ChemicalBook > Product Catalog >Pharmaceutical intermediates >Heterocyclic compound >N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide

N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide

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N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide manufacturers

N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide Basic information
Product Name:N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide
Synonyms:N-Acetyl-di-O-acetyl Ganciclovir;N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide;Three acetyl ganciclovir;2-((2-Acetamido-6-oxo-1H-purin-9(6H)-yl)methoxy)propane-1,3-diyl diacetate;Acetamide,N-[9-[[2-(acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]-;Ganciclovir Triacetate;acetic acid [2-[(2-acetamido-6-oxo-3H-purin-9-yl)methoxy]-3-acetyloxypropyl] ester;ACETIC ACID 3-ACETOXY-2-(2-ACETYLAMINO-6-OXO-1,6-DIHYDRO-PURIN-9-YLMETHOXY)-PROPYL ESTER (TRIACETYL-GANCICLOVIR)
CAS:86357-14-4
MF:C15H19N5O7
MW:381.34
EINECS:617-838-3
Product Categories:Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;86357-14-4
Mol File:86357-14-4.mol
N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide Structure
N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide Chemical Properties
Melting point 174 °C
density 1.50
storage temp. Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly, Heated)
form Solid
pka8.74±0.20(Predicted)
color White to Pale Beige
InChIInChI=1S/C15H19N5O7/c1-8(21)17-15-18-13-12(14(24)19-15)16-6-20(13)7-27-11(4-25-9(2)22)5-26-10(3)23/h6,11H,4-5,7H2,1-3H3,(H2,17,18,19,21,24)
InChIKeyPEZKHGVZZSQDPY-UHFFFAOYSA-N
SMILESC(NC1NC(=O)C2=C(N=1)N(COC(COC(C)=O)COC(C)=O)C=N2)(=O)C
CAS DataBase Reference86357-14-4(CAS DataBase Reference)
Safety Information
HS Code 2933.99.9701
MSDS Information
N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide Usage And Synthesis
Chemical PropertiesLight Brown Solid
UsesGanciclovir derivative.
Synthesis
1,3-Diacetoxy-2-(acetoxymethoxy)propane

86357-13-3

N2,9-Diacetylguanine

3056-33-5

N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide

86357-14-4

The general procedure for the synthesis of 2-((2-acetylamino-6-oxo-1H-purin-9(6H)-yl)methoxy)propane-1,3-diyl diacetate from 2-(acetyloxymethoxy)-1,3-propanediol diacetate and N-(9-acetyloxy-6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide is as follows: first, 50.0 g ( 0.21 mol, 1.0 eq.) of 20.0-diacetylguanine, 104.2 g (0.42 mol, 2.0 eq.) of 1,3-diacetoxy-2-(acetyloxymethoxy)propane and 3.0 g (0.021 mol, 0.1 eq.) of boron trifluoride ether compounds were mixed with 200 g of N,N-dimethylformamide in a microwave reactor. The reaction mixture was heated to 100 °C and maintained at this temperature for 10 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the mixture was cooled to room temperature. Subsequently, 450 g of ethyl acetate was added to the mixture and refluxed for 1 hour, after which the temperature was reduced to 0-5 °C and maintained for 1 hour. After filtration and drying process, 68.3 g of triacetyl ganciclovir compound (2) was obtained in 85.3% yield and 95.6% purity, while 3.1% of compound (3) was obtained.

References[1] Patent: CN108467396, 2018, A. Location in patent: Paragraph 0030; 0031; 0036; 0037; 0040; 0041; 0044; 0045
N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide Preparation Products And Raw materials
Raw materialsGanciclovir-->1,3-Diacetoxy-2-(acetoxymethoxy)propane-->N2,9-Diacetylguanine-->Acetic anhydride-->Boron trifluoride diethyl etherate-->N,N-Dimethylformamide
Preparation ProductsGanciclovir Mono-O-acetate
Tag:N-[9-[[2-(Acetyloxy)-1-[(acetyloxy)methyl]ethoxy]methyl]-6,9-dihydro-6-oxo-1H-purin-2-yl]acetamide(86357-14-4) Related Product Information
2-Ethoxyphenol acetic acid, triethoxy-, ethyl ester Ethoxyquin Dihydromyrcenol Ganciclovir Methyl acrylate Methyl salicylate 4-Ethoxyphenol Methanol Kresoxim-methyl Valganciclovir Methylparaben Tribenuron methyl Basic Violet 1 Ganciclovir sodium Diethoxymethane Methyl 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine