Synthetic method of 2-(N-alkyl)aminooimidazole derivatives

A technology of aminoimidazole and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of low atomic efficiency and environmental pollution, and achieve the effect of high economic efficiency and broad development prospects

Inactive Publication Date: 2013-04-17
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw materials used in these methods will be prepared by cumbersome multi-step organic synthesis reactions, and highly toxic phosphorus oxychloride, mercuric oxide, etc. will be used in the preparation process, and the reaction will gener

Method used

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  • Synthetic method of 2-(N-alkyl)aminooimidazole derivatives
  • Synthetic method of 2-(N-alkyl)aminooimidazole derivatives
  • Synthetic method of 2-(N-alkyl)aminooimidazole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0024] Example 1: Preparation of N-benzyl-1H-benzimidazol-2-amine

[0025] N-benzyl-1H-benzo[d]imidazol-2-amine

[0026]

[0027] Under nitrogen protection, add 2-aminobenzimidazole (133 mg, 1 mmol), [Cp*IrCl 2 ] 2 (1.6 mg, 0.002 mmol, 0.2 mol%), potassium carbonate (13.8 mg, 0.1 mmol, 10 mol%) and benzyl alcohol (432 mg, 4 mmol) were added to a 20 ml Schlenk reaction flask. Reaction mixture at 130 o After reacting at C for 12 hours, cool to room temperature. The solvent was removed by rotary evaporation, and then column chromatography (developing solvent: ethyl acetate / petroleum ether) was used to obtain the pure target compound with a yield of 96%. The product NMR spectrum and high-resolution mass spectra were as follows figure 1 with figure 2 As shown,

[0028] 1 H NMR (500 MHz, DMSO-d 6 ) δ 7.37 (d, J = 7.3 Hz, 2H, ArH), 7.32 (t, J = 7.6 Hz, 2H, ArH), 7.23 (t, J = 7.2 Hz, 1H, ArH), 7.13-7.11 (m, 2H, ArH), 6.86 (dd, J = 5.7 Hz and 3.2 Hz, 2H, ArH), 4.51 (d, J = 5.3 Hz,...

Example Embodiment

[0029] Example 2: Preparation of N-(4-methylphenyl)-1H-benzimidazole-2-amine

[0030] N-(4-methylbenzyl)-1H-benzo[d]imidazol-2-amine

[0031]

[0032] Under nitrogen protection, add 2-aminobenzimidazole (133 mg, 1 mmol), [Cp*IrCl 2 ] 2 (1.6 mg, 0.002 mmol, 0.2 mol%), potassium carbonate (13.8 mg, 0.1 mmol, 10 mol%) and 4-methylbenzyl alcohol (488 mg, 4 mmol) were added to a 20 ml Schlenk reaction flask. Reaction mixture at 130 o After reacting at C for 12 hours, cool to room temperature. The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether). The yield: 84%. The product NMR spectra and high-resolution mass spectra such as image 3 with Figure 4 As shown,

[0033] 1 H NMR (500 MHz, DMSO-d 6 ) δ 10.77 (s, 1H, NH), 7.26 (d, J = 7.4 Hz, 2H, ArH), 7.12 (d, J = 7.1Hz, 4H, ArH), 6.87 (s, 1H, ArH), 6.83 (s, 1H, ArH), 4.45 (br s, 2H, CH 2 N), 2.26 (s, 3H, CH 3 ); HRMS-EI...

Example Embodiment

[0034] Example 3: Preparation of N-(4-methoxyphenyl)-1H-benzimidazole-2-amine

[0035] N-(4-methoxybenzyl)-1H-benzo[d]imidazol-2-amine

[0036]

[0037] Under nitrogen protection, add 2-aminobenzimidazole (133 mg, 1 mmol), [Cp*IrCl 2 ] 2 (1.6 mg, 0.002 mmol, 0.2 mol%), potassium carbonate (13.8 mg, 0.1 mmol, 10 mol%) and 4-methoxybenzyl alcohol (552 mg, 4 mmol) were added to a 20 ml Schlenk reaction flask. Reaction mixture at 130 o After reacting at C for 12 hours, cool to room temperature. The solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: ethyl acetate / petroleum ether), yield: 87%

[0038] 1 H NMR (500 MHz, DMSO-d 6 ) δ 10.75 (s, 1H, NH), 7.30 (d, J = 7.7 Hz, 2H, ArH), 7.11 (d, J = 6.1 Hz, 2H, ArH), 7.01 (br s, 1H, NH), 6.88 (m, 4H, ArH), 4.42 (s, 2H, CH 2 N), 3.71 (s, 3H, OCH 3 ); HRMS-EI (70 eV) m / z calcd for C 15 H 16 N 3 O [M+H] + 254.1293, found 254.1300.

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Abstract

The invention relates to a synthetic method of 2-(N-alkyl)aminooimidazole derivatives. The synthetic method comprises the steps of adding a 2-aminooimidazole derivative, an iridium or rhodium metal complex catalyst, alkali (or no alkali) and alcohol in a reactor under the protection of nitrogen or in an air atmosphere, reacting the reaction mixture for a plurality of hours at a temperature of 100-130 DEG C, cooling to a room temperature, removing the solvent by rotary evaporation, and then obtaining a target compound by column separation. The synthetic method shows three significant advantages that 1) nearly non-toxic alcohol is used as an alkylating agent; 2) the reaction only generates water as a by-product and has no environmental hazards; and that 3) the reaction has high atomic economy. Therefore, the reaction has wide development prospects.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, and in particular relates to a synthesis method of 2-(N-alkyl)aminoimidazole derivatives. Background technique [0002] 2-(N-Alkyl)aminoimidazole derivatives are important biologically active compounds that exhibit broad pharmacological and physiological activities, such as using them as antiallergic and antihistamine drugs, human arginase Inhibitors, conductance calcium-activated potassium channel inhibitors, respiratory polycystic virus inhibitors (M. Ilies, L. D. Costanzo, M. L. North, J. A. Scott, D. W. Christianson, J. Med. Chem. , 2010, 53 , 4266–4276; U. S. S?rensen, D. Str?b?k, P. Christophersen, C. Hougaard, M. L. Jensen, E. ?. Nielsen, D. Peters, L. Teuber, J. Med. Chem. , 2008, 51, 7625-7634; J. F. Bonfanti, F. Doublet, J. Fortin, J. Lacrampe, J. Guillemont, P. Muller, L. Queguiner, E. Arnoult, T. Gevers, P. Janssens, H. Szel, R. Willebrords, P. Timmerman, K. Wuyts, F. Jan...

Claims

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Application Information

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IPC IPC(8): C07D235/30
Inventor 李峰单海霞陈琳康麒凯
Owner NANJING UNIV OF SCI & TECH
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