117976-90-6

Basic information

• Product Name: Rebeprazole sodium
• Synonyms: 2-[[[4-(3-METHOXYPROPOXY)-3-METHYL-2-PYRIDINYL]METHYL]SULFINYL]-1H-BENZIMIDAZOLE, SODIUM SALT;2-[[[4-(3-METHOXYPROPOXY)-3-METHYLPYRIDIN-2-YL]METHYL]SULFINY]-1H-BENZIMIDAZOLE SODIUM SALT;rebeprazole sodium;sodium 2-[[4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl]methylsulfinyl]benzoimidazole;SODIUM RABEPRAZOLE;PARIET;RABEPRAZOLE SODIUM;RABEPRAZOLE, SODIUM SALT
• CAS NO: 117976-90-6
• Molecular Formula: C₁₈H₂₀N₃O₃S*Na
• Molecular Weight: 381.42
• EINECS: 222-630-7
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Rabeprazole
• Mol File: 117976-90-6.mol

Chemical Properties

• Melting Point: 140-141°C dec.
• Boiling Point: 603.9 °C at 760 mmHg
• Flash Point: 319.1 °C
• Appearance: white to beige/
• Density: 0.45~0.55 g/mL
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: H2O: soluble10mg/mL (clear solution)
• Stability: Hygroscopic
• Merck: 14,8089
• CAS DataBase Reference: Rebeprazole sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Rebeprazole sodium(117976-90-6)
• EPA Substance Registry System: Rebeprazole sodium(117976-90-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 117976-90-6(Hazardous Substances Data)

Usage

Anti-ulcer drug

Rabeprazole sodium is a anti-ulcer disease drug belonging to proton pump inhibitor and is the sodium salt form of Rabeprazole. The Japanese company Eisai had successfully developed it for the first time with the trade name being “Bolite”. The function of the proton pump inhibitors is reducing the gastric acid secretion so that the lesion site can be stable in order to achieving the effect of curing gastric and duodenal ulcers and stomach-esophageal reflux disease. Clinically it is majorly used for the treatment of acid-related diseases such as stomach and duodenal ulcers, peptic ulcer, gastroesophageal reflux disease and zollinger-ellison syndrome. Rabeprazole is a kind of benzimidazole-substituted compounds. It inhibits the secretion of gastric acid through forming bond with the cytoplasmic proton pump in the gastric cavity wall. This product can specifically inhibit the effect of the adenosine triphosphatase that is the key enzyme during the production of stomach acid. It has inhibitory effect on both basal gastric acid and the gastric acid secretion caused by the stimulation. Rabeprazole is white-yellowish-white powder with no odor and a molecular weight being 381.43. This product is highly soluble in water or methanol, also soluble in ethanol or ethyl acetate but almost insoluble in ether or ethane. This product does not exhibit optical activity, has hygroscopic effect. Its melting point is 225 ℃ and its partition coefficient at water/octane system of pH 7.0 is about 214. This product is light yellow film-coated tablets (enteric-coated tablets). Adverse reactions and precautions: gastric cancer should be excluded after use of the drug. Adverse reactions include allergic reactions, palpitations, constipation, diarrhea, headache, edema, leukopenia, AST, ALT, total bilirubin and proteinuria. The combination of Rabeprazole sodium and digoxin can cause increased digoxin concentration. It can’t be taken simultaneously with antacids. Patients of history of drug allergy, cirrhosis, the elderly, pregnant and lactating women, children should take with caution. The above information is edited by the lookchem of Dai Xiongfeng.

Originator

Eisai (Japan)

Biochem/physiol Actions

Rabeprazole sodium is gastric proton pump inhibitor. It suppresses the production of acid in the stomach by inhibiting the gastric H+/K+ATPase (hydrogen-potassium adenosine triphosphatase) at the secretory surface of the gastric parietal cell. Rabeprazole sodium has been used clinically to treat acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevent gastroinetestinal bleeds associated with NSAID use.

Clinical Use

Gastric acid suppression

Drug interactions

Potentially hazardous interactions with other drugs Antifungals: absorption of itraconazole and ketoconazole reduced; avoid with posaconazole. Antivirals: concentration of atazanavir and rilpivirine reduced - avoid; concentration of raltegravir and saquinavir possibly increased - avoid. Clopidogrel: possibly reduced antiplatelet effect. Cytotoxics: possibly reduced excretion of methotrexate; avoid with dasatinib, erlotinib and vandetanib; possibly reduced lapatinib absorption; possibly reduced absorption of pazopanib. Ulipristal: reduced contraceptive effect, avoid with high dose ulipristal.

Metabolism

Rabeprazole is mainly metabolised via nonenzymatic reduction and, to a lesser extent, via the cytochrome P450 isoenzymes CYP2C19 and CYP3A4. Metabolites are excreted principally in the urine (about 90%) with the remainder in the faeces.

InChI:InChI=1/C18H20N3O3S.Na/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18;/h3-4,6-9H,5,10-12H2,1-2H3;/q-1;+1/rC18H20N3NaO3S/c1-13-15(19-9-8-17(13)25-11-5-10-24-2)12-26(23)18-20-14-6-3-4-7-16(14)21(18)22/h3-4,6-9H,5,10-12H2,1-2H3

Synthetic route

rabeprazole (117976-89-3) → Rabeprazole sodium (117976-90-6)

Conditions	Yield
With sodium hydroxide In ethanol Product distribution / selectivity;	100%
With sodium hydroxide In water Product distribution / selectivity;	100%
With sodium carbonate; 2-fluoro-3-chloro-5-(trifluoromethyl)pyridine In ethanol at 35 - 40℃; for 2h; pH=9; Reagent/catalyst; Solvent;	98%

2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylsulfinyl]-1H-benzimidazole, cyclopentylamine salt → Rabeprazole sodium (117976-90-6)

Conditions	Yield
With sodium hydroxide In water Product distribution / selectivity;	100%

2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methysulfinyl]-1H-benzimidazole, sec-butylamine salt → Rabeprazole sodium (117976-90-6)

Conditions	Yield
With sodium hydroxide In water Product distribution / selectivity;	99.3%

2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-vl}methylsulfinyl]-1H-benzimidazole, isopropylamine salt → Rabeprazole sodium (117976-90-6)

Conditions	Yield
With sodium hydroxide In water Product distribution / selectivity;	98%

rabeprazole (117976-89-3) + LY 307640 sulfone (117976-47-3) → rabeprazol sulphone sodium salt + Rabeprazole sodium (117976-90-6)

Conditions	Yield
With sodium hydroxide In methanol at 0 - 50℃; for 4 - 5h; Product distribution / selectivity;	A 0.2% B 95%

2-[4-(3-methoxypropoxy)-3-methyl-1-oxypyridin-2-yl-methylsulfinyl]-1H-benzimidazole sodium salt → Rabeprazole sodium (117976-90-6)

Conditions	Yield
Stage #1: 2-[4-(3-methoxypropoxy)-3-methyl-1-oxypyridin-2-yl-methylsulfinyl]-1H-benzimidazole sodium salt With 2,3-dimethyl-2,3-diaminobutane; sodium methylate; ruthenium trichloride In methanol at 50℃; for 10h; Stage #2: With acetic acid; sodium sulfite In methanol; water at 20℃; pH=6 - 7; Stage #3: With sodium hydroxide; water In ethyl acetate at 20℃; for 24h;	91%
With morpholine; ruthenium trichloride In ethanol at 50℃; for 8h; Product distribution / selectivity;	70%
With morpholine; ethanol; ruthenium trichloride at 50℃; for 8h; Product distribution / selectivity;	70%
With triethyl phosphite; MoCl2O2(dmf)2 In ethanol at 50℃; for 2h; Product distribution / selectivity;	40%
With triethyl phosphite; bis(N,N-dimethylformamide)dichloridodioxidomolybdenum(VI) In ethanol at 50℃; for 2h; Product distribution / selectivity;	40%

2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole sodium salt acetone complex → Rabeprazole sodium (117976-90-6)

Conditions	Yield
Stage #1: 2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole sodium salt acetone complex In methanol at 25℃; Stage #2: In n-heptane at 25℃; for 19h; Product distribution / selectivity;	90%
Stage #1: 2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole sodium salt acetone complex In methanol; isopropyl alcohol Stage #2: In n-heptane at 25℃; for 0.75h; Product distribution / selectivity;	89%
In tert-butyl methyl ether at 25℃; for 1h; Product distribution / selectivity;	89%
Stage #1: 2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole sodium salt acetone complex In isopropyl alcohol at 40℃; Stage #2: In n-heptane at 25℃; for 20h; Product distribution / selectivity;	79%
In n-heptane at 25℃; for 1h; Product distribution / selectivity;

rabeprazole sulfide (117977-21-6) → Rabeprazole sodium (117976-90-6)

Conditions	Yield
Stage #1: rabeprazole sulfide With sodium hydroxide; sodium hypochlorite In pyridine; water at 5 - 8℃; for 4h; Stage #2: With sodium hydroxide; ammonia In methanol; ethyl acetate
With sodium hydroxide; sodium hypochlorite In pyridine; water at 5 - 10℃; for 4h;
Stage #1: rabeprazole sulfide With sodium hypochlorite; sodium hydroxide In methanol; water at -5 - 30℃; Stage #2: With acetic acid In water at 10 - 15℃; pH=8.8 - 9.2; Stage #3: With sodium hydroxide In dichloromethane; water at 25 - 30℃; Concentration;
Multi-step reaction with 2 steps 1: sodium hydroxide; sodium hypochlorite / water; acetonitrile / -8 - -2 °C 2: sodium hydroxide / ethanol / 20 - 25 °C View Scheme
Stage #1: rabeprazole sulfide With sodium hypochlorite; sodium hydroxide In dichloromethane at -5 - 5℃; for 1h; Stage #2: With pyrographite; sodium hydroxide In methanol at 20 - 25℃; for 2h; Concentration;

2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]-methylsulfinyl]-1H-benzimidazole sodium salt; acetone complex → Rabeprazole sodium (117976-90-6)

Conditions	Yield
at 20 - 115℃; under 4 - 650 Torr; for 6.25 - 137h; Product distribution / selectivity;

2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt; acetonitrile complex → Rabeprazole sodium (117976-90-6)

Conditions	Yield
at 105℃; for 5h; Product distribution / selectivity;

2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride + Benzimidazol-2-thiol (134469-07-1) → Rabeprazole sodium (117976-90-6)

Conditions	Yield
Stage #1: 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride; Benzimidazol-2-thiol With sodium hydroxide In water at 20 - 30℃; for 2h; Stage #2: With sodium hydroxide; sodium hypochlorite In pyridine; water at 5 - 10℃; for 4 - 6h;

sodium hydroxide (1310-73-2) + rabeprazole sulfide (117977-21-6) → Rabeprazole sodium (117976-90-6)

Conditions	Yield
With pyrographite In methanol for 0.5h;

sodium hydroxide (1310-73-2) + rabeprazole (117976-89-3) → Rabeprazole sodium (117976-90-6)

Conditions	Yield
In isopropyl alcohol at 30℃; for 0.833333h;

2-chloromethyl-4-(3-methoxy propyloxy)-3-methyl pyridine (117977-20-5) → Rabeprazole sodium (117976-90-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water; ethanol / 25 - 30 °C 1.2: 25 - 30 °C 2.1: sodium hydroxide; sodium hypochlorite / water; acetonitrile / -8 - -2 °C 3.1: sodium hydroxide / ethanol / 20 - 25 °C View Scheme

