Category: 33016-47-6

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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 1-Trityl-1H-imidazole-4-carbaldehyde

Step 8.c. 7-((1-Triphenylmethyl-imidazol-4-yl)methyl)-2-(2-methoxyphenyl)-8-(1-methylpropyl)- 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine 8-(1-Methylpropyl)-2-(2-methoxyphenyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine dihydrochloride (compound vii where R3 is 1-methylpropyl, R4 is 2-methoxyphenyl, and R5-R7 are H) (from Step 4.g.)(179 mg, 0.50 mmol) and the product from Step 8.b. (compound xiv where R2 is H) (338 mg, 1.00 mmol) were combined in 1,2-dichloroethane (2.0 ml). NaBH(OAc)3 (212 mg, 1.00 mmol) was added and the reaction was allowed to stir at room temperature for about 1 hour.. The reaction mixture was poured onto a silica gel column and the product was eluted using EtOAc as eluant.. Product fractions were combined and concentrated to yield pure product as white foam (150 mg, 49%).. Mass spec. 608.2, MH+.

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

Reference:
Patent; SOCIETE DE CONSEILS DE RECHERCHES ET D’APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.); EP1382607; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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.

A mixture comprising compound 158B (350 mg; 0.88 mmol) and 1-trityl-1H-imidazole-4-carboxaldehyde (352 mg; 1.00 mmol) dissolved in 1,2-dichloroethane (DCE) (4.5 ml) in the presence of acetic acid (0.3 ml) is stirred for 5 minutes at room temperature and sodium triacetoxyborohydride (233 mg; 1.10 mmol) is then added. The mixture is stirred overnight at room temperature and is then diluted with ethyl acetate and washed successively with saturated NaHCO3 solution, with water, and with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated. This crude reaction, product is then purified by flash chromatography (gradient: 4/1 and then 2/1 CH2Cl2/acetone) to give the desired product (304 mg; 48%). [0268] 1H NMR, DMSO-d6 (ppm): 1.88 (m, 2H); 2.00 (s, 3H); 2.33 (m, 2H); 3.63 (s, 3H); 4.03 (d, 2H, 5.2 Hz); 4.50 (m, 1H); 5.45 (t, 1H, 5.6 Hz); 6.55 (s, 1H); 6.70 (s, 1H); 6.76 (d, 1H, 8.7 Hz); 7.01 (m, 6H); 7.21 (d, 1H, 8.7 Hz); 7.25 (s, 1H); 7.31-7.41 (m, 13H); 7.55 (d, 1H, 7.4 Hz); 7.73 (d, 3H, 9.4 Hz); 11.35 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Trityl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Perez, Michel; Lamothe, Marie; Hill, Bridget; Etievant, Chantal; US2004/204417; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33016-47-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 33016-47-6 name is 1-Trityl-1H-imidazole-4-carbaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(a) 1-triphenylmethyl-4-[(1-hydroxy-1-phenyl)methyl]-1H-imidazole Prepared by reacting 4-formyl-1-triphenylmethyl-1H-imidazole (melting point: 202-205 C.; prepared by oxidation of the corresponding 4-hydroxymethyl compound with manganese dioxide in dioxane) with phenylmagnesium bromide in dry THF. Yield: 94% of theory; Melting point: 187-191 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Trityl-1H-imidazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6043254; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33016-47-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 2a (0.50 g, 1.48 mmol), propyl triphenylphosphonium bromide (0.63 g, 1.63 mmol) and NaH (powered 95%, 0.05 g, 2.22 mmol) in anhydrous THF (8 mL), was stirred at rt for 8 h under Ar atmosphere. Then, the reaction mixture was quenched with saturated aqueous NaHCO3 (5 mL) solution and extracted with CH2Cl2 (3 × 15 mL). The organic layer was washed with H2O (1 × 10 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, EtOAc/Hex 1:1) to furnish the Z-3 isomer (0.44 g) which is the sole isolated product. Yield: 81%; Rf 0.63 (EtOAc/Hex 4:1); tR 12.42 min (30% MeCN ? 100% MeCN in 30 min); ESI-MS (m/z): 123.18 [M + H], 243.26 [Tr]; 1H NMR (400 MHz, CDCl3): delta 7.64 (br s, 1H), 7.36-7.35 (m, 9H), 7.16-7.13 (m, 6H), 6.75 (br s, 1H), 6.25 (dt, 1H, J = 1.5, 11.6 Hz), 5.60 (dt, 1H, J = 7.5, 11.6 Hz), 2.28 (quint d, 2H, J = 1.7, 7.5 Hz), 1.00 (t, 3H, J = 7.5 Hz); 13C NMR (160 MHz, CDCl3): delta 141.70, 137.64, 137.15, 134.53, 129.66, 128.29, 128.18, 120.20, 119.00, 76.03, 22.55, 13.79.

