Month: January 2021

Synthetic Route of 71759-89-2,Some common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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: Method B: In a20 mL microwave Biotage tube, a 1M Na2CO3 aqueous solution(5 mL) purged with argon were introduced into a mixture purged with argon of 4-iodo-1H-imidazole (1a) (0.194 g, 1.0 mmol), a boronicacid 2 (1.6 mmol) and Pd(PPh3)4 (0.80 g, 0.05 mmol) in DMF (15 mL). The mixture washeated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3j and 3p-3u in yields ranging from 30 to 95%. Time and temperaturereactions were collected in Table 1.

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

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 17325-26-7

Step 1: To a stirred mixture of 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole (500 mg, 2.2 mmol) from Example36 and methyl 4-imidazole carboxylate (400 mg, 3.3 mmol) in DMF (15 mL) was added K2CO3 (0.9 g, 6.5 mmol).After the mixture was stirred for 3 h at rt, it was partitioned between EtOAc (100 mL) and water (50 mL). The EtOAclayer was separated and washed with water (50 mL) and brine (50 mL), then dried over Na2SO4, filtered, and concentratedunder reduced pressure. The residue was purified by silica gel flash chromatography eluting with 2% MeOH in CH2Cl2to afford methyl 1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-1H-imidazole-4-carboxylate (130 mg, 19%) as a whitesolid. The regiochemistry of the alkylation was determined by 2-dimensional nuclear Overhauser effect (NOE) experiment.1H NMR (300 MHz, DMSO-d6) delta 8.01 (d, J = 0.9 Hz, 1H), 7.98 (d, J = 1.1 Hz, 1H), 7.93 (d, J = 0.9 Hz, 1H), 7.84 (d, J =8.3 Hz, 1H), 7.43 (dd, J = 1.7, 8.3 Hz, 1H), 5.35 (s, 2H), 3.72 (s, 3H), 2.78 (s, 3H). LCMS (ESI) m/z 322 (M+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; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 760212-58-6, These common heterocyclic compound, 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, 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.

Synthesis Example 15: Synthesis of Compound A82 (0371) Pd(dba)3 (0.03 eq), (t-Bu)3P (0.06 eq), and toluene (based on a reagent (0.1 M 1 eq)) were added to a flask containing Int C-2 (1 eq) and R?-4 (1.2 eq) to form a mixed solution, and then, the mixed solution was stirred under reflux for 5 hours. After the reaction solution was cooled to room temperature, an extraction process was performed thereon using MC, followed by a washing process performed thereon using distilled water. Then, the resulting product obtained from the washing process was subjected to a drying process using MgSO4 and a vacuum distillation process. The residue obtained therefrom was purified by column chromatography, thereby completing the preparation of Compound A82 (yield: 74.9%). (0372) HRMS for C37H23N3O [M]+: calculated: 525.61, found: 524. (0373) Elemental Analysis for C37H23N3O calculated: C, 84.55; H, 4.41; N, 7.99; O, 3.04

The synthetic route of 760212-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Display Co., Ltd.; Lee, Jungsub; (107 pag.)US2017/271596; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, The chemical industry reduces the impact on the environment during synthesis 7189-69-7, name is 1,1′-Sulfonyldiimidazole, I believe this compound will play a more active role in future production and life.

Zn(NO3)26H2O (75 mg, 0.25 mmol), sdi (10 mg, 0.05 mmol) andmalonic acid (52 mg, 0.05 mmol) were mixed in 5 mL of methanol.The pH of the solution was adjusted to 4.0 by the addition of HNO3solution. The mixture was stirred for 30 min at room temperatureand filtered into a glass tube. Colorless crystals of 1 were obtainedin 5 days and collected by filtration, washed with water, and thendried in air. 85% yield (based on sdi). Anal. calcd (%): C, 23.87; H,2.32; N, 23.20. Found (%): C, 23.95; H, 2.13; N, 23.11. IR (KBr, cm1):3427 (m), 3111 (m), 3010 (m),1652 (m),1551 (m),1453 (m),1384 (s),1325 (m), 1207 (m), 1167 (s), 1070 (m), 931 (m), 830 (m), 758 (m),633 (s), 614 (s), 573 (m).

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, 1,1′-Sulfonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Kang; Hu, Hanbin; Sun, Jing; Zhang, Yiheng; Han, Jishu; Wang, Lei; Journal of Molecular Structure; vol. 1134; (2017); p. 174 – 179;,
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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., Safety of 1H-Imidazole

General procedure: A 10-mL vial was charged with aryl halide (0.5 mmol), Cs2CO3 (1 mmol), Cu2O (0.05 mmol), N-containing heterocycles (0.75 mmol), DMF (1 mL), and a magnetic stir bar. The mixture was stirred at 120 C (130 C for entry 19). The reaction mixture was held at this temperature for 12 h (24 h for entry 18, 20, 21, and 25). After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 10 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether as the eluent) to provide the target products 3a-3t.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xiaochuang; Wang, Meiji; Xie, Jianwei; Synthetic Communications; vol. 47; 19; (2017); p. 1797 – 1803;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference 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.

To a solution of 1-(2-(3-cyclopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-4- fluorophenyl)-3-(piperidin-3-yl)-1H-pyrrolo[2,3-c]pyridine (4 mg, 9.6 mumol) in 1 mL anhydrous MeOH was added pyridine (3.8 mg, 48.02 mumol), 2-oxo-2,3-dihydro-1H- benzo[d]imidazole-5-carbaldehyde (2.3 mg, 14.41mumol) and NaBH3CN (3 mg, 48.02 mumol) and the mixture was stirred at 50 oC for 16 h under N2. The solvent was removed under reduced pressure and the resulting residue was purified by preparative HPLC method E followed by lyophilization to give 5-((3-(1-(2-(3-cyclopropyl-5-methyl-4H- 1,2,4-triazol-4-yl)-4-fluorophenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl)piperidin-1-yl)methyl)- 1H-benzo[d]imidazol-2(3H)-one as white solid. Yield: 1.60 mg (30%); LCMS method D: tR: 1.517 min; (M+H)+ = 563.2.1H NMR (CD3OD): delta ppm 8.59 (d, J = 3.2 Hz, 1H), 8.16-8.18 (m, 1H), 7.92-7.96 (m, 1H), 7.60-7.71 (m, 3H), 7.05 (s, 1H), 6.99-7.00 (m, 2H), 6.90 (d, J = 9.2 Hz, 1H), 3.60 (s, 2H), 2.88-3.08 (m, 3H).1.93-2.15 (m, 6H), 1.74- 1.75 (m, 2H).1.34-1.40 (m, 2.5H), 0.86-0.95 (m, 2.5H).19F NMR (CD3OD): delta ppm – 110.97.

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.; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen D.; SINGH, Suresh B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; (285 pag.)WO2018/53267; (2018); A1;,
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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, A new synthetic method of this compound is introduced below., SDS of cas: 1615-14-1

Example 24 A solution of 1,1′-(azodicarbonyl)dipiperidine (378 mg, 1.5 mmol) in methylene chloride (5 ml) was added dropwise to a suspension of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (160 mg, 0.5 mmol), tributylphosphine (303 mg, 1.5 mmol) and 2-(imidazol-1-yl)ethanol (67 mg, 0.6 mmol), (J. Med. Chem. 1993, 25, 4052-4060), in methylene chloride (8 ml) and the mixture was stirred for 3 hours at ambient temperature. Acetic acid (60 mg, 1 mmol) was added and the solvent was removed by evaporation. The solid residue was adsorbed on silica and purified by column chromatography eluding with methylene chloride/methanol (9/1 followed by 8/2). The resulting white solid was dissolved in methylene chloride/methanol and a solution of 5M hydrochloric acid in isopropanol was added. The solvent was removed by evaporation and the solid was triturated with ether, filtered, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline hydrochloride (1 80 mg, 74%). 1 H NMR Spectrum: (DMSOd6) 4.01(s, 3H); 4.62(t, 2H); 4.76(t, 2H); 7.44(dd, 1H); 7.48(s, 1H); 7.59(t, 1H); 7.66(dd, 1H); 7.72(s, 1H); 7.84(s, 1H); 8.41(s, 1H); 8.78(s, 1H); 9.22(s, 1H) MS – ESI: 414 [MH]+ Elemental Analysis: Found C 48.3 H 4.1 N 14.0 C20 H17 N5 O2 ClF 0.4H2 O 2HCl Requires C 48.6 H 4.0 N 14.2%

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; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 693-98-1, 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 693-98-1 as follows.

