1467-16-9, 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. 1467-16-9, name is 1H-Imidazole hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.
TFA (991 muIota, 13.0 mmol) was added to a solution of 3-amino-7-cyano-5-{[2- (trimethylsilyl)ethoxy]methyl}-5/-/-pyrrolo[2,3- 5]pyrazine-2-carboxylate, Intermediate 166 (150 mg, 0.43 mmol) in CH2CI2 (2 ml). The resultant mixture was stirred at RT for 4.5 h. The reaction mixture was concentrated in vacuo, azeotroped with toluene (2 x 5 ml), then dried in vacuo to afford a red/orange solid (1 14 mg). A portion (83 mg) of the solid thus obtained was dissolved in MeOH (3 ml). Aqueous NaOH solution (5.0 M, 0.67 ml, 3.4 mmol) was added then the resulting mixture was heated at 60 C for 1 h then at 80 C for 1.5 h. The reaction mixture was allowed to cool to RT then filtered. The collected solid was washed with water then dried in vacuo to afford a brown solid (60 mg). The solid thus obtained was dissolved in DMF (1 ml) then CDI (78 mg, 0.48 mmol) and imidazole hydrochloride (25 mg, 0.24 mmol) were added. The reaction was stirred at RT for 10 min. Water (3 ml) was added then the reaction was stirred at RT for 5 min. The solid was collected by filtration, washed with water, then dried in vacuo to afford a brown solid (39 mg). The solid thus obtained was dissolved in DMF (1 ml) then 2-(aminomethyl)-1 ,3- diethyl-6-methoxy-1 /-/-1 ,3-benzodiazol-3-ium iodide, Intermediate 36 (45 mg, 0.13 mmol) was added. The resultant mixture was stirred at RT for 2.5 h then concentrated in vacuo. The crude material was purified by flash column chromatography on C18 (12 g). The column was eluted with MeCNihbO + 0.1 % TFA using the following gradient (% MeCN, column volumes): 2%, 2 CV; 2-37%, 18 CV; 37-48%, 1 CV; 48-89%, 3 CV; 89-100%, 1 CV; 100% 2 CV. The desired fractions were combined and lyophilised. The material thus obtained was further purified by preparative HPLC (Method A). The desired fractions were combined and lyophilised to afford the product as a yellow solid (3.5 mg, 1.7%). 1 H NMR (500 MHz, DMSO-cfe) delta 9.41 (t, J = 5.0 Hz, 1 H), 8.34 (s, 1 H), 8.23 (s, 1 H), 7.89 (d, J = 9.1 Hz, 1 H), 7.51 (d, J = 2.3 Hz, 1 H), 7.21 (dd, J = 9.1 , 2.3 Hz, 1 H), 7.09 (s, 2H), 5.01 (d, J = 5.4 Hz, 2H), 4.66 – 4.56 (m, 4H), 3.84 (s, 3H), 1.38 – 1.28 (m, 6H). LC/MS (System C): m/z (ESI+) = 419 [M+], Rt = 1.85 min, UV purity = 99%.
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Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem