using petrol/EtOAc (3:1, v:v) as eluent to give c.

The chemical industry reduces the impact on the environment during synthesis 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Cui, Jichun; Zhang, Tongxin; Wang, Jianhua; Liu, Dezhi; Wang, Jiaqian; Liu, Jie; Shen, Guodong; Synthetic Communications; vol. 49; 8; (2019); p. 1076 – 1082;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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.

Scheme A, step a [4S-[4alpha, 7alpha(R*), 12bbeta]]-7-[(5-(4-methoxybenzylthio)-5-oxo-1-(carbo-t-butyloxy)-4,5-dihydrocyclopentimidazole)methylamino]-3,4,6,7,8,12b-hexahydro-6-oxo-1H-[1,4]-oxazino[3,4-a][2]benzazepine Dissolve 4,5-imidazoledicarboxylic acid (31.2 g, 0.2 mol) in ethanol (500 mL) and treat with concentrated sulfuric acid (0.5 mL). Heat to 60 C. for 16 hours, cool and reduce the solvent by 50% in vacuo. Dilute with ethyl ether (500 mL), wash with saturated sodium hydrogen carbonate, then brine. Dry (MgSO4) and evaporate the solvent in vacuo to give 4,5-(dicarboethoxy)imidazole.

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merrell Dow Pharmaceuticals, Inc.; US5420271; (1995); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 128293-62-9, name is Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate, 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 128293-62-9, HPLC of Formula: C7H11N3O2

The compound 7 was dissolved in methanol (94.4 ml), mixed with 10 % Pd/C (1.18 g) and stirred for four hours under hydrogen atmosphere. 10% Pd/C was removed from the reaction system with cerite filtration, so that the solvent was distilled out under a reduced pressure. Dimethylformamide (10 ml) was added to the residue and distilled out again under a reduced pressure. The residue was dissolved in dimethylformamide (10 mL) again, and mixed with the compound 8 (5. 9 g, 23.6mmol) (Baird, E. E. ; Dervan, P. B. J. Org. Chem. 1996, 118, 6141-6146), EDC (9.05 g, 47.2 mmol) and dimethylaminopyridine (288 mg, 2. 36 mmol), and stirred for 12 hours at a room temperature. Re-precipitation treatment with chloroform and ethyl acetate gave the compound 9 as white powder (5.9 g, 63%). 1HNMR(DMSO-d6) delta 1.28-1.30 (3H, t, J = 7.1 Hz), 3.85(3H, s), 3.93(3H, s), 3.98(3H, s), 4.25-4.29 (2H, dd, J = 7.1 Hz), 7.03(1H, d, J = 0.7 Hz), 7.22(1H, d, J = 2.0 Hz), 7.38(1H, s), 7.38(1H, s), 7.66(1H, s), 10.35(1H, s), 10.74(1H, s) ; 13CNMR(DMSO-d6) delta 14.3, 35.3, 35.7, 36.5, 60.8, 106.4, 115.6, 119.8, 121.6, 122.2, 126.5, 127.2, 131.0, 138.0, 139.0, 156.3, 158.7, 158.9: Anal. Calcd. for C18H12N4O3·H2O: C, 53.22; H, 4.89; N, 22.57. Found: C, 50.88; H,4.88; N,23.13.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Japan Science and Technology Agency; EP1719777; (2006); 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

General procedure: Benzimidazole 1 (1mmol) was added to the mixture of AlCl3 or AlBr3 (5.0 mmol) in benzene (3 mL). The reactionmixture was stirred at room temperature for the time as indicated in Table 1. The mixture wasquenched with ice water (50 mL), extracted and worked-up as described above.

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 3012-80-4.

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 25676-75-9, The chemical industry reduces the impact on the environment during synthesis 25676-75-9, name is 4-Bromo-1-methylimidazole, I believe this compound will play a more active role in future production and life.

Borylation: A flask is charged with Int 39 (458 mg, 1 mmol, 1 eq.), E^pim (381 mg, 1.5 mmol, 1.5 eq.), dioxane previously degassed with N2 (5 mL), potassium acetate (295 mg, 3 mmol, 3 eq.) and Pd(dppf)Cl2-DCM (82 mg, 0.10 mmol, 0.1 eq.). The mixture is stirred to 100 C overnight, concentrated in vacuo. The residue is diluted in DCM and water. The organic layer is separated and concentrated in vacuo, purified by flash chromatography on silica gel (eluting with DCM/MeOH 100/0 to 95/5) to afford the expected boronic ester and boronic acid mixture.LCMS: MW (calcd): 505.3; m/z MW (obsd): 506.3 (M+H).LCMS: MW (calcd): 423.1 ; m/z MW (obsd): 424.1 (M+H).; Suzuki coupling: To a stirred solution of boronic ester and boronic acid mixture (51 mg, 0.10 mmol, 1 eq.) and 4-bromo-l -methyl-imidazole (CAS 25676-75-9; 10 pL, 0.10 mmol, 1 eq.) in dioxane (2 mL) is added CS2CO3 (65 mg, 0.20 mmol, 2 eq.), Pd(PPh3)4 (12 mg, 0.01 mmol, 0.1 eq.) in water (0.5 mL). The mixture is heated to 90 C for 1 h then concentrated in vacuo. The residue is diluted in DCM and water. The organic layer is separated and concentrated in vacuo, purified by flash chromatography on Biotage SNAP KP-NH cartridge (eluting with DCM/MeOH 100/0 to 98/2) to afford the expected compound.

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, 4-Bromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; ALVEY, Luke, Jonathan; ANNOOT, Denis, Maurice; BONNATERRE, Florence, Marie-Emilie; BUCHER, Denis; DUTHION, Beranger; JARY, Helene; PEIXOTO, Christophe; TEMAL-LAIB, Taoues; TIRERA, Amynata; (340 pag.)WO2019/105886; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem