Application of 1-Trityl-1H-imidazole-4-carbaldehyde

Electric Literature of 33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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.

3-[2-(aminomethyl)-5-chlorophenyl]propanoic acid hydrochloride a125 (0.54 g, 2.16 mmol), EtbetaN (1.8 ml_, 13.0 mmol), and trimethylorthoformate (0.30 ml_, 2.16 mmol) are added under stirring and prevention from entrance of air moisture to a solution of 1-trityl-1 H- imidazole-4-carbaldehyde (0.73 g, 2.16 mmol) in absolute methanol (76 ml_), and the mixture is stirred at room temperature for 16 h. NaBH4 (0.13 g, 3.45 mmol) is added, and the mixture is stirred for 1 h and quenched by the addition of a saturated NaHCtheta3 solution to pH 5-6. The solvents are removed under reduced pressure, and the obtained mass is subjected to extraction with ethyl acetate. Water is added to the residue, and undissolved residue is separated by filtration and dried to give 3-[5-chloro-2-({[(1-trityl-1 H-imidazol-4- yl)methyl]amino}methyl)phenyl]propanoic acid a128 (0.71 g). The organic extract is dried over anhydrous Na2SO4 and evaporated to give additionally intermediate a128 (0.40 g).The total yield of intermediate a128 is 1.11 g. Yield: 96 %.1 H NMR deltaH (DMSO, ppm): 2.48 (m, 2 H), 2.81 (t, J = 7.6 Hz, 2 H), 3.86 (s, 2 H), 3.93 (s, 2H), 6.96 (s, 1 H), 7.10 (m, 6 H), 7.20-7.48 (m, 13 H).

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; WO2008/132139; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem