OMeprazole N-Methyl 5-Methoxy Analog

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OMeprazole N-Methyl 5-Methoxy Analog Basic information
Synthesis
Product Name:OMeprazole N-Methyl 5-Methoxy Analog
Synonyms:EsoMeprazole related substance H193/61;omeprazole Impurity III (CP);N-Methyl OMeprazole;5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]sulfinyl]-1-Methyl-;5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]sulfinyl]-1-Methyl-1H-benziMidazole;6-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]sulfinyl]-1-Methyl-1H-benziMidazole;N-Methyl OMeprazole (Mixture of isoMers with the Methylated nitrogens of iMidazole);EsoMeprazole H193/61
CAS:89352-76-1
MF:C18H21N3O3S
MW:359.44
EINECS:
Product Categories:Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds
Mol File:89352-76-1.mol
OMeprazole N-Methyl 5-Methoxy Analog Structure
OMeprazole N-Methyl 5-Methoxy Analog Chemical Properties
Melting point 132-135°C
Boiling point 585.8±60.0 °C(Predicted)
density 1.30
storage temp. -20°C Freezer
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form Solid
pka4.74±0.40(Predicted)
color White to Light Brown
Major Applicationpharmaceutical (small molecule)
InChIInChI=1S/C18H21N3O3S/c1-11-9-19-15(12(2)17(11)24-5)10-25(22)18-20-14-8-13(23-4)6-7-16(14)21(18)3/h6-9H,10H2,1-5H3
InChIKeyRUGQJBJNYIHOIW-UHFFFAOYSA-N
SMILESC1(S(CC2=NC=C(C)C(OC)=C2C)=O)N(C)C2=CC=C(OC)C=C2N=1
Safety Information
WGK Germany WGK 3
HS Code 29339900
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 3 Oral
MSDS Information
OMeprazole N-Methyl 5-Methoxy Analog Usage And Synthesis
Synthesis

Synthetic route of N-Methyl OMeprazole (Mixture of isoMers with the Methylated nitrogens of iMidazole)

A solution of dimethyl sulfate (2.0 equivalents) in CH2Cl2 was added to a solution of esomeprazole and DBU (1,8-diazabicyclo-[5.4.0]undec-7-ene, 1.2 equivalents) at room temperature. The mixture was then stirred while monitoring the reaction by thin-layer chromatography. After the reaction was complete, water was added to the reaction mixture and it was stirred vigorously for 30 minutes.

The mixture was then extracted with CH₂Cl₂, the organic layer was washed with 1N NaHCO₃ and water, dried over anhydrous MgSO₄, and concentrated on a rotary evaporator. The resulting oil was purified by short silica gel column chromatography (CH₂Cl₂ to 2% MeOH CH₂Cl₂ solution) to give OMeprazole N-Methyl 5-Methoxy Analog.
Chemical PropertiesLight Tan Solid
Uses(5-Desmethoxy-6-methoxy) 1-N-Methyl Omeprazole is an impurity of Omeprazole (O635000). Omeprazole covalently binds to proton pump. It inhibits gastric secretion and it is used as an anttiulcerative.
UsesOmeprazole (O635000) impurity.
OMeprazole N-Methyl 5-Methoxy Analog Preparation Products And Raw materials
Tag:OMeprazole N-Methyl 5-Methoxy Analog(89352-76-1) Related Product Information
5-Methoxy-2-[((4-methoxy-3,5-dimethyl-1-oxido-2-pyridinyl)methyl)sulfinyl]-benzimidazole Omeprazole EP Impurity G Esomeprazole Ufiprazole 8-Methoxy-1,3-dimethyl-12-thioxo-pyrido[123,4]imidazo[1,2-a]benzimidazol-2- (12H)-one OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS) EsoMeprazole related substance H193/61 (R)-Omeprazole Sodium Salt Omeprazole