Step 3aIodine (18.5 g, 73.1 mmol) was dissolved in 90 mL of chloroform. 2-Methylimidazole (3.0 g, 36.5 mmol) in 90 mL of 2M NaOH solution was added slowly.The cloudy mixture cleared to two phases by 2.5 h.The layers were separated and acetic acid (10.5 mL, 183 mmol) was added to the organic layer to neutralize the reaction (to pH~5-6).A solid appeared which was filtered off and recrystallized from warm acetonitrile to afford 8.5 g (69percent) of 4,5-diiodo-2-methyl-1H-imidazole. (M+H)+=334.

According to the analysis of related databases, 693-98-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5805-57-2, A common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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.

A mixture of 6,9-dichloro-2-methoyl-anzacridine (278 mg,1 mmol) and benzimidazoles (220 mg, 1 mmol) was heated in phenolunder 120 C for 2 h with nitrogen protection. Then the mixturewas poured into ethyl acetate to give yellow precipitates,which were purified by washing with ethyl acetate twice. 4.1.2.1. 6-Chloro-2methyl-9-((1H-benzo[d]imidazol-2-yl)methyl)-azaacridine (9). Yield 73%; mp: 289-291 C; 1H NMR (400 MHz,DMSO-d6) d 8.51-8.48 (d, J = 14.4 Hz 1H), 8.37 (s, 1H), 8.13-8.11(d, 1H), 7.92 (s, 1H), 7.47-7.42 (m, 3H), 7.22-7.20 (d, J = 8.8 Hz,1H), 7.12-7.10 (m, 2H), 3.81 (s, 3H). 13C NMR (101 MHz, DMSOd6)d 157.82, 153.67, 147.62, 146.32, 143.49, 140.36, 140.33, 140.28, 133.72, 127.24, 126.19, 125.45, 123.24, 118.35, 115.08,53.37, 44.72. HRMS (ESI): [M+H]+ 390.1043; found 390.1115.

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:
Article; Li, Dan; Yuan, Zigao; Chen, Shaopeng; Zhang, Cunlong; Song, Lu; Gao, Chunmei; Chen, Yuzong; Tan, Chunyan; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3437 – 3446;,
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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-(Trifluoromethyl)-1H-imidazole

EXAMPLE 1 2-(2,4-Dichlorophenyl)-1-(1,2,4-triazol-1-yl)-3-(5-trifluoromethylimidazol-1-yl)-propan-2-ol A mixture of 4-trifluoromethylimidazole (0.7 g, 5 mmole), 2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-oxirane mesylate salt (1.88 g, 5 mmole) and anhydrous potassium carbonate (2.0 g, 14 mmole) in dry N,N-dimethylformamide (20 ml) was heated at 75-80 C. for 18 hours. The solvent was evaporated under vacuum and the residue was partitioned between water (20 ml) and methylene chloride (50 ml). The aqueous layer was separated and extracted twice with methylene chloride (30 ml). The organic layers were combined, dried over magnesium sulphate and evaporated to yield the crude product containing the 4- and 5-trifluoromethyl-imidazolyl isomers. The residue was chromatographed on silica eluding with a mixture of hexane, isopropyl alcohol and concentrated ammonium hydroxide (80:20:1.5); fractions containing the minor component were evaporated and the product recrystallized from a mixture of acetone and water to give the desired title compound (0.02 g, 1%), m.p. 190-192 C. C14 H12 Cl2 F3 N5 O requires C, 44.3; H, 3.0; N, 17.2%. Found: C, 44.5; H, 3.1; N, 17.3%.

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; Pfizer Inc.; US4554286; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem