Tag: M.W=100-200

Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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. COA of Formula: C8H6F2N2

A mixture of 2-difluoromethyl-lH-benzimidazole (2.22 g), 2,4-dichloro- 6-morpholinopyrimidine (2.81 g), potassium carbonate (6.63 g) and DMF (50 ml) was stirred under nitrogen and heated to 90C for 16 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate in methylene chloride as eluent. The solid so obtained was washed with a 1 : 1 mixture of isohexane and diethyl ether. There was thus obtained 4-chloro-2-(2-difiuoromethylbenzimidazol- 1 -yl)-6-morpholinopyrimidine (3.17 g); NMR Spectrum: (DMSOd6) 3.75 (s, 8eta), 7.09 (s, IH), 7.45-7.47 (m, IH), 7.50-7.54 (m, IH), 7.57-7.83 (t, IH), 7.87 (d, IH), 8.31 (d, IH); Mass Spectrum: M+H+ 366.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 705-09-9, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32072; (2008); 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 17289-20-2 as follows. Computed Properties of C6H8N2O2

EXAMPLE 8 Preparation of 1-methyl-5-hydroxymethylimidazole To a suspension of 1.4 g (0.01 mol) of 1-methyl-5-carbmethoxyimidazole in 5 ml of water is added 0.8 g (0.02 mol) of sodium hydroxide, and the mixture was heated to reflux for 2 hours. To the mixture is added 4 ml of ~37percent aqueous formaldehyde solution, and the resultant mixture is heated at 80-90 for 2 hours. After completion of the reaction, the solvent is stripped off and the residue is extracted with ethyl acetate. The ethyl acetate extract was concentrated to give 1-methyl-5-hydroxymethylimidazole as a solid, m.p. 112¡ã-114¡ã C.

According to the analysis of related databases, 17289-20-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Korea Institute of Science and Technology; US4292431; (1981); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 20075-26-7, A common heterocyclic compound, 20075-26-7, name is 1-(Methoxymethyl)-1H-imidazole, molecular formula is C5H8N2O, 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.

The title compound was prepared as follows. To a solution of 1-methoxymethyl- imidazole (216 mg, 1. 95 MMOL) in dry THF (20 mi) AT-78 C was added slowly a solution of t- butyllithium (2. 4 ml of 1. 7 M in THF). After 20 minutes, ZNCI2 (663 mg, 4. 86 MMOL) was added, the mixture was allowed to warm to room temperature and stirred for another 60 min. 1- 4-AMINO-2- [1- (6-CHLORO-PYRIDINE-3-SULFONYL)-PIPERIDIN-4-YLAMINO]-THIAZOL-5-YL}-1-PHENYL- methanone (Example F21 ; 200 mg, 0. 390 MMOL) AND TETRAKIS (TRIPHENYLPHOSPHINO) PALLADIUM (0) (Pd (Ph3P) 4 ; 12 mg, 0. 013 MMOL) were added and the mixture REFLUXED under argon for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with 0. 1 NAOH, dried over MGS04, filtered, and concentrated. The resultant solid was dissolved in a solution of 38% HCI (10 ML), ethanol (15 MI), and H20 (15 ml) and REFLUXED for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with sat. NaHCO3, dried over MGS04, filtered, concentrated, and purified via preparative HPLC. The concentrate from fractions was dissolved in EtOAc, washed with sat NAHC03, dried over MGS04, filtered, and concentrated. The resultant solid was placed in acetonitrile (30 ML), water (90 ML), and 38% HCI (0. 5 mL) and evaporated to give 26 mg of white powder in 11 % yield. ‘H NMR (CD30D) : 8 9. 13 (d1H, J=2. 5 Hz), 8. 44 (dd, 1H, J=2. 5, 8. 3 Hz), 8. 23 (d, 1H, J=8. 3 Hz), 7. 78 (s, 2H), 7. 50-7. 40 (m, 1H), 7. 08-6. 97 (m, 2H), 4. 02-3. 90 (m, 3H), 2. 98-2. 87 (m, 2H), 2. 37-2. 13 (m, 2H), 1. 96-1. 78 (m, 2H). ESIMS (MH+) : 546. Anal. Calcd for C23H2, F2N703S2 O 2. 4 HCI * 1. 0 H2O # 0. 5 EtOAc : C, 43. 19 ; H, 4. 26 ; N, 14. 10 ; S, 9. 23. Found : C, 42. 85 ; H, 4. 67 ; N, 14. 50 ; S, 9. 27.

The synthetic route of 20075-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2004/74283; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, 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 137049-00-4 as follows.

