Alternatived Products of [ 97980-71-7 ]
Product Details of [ 97980-71-7 ]
CAS No. : | 97980-71-7 |
MDL No. : | MFCD00708020 |
Formula : |
C17H12O6
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
312.27
|
Pubchem ID : | - |
Synonyms : |
|
Safety of [ 97980-71-7 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 97980-71-7 ]
* 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 [ 97980-71-7 ]
- 1
-
[ 97980-71-7 ]
-
[ 629-96-9 ]
-
[ 1217342-37-4 ]
Yield | Reaction Conditions | Operation in experiment |
33% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 80 - 90℃; for 12h; |
|
Reference:
[1]Location in patent: experimental part
Lv, Peng-Cheng; Wang, Kai-Rui; Li, Qing-Shan; Chen, Jin; Sun, Juan; Zhu, Hai-Liang
[Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1117 - 1123]
- 2
-
[ 2150-45-0 ]
-
[ 97980-71-7 ]
-
2-hydroxy-6-(2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)benzoic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
71% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 3
-
[ 97980-71-7 ]
-
[ 2150-46-1 ]
-
[ 1235837-61-2 ]
Yield | Reaction Conditions | Operation in experiment |
74% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 4
-
[ 97980-71-7 ]
-
[ 391-92-4 ]
-
[ 1235837-69-0 ]
Yield | Reaction Conditions | Operation in experiment |
75% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 5
-
[ 97980-71-7 ]
-
[ 4068-78-4 ]
-
[ 1235837-67-8 ]
Yield | Reaction Conditions | Operation in experiment |
73% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 6
-
[ 97980-71-7 ]
-
[ 22717-57-3 ]
-
[ 1235837-63-4 ]
Yield | Reaction Conditions | Operation in experiment |
71% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; |
4.3.3. General procedure for the preparation of compounds 5a-5t
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 7
-
[ 97980-71-7 ]
-
[ 4670-56-8 ]
-
[ 1235837-71-4 ]
Yield | Reaction Conditions | Operation in experiment |
70% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; |
4.3.3. General procedure for the preparation of compounds 5a-5t
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 8
-
[ 97980-71-7 ]
-
[ 6342-70-7 ]
-
[ 1235837-77-0 ]
Yield | Reaction Conditions | Operation in experiment |
73% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 9
-
[ 97980-71-7 ]
-
[ 22717-56-2 ]
-
[ 1235837-75-8 ]
Yield | Reaction Conditions | Operation in experiment |
74% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 10
-
[ 97980-71-7 ]
-
[ 22717-55-1 ]
-
[ 1235837-73-6 ]
Yield | Reaction Conditions | Operation in experiment |
71% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 11
-
[ 97980-71-7 ]
-
[ 52159-67-8 ]
-
3-chloro-2-(2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)benzoic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
73% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12.0h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 12
-
[ 97980-71-7 ]
-
[ 176750-70-2 ]
-
2-chloro-6-(2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)benzoic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
72% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20.0℃; for 12.0h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 13
-
[ 97980-71-7 ]
-
[ 28165-45-9 ]
-
3-bromo-2-(2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)benzoic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
70% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 14
-
[ 97980-71-7 ]
-
[ 72373-81-0 ]
-
2-fluoro-6-(2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetoxy)benzoic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
70% |
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; |
General procedure: A solution of compound 3, substituted methyl salicylate (4a-4t), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC.HCl), N-Hydroxybenzotriazole (HOBt) and 4-dimethylaminopyridine (DMAP) in DMF (50 mL) was stirred for 12 h at room temperature. Then, compounds 5a-5t were obtained by subsequent purification with flash chromatography (acetate: petroleum ether = 1:5-1:2). |
- 15
-
[ 98198-48-2 ]
-
[ 97980-71-7 ]
-
N-(4-bromo-3-methylphenyl)-2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
50% |
|
General procedure: To a solution of the carboxylic acid 7 (31.4 mg, 0.1 mmol) in anhydrous CH2Cl2 was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (5.0 equiv) and 4-dimethylaminopyridine (1.0 equiv) at 0 C. The reaction mixture was stirred for 10 min at the same temperature. To the reaction mixture was added amine (3.0 equiv) and then the reaction mixture was slowly warmed to room temperature. After 12 hours at the same temperature, the reaction mixture was diluted with CH2Cl2 and washed with aqueous NH4Cl. The organic layer was dried over MgSO4. The mixture was concentrated at reduced pressure. The residue was purified by flash chromatography on silica gel (CH2Cl2/methanol, 15:1) to give desired amide 12 (32.7 mg, 70%). |
- 16
-
[ 97980-71-7 ]
-
[ 21717-95-3 ]
-
[ 1447463-72-0 ]
Yield | Reaction Conditions | Operation in experiment |
63% |
|
General procedure: To a solution of the carboxylic acid 7 (31.4 mg, 0.1 mmol) in anhydrous CH2Cl2 was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (5.0 equiv) and 4-dimethylaminopyridine (1.0 equiv) at 0 C. The reaction mixture was stirred for 10 min at the same temperature. To the reaction mixture was added amine (3.0 equiv) and then the reaction mixture was slowly warmed to room temperature. After 12 hours at the same temperature, the reaction mixture was diluted with CH2Cl2 and washed with aqueous NH4Cl. The organic layer was dried over MgSO4. The mixture was concentrated at reduced pressure. The residue was purified by flash chromatography on silica gel (CH2Cl2/methanol, 15:1) to give desired amide 12 (32.7 mg, 70%). |
- 17
-
[ 2038-03-1 ]
-
[ 97980-71-7 ]
-
[ 1447463-78-6 ]
Yield | Reaction Conditions | Operation in experiment |
68% |
Stage #1: 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 4-(2-AMINOETHYL)MORPHOLINE In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; |
General Procedure (GP) for Synthesis Amide
General procedure: To a solution of the carboxylic acid 7 (31.4 mg, 0.1 mmol) in anhydrous CH2Cl2 was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (5.0 equiv) and 4-dimethylaminopyridine (1.0 equiv) at 0 °C. The reaction mixture was stirred for 10 min at the same temperature. To the reaction mixture was added amine (3.0 equiv) and then the reaction mixture was slowly warmed to room temperature. After 12 hours at the same temperature, the reaction mixture was diluted with CH2Cl2 and washed with aqueous NH4Cl. The organic layer was dried over MgSO4. The mixture was concentrated at reduced pressure. The residue was purified by flash chromatography on silica gel (CH2Cl2/methanol, 15:1) to give desired amide 12 (32.7 mg, 70%). |
63.4% |
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In dichloromethane at 60℃; |
|
Reference:
[1]Choe, Hyeonjeong; Kim, Jieun; Hong, Sungwoo
[Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 15, p. 4324 - 4327]
[2]Xiao, Zhu-Ping; Wei, Wei; Liu, Qi; Wang, Peng-Fei; Luo, Xing; Chen, Fang-Yuan; Cao, Yang; Huang, Hong-Xia; Liu, Mi-Mi; Zhu, Hai-Liang
[RSC Advances, 2017, vol. 7, # 11, p. 6193 - 6201]
- 18
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[ 5805-57-2 ]
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[ 97980-71-7 ]
-
N-((1H-benzo[d]imidazol-2-yl)methyl)-2-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
79% |
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1.25h; |
General procedure: To a stirring solution of appropriately substituted 11 or 12 (0.76 mmol) in DMF at RT, HATU (0.83 mmol) and diisopropylethylamine (2.29 mmol) were added. Appropriately, substituted amine (0.76 mmol) was added after 15 min and stirring continued for another 1 h at rt. The reaction was monitored by TLC and then poured into ice water with stirring. On complete consumption of reactants, the reaction mixture was cooled to room temperature. The so-formed precipitate was filtered off and chromatographed on a silica gel (Hexane/EtOAc) on silica gel (100?200 mesh). |
- 19
-
[ 7720-39-0 ]
-
[ 97980-71-7 ]
-
2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)-N-(1H-imidazol-2-yl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
86% |
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1.25h; |
General procedure: To a stirring solution of appropriately substituted 11 or 12 (0.76 mmol) in DMF at RT, HATU (0.83 mmol) and diisopropylethylamine (2.29 mmol) were added. Appropriately, substituted amine (0.76 mmol) was added after 15 min and stirring continued for another 1 h at rt. The reaction was monitored by TLC and then poured into ice water with stirring. On complete consumption of reactants, the reaction mixture was cooled to room temperature. The so-formed precipitate was filtered off and chromatographed on a silica gel (Hexane/EtOAc) on silica gel (100-200 mesh). |