Tag: M.W=200-300

Related Products of 71759-88-1,Some common heterocyclic compound, 71759-88-1, name is 5-Iodo-1-methyl-1H-imidazole, molecular formula is C4H5IN2, 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 64 3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(1-methyl-1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine A solution of 5-iodo-1-methyl-1H-imidazole (0.0217 g, 0.104 mmol), 3-[(S)-1-(2-chloro-3-fluoro-6-methoxy-phenyl)-ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.030 g, 0.070 mmol), potassium carbonate (0.0289 g, 0.209 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, dichloromethane (2.84 mg, 0.00348 mmol) in previously degassed 4:1 dioxane:water (1.50 mL) was evacuated and charged with N2 (2*) and heated under microwave conditions [Biotage, 100 C., 30 min, high absorption]. The reaction mixture was partitioned between EtOAc and H2O and separated. The aqueous was back extracted with EtOAc (3*) and the combined organic fractions were dried over Na2SO4, filtered and concentrated in vacuo resulting in a crude brown oil. The crude was purified by chromatography on silica gel [ISCO Combiflash, 12 g cartridge, eluting with 100% DCM-8% MeOH in DCM]. This resulted in the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD): delta=1.82 (d, J=7.3 Hz, 3H), 3.51 (s, 3H), 3.66 (br. s., 3H), 5.12 (q, J=7.1 Hz, 1H), 6.90 (dd, J=4.2, 9.0 Hz, 1H), 6.95 (s, 1H), 7.08 (dd, J=8.8, 8.8 Hz, 1H), 7.41 (d, J=1.0 Hz, 1H), 7.51 (s, 1H), 7.69 (s, 1H), 8.17 (d, J=2.0 Hz, 1H). MS (ES+): m/z 385.11, 387.07 (76/24) [MH+]. HPLC: tR=2.87 min (polar-5 min, ZQ3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Iodo-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; OSI Pharmaceuticals, LLC; US2011/281888; (2011); 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. 1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1243204-92-3

Example B3 a) Preparation of compound 4 A mixture of intermediate 1 (443 mg, 2.08 mmol), 4-fluorobenzoic acid hydrazide (320 mg, 2.08 mmol) and K2CO3 (143 mg, 1.04 mmol) in n-BuOH (15 ml) was heated in the microwave at 120 0C for 12 h. The solvent was removed under reduced pressure and the resulting residue partitioned between EtOAc/H2O. The phases were separated. The aq. phase was extracted with EtOAc, and the combined organic extracts were washed with brine and dried (MgSO^. Filtration and concentration under reduced pressure gave the crude product which was purified by column chromatography over silica gel (eluent: 100:0 to 90: 10 DCM/MeOH, gradient elution). The product fractions were collected and evaporated to yield 450 mg of compound 4 (62.0 %).

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 1243204-92-3.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; WU, Tongfei; GIJSEN, Henricus, Jacobus, Maria; ROMBOUTS, Frederik, Jan, Rita; BISCHOFF, Francois, Paul; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; DE CLEYN, Michel, Anna, Jozef; PIETERS, Serge, Maria, Aloysius; MINNE, Garrett, Berlond; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; WO2011/6903; (2011); 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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 144689-93-0

