Alternatived Products of [ 209216-23-9 ]
Product Details of [ 209216-23-9 ]
| CAS No. : | 209216-23-9 |
MDL No. : | MFCD09754448 |
| Formula : |
C12H17N5O4
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | YXPVEXCTPGULBZ-WQYNNSOESA-N |
| M.W : |
295.29
|
Pubchem ID : | 135526609 |
| Synonyms : |
BMS200475 monohydrate;SQ34676 monohydrate;SQ 34,676;BMS 200475;Entecavir (hydrate);Entecavir Hydrate
|
Chemical Name : | 2-amino-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-1,9-dihydro-6H-purin-6-one hydrate |
Safety of [ 209216-23-9 ]
Application In Synthesis of [ 209216-23-9 ]
* 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 [ 209216-23-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|
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7 EXAMPLE 7
EXAMPLE 7 Employing the above procedures a tablet of 0.5 milligram strength entecavir was prepared. The entecavir was dissolved in upto 17% w/w aqueous povidone solution which was heated at 60 to 70° C. |
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and a second pharmaceutically acceptable agent which comprises one or more of the following: lamivudine;entecavir;telbivudine; |
- 2
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[ 209216-23-9 ]
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[ 544-63-8 ]
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[ 2221944-50-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In pyridine at 20℃; for 6h; |
2.2. Synthesis of lipidic prodrugs of EV
General procedure: We added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 2equiv.) to a solution of EV monohydrate (500 mg, 1.69 mmol) in pyridine(20 ml), corresponding FA (1 equiv.), and N,N-dimethylaminopyridine(DMAP, 0.05 equiv.) at ambient temperature. The reactionmixture was stirred for 6 h at the same temperature and quenched bywater. The reaction mixture was concentrated in vacuo, and dilutedwith 10% methanol in dichloromethane and water. The organic layerwas washed with 1 N HCl and brine, dried over magnesium sulfate, andconcentrated in vacuo. Purification of the residue via flash columnchromatography on silica gel methanol/chloroform=1:20-1:10) yielded the lipidic compounds as white solids. |
Reference：
[1]Ho, Myoung Jin; Lee, Dae Ro; Im, Sung Hyun; Yoon, Jeong A.; Shin, Chang Yong; Kim, Hyun Jung; Jang, Sun Woo; Choi, Young Wook; Han, Young Taek; Kang, Myung Joo
[International Journal of Pharmaceutics, 2018, vol. 543, # 1-2, p. 52 - 59]
- 3
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[ 209216-23-9 ]
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[ 57-10-3 ]
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[ 2221944-51-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In pyridine at 20℃; for 6h; |
2.2. Synthesis of lipidic prodrugs of EV
General procedure: We added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 2equiv.) to a solution of EV monohydrate (500 mg, 1.69 mmol) in pyridine(20 ml), corresponding FA (1 equiv.), and N,N-dimethylaminopyridine(DMAP, 0.05 equiv.) at ambient temperature. The reactionmixture was stirred for 6 h at the same temperature and quenched bywater. The reaction mixture was concentrated in vacuo, and dilutedwith 10% methanol in dichloromethane and water. The organic layerwas washed with 1 N HCl and brine, dried over magnesium sulfate, andconcentrated in vacuo. Purification of the residue via flash columnchromatography on silica gel methanol/chloroform=1:20-1:10) yielded the lipidic compounds as white solids. |
Reference：
[1]Ho, Myoung Jin; Lee, Dae Ro; Im, Sung Hyun; Yoon, Jeong A.; Shin, Chang Yong; Kim, Hyun Jung; Jang, Sun Woo; Choi, Young Wook; Han, Young Taek; Kang, Myung Joo
[International Journal of Pharmaceutics, 2018, vol. 543, # 1-2, p. 52 - 59]
- 4
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[ 209216-23-9 ]
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[ 57-11-4 ]
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[ 2221944-52-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In pyridine at 20℃; for 6h; |
2.2. Synthesis of lipidic prodrugs of EV
General procedure: We added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 2equiv.) to a solution of EV monohydrate (500 mg, 1.69 mmol) in pyridine(20 ml), corresponding FA (1 equiv.), and N,N-dimethylaminopyridine(DMAP, 0.05 equiv.) at ambient temperature. The reactionmixture was stirred for 6 h at the same temperature and quenched bywater. The reaction mixture was concentrated in vacuo, and dilutedwith 10% methanol in dichloromethane and water. The organic layerwas washed with 1 N HCl and brine, dried over magnesium sulfate, andconcentrated in vacuo. Purification of the residue via flash columnchromatography on silica gel methanol/chloroform=1:20-1:10) yielded the lipidic compounds as white solids. |
Reference：
[1]Ho, Myoung Jin; Lee, Dae Ro; Im, Sung Hyun; Yoon, Jeong A.; Shin, Chang Yong; Kim, Hyun Jung; Jang, Sun Woo; Choi, Young Wook; Han, Young Taek; Kang, Myung Joo
[International Journal of Pharmaceutics, 2018, vol. 543, # 1-2, p. 52 - 59]
- 5
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[ 209216-23-9 ]
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[ 1383812-22-3 ]
| Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: triethylamine; dmap / acetonitrile / 20 °C
2: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / acetonitrile; <i>N</i>,<i>N</i>-dimethyl-aniline / 1 h / 70 °C / Cooling with ice |
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- 6
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[ 209216-23-9 ]
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[ 701278-58-2 ]
| Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 3 steps
1: triethylamine; dmap / acetonitrile / 20 °C
2: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / acetonitrile; <i>N</i>,<i>N</i>-dimethyl-aniline / 1 h / 70 °C / Cooling with ice
3: ammonia / methanol / 5 h / 20 °C |
|
- 7
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[ 209216-23-9 ]
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[ 2630939-36-3 ]
| Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 4 steps
1: triethylamine; dmap / acetonitrile / 20 °C
2: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / acetonitrile; <i>N</i>,<i>N</i>-dimethyl-aniline / 1 h / 70 °C / Cooling with ice
3: ammonia / methanol / 5 h / 20 °C
4: zinc; ammonium hydroxide / 55 °C |
|
- 8
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[ 209216-23-9 ]
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[ 108-24-7 ]
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[ 2630942-02-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 88% |
With dmap; triethylamine In acetonitrile at 20℃; |
18 Synthesis of Intermediate 18-2:
Entecavir monohydrate (purchased from Taizhou Bona ChemicalCo., Ltd.) (295mg, 1.0mmol), triethylamine (1.01g, 10mmol), DMAP (24mg, 0.2 mmol) was added to acetonitrile (10 mL), followed by acetic anhydride (357.3 mg, 3.5 mmol), and stirred at room temperature. The reaction liquid gradually changed from turbidity to clear, and then insolublematter gradually precipitated out. After reacting overnight, it was filtered and washed with acetonitrile to obtain 320mg of white solid with a yield of 88%. |
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