Related Products of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride. A new synthetic method of this compound is introduced below.
Iminodibenzyl (50.0 g, 0.256 mol) was dissolved in DMF (700 mL), sodium hydride (12.3 g, 0.306 mol, 60% dispersion in oil) was slowly added in portions and the mixture was stirred at 50 C. for 2 h. Ethyl 3-bromopropionate (100 mL, 0.77 mol) was slowly added dropwise and the mixture was heated at reflux temperature overnight. The mixture was cooled and evaporated. The residue was suspended in DCM (150 mL), filtered and the solvent was evaporated. The resulting residue was purified in portions by column chromatography (silica gel, DCM) to give 5.1 g (7%) of 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid ethyl ester.TLC: Rf=0.69 (silica gel, DCM).3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid ethyl ester (1.41 g, 4.77 mmol) was dissolved in ethanol (30 mL) and a solution of sodium hydroxide (0.75 g, 18.8 mmol) in water (5 mL) was added. The mixture was stirred for 3.5 h. 1 N Hydrochloric acid (17 mL) was added and the mixture was extracted with DCM (2×25 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4) and the solvent was evaporated to give 1.18 g (92%) of 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propionic acid.Carbonyldiimidazole (0.33 g, 2.1 mmol) was dissolved in DCM (5 mL) and 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propionic acid (0.56 g, 2.1 mmol) was added. The mixture was stirred at room temperature for 1.5 h under a nitrogen atmosphere. Simultaneously, sodium methoxide (0.8 mL of a 30% solution in water, 4.4 mmol) was added to a solution of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (0.43 g, 2.2 mmol) in methanol (5 mL). The mixture was stirred at room temperature for 1.5 h under a nitrogen atmosphere. The solvent was evaporated and the residue was stripped with DCM (6 mL). The above solution of the activated carboxylic acid was added to the residue and the reaction mixture was stirred at room temperature overnight. Water (10 mL) was added followed by DCM (50 mL) and the phases were separated. The aqueous phase was extracted with DCM (20 mL) and the combined organic phases were dried (MgSO4). After evaporation of the solvent, the residue was purified by column chromatography (silica gel, 150 mL, methanol/ethyl acetate 1:5). Evaporation of the solvent afforded 0.41 g (52%) of the title compound as a solid.TLC: Rf=0.28 (silica gel, methanol/ethyl acetate 1:5). LC-MS: Calcd. for MH+: 373; found: 373.1H NMR (400 MHz, DMSO-d6, two rotamers, 1:1): delta2.49 (m, 1H), 2.60-2.72 (m, 3H), 3.07 (d, 4H), 3.47 (t, 1H), 3.86 (t, 1H), 4.08-4.20 (m, 2H), 4.22 (s, 1H), 4.62 (s, 1H), 6.90 (m, 2H), 7.01-7.16 (m, 6H), 7.40 (s, 0.5H), 7.45 (s, 0.5H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62002-31-7, its application will become more common.
Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
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