Category: 29043-48-9

Synthetic Route of 29043-48-9, A common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, 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.

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2·2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 × 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3×10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

The synthetic route of 29043-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 29043-48-9, 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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: First, a mixture of 4-nitrobenzene-1,2-diamine (1 g) and formic acid (0.74 mL) in 5 N HCl (70 mL) was stirred and heated to reflux for 24 h. The mixture was cooled to room temperature and neutralized by 10% NaOH, and precipitate was isolated, recrystallised from water and dried to produce 5-nitrobenzoimidazole (0.69 g) [37]. Next, 5-nitrobenzoimidazole (0.25 g) was dissolved in ethanol (20 mL). The solution was stirred and heated to reflux, and the palladium-on-charcoal catalyst (0.15 g) and hydrazine hydrate (1.6 mL) were added. Then the mixture was stirred for 4 h, and filtered in hot. The filtrate was evaporated, and the residue was recrystallised from ethanol to give rise to the precursor compound 5-aminobenzoimidazole (0.163 g). Finally, a mixture of 4-chloro-6,7-dimethoxyquinazoline hydrochloride (0.25 g), 5-aminobenzoimidazole (0.15 g) in isopropanol (25 mL) was stirred and heated to reflux for 4 h. The precipitate was filtered off, recrystallised from methanol and dried to afford 12 as yellow powder (0.32 g, yield 73%).

The chemical industry reduces the impact on the environment during synthesis 2-Methyl-1H-benzoimidazol-5-ylamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Lue, Shuang; Zheng, Wei; Ji, Liyun; Luo, Qun; Hao, Xiang; Li, Xianchan; Wang, Fuyi; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 84 – 94;,
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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Example No. 302Preparation of 5- (3 , 4 -dihydro-2H-benzo [b] [1,4] oxazin-6-yl) -N- (2-methyl-lH-benzo [d] imidazol-5-yl) -lH-pyrazolo [4,3- d] pyrimidin-7-amine6- (7-chloro-2- (4 -methoxybenzyl) -2H-pyrazolo [4 , 3-d] pyrimidin-5- yl) -2H-benzo [b] [1 , 4] oxazin-3 (4H) -one (0.16 mmol) and 2 -methyl – lH-benzo [d] imidazol-5-amine (0.3 mmol 2 eq.,) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was evaporated and used without further purification. The reaction mixture was dissolved in THF (dry) LiAlH4 powder was added (excess, 2 by 2 eq) until completion of reaction is observed (by LCMS) . The reaction was quenched with water (lmL per gram LiAlH4) , then NaOH (ca. 15% aq. , lmL per g LiAlH4) , water (3mL per gram LiAlH4) . The mixture was filtered, washed with THF, MeOH, MeCN (ca. 10ML each) . The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140 C. The reaction mixture was concentrated and purified by semi-preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 398.1840 g/molHPLC-MS: analytical method Lrt: 3.09 min – found mass: 399 (m/z+H)

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 29043-48-9.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; TRAUBE, Nadine; WO2012/143144; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 29043-48-9,Some common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, molecular formula is C8H9N3, 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: Example 2C 5-methyl-N-(2-methyl-2H-indazol-5-yl)-4-oxo-4,5,6,7-tetrahydrofuro[3,2-c]pyridine-3-carboxamide To a solution of the product from Example 2B (0.1 g, 0.512 mmol) in N,N-dimethylformamide (4 mL) was added 2-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (0.195 g, 0.512 mmol) and triethylamine (0.071 mL, 0.512 mmol). After mixing, 2-methyl-2H-indazol-5-amine (0.075 g, 0.512 mmol) was added, and the vial was shaken for 4 hours. The mixture was concentrated and triturated with methanol to provide the titled compound. 1H NMR (DMSO-d6) delta ppm 12.76 (s, 1H), 8.32 (s, 1H), 8.29 (s, 1H), 8.25 (d, J=4 Hz, 1H), 7.60 (d, J=12 Hz, 1H), 7.29 (d, J=12 Hz, 1H), 4.41 (s, 3H), 3.75 (t, J=8 Hz, 2H), 3.11 (t, J=8 Hz, 2H), 3.06 (s, 3H); MS (ESI) m/z 325 (M+H)+.

The synthetic route of 29043-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Altenbach, Robert J.; Liu, Huaqing; Clapham, Bruce; Aguirre, Ana L.; Cowart, Marlon; Koenig, John R.; Sarris, Kathy; Scanio, Marc J.; Swinger, Kerren K.; Vasudevan, Anil; Villamil, Clara I.; Woller, Kevin R.; (95 pag.)US9777020; (2017); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 29043-48-9, These common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, 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 coupling reaction of 3-chloro-2-methylbenzenesulphonyl chloride (2 eq. ) with 2- methylbenzimidazoel (1 eq. ) under the condition described above yielded a mixture of 3- CHLORO-N- [1- (3-CHLORO-2-METHYLBENZENESULPHONYL)-2-METHYL-1 H-BENZOIMIDAZOL-5-YL]-2- methyl-benzenesulphonamide and 3-chloro-N-[1-(3-chloro-2-methylbenzenesulphonyl)- 2-METHYL-1 H-BENZOIMIDAZOL-6-YL]-2-METHYL-BENZENESULPHONAMIDE in 1: 1 ratio as judged by HNMR.’H NMR (270 MHz, DMSO): 5 10.7 (2H, s, 2 x NH), 7.86-7. 96 (3H, m, ArH), 7.65-7. 78 (5H, m, ArH), 7.52-7. 58 (5H, m, ArH), 7.25-7. 40 (3H, m, ArH), 7.07 (2H, t, J = 8.2 Hz, ArH), 2.61 (3H, s, CH3), 2.58 (3H, s, CH3), 2.54 (6H, s, 2 x CH3), 2.39 (3H, S, CH3), 2.33 (3H, s, CH3). The mixture (200 mg) was dissolved in THF (15 mL), N- hydroxybenzotriazole (200 mg) was added. After stirred at rt for 48h, the mixture was partitioned between ethyl acetate and 5% sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulphate and concentrate in vacuo to give a yellow residue, which was purified with flash chromatography (methanol/DCM gradient elution). Off white amorphous powder was obtained. TLC single spot at Rf 0.38 (10% methanol/DCM) ; HPLC purity 99% (tR 2.0 min in 10% WATER-METHANOL) ;’H NMR (270 MHz, DMSO): 5 12.1 (1H, s, NH), 10.3 (1H, s, NH), 7.78 (1H, d, J = 7.9 Hz, ArH), 7.68 (1H, d, J= 7.9 Hz, ArH), 7.29-7. 35 (2H, m, ArH), 7.12 (1H, s, ArH), 6.83 (1H, dd, J= 8.4, 1.8 Hz, ArH), 2.63 (3H, s, CH3), 2.41 (3H, s, CH3) ; APCI-MS 334 (M-H+) ; FAB-HRMS calcd for C1SH1SCIN302S (MH+) 336.0573, found 336.0583.

Statistics shows that 2-Methyl-1H-benzoimidazol-5-ylamine is playing an increasingly important role. we look forward to future research findings about 29043-48-9.

Reference:
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 29043-48-9, A common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, 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.

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2¡¤2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 ¡Á 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3¡Á10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

The synthetic route of 29043-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Example No. 289Preparation of 6- (7- ( (2-methyl -lH-benzo [d] imidazol-5- yl)amino) -IH-pyrazolo [4, 3-d] pyrimidin- 5 -yl) -2H- benzo [b] [1 , 4] oxazin-3 (4H) -one6- (7-chloro-2- (4-methoxybenzyl) -2H-pyrazolo [4 , 3 -d] pyrimidin- 5- yl) -2H-benzo [b] [1, 4] oxazin-3 (4H) -one (0.16 mmol) and 2-methyl- lH-benzo [d] imidazol-5-amine (0.3 mmol 2 eq. , ) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140 C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was concentrated and purified by semi- preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 412.1584 g/molHPLC-MS: analytical method Drt: 3.81 min – found mass: 413 (m/z+H)

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 29043-48-9.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; TRAUBE, Nadine; WO2012/143144; (2012); 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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Methyl-1H-benzoimidazol-5-ylamine

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2¡¤2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 ¡Á 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3¡Á10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

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; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, 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. Recommanded Product: 29043-48-9

A solution of 75 mg (0.10 mmol) of (2S) -2- {[(iraws-4- {[(ieri-butoxycarbonyl) – amino] methyl}cyclohexyl) carbonyl] amino} -3- (4 ‘- {[1 – (ieri-butoxycarbonyl) -piperidin-4-yl] – carbamoyl} -2’-methyl-biphenyl-4-yl) propanoic acid and 31 mg (0:21 mmol) of 2-methyl-l / ibenzimidazol-5-aminewas dissolved in 1 ml of dichloromethane containing 0.05 ml (0:31 mmol) of N, N-diisopropylamineand 81 mg (0:16 mmol) of (l / i-benzotriazol-l-yloxy) (tripyrrolidin-lyl) phosphoniumhexafluorophosphate was added and stirred for 16 h at RT. The reaction solution was separatedby preparative HPLC (eluent: acetonitrile / water gradient, 0.01% to trifluoroacetic acid). Theproduct-containing fractions were combined and concentrated on a rotary evaporator. There were23 mg (26% d. Th.) Of the title compound.

The synthetic route of 29043-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROEHN, ULRIKE; ELLERMANN, MANUEL; STRASSBURGER, JULIA; WENDT, ASTRID; ROEHRIG, SUSANNE; WEBSTER, ROBERT ALAN; SCHMIDT, MARTINA VICTORIA; TERSTEEGEN, ADRIAN; BEYER, KRISTIN; SCHAEFER, MARTINA; BUCHMUELLER, ANJA; GERDES, CHRISTOPH; SPERZEL, MICHAEL; SANDMANN, STEFFEN; HEITMEIER, STEFAN; HILLISCH, ALEXANDER; ACKERSTAFF, JENS; TERJUNG, CARSTEN; (489 pag.)TW2016/5810; (2016); A;,
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 29043-48-9 as follows. SDS of cas: 29043-48-9

To a stirred solution of 2-methyl-1 H-benzo[d]imidazol-5-amine (187 mg) in DCM (5 mL) at 0 C was added 3-carbamoyl-4-hydroxybenzene-1 -sulfonyl chloride (lnt-1 , 300 mg). The reaction mixture was allowed to warm to RT and stirred for 16 hr. The reaction mixture was diluted with water (30 mL) and extracted with DCM (2 x 50 mL). The combined DCM extracts were washed with saturated brine (25 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product (300 mg). The crude product was purified by reversed phase preparative HPLC (Sunfire C18, 30 x 250 mm) using a gradient of 10-100% acetonitrile in 10 mM ammonium bicarbonate (aq). The desired fraction was concentrated under reduced pressure and the resulting solid was collected by filtration, washed with water (10 mL) and dried under vacuum to afford the titled compound (55.6. mg). LCMS m/z 347.04 (M+H)+. NMR after D20 exchange (400 MHz, DMSO-c/6) delta ppm 2.27 – 2.50 (m, 3 H) 6.76 (d, J=8.33 Hz, 1 H) 6.85 (dd, J=8.55, 1 .75 Hz, 1 H) 7.02 – 7.21 (m, 1 H) 7.28 (d, J=8.33 Hz, 1 H) 7.40 – 7.61 (m, 1 H) 8.19 (d, J=2.19 Hz, 1 H).

According to the analysis of related databases, 29043-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem