Alternatived Products of [ 20389-10-0 ]
Product Details of [ 20389-10-0 ]
| CAS No. : | 20389-10-0 |
MDL No. : | MFCD02055964 |
| Formula : |
C16H10ClNO2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | QPDXYIKQOBZSGQ-UHFFFAOYSA-N |
| M.W : |
283.71
|
Pubchem ID : | 276278 |
| Synonyms : |
|
Application In Synthesis of [ 20389-10-0 ]
* 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.
- Downstream synthetic route of [ 20389-10-0 ]
- 1
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[ 20389-10-0 ]
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[ 883526-41-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With oxalyl dichloride In N,N-dimethyl-formamide for 24h; |
|
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With thionyl chloride Heating; |
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With thionyl chloride In toluene Reflux; |
5.12 General procedure for preparation of 2-arylquinoline-4-carbonyl chloride (13a-h and 14a-g)
General procedure: Various substituted 2-arylquinoline-4-carboxylic acids 11a-h and 12a-g (0.01mol) were added to thionyl chloride (15mL), respectively, and refluxed for 5-7h. The reaction mixture was evaporated to yield corresponding 2-arylquinoline-4-carbonyl chloride 13a-h and 14a-g. |
Reference：
[1]Giardina, Giuseppe A. M.; Sarau, Henry M.; Farina, Carlo; Medhurst, Andrew D.; Grugni, Mario; Raveglia, Luca F.; Schmidt, Dulcie B.; Rigolio, Roberto; Luttmann, Mark; Vecchietti, Vittorio; Hay, Douglas W. P.
[Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1794 - 1807]
[2]Li, Jian; Chen, Jing; Gui, Chunshan; Zhang, Li; Qin, Yu; Xu, Qiang; Zhang, Jian; Liu, Hong; Shen, Xu; Jiang, Hualiang
[Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2209 - 2224]
[3]Li, Sai; Huang, Qiang; Liu, Yajing; Zhang, Xiaolong; Liu, Shuang; He, Chao; Gong, Ping
[European Journal of Medicinal Chemistry, 2013, vol. 64, p. 62 - 73]
- 2
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[ 20389-10-0 ]
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[ 63-74-1 ]
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2-(3-chlorophenyl)-N-(4-sulfamoylphenyl)quinoline-4-carboxamide
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 93% |
Stage #1: 2-(3-Chlor-phenyl)-chinolin-4-carbonsaeure With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: sulfanilamide In N,N-dimethyl-formamide at 20℃; |
4.1.2 General procedure for the synthesis of benzene sulfonamide linked 2-phenylquinoline derivatives (5a-j, 7a-k, 9a-k)
General procedure: To a solution of compound 3 (1 equiv.) in dry DMF (2mL) were added EDCI (1.2 equiv.), HOBt (1.2 equiv.) and kept on stirring for 1h at room temperature. The benzene sulfonamide amine (4, 6, 8) (1 equiv.) was added to the reaction mixture and continued stirring until completion and monitored by TLC. The reaction mixture was quenched with ice and the solid was filtered and washed 2-3 times with cold water and dried and purified using column chromatography to give the pure products (5a-j, 7a-k, 9a-k) with 78-98% yield. |
| 93% |
Stage #1: 2-(3-Chlor-phenyl)-chinolin-4-carbonsaeure With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: sulfanilamide In N,N-dimethyl-formamide at 20℃; |
4.1.2 General procedure for the synthesis of benzene sulfonamide linked 2-phenylquinoline derivatives (5a-j, 7a-k, 9a-k)
General procedure: To a solution of compound 3 (1 equiv.) in dry DMF (2mL) were added EDCI (1.2 equiv.), HOBt (1.2 equiv.) and kept on stirring for 1h at room temperature. The benzene sulfonamide amine (4, 6, 8) (1 equiv.) was added to the reaction mixture and continued stirring until completion and monitored by TLC. The reaction mixture was quenched with ice and the solid was filtered and washed 2-3 times with cold water and dried and purified using column chromatography to give the pure products (5a-j, 7a-k, 9a-k) with 78-98% yield. |
Reference：
[1]Angeli, Andrea; Arifuddin, Mohammed; Sahoo, Santosh Kumar; Singh, Priti; Supuran, Claudiu T.; Swain, Baijayantimala; Yaddanapudi, Venkata Madhavi
[European Journal of Medicinal Chemistry, 2022, vol. 234]
[2]Angeli, Andrea; Arifuddin, Mohammed; Sahoo, Santosh Kumar; Singh, Priti; Supuran, Claudiu T.; Swain, Baijayantimala; Yaddanapudi, Venkata Madhavi
[European Journal of Medicinal Chemistry, 2022, vol. 234]
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