Tag: M.W=100-200

Reference of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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 stirred solution of 2-chloro-3-methoxy-5-nitropyridine (2 g, 10.60 mmol) in DMSO (30 mL) under an argon atmosphere were added potassium carbonate (6.70 g, 48.61 mmol) and 4-(trifluoromethyl)-1H-imidazole (1.7 g, 12.76 mmol) at room temperature. The reaction mixture was stirred at 50 oC for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL). The obtained solid was filtered and dried in vacuo to afford 3-methoxy-5-nitro-2-(4-(trifluoromethyl)-1H- imidazol-1-yl) pyridine (1.4 g, 46%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.97 (s, 1H), 8.65 (s, 1H), 8.45 (s, 1H), 8.44 (s, 1H), 4.11 (s, 3H); LCMS: 288.8 (M+1); (column; X-Select CSH C-18 (50 ¡Á 3.0 mm, 3.5 mum); RT 3.46 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH/ CH2Cl2 (Rf: 0.4).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethyl)-1H-imidazole, its application will become more common.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-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.

To a solution of OI-14a (4 g, 36.36 mmol, 1.0 eq) in chloroform (40 mL) was added NBS (7.12 g, 40 mmol, 1.1 eq). The mixture was stirred at 70 C. for 3 h. Then the mixture was cooled to room temperature and diluted with a saturated aqueous solution of Na2CO3 (50 mL) and DCM (100 mL). The organic layer washed with brine and water, dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give OI-14b (333 mg, 4.8%).

The synthetic route of 17289-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Foresee Pharmaceuticals Co., Ltd.; YANG, Wenjin; CHANG, Kai-Wei; LIU, Suying; TSAI, Cheng-Han; (98 pag.)US2019/352288; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 20034-02-0, name is (6-Methyl-1H-benzo[d]imidazol-2-yl)methanol, molecular formula is C9H10N2O, 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. Application In Synthesis of (6-Methyl-1H-benzo[d]imidazol-2-yl)methanol

N-Methyl-2-methanol-5-methylbenzimidazole 48 was prepared according to using the procedure by Harisha et al. [28]. A solution of 5-methyl-(1H-benzimidazole-2-yl)-methanol 25 (1.62 g, 0.01 mol), and sodium hydroxide (0.40 g, 0.01 mol) were stirred in dry acetone (30 mL) was stirred for 30 min. Then, iodomethane (1.41 g, 0.01 mol) was added to the mixture and the mixture was stirred for 24 h. The reaction mixture was concentrated to a quarter and then poured into ice-cold water. The solid was filtered and washed with 50% HCl to neutralize the excess potassium carbonate. Then, wash the solid with cold water (100 mL) and then aqueous ethanol. The product was purified by column chromatography (9:1 chloroform/ethanol) to give the desired product (FAS37) as a brown powder Yield 46%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20034-02-0, its application will become more common.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
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Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1, 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 33543-78-1 as follows.

Compound 52 was alkylated in sequence with ethyl bromoacetate, isopentyl iodide, and iodomethane to give compound 55. Hydrolysis of compound 55, followed by a treatment with TMS-Eto-acetylene, gave the cyclic anhydride 57. Reaction of compound 57 with diethyl malonate gave compound 58, which coupled with compound 11 to yield the compound 215.

According to the analysis of related databases, 33543-78-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERMUNE, INC.; US2009/257979; (2009); 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. 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

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;,
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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

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

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. 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