Example 6:; (5-MethyI-2-oxo-l,3-dioxol-4-yI)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2- (2H-tetrazoI-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate (olmesartan medoxomil) (Ie); Step I: 5-(2-Hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(N-(2-trimethylsilylethoxymethyl) tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-ethylcarboxylate (Vd); 2-Propyl-5-[(l-hydroxy-l-methyl)ethyl]-3H-imidazole-4-ethylcarboxylate (0.808 g, 0.0033675 mol) was added to the two isomers (IVb) (1.5 g, 0.0033675 mol) and K2CO3 (0.558 g, 0.0040382 mol) in anhydrous DMF (10 mL) under N2 atmosphere. The mixture was stirred at room temperature for 17 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The mixture was partitioned between water and AcOEt. The organic layer was washed with water (3 times), dried over Na2SO4 and concentrated under reduced pressure to give a residue (1.8 g) that was purified by flash chromatography on silica (cyclohexane/AcOEt 6:4) to give the isomer (Vd1) (0.499 g) and the isomer (Vd2) (0.206 g) as oils. Yield: 35%. (Vd1) (isomer with lower elution time):1H-NMR (400 MHz, CDCl3, delta): -0.03 (s, 9H, Me3Si), 0.92 (t, J=8.2Hz, 2H, SiCH2CH2O), 0.96 (t, J=7.2Hz, 3H, CH2CH2CH3), 1.18 (t, J=7.2etaz, 3H, OCH2CHi), 1.64 (s, 6eta, CMe2), 1.67-1.76 (m, 2H5 CH2CH2CH3), 2.66 (t, J=7.6Hz, 2H, CH2CH2CH3), 3.66 (t, J=8.2Hz, 2H, SiCH2CH2O), 4.22 (q, J=7.2etaz, 2H, OCH2CH3), 5.44 (s, 2H, ArCH2N), 5.78 (s, 2H, OCH2N), 6.84-6.86 (m, 2H) 7.14-7.16 (m, 2H) 7.41-7.43 (m, IH) 7.46-7.56 (m, 2H) 7.84- 7.86 (m, IH) (aromatic protons).(Vd2) (isomer with higher elution time): 1H-NMR (400 MHz, CDCl3, delta): -0.10 (s, 9H, Me3Si), 0.70 (t, J=8.4Hz, 2H, SiCH2CH2O), 0.92 (t, J=7.4Hz, 3H, CH2CH2CH5), 1.13 (t, J=7.0etaz, .3eta, OCH2CH3), 1.60 (s, 6eta, CMe2), 1.62-1.71 (m, 2H, CH2CH2CH3), 2.58 (t, J=7.8Hz, 2H, CH2CH2CH3), 3.39 (t, J=8.4Hz, 2H, SiCH2CH2O), 4.17 (q, J=7.2etaz, 2H, OCH2CH3), 5.05 (s, 2H, ArCH2N), 5.38 (s, 2H, OCH2N), 6.81-6.83 (m, 2H) 7.05-7.07 (m, 2H) 7.49-7.52 (m, 2H) 7.55-7.57 (m, IH) 7.61- 7.65 (m, IH) (aromatic protons).

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; S.I.M.S. S.r.l. – SOCIETA ITALIANA MEDICINALI SCANDICCI; WO2008/12852; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 621-72-7, 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. 621-72-7, name is 2-Benzyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Metallic Na (76 mg,3.3 mmol) was added to t-BuOH (30 ml), and the mixturewas heated under reflux until effervescence ceased. Thenazole 3b-d or 6b,d,e (3 mmol) and 3,5-dibromo-1-(1,1-dioxidothietan-3-yl)-1H-1,2,4-triazole (1) (0.99 g, 3 mmol)were added. The reaction mixture was heated under refluxfor 2 h (for compounds 4b-d, 7d,e) or 3 h (for compound7b). The solvent was evaporated under reduced pressure,and H2O (15 ml) was added to the residue. The precipitatewas filtered off, dried at 60C, and recrystallized from asuitable solvent.

The synthetic route of 2-Benzyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Makarova, Nadezhda N.; Klen, Elena E.; Khaliullin, Ferkat ?.; Chemistry of Heterocyclic Compounds; vol. 55; 9; (2019); p. 823 – 826; Khim. Geterotsikl. Soedin.; vol. 55; 9; (2019); p. 823 – 826,4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C12H11N3O

3-Methoxy-4-(4-methyl-lH-imidazol-l-yl)benzonitrile (100 mg, 0.469 mmol) was placed in a reaction vessel, and a 5 M aqueous sodium hydroxide solution (1 mL) and methanol (2 mL) were successively added to the vessel. The resultant mixture was stirred at room temperature for 2 hours, and then further stirred at 65C for 5 hours. The resultant reaction mixture was concentrated under a reduced pressure, and a 2 M aqueous hydrochloric acid solution (4 mL) and water (4 mL) were successively added to the concentrate. The solids collected by filtration were dried under a reduced pressure to obtain 98 mg of a title compound. Yield: 78%.

The synthetic route of 1243204-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management CO., LTD.; YOSHIKAWA, Seiji; KAYANO, Akio; WO2011/37244; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 28890-99-5,Some common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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) 20.0 g (78.8 mmol) 1 ,3-dibromo-5-fluoro-benzene, 16.3 g (78.8 mmol) 6H- benzimidazolo[1 ,2-a]benzimidazole and 43.5 g (0.315 mmol) potassium carbonate in 200 ml DMF are stirred for 17 h at 170 C. The reaction mixture is filtered hot and the precipitate from the mother liquor is filtered after cooling. The product is washed with water and ethanol and decocted with diethyl ether and ethanol. Yield 21.2 g (61 %).1 H NMR (400 MHz, THF-d8): delta 8.21-8.26 (m, 4H), 7.98-7.8.00 (m, 1 H), 7.68-7.73 (m, 2H), 7.31-7.49 (m, 4H).

The synthetic route of 28890-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole, 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 71759-87-0, Recommanded Product: 71759-87-0

3 -Cyclopropyl- 1 H-pyrazol-5-amine (910 mg, 7.4 mmol), 4-iodo- 1-methyl-i Himidazole (1.85 g, 8.9 mmol), potassium carbonate (2.2 g, 15.5 mmol) and CuT (140 mg, 0.74 mmol) were placed in a dry round-bottom flask. Anhydrous toluene was added via a syringe and the system was degassed. trans-N,N?-Dimethylcyclohexane1,2-diamine (420 mg, 2.96 mmol) was added in one portion and the system was degassed followed by heating at reflux for 24 h. The reaction mixture was quenched with water. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with brine, then dried over anhydrous Na2504. The volatile components were removed on a rotary evaporator and the residues were purified by flash column chromatography to yield the titled compound in 479 mg. ?H NMR (400 MHz, CDC13): 7.16 (s, 1H), 6.94 (s, 1H), 5.16 (br, 1H), 5.03 (s, 1H), 3.59 (s, 3H), 1.84- 1.74 (m, 1H), 0.84-0.76 (m, 2H), 0.66-0.58 (m, 2H). ESI-MS calculated for C,0H,4N5 [M+Hj = 204.12; Observed: 204.1.

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; ZHAO, Yujun; ZHOU, Bing; AGUILAR, Angelo; (114 pag.)WO2016/138332; (2016); 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H10F3N3

Method C[95] A pale yellow solid final compound (16.3g, yield 76%) was obtained by reacting3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) with 3-(4-imidazole-l-yl-pyrimidine-2-yl amino)-4-methyl-benzoic acid methyl ester (14. Ig, 45.60mmol) in a similar manner as described in Method A of Example 1, except that sodium tert-butoxide was used, instead of potassium tert-butoxide.

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 641571-11-1.

Reference:
Patent; IL-YANG PHARM. CO., LTD.; KIM, Dong Yeon; CHO, Dae Jin; LEE, Gong Yeal; KIM, Hong Youb; WOO, Seok Hun; WO2010/18895; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39513-26-3, A common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, molecular formula is C7H5BrN2O, 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 1095 Step 1 A solution of Compound 1095A in DMF (2 ml) was treated sequentially with sodium hydride (28 mg, 60% dispersion in oil, 0.70 mmol) and iodomethane (0.04 ml, 80 mg, 0.56 mmol). The reaction mixture was stirred overnight at rt. The reaction was quenched with water, diluted with EtOAc, and washed sequentially with water and brine. The organic phase was dried over anhydrous MgSO4, filtered and concentrated to give crude Compound 1095B (37 mg, 68%), which was used without further purification.

