* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With 8-quinolinol; sodium hydroxide; copper dichloride In water at 20℃; for 0.333333 h; Sealed tube; Microwave irradiation
General procedure: In a 10 mL glass tube 2-iodobenzoic acid (1.0 mmol), acetamidine hydrochloride (1.2 mmol), CuCl2 (0.1 mmol), L2 (0.1 mmol), and NaOH (4.0 equiv.) and 3.0 mL water were placed. The vessel was then sealed with a septum and placed into the microwave cavity. Initial microwave irradiation of 120 W by using a CEM Discover microwave synthesizer was used at the room temperature for 20 min. The reaction mixture was stirred continuously during the reaction. After completion of the reaction, the solvent was removed in vacuo. The residue was purified by silica gel column chromatography to afford the corresponding product. All the products were confirmed by NMR and MS spectroscopic analysis.
With ytterbium(III) triflate In 1,3,5-trimethyl-benzene at 165℃; for 6 h; Inert atmosphere
General procedure: A mixture of 2-aminobenzamide (1, 4.0 mmol), carboxamide (2, 6.0 mmol), Yb(OTf)3 (0.20 mmol,5.0 molpercent), and mesitylene (5.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 120-165 oC (bath temp.) for 6 h with stirring. Then, the reaction mixture was cooled to room temperature, and analyzed by GLC, GC-MS (EI), and LC-MS (ESI). After evaporation of mesitylene under vacuum,the products (3) were isolated by recrystallization from MeOH/hexane and/or medium pressure column chromatography on silica gel (eluent: EtOAc/hexane = 50/50 ~ EtOAc 100percent. For 3j, eluent:MeOH/CHCl3 = 50/50). 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6. The analytical and spectral data of 3a-e,38 3f,39 3g,40 3h,41 and3j,42 were consistent with those reported previously. The product, 3i, was characterized below.
50%
at 160℃; for 0.333333 h; Microwave irradiation
Example30: (4-Chloro-phenyl)-{4-[(3S,4S)-4-hydroxy-l-(6-methoxy-quinazolin-4yl)- pyrrolidin-3-yl]-piperazin-l-yl}-methanone[00243] Step 1. 6-Methoxy-3H-quinazolin-4-one[00244] To 1.025 mmoles of 2-amino-5-methoxy anthranilic acid add 6.14 mmoles of formamide and microwave reaction mixture for 20mins at 1600C. After cooling the solid was diluted with 1OmL ethanol, the mixture was heated to reflux and allowed to cool slowly. The solid obtained was filtered and washed with cold ethanol and vaccum dried to give the title compound in 50percent yield.[00245] LC-MS: m/z = 177 (M+ +1)
[0144] A mixture of 2-amino-5-methoxybenzoic acid (10.0 g, 59.9 mmol), formamidine acetate (12.3 g, 119 mmol) in 80 mL of 2-methoxyethanol was heated at 125 °C for 18 hours. After being cooled to room temperature, the precipitate was collected by filtration, washed twice with 2-methoxyethanol and dried in the vacuum to provide 6-methoxyquinazolin- 4(3H)-one (9.1 g, 87percent yield).
at 130℃; for 2 h; Inert atmosphere; Microwave irradiation
5-methoxybenzamide (83 mg, 0.5 mmol), [Cp * Ir (2,2'-bpyO) (H2O)](5.4 mg, 0.005 mmol, 1 molpercent), cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.) And methanolInto a dry 5mL microwave reaction tube. Nitrogen protection in microwave tube placed in a single mode pressure microwave synthesizerCEM, USA). After the reaction mixture was reacted at 130 ° C for 2 hours, it was cooled to room temperature. Solvent was removed by rotary evaporation and then passedColumn chromatography (developing solvent: petroleum ether / ethyl acetate) gave the pure target compound in a yield of 91percent
Reference：
[1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337646, 2017, A, . Location in patent: Paragraph 0045; 0046; 0047; 0048
5
[ 6313-33-3 ]
[ 22921-68-2 ]
[ 19181-64-7 ]
Yield
Reaction Conditions
Operation in experiment
55%
With 8-quinolinol; sodium hydroxide; copper dichloride In water at 20℃; for 0.333333 h; Sealed tube; Microwave irradiation
General procedure: In a 10 mL glass tube 2-iodobenzoic acid (1.0 mmol), acetamidine hydrochloride (1.2 mmol), CuCl2 (0.1 mmol), L2 (0.1 mmol), and NaOH (4.0 equiv.) and 3.0 mL water were placed. The vessel was then sealed with a septum and placed into the microwave cavity. Initial microwave irradiation of 120 W by using a CEM Discover microwave synthesizer was used at the room temperature for 20 min. The reaction mixture was stirred continuously during the reaction. After completion of the reaction, the solvent was removed in vacuo. The residue was purified by silica gel column chromatography to afford the corresponding product. All the products were confirmed by NMR and MS spectroscopic analysis.
Reference：
[1] Journal of Medicinal Chemistry, 1983, vol. 26, # 3, p. 420 - 425
[2] Chemistry and Biodiversity, 2017, vol. 14, # 4,
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 1301
[4] Journal of the Chemical Society, 1947, p. 890,894
[5] Yakugaku Zasshi, 1943, vol. 63, p. 445,447[6] Chem.Abstr., 1951, p. 5156
7
[ 1882-69-5 ]
[ 19181-64-7 ]
Reference：
[1] Journal of the American Chemical Society, 1946, vol. 68, p. 1301
[2] Journal of the Chemical Society, 1947, p. 890,894
[3] Yakugaku Zasshi, 1943, vol. 63, p. 445,447[4] Chem.Abstr., 1951, p. 5156
With 8-quinolinol; sodium hydroxide; copper dichloride; In water; at 20℃; for 0.333333h;Sealed tube; Microwave irradiation;
General procedure: In a 10 mL glass tube 2-iodobenzoic acid (1.0 mmol), acetamidine hydrochloride (1.2 mmol), CuCl2 (0.1 mmol), L2 (0.1 mmol), and NaOH (4.0 equiv.) and 3.0 mL water were placed. The vessel was then sealed with a septum and placed into the microwave cavity. Initial microwave irradiation of 120 W by using a CEM Discover microwave synthesizer was used at the room temperature for 20 min. The reaction mixture was stirred continuously during the reaction. After completion of the reaction, the solvent was removed in vacuo. The residue was purified by silica gel column chromatography to afford the corresponding product. All the products were confirmed by NMR and MS spectroscopic analysis.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