The synthetic route of 1-Trityl-1H-imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Agelis, George; Resvani, Amalia; Koukoulitsa, Catherine; Tumova, Tereza; Slaninova, Jirina; Kalavrizioti, Dimitra; Spyridaki, Katerina; Afantitis, Antreas; Melagraki, Georgia; Siafaka, Athanasia; Gkini, Eleni; Megariotis, Grigorios; Grdadolnik, Simona Golic; Papadopoulos, Manthos G.; Vlahakos, Demetrios; Maragoudakis, Michael; Liapakis, George; Mavromoustakos, Thomas; Matsoukas, John; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 352 – 370;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33016-47-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 33016-47-6 as follows.

E (R)-N-[1-(Phenylmethyl)-4-[1-(triphenylmethyl)-1H-imidazol-4-yl]-3-butenyl]benzenesulfonamide A solution of compound D (400 mg, 0.63 mmol) and 1-trityl-4-formylimidazole (320 mg, 0.94 mmol) in methylene chloride was dried over MgSO4. The solids were filtered and the filtrate evaporated to dryness. The white foam residue was diluted with of THF (24 mL) and 3A molecular sieves added. After 1 hour, a solution of lithium bis(trimethylsilyl)amide (1.4 mL, 1M) in THF was added dropwise. After 1 hour, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate and the solution washed with brine, dried (MgSO4) and concentrated. The resulting residue was purified by flash chromatography on silica gel. Elution with 40% ethyl acetate in hexane afforded (108 mg) of the title compound, and (149 mg) of the Z-isomer (Combined yield 67%). MS; (M+H)+=610.

According to the analysis of related databases, 33016-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US6387926; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 33016-47-6, Recommanded Product: 33016-47-6

Under argon atmosphere, 5.6 ML (2.96 mmol, 1 equivalent) of the solution of ethyl bromozincacetate in tetrahydrofuran obtained in Example 43 was added dropwise to a solution of 1 g (2.96 mmol) of 1-trityl-1H-imidazol-4-carbaldehyde in 10 ML of THF at 3?6C. The mixture was stirred at 0?5C for 1 hour and 25 minutes. 5.6 ML (2.96 mmol, 1 equivalent) of the solution of ethyl bromozincacetate in tetrahydrofuran obtained in Example 43 was added dropwise at 0?3C. The mixture was stirred at 2?3C for 5 hours and 30 minutes. 5 ML of 1N hydrochloric acid was added dropwise at 20C or lower, followed by dilution with 30 ML of ethyl acetate.. Then, the layers were separated.. The organic layer was washed successively with 5 ML of 1N hydrochloric acid, 5 ML of water, 5 ML (*2) of an aqueous saturated sodium bicarbonate solution, and 5 ML (*2) of an aqueous saturated sodium chloride solution.. After washing, the organic layer was dried with anhydrous magnesium sulfate.. After concentration under reduced pressure, recrystallization with 3 ML of IPE afforded 1.16 g of the desired product (yield 92%).1H NMR (CDCl3): delta 1.22 (3H, t, J=7.1 Hz), 2.83-2.86 (2H, m), 4.13 (2H, q, J=7.1 Hz), 5.09-5.13 (1H, m), 6.78 (1H, s), 7.10-7.15 (6H, m), 7.26-7.39 (10, m).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Trityl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1471056; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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,
Imidazole | C3H4N2 – PubChem

Related Products of 33016-47-6, A common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, its 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.

In a 100 ml, three-necked flask fitted with a magnetic stirrer, under inert atmosphere, ethyl iodide (1.1 ml, 0.0136 mol) is dissolved in Et2theta (25 ml). At -70 0C, a1.5 M solution of t-BuLi in pentane (17 ml, 0.026 mol) is added dropwise. The mixture is stirred 0.3 h at this temperature and 0.75 h at room temperature. A solution of 1-trityl-1 H- imidazole-4-carbaldehyde x43 (2 g, 0.00591 mole) in THF (25 ml) is added dropwise at 0 0C. The mixture is stirred for 1 h and poured onto ice. HCI is added until the pH is slightly acid (pH : 3-5) and the aqueous phase is extracted twice with Et^O. The combined organic phases are dried over MgSOphi filtered and concentrated to dryness. The crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4thetaH: 95/4.5/0.5 (v/v/v)) to afford 1.21 g of 1-(1-trityl-1H-imidazol-4-yl)propan-1-ol x88. Yield: 56 %.LC-MS (MH+): 369.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Application of 33016-47-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under argon atmosphere, cinchonine (220 mg, 0.5 mmol) was suspended in tetrahydrofuran (absolute, 1.0 mL), and to this suspension was added a Reformatsky reagent (0.52 M; 7.7 mL, 1.51 mmol) dropwise under ice-cooling. After stirring for 10 minutes, pyridine (0.15 mL, 2 mmol) was added thereto dropwise. After stirring for 20 minutes under ice-cooling, the mixture was cooled to -40C. A solution of 4-formyl-1-trityl-1H-imidazole (0.5 mmol) in tetrahydrofuran (absolute, 2.0 mL) was added dropwise over 10 minutes, and the mixture was stirred at -40 C for 4 hours. To this reaction solution was added 1N HCl (10 mL), which was then extracted with ethyl acetate (10 mL×2). The extracted solution was washed successively with an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution. After the organic layer was dried with sodium sulfate, the solvent was removed under reduced pressure. The residue was analyzed with high performance liquid chromatography. Consequently, the yield was 84% and the enantiomer excess was 66%.1H NMR (400 MHz, CDCl3) delta: 1.42 (9H, s), 2.74 (1H, dd, J = 16.4 and 7.8 Hz), 2.81 (1H, dd, J = 16.4 and 4.6 Hz), 3.42 (1H, d, J = 4.9 Hz), 5.06 (1H, m), 6.79 (1H, s), 7.1-7.2 (7H, m), 7.29-7.36 (8H, m), 7.37 (1H, d, J = 1.4 Hz). IR (KBr) nucm-1: 3197, 2974, 1726, 1493, 1444, 1148, 701. High Performance Liquid Chromatography Column: CHIRALPAK AD Mobile phase: Hexane/2-Propanol (90/10) Flow rate: 1.0 mL/min. Detection: UV (220 nm) Temperature: 30 C Retention Time: 22.5 minutes (enantiomer 16.8 minutes)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Trityl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference of 33016-47-6, The chemical industry reduces the impact on the environment during synthesis 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

1-Trityl-1H-imidazole-4-carboxaldehyde (Daminos-Zeghal S. et al., Tetrahedron, 1997, 53(22), 7605-14) (5 g; 14.8 mmol) is dissolved in dichloromethane (35 ml) under a nitrogen atmosphere and then cooled to -78 C. Methyl trifluoromethanesulfonate (1.7 ml; 14.8 mmol) is added dropwise and the reaction mixture is allowed to warm slowly to room temperature (over 2 hours). Phosphate buffer solution (pH 7; 50 ml) is added and the two-phase mixture is stirred vigorously for 15 minutes. The two phases are then separated and the aqueous phase is extracted three times with dichloromethane. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated. The orange-colored solid obtained is purified by flash chromatography (CH2Cl2, then 10/90 acetone/CH2Cl2 and then 5/95 MeOH/CH2Cl2) to give the desired product (1.39 g; 85%). [0250] 1H NMR, DMSO-d6 (ppm): 3.87 (s, 3H); 7.88 (s, 1H); 8.00 (s, 1H); 9.75 (s, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Trityl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.