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2007/84451; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 219814-29-6,Some common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, molecular formula is C4H4Br2N2, 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 A : (5-Bromo-6-methyl-3 H- 1 ‘ -azaspiro [imidazo [2, 1 -b] oxazole-2,3 ‘ – bicyclo[2.2.2]octan]-l ‘-yl-8-ium)trihydroborate and (6-bromo-5-methyl-3H-l ‘- azaspiro[imidazo[2, l-b]oxazole-2,3 ‘-bicyclo[2.2.2]octan]- -yl-8-ium)trihydroborate To 2,4-dibromo-5-methyl-lH-imidazole (0.8 g, 3.3 mmol) in THF (25 niL) was added N-butyllithium (1.3 niL, 3.3 mmol) dropwise at -78C. After 45 minutes, a solution of racemic r-azaspiro[oxirane-2,3′-bicyclo[2.2.2]octan]-l’-yl-4- ium)trihydroborate (0.56 g, 3.7 mmol) from the reference example, in THF (20 mL) was added dropwise at -78C. The cooling bath was removed and the reaction mixture warmed to room temperature. After 15 minutes, the mixture was heated to 75C for 2 hours and then cooled to room temperature. The reaction was quenched with water and the product was extracted with ethyl acetate (100 mL). The organics were dried with MgS04, filtered and the solvent was removed to yield the crude product. The crude material was purified by chromatography (Biotage) to yield the regioisomeric products. These regioisomers were separated by reverse phase chromatography using a Sunfire column with gradients of acetonitrile-water containing 0.1% of trifluoroacetic acid (TFA), and at 40 mL/min flow rate. The pure fractions for peak 1 and peak 2 were then neutralized with 1 N NaOH (pH ~8-9) and the products were extracted with ethyl acetate. The organic layers were dried with MgS04, filtered and the solvent was removed to yield racemic (5-bromo-6-methyl-3H-l’-azaspiro[imidazo[2,l-b]oxazole-2,3′- bicyclo[2.2.2]octan]-l’-yl-8-ium)trihydroborate (0.32 g, 1.0 mmol, 30.8 % yield) XH NMR (500MHz, DMSO-d6) delta 4.23 (d, J=9.8 Hz, IH), 4.12 (d, J=9.9 Hz, IH), 3.36 (dd, J=15.2, 2.5 Hz, IH), 3.19 (dd, J=15.3, 2.1 Hz, IH), 3.04 – 2.95 (m, IH), 2.91 – 2.73 (m, 3H), 2.35 (br. s., IH), 2.03 – 1.88 (m, 4H), 1.84 – 1.67 (m, 3H), 1.64 – 1.11 (m, 3H). MS (LC/MS) R.T. = 2.09; [M+2]+ = 300.04 and racemic (6-bromo-5-methyl-3H-l’- azaspiro[imidazo[2,l-b]oxazole-2,3′-bicyclo[2.2.2]octan]-r-yl-8-ium)trihydroborate (0.33 g, 1.1 mmol, 31.7 % yield) as powders. NMR (500MHz, DMSO-de) delta 4.32 (d, J=10.1 Hz, IH), 4.12 (d, J=10.2 Hz, IH), 3.36 (d, J=2.4 Hz, IH), 3.18 (dd, J=15.2, 2.2 Hz, IH), 2.99 (d, J=2.9 Hz, IH), 2.93 – 2.78 (m, 3H), 2.31 (d, J=2.0 Hz, IH), 2.06 – 1.94 (m, 4H), 1.84 – 1.69 (m, 3H), 1.62 – 1.22 (m, 3H). MS (LC/MS) R.T. = 2.64; [M+2]+ = 300.04.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dibromo-4-methylimidazole, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; ZUSI, F. Christopher; HILL, Matthew D.; (87 pag.)WO2016/73407; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem