Category: 934-22-5

Electric Literature of 934-22-5, These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, 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: HATU (60 mg, 0.16 mmol) was added to a solution of DIPEA(0.069 ml, 0.39 mmol), 1H-indazole-5-amine (26 mg, 0.2 mmol) and 9a(33 mg, 0.13 mmol) in DMF (5 ml) at room temperature. The mixturewas stirred at room temperature overnight. The reaction was quenchedwith sat. aq. NaHCO3 at room temperature and extracted with AcOEt.The organic layer was separated, washed with water and sat. aq. NaCl,passed through a pad of NH silica gel (eluent: AcOEt). The residue waswashed with AcOEt to afford 1c (33 mg, 68%) as a white solid.

The synthetic route of 934-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mizojiri, Ryo; Nii, Noriyuki; Asano, Moriteru; Sasaki, Masako; Satoh, Yoshihiko; Yamamoto, Yukiko; Sumi, Hiroyuki; Maezaki, Hironobu; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2521 – 2530;,
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 934-22-5 as follows. Quality Control of 6-Aminobenzimidazole

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.

According to the analysis of related databases, 934-22-5, the application of this compound in the production field has become more and more popular.

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

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 934-22-5 as follows. Recommanded Product: 6-Aminobenzimidazole

To a stirred solution of 5-amino-benzimidazole (290mg, 2. 2MMOL) in anhydrous DMF (lOmL) under N2 was added caesium carbonate (980mg) The resulting mixture was stirred at 70C for 60 min. To this was added a solution of 6-CHLORO-N-[(15)-1-PHENYLETHYL] PYRAZIN-2-AMINE (470mg) in DMF (5mL) and the resulting mixture was then heated at reflux for 48h. The DMF was removed under reduced pressure and the residue diluted with chloroform. The organic layer was washed with aqueous NA2CO3, dried (NA2SO4) and the solvent removed under reduced pressure to furnish the crude product. Column chromatography using dichloromethane-methanol (95: 5 No. 92: 8) as eluant separated two fractions from unreacted starting material. The higher Rf fraction was assigned as the 6-isomer (276mg, 42%). 1H-n. m. r. (CDCl3) 81. 64 (d, 3H, J= 6.9Hz, CH3), 2.90 (br s, 2H, NH2), 5.05 (m, 1H, CH), 5.21 (d, 1H, NH), 6.70 (dd, 1H, /= 8.7, 2. 1Hz, benzimid-H), 6.97 (d, 1H, J = 1. 8Hz, benzimid-H), 7.28-7. 43 (m, 5H, Ph-H), 7.58 (d, 1H, J= 8.4Hz, benzimid-H), 7.84 (s, 1H, pyraz-H), 8.08 (s, 1H, pyraz-H), 8.21 (s, 1H, benzimid-H). m/z (ES) 331 (M++H). The lower fraction was assigned as the 5-isomer (170mg, 26%),’H-n. m. r. (CDCl3) 81. 64 (d, 3H, J= 6. 9HZ, CH3), 2.85 (BR S, 2H, NHZ), 5.01 (m, 1H, CH), 5.19 (d, 1H, NH), 6.70 (dd, 1H, J= 8.7, 2. 1Hz, benzimid-H), 7.11 (d, 1H, J= 1. 8Hz, benzimid-H), 7.29-7. 40 (m, 5H, Ph-H), 7.51 (d, 1H, YE8. 7Hz, benzimid-H), 7.81 (s, 1H, pyraz-H), 8.10 (s, 1H, pyraz-H), 8.32 (s, 1H, benzimid-H). m/z (ES) 331 (M++H).

According to the analysis of related databases, 934-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOPIA PTY LTD; WO2003/99811; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, 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. Computed Properties of C7H7N3

Example 38 N-(1H-benzo[d]imidazol-5-yl)-2-(4-(5-chloro-2-propionylphenyl)-5-methoxy-2-oxopyri din-1(2H)-yl)-3-phenylpropanamide 38 Compound 8i (80 mg, 181.86 mumol), 1H-benzo[d]imidazol-5-amine 38a (24.22 mg, 181.86 mumol, prepared by a known method disclosed in “”) and N,N-diisopropylethylamine (70.51 mg, 545.59 mumol) were added to 10 mL of tetrahydrofuran, followed by addition of a solution of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide in ethyl acetate (50%, 231.34 mg, 363.73 mumol). After completion of the addition, the reaction solution was warmed up to 50C, and stirred for 1.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was added with 25 mL of saturated sodium bicarbonate solution, and extracted with ethyl acetate (50 mL*2). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by the silica gel column with elution system A to obtain the title compound 38 (75 mg, yield: 74.3%). MS m/z (ESI): 555.5 [M+1] 1H NMR (400 MHz, DMSO-d6) delta 10.84 (s, 1H), 9.05 (s, 1H), 9.14 (s, 1H), 8.27 (s, 1H), 7.79-7.77 (d, 1H), 7.72-7.69 (d, 1H), 7.59-7.52 (m, 2H), 7.41 (s, 1H), 7.34 (s, 1H), 7.30-7.24 (m, 4H), 7.19-7.17 (m, 1H), 6.30 (s, 1H), 6.03-5.99 (m, 1H), 3.52-3.50 (m, 4H), 3.48-3.44 (m, 1H), 2.85-2.75 (m, 2H), 1.25-1.18 (m, 3H).

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

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; YANG, Fanglong; WANG, Weimin; LI, Xiaodong; CHEN, Gang; HE, Feng; TAO, Weikang; (198 pag.)EP3486242; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 934-22-5,Some common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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 respective 2-oxo benzoic acid (1 eq.) was dissolved in THF (5 ml in case of 1 mmol) and DCC (1 eq.) was added. After stirring at r.t. for 1 h, benzimidazol-5(6)-amine (1 eq.) was added and stirring at r.t. was continued for 24 h. The mixture was put into the fridge for 2 h and afterwards the precipitated solid was filtered off. The filtrate was concentrated in vacuo, re-dissolved in a mixture of AcOH and toluol (3 ml and 7 ml in case of 1 mmol batch) and refluxed over night. After cooling the solvents were evaporated. The resulting residue was dissolved in CH2Cl2 (10 ml in case of 1 mmol batch), cooled to 0 C. and treated with TFA (1 ml (4 ml) per mmol). After stirring at r.t. for 10 min, triethylsilane (2 eq. (4 eq.)) was added. The reaction was allowed to warm up to room temperature and stirred for 3 h. After that time, the mixture was quenched with saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with EtOAc (3¡Á25 ml). The combined organic layers were dried over Na2SO4, concentrated in vacuo and the remaining residue was purified by flash-chromatography using silica gel and a CHCl3/MeOH gradient. Example 1262-(1H-benzo[d]imidazol-5-yl)-3-(4-biphenyl)isoindolin-1-oneThe compound was synthesized according to method 11.2-(4-Phenylbenzoyl)benzoic acid (1.0 g; 3.3 mmol), DCC (680 mg; 3.3 mmol), benzimidazol-5(6)-amine (440 mg; 3.3 mmol), TFA (3.92 ml) and triethylsilane (0.624 ml; 3.92 mmol; 4 eq.) and was additional purified by semi-preparative HPLC; yield: 0.120 g (9.1%); MS m/z: 402.1 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): delta 6.79 (s, 1H); 7.28-7.32 (m, 1H); 7.36-7.40 (m, 5H); 7.53-7.60 (m, 5H); 7.63-7.66 (m, 1H); 7.72-7.74 (d, 1H, 3J=8.7 Hz); 7.76-7.79 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 7.89-7.91 (m, 1H); 8.17-8.18 (d, 1H, 4J=1.7 Hz); 9.06 (s, 1H); HPLC (Gradient 3): rt 15.20 min (97.0%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Aminobenzimidazole, its application will become more common.

Reference:
Patent; PROBIODRUG AG; US2011/92501; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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. Formula: C7H7N3

To a solution of 2,4-dichloropyrimidine (1 mmol) and 5-Aminobenzimidazole (1 mmol) in 5 ml EtOH, was added Et3N(1 mmol). The reaction mixture was refluxed for 5 hours. After removal of the solvent in vacuo and addition of H2O, the mixture was extracted with EtOAc. The organic layers were combined, washed with a saturated NaCl aqueous solution, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography to give N-(2-chloropyrimidin-4-yl)-1H-benzo[d]imidazol-5-amine in a yield of 80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 934-22-5, its application will become more common.

Reference:
Patent; Hutchison MediPharma Enterprises Limeted; US2008/255172; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, A common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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 1; The preparation of 3-(1H-benzimidazol-5-ylamino)-4-(3-hydroxybenzylamino)cyclobut-3-ene-1,2-dione (?A1?) is carried out analogously to the following scheme 1.1 6.2 g (35.7 mmol) of 3,4-diethoxy-3-cyclobutene-1,2-dione 1 are dissolved in 50 ml of ethanol, 5.0 g (35.7 mmol) of 3H-benzimidazol-5-ylamine 2 are added, and the mixture is stirred at 75 C. for 20 h. The mixture is then subjected to conventional work-up, giving 8.93 g (97%) of 3-(1H-benzimidazol-5-ylamino)-4-ethoxycyclobut-3-ene-1,2-dione 3; MS-FAB (M+H+)=358, m.p. 243-244.

The synthetic route of 934-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mederski, Werner; Emde, Ulrich; Barnickel, Gerhard; Zenke, Frank; Greiner, Hartmut; Stieber, Frank; US2008/234266; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 934-22-5 name is 6-Aminobenzimidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

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

934-22-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 934-22-5 name is 6-Aminobenzimidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To the solution of 1H-benzimidazol-5-amine 121 (0.68 g, 5.11 mmol) in acetic acid (20 mL), the Compound 120a (1.06 g, 5.62 mmol) was added and stirred at room temperature for 20 minutes. TMSCN (1 mL) was added dropwise to the reaction mixture and continuously stirred for 2 hours. After reaction completing, the reaction mixture was concentrated under reduced pressure to yield a viscous liquid. The viscous liquid was diluted with ethyl acetate (10 mL) and water. The diluted solution was adjusted to the pH 6-7 with ammonia at an ice-bath. The neutralized solution was extracted with ethyl acetate (20 mL x 4), dried over sodium sulfate, filtered and concentrated under reduced pressure to yield a viscous dark-yellow solid. The solid was dissolved in ethyl acetate (15 mL) and brine (15 mL). The mixture was stirred at room temperature for 2 minutes to form the pale-yellow precipitates. The pale-yellow precipitates was filtered and washed with water. The filtrate was dried over sodium sulfate and concentrated under reduced pressure to obtain the pale- yellow solid. Those pale-yellow solids were combined as the desired product 122a at a yield of 96%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

Reference:
Patent; SHIH, Chuan; NATIONAL HEALTH RESEARCH INSTITUTES; ACADEMIA SINICA; CHEN, Chih-Hao; CHEN, Chiung-Tong; WANG, Hwei-Jiung; HUANG, Kai-Fa; (130 pag.)WO2020/47360; (2020); 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. 934-22-5, name is 6-Aminobenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., 934-22-5

1 equivalent of the aldehyde was dissolved in AcOH (5 mL in case of 4 mmol starting material) and 1.1 equivalents of the amine were added. 1 equivalent of TMSCN was then added to the mixture. The mixture was stirred for 1.5 h at r.t.The mixture was then poured on ice/ammonia (containing 12 mL of a 25% NH3 solution in case of 4 mmol starting material). The aqueous layer was extracted 3 times by means of CH2Cl2 the organic phases were combined, dried, filtrated and the solvent was removed. The remains were re-dissolved in concentrated HCl and kept at 40 C. overnight. Water was added and the solution was neutralized by adding NaOH. The aqueous phase was extracted three times by means of CH2Cl2, thereafter the organic phases were combined and dried. The solvent was removed and the remains were taken up in triethyl-ortho formate. The mixture was kept under reflux for 1 h. The orthoester was removed and the remaining oil was dissolved in MeOH and NaBH4 (1.5 equivalents) were added. The mixture was kept at ambient temperature for 1 h, followed by 60 C. for 1 h and the reaction was quenched by addition of an aqueous solution of ammonia (12%). The aqueous layer was extracted three times by means of CH2Cl2, thereafter the organic phases were combined and dried. The solvent was removed and the remaining mixture was subjected to preparative HPLC. Example 631-(1H-benzo[d]imidazol-5-yl)-5-phenylimidazolidin-4-oneThe compound was synthesized starting from 5-aminobenzimidazole (0.75 g, 5.61 mmol), benzaldehyde (0.52 mL, 5.1 mmol), TMSCN (0.64 mL, 5.1 mmol), conc. aqueous HCl (10 mL), triethyl orthoformate (13 mL, excess), NaBH4 (0.227 g, 6 mmol) as described in method 4. Yield: 0.088 g (6.2%); MS m/z 279.3 (M+H)+; 1H NMR (400 MHz, DMSO-D6): delta 4.78-4.80 (m, H); 5.04-5.05 (m, H); 5.17-5.19 (m, H); 6.23 (d, H, J=2.1 Hz); 6.79 (dd, H, 3J=9.1 Hz, 4J=2.1 Hz); 7.24-7.27 (m, H); 7.30-7.36 (m, 4H); 7.59 (d, H, J=9.1 Hz); 8.89 (s, H); 9.16 (s, H), HPLC (lambda=214 nm), [B]: rt 6.43 min (97.8%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; PROBIODRUG AG; US2011/92501; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem