Tag: M.W=100-200

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 106429-59-8 as follows. Application In Synthesis of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde

A solution of intermediate 2 (100 mg, crude HCI salt, 0.29 mmol) and 2-oxo-2,3-dihydro-1H-benzo[d]jimidazole-5-carbaldehyde (CAS: 106429-59-8) (71 mg, 0.44 mmol) in MeOH (2 mL) was stirred at room temperature for 2 h. NaBH3CN (37 mg, 0.58 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with H2O and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na,SOu, filtered and concentrated. The residue was purified by prep-HPLC (Waters 2767/Qda, Column: Waters Xbridge 19*150 mm 10 um, Mobile Phase A: H20 (0.1% TFA), B: ACN)to give the racemic Compound 14 (49 mg, TFA salt). The obtained racemic Compound 14 was separated by SFC (SFC80, Waters, IC 2.5*25 cm, 10 um, A: Supercritical COQ., B: MeOH/DEA= 100/0.03; A:B = 70/30; Flow rate: 70 mL/min; column temperature (T): 25 C; Backpressure (BPR): 100 bar) to give Compound 108 (12 mg as TFA salt, 6.8% yield) as a white solid and Compound 109 (13 mg as TFA salt, 7.3% yield) as a white solid.

According to the analysis of related databases, 106429-59-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
Imidazole – Wikipedia,
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1848-84-6, name is 2-Ethyl-1H-benzo[d]imidazole, 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. SDS of cas: 1848-84-6

A mixture of 4-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8- yl)piperidine-l -carboxylic acid tert-butyl ester (375 mg, 0.858 mmol), 2-ethylbenzimidazole (151 mg, 1.03 mmol), Xphos (43 mg, 0.09 mmol) and Cs2CO3 (421 mg, 1.29 mmol) in dioxane (5 niL) was degassed with nitrogen bubbling for 15 minutes.Tris(dibenzylideneacetone)dipalladium (20 mg, 0.022 mmol) was added and the mixture was heated to 120 0C for 20 hours. The reaction mixture was diluted with EtOAc, filtered, concentrated in vacuo and purified by column chromatography (Si-PCC, EtOAcxyclohexane, 40-90percent) affording 647 (390 mg, 83percent). LCMS: Rx 4.54 min, [M+H]+ 547.24 1H NMR (400 MHz, DMSO): delta 8.00-7.99 (m; 1 H); 7.68-7.60 (m; 1 H); 7.25-7.24 (m; 2 H); 4.45-4.12 (m; 4 H); 4.12-4.01 (d; J = 13.26 Hz, 2 H); 3.85-3.70 (m; 6 H); 3.25- 3.10 (m, 4 H); 3.04-2.82 (m, 2 H); 2.00-1.90 (d; J = 13.26 Hz, 2 H); 1.76-1.59 (m, 2 H); 1.43 (s; 9 H); 1.35 (t, J = 7.44 Hz, 3 H).

The synthetic route of 1848-84-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); A1;,
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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. 58089-25-1, name is 2-Mercapto-5-benzimidazolecarboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Mercapto-5-benzimidazolecarboxylic Acid

EXAMPLE 48 5-Carboxy-2-[{4-(2-benzyloxy)ethoxy-3-methylpyridine-2-yl}methylthio]-1H-benzimidazole STR110 A mixture comprising 1.26 g of 5-carboxy-2-mercaptobenzimidazole, 1.8 g of 4-(2-benzyloxyethoxy)-2-chloromethyl-3-methylpyridine, 0.57 g of sodium hydroxide and 150 ml of methanol was stirred at 50 C. for 1.5 hours and distilled under a reduced pressure to remove the methanol. The obtained residue was purified by silica gel column chromatography and recrystallized from a methanol/ethyl acetate mixture to obtain 1.52 g of the title compound. 1 H-NMR(DMSO-d6) delta; 2.25(s, 3H), 3.65~3.9(m, 2H), 4.1~4.3(m, 2H), 4.58(s, 2H), 4.74(s, 2H), 6.95(d, J=5.7 Hz, 1H), 7.32(s, 5H), 7.50(d, J=8.3 Hz, 1H), 7.79(dd, J=1.3 Hz, 8.3 Hz, 1H), 8.04(s, 1H), 8.24(d, J=5.7 Hz, 1H).

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 58089-25-1.

Reference:
Patent; Eisai Co., Ltd.; US5045552; (1991); 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. 78581-99-4, name is 5,6-Difluorobenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 78581-99-4

27: Methyi 3-{[(1 /?)-1-(2-chioro-3-hydroxyphenvi)ethv?oxv}-5- (5.6-dif iuoro-1 MbenzimidazoS-1 -yl)-2-thiophenecarboxyiateStep A – Methyl 5-{5,6-dif.uoro-1 Mbe?zimidazoi-1-yl)~3-hydroxy~2- thiophe?ecarboxylate To a mixture of 5,6-dif.upsilonoro-1 Mbenzsmidazoie (0.5 g, 3.2 rnmol) and 2-chioro- 3-oxo-2,3~dihydro~2-thiophenecarboxyiate (0.72 g, 3.7 mrnof) in 10 mL of CHCI3 was added Mmefhyiimidazole (0.4 g, 4.9 mrnol) and NaHCO3 (0.82 g, 5 9.7 mmol). The mixture was heated to 550C for 24 h. Silica gel (2 g) was added and the voiatites were evaporated under reduced pressure and the residue was purified by flash column chromatography (0 to 50% EtOAc: DCIVI) to afford 0.71 g of the tilted compound, MS (ESI): 311 [M+H]*.

According to the analysis of related databases, 78581-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143456; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, 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. HPLC of Formula: C4H5BrN2

5-bromo-1-methyl-1H-imidazole (47.96 g, 297.9 mmol) followed by THF (537 mL) was added to a 3 L four necked flask equipped with an overhead stirrer, nitrogen bubbler and thermocouple. To this room temperature solution was added isopropyl magnesium chloride / lithium chloride complex (246.8 mL, 320.8 mmol, 1.3 M in THF) (addition temperature maintained at 16.6-25 [deg.] C) to give a lean pumice suspension and stir the reaction for 60 min And then cooled to 5.3 in an ice bath. To this mixture was added a solution of N-methoxy-N-methyl-6- (trifluoromethyl) nicotinamide (53.66 g, 229.1 mmol, intermediate 4: step b) in THF (268 mL) 5.3 to 5.6 & lt; 0 & gt; C) to give an orange mixture. After the addition, the reaction was allowed to warm to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C with an ice bath, carefully quenched with a 2N HCl aqueous solution at pH = 7, and the quenching temperature reached 12 C. The mixture was diluted with ethyl acetate (500 mL), the phases were separated and the organic layer was washed with brine (2 x 200 mL), dried over sodium sulfate, filtered and the solvent removed. After addition of hot ether, filtration yielded the title compound as a solid.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica, N.V; Leonardo, Christie.A; Barubay, Kent; Edward, James P.; Kirsten, Kevin D.; Kumar, David A.; Maharupe, Uma; Nishimura, Rachel; Urbanski, Modu; Venkatesan, Hariharan; Wang, Ai Hua; OhLynn, Ronald L.; Woods, Craig R.; Fourier, Anne; Shu, Jia Hu; Cummings, Maxwell D.; (50 pag.)KR2016/70823; (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 5805-57-2 as follows. Product Details of 5805-57-2

General procedure: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

According to the analysis of related databases, 5805-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17289-26-8, The chemical industry reduces the impact on the environment during synthesis 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

COMPOUND 12.1. 32: 4-(f6. 7-DIMETHOXY-2-[(4-METHYL-lH-IMIDAZOL-5- YL) METHYL]-1, 2, 3, 4-TETRAHYDROISOOUINOLIN-1-YLMETHYL)-N,- DIETHYLBENZAMIDE; INTERMEDIATE 5.1. 5 (25 mg, 0.05 mmol) and 1-methyl-4-imidazolecarbaldehyde (12 mg, 0.10 mmol) were dissolved in DCE (5 mL). After stirring for 10 min at room temperature, sodium triacetoxyborohydride (33 mg, 0.16 mmol) was added and the mixture was stirred for 18 h at room temperature. Resin-bound tosylhydrazine (100 mg, 1.5 mmol/g) was added and the mixture was agitated for another 2 h. DCM and 1 M sodium hydroxide solution were added and the mixture was passed through a Whatman IPS silicon-treated filter paper. The organic phase was evaporated and the crude product was purified by preparative LCMS to yield the desired product (10 mg, 0.02, 39%). 1H NMR (500 MHz, CDC13): 1.14, 1.28 (2 brs, 6H), 2.17 (s, 3H), 3.10- 3.60, 3.80 (2 m, 10H), 4.35 (brs, 2H), 4.41 (s, 1H), 6.14, 6.59 (2 s, 2H), 7.29 (m, 4H), 8.50 (brs, 1H). (+) LRESIMS m/z 369 (100), 463 (35).

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-Methyl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 56248-10-3, name is 5-Phenyl-1H-imidazole-2-carbaldehyde, molecular formula is C10H8N2O, 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. Recommanded Product: 56248-10-3

General procedure: To a stirred solution of compound 3 (100mg, 0.40 mmol) in ethanol was added corresponding benzohydrazides (4a-m) (1.0 mmol) and refluxed for 1 h. The reaction mass was washed with pet ether, filtered and dried undervacuum to obtain the pure hydrazone compounds. Yields ofthe products varied between 78 and 88 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 56248-10-3, its application will become more common.

Reference:
Article; Prasanna, V. Laxmi; Narender; Asian Journal of Chemistry; vol. 27; 10; (2015); p. 3605 – 3608;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, 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. SDS of cas: 32673-41-9

A mixture of 1,2,3,4-tetrahydro-quinoline (Intermediate F1) (Commercially available from Aldrich) (1.62 mL, 12.6 mmol) and 4-hydroxymethyl-imidazole hydrochloride salt (commercially available from Aldrich) (Intermediate F2) (0.70 g, 5.1 mmol) and sodium carbonate (1.6 g, 15.1 mmol) in water (20 mL) and dioxane (10 mL) were heated at reflux for 24 h. The mixture was cooled to rt and extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and freed of solvent. The resultant oil was purified by chromatography on silica gel with 5% NH3-MeOH: dichloromethane to give 1-(1H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (Intermediate F3) as a solid, 0.54 g (50%). 1-(1H-Imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (Intermediate F3)was subjected to the appropriate process steps in Method A to produce 4-(3,4-dihydro-2H-quinolin-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 11). 1H NMR (300 MHz, DMSO-d6): delta12.0 (s, 1H), 11.8 (s, 1H), 6.93 (t, J=6.9 Hz, 1H), 6.87 (d, J=7.2 Hz, 1H), 6.66-6.63 (m, 1H), 6.63 (s, 1H), 6.50 (t, J=6.9 Hz, 1H), 4.18 (s, 2H), 3.28 (t, J=6.3 Hz, 2H), 2.67 (t, J=6.3 Hz, 2H), 1.90-1.84 (m, 2H).

The synthetic route of 4-Imidazolemethanol hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2006/69143; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 934-32-7, These common heterocyclic compound, 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, 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 the requested benzylic aldehyde (1 mmol),2-aminobenzimidazole or 3-amino-1,2,4-triazole (1 mmol),beta-diketone (1 mmol) and NS-C4(DABCO-SO3H)2·4Cl(20 mg, 10 mol %) was heated at 90 C under solvent-freeconditions. The progress of the reaction was monitoredby TLC (n-hexane: EtOAc, 70:30). After completion ofthe reaction, the reaction mixture was cooled to roomtemperature and 3 mL of water was added to it. Thecatalyst was dissolved in water and filtered for separation ofthe crude product. The separated product was washed twicewith water (2 × 5 mL), and the crude product was purifiedby recrystallization in ethanol.

The synthetic route of 934-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Goli-Jolodar, Omid; Shirini, Farhad; Journal of the Iranian Chemical Society; vol. 14; 11; (2017); p. 2275 – 2286;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem