Related Products 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.
Example 1Under a nitrogen atmosphere, 6-bromo-N-methyl-2- naphthamide (7.0 g, 26.5 mmol) was added to tetrahydrofuran (175 mL) , and then 2.0 mol/L isopropylmagnesium chloridetetrahydrofuran solution (13.7 mL) was added dropwise thereto at room temperature. The reaction mixture was cooled to -30C, 1.6 mol/L n-butyllithium hexane solution (26.6 mL) was added dropwise thereto, and the mixture, was stirred at the same temperature for 2 hr. To the reaction mixture was addeddropwise a solution of l-trityl-4-formyl-lH-imidazole (13.5 g, 39.9 mmol) in tetrahydrofuran (140 mL) at -20C, and themixture was stirred at the same temperature for 2 hr. The reaction mixture was allowed to warm to 0C, and stirred for 1 hr, and 20w/v% aqueous ammonium chloride solution (105 mL) was added dropwise thereto. The organic layer was separated, and concentrated to the volume of about 90 mL under reducedpressure. To the residue was added tetrahydrofuran (140 mL) , and the mixture was concentrated to the volume of about 90 mL under reduced pressure. To the residue was added acetone (140 mL) , and the mixture was concentrated to the volume of about 140 mL under reduced pressure. These operations were repeated three times. To the residue was added acetone to adjust the volume to about 180 mL, and the mixture was stirred at room temperature. The crystals were collected by filtration, and washed with acetone (70 mL) . The obtained wet crystals were dried under reduced pressure to give 6- [hydroxy ( 1-trityl-lH- imidazol-4-yl) methyl] -N-methyl-2-naphthamide (10.3 g, 19.7 mmol) . yield 74%.½ NMR (500 MHz , DMSO-d6) delta 2.84 (d, J = 4.7 Hz, 3H) , 5.76 (d, J = 5.0 Hz, 1H), 5.82 (d, J = 4.7 Hz, 1H) , 6.80 (s, 1H) , 6.98- 7.13 (m, 6H) , 7.28 (d, J = 1.6 Hz, 1H) , 7.32-7.50 (m, 9H) , 7.55 (dd, J = 8.5, 1.6. Hz, 1H) , 7.83-7.99 (m,. 4H) 8.37 (s, 1H) 8.58 (d, J = 4.4 Hz, 1H) ; HRMS (ESI) m/z Calcd for aC35H30 3O2 [M+H] +: 524.2338, Found: 524.2325; Anal. Calcd for a C35H29 3O2: C, 80.28; H, 5.58; N, 8.02. Found: C, 80.17; H, 5.80; N, 7.81.[0097]
The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAWABATA, Yoichi; SAWAI, Yasuhiro; KANNO, Kazuaki; SAWADA, Naotaka; WO2012/173280; (2012); A1;,
Imidazole – Wikipedia,
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