Cas no 924663-38-7 (Rabeprazole N-Oxide)

Rabeprazole N-Oxide structure
Rabeprazole N-Oxide structure
Product Name:Rabeprazole N-Oxide
CAS No:924663-38-7
MF:C18H21N3O4S
MW:375.442043066025
CID:827169
PubChem ID:16095899
Update Time:2024-12-09

Rabeprazole N-Oxide Chemical and Physical Properties

Names and Identifiers

    • 2-(((1H-Benzo[d]imidazol-2-yl)sulfinyl)methyl)-4-(3-methoxypropoxy)-3-methylpyridine 1-oxide
    • Rabeprazole N-Oxide
    • 2-[[4-(3-methoxypropoxy)-3-methyl-1-oxidopyridin-1-ium-2-yl]methylsulfinyl]-1H-benzimidazole
    • 2-[[[1-Oxide-4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-1H-benzimida
    • 2-[[[4-(3-METHOXYPROPOXY)-3-METHYL-1-OXIDO-PYRIDIN-2-YL]METHYL]SULFINYL]-1H-BENZO[D]IMIDAZOLE
    • 2-[[[4-[3-methoxypropoxy]-3-methyl-2-pyridinyl]-methyl]sulfinyl]-1H-benzimidazole N-oxide
    • 2-[4-(3-methoxypropoxy)-3-methyl-1-oxypyridin-2-yl-methylsulfinyl]-1H-benzimidazole
    • 2-{[4-(3-methoxypropoxy)-3-methyl-1-oxidopyridin-2-yl]methylsulfinyl}-1H-benzoimidazole
    • 2-[[4-(3-Methoxypropoxy)-3-methyl-1-oxypyridin-2-yl]methylsulfinyl]-1H-benzimidazole
    • 2-[[[4-(3-Methoxypropoxy)-3-methyl-1-oxido-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole (ACI)
    • 2-(((4-(3-Methoxypropoxy)-3-methyl-1-oxopyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole
    • 2-(((4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl-1-oxide)methyl)sulphinyl)-1H-benzimidazoleRabeprazole N-oxide
    • DTXSID70582520
    • 2-({[4-(3-Methoxypropoxy)-3-methyl-1-oxido-2-pyridinyl]methyl}sulfinyl)-1H-benzimidazole
    • RABEPRAZOLE SODIUM IMPURITY D (EP IMPURITY)
    • DB-226381
    • 1H-BENZIMIDAZOLE, 2-(((4-(3-METHOXYPROPOXY)-3-METHYL-1-OXIDO-2-PYRIDINYL)METHYL)SULFINYL)-
    • RABEPRAZOLE N-OXIDE (USP IMPURITY)
    • AKOS022186226
    • EC 642-214-2
    • 2-(((1H-benzo[d]imidazol-2-yl)sulfinyl)methyl)-4-(3-methoxypropoxy)-3-methylpyridine 1-oxide (Rabeprazole Impurity
    • CS-0166555
    • 17Q1V00385
    • AS-83386
    • Rabeprazole Impurity
    • F19231
    • 2-((4-(3-Methoxypropoxy)-3-methyl-1-oxypyridin-2-yl)methylsulfinyl)-1H-benzimidazole
    • RABEPRAZOLE N-OXIDE [USP IMPURITY]
    • Q27251924
    • 924663-38-7
    • RABEPRAZOLE SODIUM IMPURITY D [EP IMPURITY]
    • Rabeprazole Impurity B
    • 2-(((RS)-(1H-BENZIMIDAZOL-2-YL)SULFINYL)METHYL)-4-(3-METHOXYPROPOXY)-3-METHYLPYRIDINE 1-OXIDE
    • NS00004508
    • UNII-17Q1V00385
    • Inchi: 1S/C18H21N3O4S/c1-13-16(21(22)9-8-17(13)25-11-5-10-24-2)12-26(23)18-19-14-6-3-4-7-15(14)20-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,19,20)
    • InChI Key: ZOEQFVVMBAVTRU-UHFFFAOYSA-N
    • SMILES: [O-][N+]1C(CS(C2NC3C(=CC=CC=3)N=2)=O)=C(C)C(OCCCOC)=CC=1

Computed Properties

  • Exact Mass: 376.13300
  • Monoisotopic Mass: 375.12527733g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 8
  • Complexity: 470
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.1
  • Topological Polar Surface Area: 109?2

Experimental Properties

  • Density: 1.4±0.1 g/cm3
  • Melting Point: 161-163°C
  • Boiling Point: 699.3±65.0 °C at 760 mmHg
  • Flash Point: 376.7±34.3 °C
  • PSA: 109.72000
  • LogP: 3.49850
  • Vapor Pressure: 0.0±2.2 mmHg at 25°C

Rabeprazole N-Oxide Security Information

Rabeprazole N-Oxide Pricemore >>

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Rabeprazole N-Oxide Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane ;  145 min, 0 °C; 15 min, 0 °C
Reference
Efficient synthesis of N-oxide derivatives: Substituted 2-(2-(pyridyl-N-oxide)methylsulphinyl)benzimidazoles
Ray, Purna C.; Mittapelli, Vasantha; Rohatgi, Amit; Tyagi, Om Dutt, Synthetic Communications, 2007, 37(17), 2861-2868

Production Method 2

Reaction Conditions
1.1 Reagents: N,N′-Diisopropylethylenediamine Solvents: Water ;  pH 6.5, rt
1.2 Reagents: Hydrogen peroxide Solvents: Chloroform ;  rt; 10 h, rt
1.3 Reagents: N,N′-Diisopropylethylenediamine ;  rt; 60 min, rt; 5 h, rt
1.4 Reagents: Hydrogen peroxide Solvents: Chloroform ;  -10 °C; 1 h, -10 °C
1.5 Reagents: Sulfuric acid Solvents: Water ;  neutralized, 25 °C
Reference
Method for preparation of Rabeprazole intermediate impurity 2-{[4-(3-methoxypropoxy)-3-methyl-pyridin-oxide-2-yl]methylthio}-1H-benzimidazole
, China, , ,

Production Method 3

Reaction Conditions
1.1 Reagents: Potassium bicarbonate Solvents: Dichloromethane ,  Water ;  rt → 0 °C
1.2 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane ;  2 h, 0 °C; 2 h, 0 °C
Reference
Synthetic studies connected with the preparation of H+/K+-ATPase inhibitors rabeprazole and lansoprazole
Radl, Stanislav; Klecan, Ondrej; Havlicek, Jaroslav, Journal of Heterocyclic Chemistry, 2006, 43(6), 1447-1453

Production Method 4

Reaction Conditions
1.1 Reagents: Acetic acid Solvents: Acetonitrile ,  Water ;  pH 5, rt; rt → 5 °C
1.2 Reagents: Chlorosuccinimide ,  Sodium hydroxide Solvents: Water ;  0 - 5 °C; 2 h, 0 - 5 °C
Reference
Process for the preparation of a gastric acid secretion inhibitor
, European Patent Organization, , ,

Production Method 5

Reaction Conditions
1.1 Solvents: Dimethyl sulfoxide ,  Water ;  12 h, rt
Reference
Preparation of high-purity sodium rabeprazole by enzymic oxidation of rabeprazole thioether
, China, , ,

Production Method 6

Reaction Conditions
1.1 Reagents: Sodium hypochlorite Solvents: Acetonitrile ,  Water ;  20 °C; 5 h
1.2 Reagents: Sodium chloride ,  Sodium sulfite
1.3 Reagents: Formic acid ;  pH 5
Reference
Process for the preparation of pyridinylmethylsulfinylbenzimidazoles (Rabeprazole) by reduction of the corresponding pyridine N-oxides
, Canada, , ,

Production Method 7

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Acetone ,  Water ;  1 h, rt
1.2 Reagents: m-Chloroperbenzoic acid Solvents: Chloroform ,  Water ;  30 min, -10 °C; -10 °C
1.3 Reagents: Sodium hydroxide Solvents: Water
1.4 Reagents: Acetic acid ;  pH 8 - 8.5
1.5 Reagents: Sodium hydroxide Solvents: Water ;  basified
1.6 Reagents: Acetic acid ;  pH 8.5 - 9
Reference
Synthesis of metabolites and related substances of rabeprazole, an anti-ulcerative drug
Reddy, Ganta Madhusudhan; Mukkanti, Kaga; Bhaskar, Boluggodu Vijaya; Reddy, Padi Pratap, Synthetic Communications, 2009, 39(2), 278-290

Rabeprazole N-Oxide Raw materials

Rabeprazole N-Oxide Preparation Products

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