2-hydroxymethyl-4-(methoxypropoxy)-3-methylpyridine hydrochloride (675198-19-3) → Rabeprazole sodium (117976-90-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride / dichloromethane / -10 - -5 °C 2.1: sodium hydroxide / water; ethanol / 25 - 30 °C 2.2: 25 - 30 °C 3.1: sodium hydroxide; sodium hypochlorite / water; acetonitrile / -8 - -2 °C 4.1: sodium hydroxide / ethanol / 20 - 25 °C View Scheme

2-hydroxymethyl-4-(3-methoxy propoxy)-3-methyl pyridine (118175-10-3) → Rabeprazole sodium (117976-90-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 10 °C 2: sodium hydroxide; sodium hypochlorite / acetonitrile; water / 2 h / 0 - 5 °C 3: sodium hydroxide / methanol / 1 h / 20 °C View Scheme

Benzimidazol-2-thiol (134469-07-1) → Rabeprazole sodium (117976-90-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 10 °C 2: sodium hydroxide; sodium hypochlorite / acetonitrile; water / 2 h / 0 - 5 °C 3: sodium hydroxide / methanol / 1 h / 20 °C View Scheme

Rabeprazole sodium (117976-90-6) → 3-(3-methoxypropoxy)-4-methyl-5H-pyrido[1',2':4,5][1,2,4]thiadiazino[2,3-a]benzimidazol-13-ium perchlorate (1052003-84-5)

Conditions	Yield
With perchloric acid In methanol; water at -25℃; for 16h;	100%

(4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester (651728-13-1) + Rabeprazole sodium (117976-90-6) → (4-{2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylmethanesulfinyl]benzoimidazole-1-sulfon-yl}phenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane at 20℃; for 8h;	92%
With sodium hydrogencarbonate In dichloromethane at 20℃; for 3h; Inert atmosphere;	92%

α-bromoacetophenone (70-11-1) + Rabeprazole sodium (117976-90-6) → 1-phenacyl-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole (1052003-67-4)

Conditions	Yield
With triethylamine In tetrahydrofuran at -26 - 20℃;	92%

Rabeprazole sodium (117976-90-6) → 3-(3-methoxypropoxy)-4-methyl-5H-pyrido[1',2':4,5][1,2,4]thiadiazino[2,3-a]benzimidazol-13-ium tetrafluoroborate

Conditions	Yield
With tetrafluoroboric acid In methanol; water at -25℃; for 14h;	86%

2,5-dichlorobenzenesulphonyl chloride (5402-73-3) + Rabeprazole sodium (117976-90-6) → 1-(2,5-dichlorophenylsulfonyl)-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole (1052003-47-0)

Conditions	Yield
With triethylamine In tetrahydrofuran at -26 - 20℃;	85%

1-bromomethyl-4-nitro-benzene (100-11-8) + Rabeprazole sodium (117976-90-6) → 1-(4-nitrobenzyl)-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole (1052003-37-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -26 - 20℃;	82%

3-chlorosulfonyl-4-methylbenzoic acid 2-(p-tolylsulfonyl)ethyl ester (651728-83-5) + Rabeprazole sodium (117976-90-6) → 3-{2-[4-(3-methoxypropoxy)-3-methylpyridin-2-yl-methanesulfinyl]benzimidazole-1-sulfon-yl}-4-methylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester

Conditions	Yield
With sodium hydrogencarbonate; triethylamine In dichloromethane at 20℃; for 0.5h;	80%
With sodium hydrogencarbonate; triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	80%

chloromethyl methyl ether (107-30-2) + Rabeprazole sodium (117976-90-6) → 1-Methoxymethyl-2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-ylmethanesulfinyl]-1H-benzoimidazole

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 24h; Ambient temperature;	78%

(4-chlorosulfonyl-3,5-dimethylphenoxy)acetic acid 2-(p-toluenesulfonyl)ethyl ester (651728-25-5) + Rabeprazole sodium (117976-90-6) → 3,5-dimethyl-4-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}-phenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester

Conditions	Yield
With sodium hydrogencarbonate; triethylamine In dichloromethane at 20℃; for 3h;	77%

3-chlorosulfonylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester (651728-72-2) + Rabeprazole sodium (117976-90-6) → 3-{2-[4-(3-methoxypropoxy)-3-methylpyridin-2-yl-methanesulfinyl]benzimidazole-1-sulfon-yl}benzoic acid 2-(toluene-4-sulfonyl)ethyl ester

Conditions	Yield
With sodium hydrogencarbonate; triethylamine In dichloromethane at 20℃; for 1.5h;	76%
With sodium hydrogencarbonate; triethylamine In dichloromethane at 20℃; for 1.5h; Inert atmosphere;	76%

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) + Rabeprazole sodium (117976-90-6) → 2-[4-(3-Methoxy-propoxy)-3-methyl-pyridin-2-ylmethanesulfinyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 20h; Ambient temperature;	72%

Benzyloxymethyl chloride (3587-60-8) + Rabeprazole sodium (117976-90-6) → 1-Benzyloxymethyl-2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-ylmethanesulfinyl]-1H-benzoimidazole (184713-27-7, 184713-30-2, 184713-31-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 17h; Ambient temperature;	64%

Rabeprazole sodium (117976-90-6) + 3-bromo-1-phenyl-1-propenyl bromide (4392-24-9) → 1-cinnamyl-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole (1052003-57-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at -26 - 20℃;	36%

Rabeprazole sodium (117976-90-6) + 2-hydroxyethanethiol (60-24-2) → 2-(2-hydroxyethylthio)-1H-benzimidazole (7673-83-8) + 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyldisulfanylethanol + rabeprazole sulfide (117977-21-6) + 1-(1H-Benzoimidazol-2-yl)-2-(2-hydroxy-ethyldisulfanylmethyl)-4-(3-methoxy-propoxy)-3-methyl-pyridinium

Conditions	Yield
With citrate buffer In acetonitrile at 25℃; for 0.25h; Product distribution; Mechanism; also omeprazole; var. pH, var. time;

Rabeprazole sodium (117976-90-6) → R-(+)-Rabeprazole

Conditions	Yield
Multi-step reaction with 3 steps 1: 64 percent / N,N-diisopropylethylamine / tetrahydrofuran / 17 h / Ambient temperature 3: aq. H2SO4 / CH2Cl2 / 0 - 5 °C View Scheme

Rabeprazole sodium (117976-90-6) → S-(-)-Rabeprazole

Conditions	Yield
Multi-step reaction with 3 steps 1: 64 percent / N,N-diisopropylethylamine / tetrahydrofuran / 17 h / Ambient temperature 3: aq. H2SO4 / CH2Cl2 / 0 - 5 °C View Scheme

Rabeprazole sodium (117976-90-6) → 1-Benzyloxymethyl-2-[(R)-4-(3-methoxy-propoxy)-3-methyl-pyridin-2-ylmethanesulfinyl]-1H-benzoimidazole

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / N,N-diisopropylethylamine / tetrahydrofuran / 17 h / Ambient temperature View Scheme

Rabeprazole sodium (117976-90-6) → 1-Benzyloxymethyl-2-[(S)-4-(3-methoxy-propoxy)-3-methyl-pyridin-2-ylmethanesulfinyl]-1H-benzoimidazole

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / N,N-diisopropylethylamine / tetrahydrofuran / 17 h / Ambient temperature View Scheme

acetonitrile (75-05-8) + Rabeprazole sodium (117976-90-6) → 2-[[4-(3-methoxypropoxy)-3-methylpyridine-2-yl]methylsulfinyl]-1H-benzimidazole sodium salt; acetonitrile complex

Conditions	Yield
at 22℃; for 18h;

Upstream product

• 117976-89-3 rabeprazole 
• 117977-21-6 rabeprazole sulfide 
• 117976-47-3 LY 307640 sulfone 
• 134469-07-1 Benzimidazol-2-thiol 
• 1310-73-2 sodium hydroxide 
• 117977-20-5 2-chloromethyl-4-(3-methoxy propyloxy)-3-methyl pyridine 
• 675198-19-3 [4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanol hydrochloride 
• 118175-10-3 2-hydroxymethyl-4-(3-methoxy propoxy)-3-methyl pyridine 

Downstream Products

• 7673-83-8 2-(2-hydroxyethylthio)-1H-benzimidazole 
• 117977-21-6 rabeprazole sulfide 
• 184713-27-7 1-Benzyloxymethyl-2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-ylmethanesulfinyl]-1H-benzoimidazole 
• 177795-59-4 R-(+)-Rabeprazole 
• 177795-59-4 S-(-)-Rabeprazole 
• 1052003-47-0 1-(2,5-dichlorophenylsulfonyl)-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole 
• 1052003-67-4 1-phenacyl-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole 
• 1052003-37-8 1-(4-nitrobenzyl)-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole 
• 1052003-57-2 1-cinnamyl-2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl}-1H-benzimidazole 
• 259183-31-8 1-benzenesulfonyl-2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole 

Relevant articles and documents

A right-handed thunder beira zuozuo sodium hydrate crystal form and its preparation method

The invention relates to a novel crystal form of rabeprazole sodium aquo-complex and a preparation method of the novel crystal form. The novel crystal form is called the Z-type crystal. The Z-type crystal of the rabeprazole sodium aquo-complex is characterized in that in the X-ray powder diffraction pattern expressed by Cu-K alpha radiation and a 2theta+/-0.2DEG diffraction angle, the Z-type crystal has characteristic diffraction peaks at 9.3, 10.7, 18.2, 19.6, 21.2, 23.0, 27.2 and 29.9.

Preparation method for key intermediate rabeprazole thioether

The invention discloses a preparation method for rabeprazole thioether 2-[[[4-(3- methoxypropoxy)-3-methylpyridin-2-yl] methyl] sulfo]-1H-benzimidazole. By using Mitsunobu reaction, the rabeprazole thioether is prepared from rabeprazole oxhydryl in one-step synthesis way without chlorination reaction. In the reaction process, the high-corrosive chloride agent, such as, thionyl chloride, is not used, so that the violent corrosion of the reaction to the device is obviously reduced, and meanwhile, the reaction yield is obviously increased due to the shortened reaction step. According to the invention, the process is simple, the reaction condition is mild, the corrosion to the device is small, the yield is higher (70%-80%) and the method is suitable for industrial production.

Method for preparing optically-pure Rabeprazole

The invention discloses a method for preparing optically-pure Rabeprazole. The method is used for preparing a chiral 2-[[4-(3-methoxypropoxy)-3-methylpyrid-2-yl]methylsulfinyl]-1H-benzimidazole compound (Rabeprazole), which is present in a single-enantiomer form or rich-enantiomer form, in an enantioselective manner. The same effects, i.e., identical enantioselectivity and conversion ratio can be achieved through complexing a tartaric acid diamide ligand and titanium and adding an organic-base additive or not in the presence of water. The invention further provides a method for preparing a sodium salt from the obtained Rabeprazole.

A process for the preparation of sodium rebeilazole for

The invention provides a preparation method of sodium rabeprazole. The preparation method comprises the following four steps of (1) adding rabeprazole into a mixed solvent of 2-fluoro-3-chloro-5-trifluoromethyl pyridines and ethanol, and regulating the temperature at 35-40 DEG C; (2) adding anhydrous sodium carbonate and anhydrous sodium sulfate into a reaction solution until the pH value of the reaction solution is 8.0-10.0, keeping the temperature at 35-40 DEG C, and reacting for 2h under stirring; (3) continuing to add n-hexane, and reacting at the temperature of 35-40 DEG C for 2h under stirring; and (4) carrying out solid-liquid separation, and drying at reduced pressure to obtain sodium rabeprazole. The method is simple in process, and sodium rabeprazole is high in purity, low in water content and good in stability.

A right-handed sodium rebeilazole for method for the synthesis of

The invention relates to a method for synthesizing rabeprazole sodium. The method comprises the following steps: performing asymmetric oxidation on raw materials with cumyl hydroperoxide, extracting through a sodium hydroxide solution, neutralizing to the pH value of 9.7 by using acid, separating out high-purity white rabeprazole sodium solids, filtering without drying, directly adding a wet sample into a mixed system of sodium hydroxide and dichloromethane and alkane solvent while stirring for reacting at the temperature of 0-30 DEG C for 3-5 hours, filtering, and drying, thereby obtaining the white rabeprazole sodium solids. According to the method disclosed by the invention, the operating steps are simplified, the yield is improved, the rabeprazole is prevented from being dried and heated, unknown impurities generated by heat instability are reduced, and use of an organic solvent is reduced.

Rabeprazole sodium crystal method for the preparation of compounds

The invention relates to the field of medicine production and in particular relates to a preparation method of a rabeprazole sodium crystal type compound. The preparation method of the rabeprazole sodium crystal type compound comprises the following steps of: by taking 2-mercapto benzimidazole and 2-chloromethyl-3-methyl-4-methoxy propoxy pyridine hydrochloride as raw materials and carrying out a condensation reaction to prepare rabeprazole thioether, and subsequently carrying out an oxidation reaction via the rabeprazole thioether and carrying out salt forming reaction via rabeprazole and sodium hydroxide to acquire the rabeprazole sodium. According to the preparation method of the rabeprazole sodium crystal type compound, the raw materials are low in cost and easy to purchase; samples are basically invariant in related substances and contents under the condition with high temperature and high humidity; the articles are stable in property and low in overall manufacturing cost; and the preparation method of the rabeprazole sodium crystal type compound has the advantages of strictly controlling the temperatures in the steps, being less in by-products, high in yield and non-toxic, and also has the advantages of being short in production period and further improving the production efficiency.

PROCESS FOR THE PREPARATION OF RABEPRAZOLE

The present invention provides a compound of Formula III, process of its preparation and its use as a reference marker or as a reference standard. The present invention further provides a process for the preparation of rabeprazole, a salt or a solvate thereof. The invention also provides a chromatographic method for testing the purity of rabeprazole, a salt or a solvate thereof.

PROCESS FOR THE PREPARATION OF 2-PYRIDINYLMETHYLSULFINYL BENZIMIDAZOLES, THEIR ANALOGS AND OPTICALLY ACTIVE ENANTIOMERS

The present invention provides a commercially viable, cost effective and energy efficient process for the preparation of 2-pyridinylmethylsulfinyl benzimidazoles, their analogs and optically active enantiomers or pharmaceutically acceptable salts, hydrates or solvates thereof in high purity via application of reactors such as plug flow reactor, microreactor, microfluidic flow reactor, tubular flow reactor, coil-type flow reactor, laminar flow reactor, packed bed reactor, fluidized bed reactor or fixed bed reactor.

PROCESS FOR OBTAINING AMORPHOUS RABEPRAZOLE SODIUM

The present invention relates to a new process for obtaining the amorphous form of rabeprazole sodium salt from the acetone solvate of said salt by means of the treatment in a solvent system formed by a C6-C8 alkane and water, and to the use of said process for obtaining rabeprazole sodium salt from the acetone solvate thereof.

A PROCESS FOR THE PREPARATION OF AMORPHOUS FORM OF RABEPRAZOLE SODIUM

The present invention relates to a process for the preparation of amorphous form of Rabeprazole sodium of formula (I).