5. SYNTHESIS OF (-)-2,4-DICHLORO-7V-(1 ‘-(l-METHYL-li-iMiDAzoL-4-YLSULFONYL)-2,3-DIHYDRO [INDENE- 1 ,4 ‘-PIPERIDINE] -2-YL)BENZAMIDE, 7B; [00235] To a solution of 6b (440 mg, 1.07 mmol) and DIPEA (384 muL, 2.14 mmol) in CH2Cl2 (12 mL) was added 1 -methyl- lH-imidazole-4-sulfonyl chloride (194 mg, 1.07 mmol). The reaction was stirred for 18 h. To the reaction mixture was added hexanes (4 mL) and isolated the white ppt by vacuum filtration to afford 7b (501 mg, 92%); Eta-nmr (400 MHz, CDCl3) delta 7.53 (s, IH), 7.46-7.44 (m, 2H), 7.37 (d, J= 2.0 Hz, IH), 7.30-7.18 (m, 5H), 6.06 (d, J= 10.0 Hz, IH), 4.91 (dd, J= 9.0, 6.0 Hz, IH), 3.88-3.72 (m, 5H), 3.43 (dd, J= 17.0, 6.0 Hz, IH), 3.14 (d, J = 12.5, 5.0 Hz, IH), 3.03 (td, J= 12.0, 3.0 Hz, IH), 2.81 (d, J= 16.0 Hz, IH), 2.27-2.21 (m, IH), 1.94 (d, J= 13.5 Hz, IH), 1.81-1.71 (m, 2H), 1.49 (dd, J= 35.0, 6.5 Hz, IH); m/z 519.1.

According to the analysis of related databases, 137049-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; CONN, Jeffrey, P.; WILLIAMS, Richard; JONES, Carrie, K.; SHEFFLER, Douglas, J.; WO2010/102003; (2010); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3752-24-7,Some common heterocyclic compound, 3752-24-7, name is 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole, molecular formula is C7H10N2, 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 Intermediate 1 (2.1 g, 17 mmol) in DMF (6 mL) were added 2- (chloromethyl)-l,4-dimethylbenzene (2.6 g, 17 mmol) and potassium carbonate (4.8 g, 35 mmol). The mixture was stirred overnight at room temperature. Water (5 mL) was added and the mixture was stirred for another 10 minutes. The reaction mixture was poured into ethyl acetate/water and the layers were separated. The organic layer was washed three times with brine, then dried over magnesium sulphate and concentrated by evaporation in vacuo, to afford the title compound (1.2 g, 29%) as a pale yellow solid, deltapi (400 MHz, d6- DMSO) 7.40 (s, IH), 7.07-7.09 (m, IH), 7.00 (d, 77.6 Hz, IH), 6.57 (s, IH), 5.02 (s, 2H), 2.50-2.51 (m, 3H), 2.31-2.35 (m, 2H), 2.22 (s, 3H), 2.20 (s, 3H). LCMS (ES+) 241 (M+H)+, RT 1.46 minutes (method A).

The synthetic route of 3752-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; HEER, Jag Paul; JACKSON, Victoria Elizabeth; KROEPLIEN, Boris; LECOMTE, Fabien Claude; PORTER, John Robert; WO2015/86513; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1122-28-7, name is 4,5-Dicyanoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H2N4

Example 19 2-Bromo-4,5-dicyanoimidazole (21) STR67 To 1.18 g (10 mmol) 4,5-dicyanoimidazole and 25 ml 0.1M NaOH was added 1.8 ml Br2 (35 mmol). The mixture was stirred overnight at room temperature and then acidified with dilute HCl. The solid was filtered, rinsed with water and recrystallized from water to give 1.5 g of dicyanobromoimidazole 21 (yield 76.4%).: m.p. 147-149 C. (lit. 141-143 C.); Rf=0.65 (ethyl acetate_methanol=4:1); MS(EI): 198([M+2], 96%), 196 (?M+!, 100%),171 (28.5), 169 (29.2), 117 (27.4), 91 (19.0), 64 (20.6), 53 (22.4), 38 (18.8).

The synthetic route of 1122-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; McGill University; US5734041; (1998); A;,
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. 35445-32-0, name is Ethyl 1,4-dimethyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H12N2O2

[2758] To a stirred solution of compound 965 (680 mg) in 10 ml THF at -78¡ã C. was added dropwise 1.0M LAH in THF (5.0 ml). Reaction was stirred and allowed to warm to room temperature overnight. Cooled reaction mixture to 0¡ã C. then added 5 ml of H2O dropwise. Allowed reaction to warm to room temperature while stirring for 1 hr. Filtered through celite and rinsed with 20 ml THF/40 ml H2O. A clear filtrate obtained. Filtrate afforded compound 966.

According to the analysis of related databases, 35445-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US2004/122018; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 89830-98-8,Some common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

J-1 a (4.84 g; 44.8 mmol) in TH F (60 mL) was added dropwise to a suspension of NaH (1 .97 g; 49.2 mmol) in TH F (200 mL) at 0¡ãC under N2. The mixture was stirred at RT for 30 min and SEM-CI (9.9 mL; 55.9 mmol) in THF(20 mL) was added dropwise at 0¡ãC. The mixture was stirred at RT under N2 for 16 h. Water was added and the product was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude was purified by preparative LC (Irregular SiOH 20-45 [Jim , 150g Merck, Mobile phase Gradient from 50percent DCM, 50percent heptane to 100percent DCM). The fractions containing pure compound were combined and the solvent was removed under reduced pressure to give 6.6 g of J-1 b as a yellow oil (62percent).Mixture of 2 regioisomers : 70/30Minoritory regioisomer : 1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.64 (s, 1 H), 6.56 (s, 1 H), 5.34 (s, 1 H), 3.45 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.52-0.57 (m, 2H), -0.04 (s, 9H).Majoritory regioisomer :1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.56 (s, 1 H), 6.94 (s, 1 H), 5.20 (s, 1 H), 3.43 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.56-0.62 (m, 2H), -0.04 (s, 9H). BuLi (1.6M in hexane)(1 1 mL; 17.6 mmol) was added to a solution of J-1 b (3.5 g; 14.7 mmol) in THF (60 mL) at -50¡ãC. The mixture was stirred at the sametemperature for 30 min and DMF (1 .7 mL; 22 mmol) was added. The mixture was warmed slowly to RT in 1 h and NH2OH,HCI (970 mg; 29.4 mmol) was added and the mixture was stirred at RT for 16h. Water was added and the product was extracted with DCM (3 times), washed with brine, dried over MgS04 and the solvent was removed under reduced pressure to give 4.1 g (quantitative yield) of the mixture of isomers K-1 as yellow oil.HPLC Rt (min) = 5.30, 5.41 and 5.90 ; MS M+ (H+): 282 (method V2002V2002) K-1 ( 3.1 g; 1 1 mmol) was dissolved in DCM (18 mL) and pyridine (19 mL) at RT. The mixture was cooled to 0¡ãC and TFAA (4.6 mL; 33 mmol) was added. The mixture was stirred at RT for 24h. The solvent was removed under reduced pressure and the residue was dissolved in AcOEt. The organic layer was washed with water and brine, dried over MgS04, filtered and the solvent was removed under reduced pressure. The crude was purified by preparative LC (irregular SiOH 15-40??? 90g merck, mobile phase Heptane/DCM 30/70 to DCM 100percent) to give 2.14 g of intermediate J-1 (73percent) as a mixture of two isomers.HPLC Rt (min) = 6.51 ; MS M+ (H+): 264 (method V2002V2002)

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; BONFANTI, Jean-Francois; DOUBLET, Frederic Marc Maurice; EMBRECHTS, Werner; FORTIN, Jerome Michel Claude; MC GOWAN, David Craig; MULLER, Philippe; RABOISSON, Pierre Jean-Marie Bernard; WO2013/68438; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 15965-31-8, name is 5-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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. Computed Properties of C3H3ClN2

A mixture of 4-chloro-lH-imidazole (102 mg, 1.00 mmol), 1,2- difluoro-3-methoxy-5-nitrobenzene (200 mg, 1.00 mmol), and cesium carbonate (325 mg, 1 mmol) in acetonitrile (6 mL) was heated at 800C for 12 h. The reaction mixture was quenched with 1 N HCl. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (20 % EtOAc/hexane) to afford 4- chloro-l-(2-fluoro-6-methoxy-4-nitrophenyl)-lH-imidazole (60 mg, 22 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15965-31-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3314-30-5, These common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-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.

Example 3 3-(1H-benzimidazol-2-methylene)-5-(N-methylphenylaminosulfo)-2-indolone (Indo 3) 0.15 g (0.5 mmol) 5-(N-methylphenylaminosulfo)-2-indolone and 0.10 g (0.685 mmol) 1H-benzimidazol-2-formaldehyde were suspended in 6 mL anhydrous ethanol, followed by addition of 2 drops of piperidine. The mixture was heated and refluxed in an oil bath for 30 min. A large quantity of yellow solid was precipitated, filtered, and washed with anhydrous ethanol, to obtain 0.14 g pale yellow solid, with a yield of 65.1percent. Analytical result by NMR spectroscopy: 1H-NMR (DMSO-d6) delta (ppm): delta13.83 (s, 1H), 11.73 (s, 1H), 8.24 (s, 1H), 8.20 (s, 1H), 7.81 (b, 2H), 7.27-7.37 (m, 6H), 7.17 (s, 1H), 7.15 (s, 1H), 7.05 (d, 1H, J=8.4 Hz), 3.21 (s, 3H). ESI-MS m/z: 429 [M-H]+ (100). Analysis showed that, the pale yellow solid is 3-(1H-benzimidazol-2-methylene)-5-(N-methylphenylaminosulfo)-2-indolone, the structural formula of which is shown in Formula I, wherein R1 is N-methylphenylaminosulfo, and R2 is hydrogen.

The synthetic route of 3314-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUTE OF RADIATION MEDICINE, CHINA ACADEMY OF MILITARY MEDICAL SCIENCES PLA; Yang, Xiaoming; Wang, Lin; Li, Changyan; Zhan, Yiqun; Liu, Jing; Luo, Teng; Yan, Haiyan; Zhang, Shouguo; Li, Wei; Wen, Xiaoxue; Peng, Tao; Li, Lu; (18 pag.)US2016/151334; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem