Category: 279226-70-9

Reference of 279226-70-9, 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. 279226-70-9, name is 1-Methyl-1H-benzimidazole-5-carboxaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 6-(l-methyl-lH-pyrazol-4-yl)-4-(6-(piperazin-l-yl)pyridin-3- yl)pyrazolo[l,5-a]pyrazine-3-carbonitrile dihydrochloride (Example 8; 30 mg, 0.078 mmol) in DCE (778 mu.) was treated sequentially with 1 -methyl- lH-benzimidazole-5-carboxaldehyde (25 mg, 0.16 mmol) and NaBH(AcO)3 (49 mg, 0.23 mmol). The mixture was stirred overnight at ambient temperature, and then concentrated in vacuo. The residue was purified first by silica chromatography (using 0-20% MeOH in DCM as the gradient eluent) and then by C18 reverse phase chromatography (using 5-95% ACN/water with 0.1% TFA the gradient eluent) to cleanly afford the title compound as its TFA salt. The TFA salt was treated with saturated NaHCCb(aq), and subsequently extracted into EtOAc (3x). The combined organic extracts were dried over anhydrous Na2S04(S), filtered, and concentrated in vacuo to cleanly afford the title compound (1.5 mg, 3.6% yield). MS (apci) m/z = 529.8 (M+H).

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-benzimidazole-5-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 279226-70-9, name is 1-Methyl-1H-benzimidazole-5-carboxaldehyde, 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. COA of Formula: C9H8N2O

To a solution of 1-methyl-1H-benzoimidazole-5-carbaldehyde (prepared as described in WO0037473) (420 mg, 2.62 mmol) in trimethylsilyl cyanide (2 mL, 15.0 mmol) was added a catalytic amount of zinc iodide. The reaction mixture was stirred at ambient temperature overnight, concentrated under vacuum and the resulting residue dissolved in a 7N solution of ammonia in methanol (10 mL, 70 mmol) in a sealed tube. The mixture was heated for 1.5 hours at 55 C. then cooled to ambient temperature and concentrated under vacuum. The residue was dissolved in 6N aqueous hydrochloric acid (?10 mL) in a sealed tube. The mixture was stirred at 110 C. for 6 hours then cooled and concentrated under vacuum to afford a solid residue. This solid was dissolved in N,N-dimethylformamide (?20 mL). Triethylamine (4 mL, 28.7 mmol) and di-tert-butyl dicarbonate (850 mg,3.93 mmol) were added and the mixture was stirred for 4 hours at ambient temperature. The solvent was then removed, the residue was washed with ether, dried and then dissolved in tetrahydrofuran (55 mL). To this solution was added (S)-2-(2-amino-3-phenylpropinylamino-thiazole-4-carboxylic acid methyl ester (prepared as described in example 3) (800 mg, 2.62 mmol) and the reaction mixture cooled to 0 C. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (500 mg, 2.61 mmol) was added and the reaction mixture was allowed to slowly warm to ambient temperature and then stirred for 48 hours. The reaction mixture was then partitioned between ethyl acetate and water, the ethyl acetate layer was dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography over silica gel gradient eluted between 0 and 50% v/v ethyl acetate in dichloromethane and then gradient eluted between 0 to 4% methanol in dichloromethane. Precipitation of the isolated product from a tetrahydrofuran solution with an excess of hexanes afforded 2-{(S)-2-[2-tert-butoxycarbonylamino-2-(1-methyl-1 H-benzoimidazol-5-yl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester as an amorphous white solid (510 mg, 33%). HRMS: Obs. Mass, 593.2167. Calcd. Mass, 593.2177 (M+H)

The synthetic route of 1-Methyl-1H-benzimidazole-5-carboxaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goodnow,, Robert Alan; Huby, Nicholas J.S.; Kong, Norman; McDermott, Lee Apostle; Moliterni, John Anthony; Zhang, Zhuming; US2006/63814; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem