Rabeprazole supplier | CasNO.117976-89-3

Name
Rabeprazole
EINECS 601-501-2
CAS No. 117976-89-3
Article Data43
CAS DataBase
Density 1.33 g/cm³
Solubility Soluble
Hazard Symbols Xi
Synonyms 2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole;1H-benzimidazole, 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-;2-({[4-(3-Methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole;Pariprazole;(RS)-2-([4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole;
PSA 96.31000
LogP 3.85510

Synthetic route

: 1080503-70-3
2,3-dimethyl-4-(3-methoxy-propoxy)pyridine

: 1080503-68-9
(-)-menthyl 2-benzimidazolylsulphinate

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
Stage #1: 2,3-dimethyl-4-(3-methoxy-propoxy)pyridine With n-butyllithium In tetrahydrofuran at -90 - -80℃; Stage #2: (-)-menthyl 2-benzimidazolylsulphinate In tetrahydrofuran at -80 - -20℃;	90%

: 117977-21-6
rabeprazole sulfide

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; sodium tungstate In methanol; water at 20℃; for 0.666667h; Product distribution / selectivity;	88%
With dihydrogen peroxide; sodium carbonate; sodium tungstate In methanol; water at 20℃; for 0.666667h; Product distribution / selectivity;	86.8%
With sodium hypochlorite; sodium hydroxide In water; acetonitrile Flow reactor;	85.1%

: 117977-21-6
rabeprazole sulfide

A: 117976-89-3
rabeprazole

B: 117976-47-3
LY 307640 sulfone

Conditions

Conditions	Yield
With sodium hydroxide; N-chloro-succinimide; water In acetonitrile at 0 - 5℃; for 2h; Product distribution / selectivity;	A 75% B 0.1%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1h; Product distribution / selectivity;	A 57% B 0.5%
With sodium hypochlorite; water In dichloromethane at 0 - 5℃; for 3 - 6h; Product distribution / selectivity;	A 52% B 0.5%

: 2-[4-(3-methoxypropoxy)-3-methyl-1-oxypyridin-2-yl-methylsulfinyl]-1H-benzimidazole sodium salt

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In acetonitrile at -10℃; for 6h; Product distribution / selectivity;	70%
With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In acetonitrile at -10℃; for 6h; Product distribution / selectivity;	70%
With methanesulfonyl chloride; triethylamine In dichloromethane at -10℃; Product distribution / selectivity;
Stage #1: 2-[4-(3-methoxypropoxy)-3-methyl-1-oxypyridin-2-yl-methylsulfinyl]-1H-benzimidazole sodium salt With methanesulfonyl chloride; triethylamine In dichloromethane at -10℃; Stage #2: With water In dichloromethane Product distribution / selectivity;

: 37699-43-7
2,3-dimethyl-4-nitropyridine N-oxide

: 1589-49-7
methoxypropanol

: 134469-07-1
Benzimidazol-2-thiol

A: 2-[(RS)-[(4-chloro-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole

B: 924663-38-7
2-[[(RS)-(1H-benzimidazol-2-yl)sulfinyl]methyl]-4-(3-methoxypropoxy)-3-methylpyridine 1-oxide

C: 102804-77-3
2-[(RS)-[(4-methoxy-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole

D: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
Multistep reaction. Further byproducts given;

...Expand

: 924663-40-1
2-[[(4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
With lithium carbonate; ruthenium trichloride; sodium vanadate In acetonitrile for 2h; Heating / reflux;	5 %Chromat.
With sodium vanadate; lithium carbonate; ruthenium trichloride In acetonitrile for 2h; Heating / reflux;

: 408332-88-7
Diethyl tartrate

: 117977-21-6
rabeprazole sulfide

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene	1.1 g (49%)

: 13811-71-7
diethyl (2S,3S)-tartrate

: 117977-21-6
rabeprazole sulfide

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; isopropylbenzene hydroperoxide; titanium(IV) isopropylate In water; toluene	1.36 g (60%)

: 937-14-4
3-chloro-benzenecarboperoxoic acid

: 117977-21-6
rabeprazole sulfide

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
Stage #1: 3-chloro-benzenecarboperoxoic acid; rabeprazole sulfide In sodium hydroxide; diethyl ether; dichloromethane at -10℃; for 1.08333h; Stage #2: With triethylamine In diethyl ether; dichloromethane at 0 - 20℃;

: 924663-38-7
2-[[(RS)-(1H-benzimidazol-2-yl)sulfinyl]methyl]-4-(3-methoxypropoxy)-3-methylpyridine 1-oxide

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
Stage #1: 2-[[(RS)-(1H-benzimidazol-2-yl)sulfinyl]methyl]-4-(3-methoxypropoxy)-3-methylpyridine 1-oxide With methanol; sodium methylate; ruthenium trichloride; N,N,N,N,-tetramethylethylenediamine at 50℃; for 10h; Stage #2: With acetic acid; sodium sulfite In water pH=6 - 7; Product distribution / selectivity;

: 5038-11-9
N,N'-thiodimorpholine

: 2-[[[4-[3-methoxypropoxy]-3-methyl-2-pyridinyl]-methyl]sulfinyl]-1H-benzimidazole N-oxide

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
With ammonium acetate; sodium hydroxide; chloro-trimethyl-silane; sodium hydrogencarbonate In methanol; ethanol; dichloromethane; water	0.34 g (79%)

: 117977-20-5
2-chloromethyl-4-(3-methoxy propyloxy)-3-methyl pyridine

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
Multi-step reaction with 2 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 View Scheme

: 675198-19-3
2-hydroxymethyl-4-(methoxypropoxy)-3-methylpyridine hydrochloride

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
Multi-step reaction with 3 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 View Scheme

: 118175-10-3
2-hydroxymethyl-4-(3-methoxy propoxy)-3-methyl pyridine

: 117976-89-3
rabeprazole

Conditions

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

: 134469-07-1
Benzimidazol-2-thiol

: 117976-89-3
rabeprazole

Conditions

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

: C13H19NO5

: 117976-89-3
rabeprazole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide 2: sodium hydride 3: 3-chloro-benzenecarboperoxoic acid View Scheme

: 117976-89-3
rabeprazole

: 117976-90-6
Rabeprazole sodium

Conditions

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%

: 117976-89-3
rabeprazole

: 117976-47-3
LY 307640 sulfone

A: rabeprazol sulphone sodium salt

B: 117976-90-6
Rabeprazole sodium

Conditions

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

...Expand

: 117976-89-3
rabeprazole

: 519183-08-5
sodium 2-[2-[[(4-methoxypropoxy-3-methyl) pyridin-2-yl]methanesulfinyl]benzimidazole-1-sulfonyl]benzenesulfonate

Conditions

Conditions	Yield
	92%

: 69986-21-6
2-[p-(chlorosulfonyl)phenoxy]acetamide

: 117976-89-3
rabeprazole

: 259183-37-4
2-(4-{[2-({[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)acetamide

Conditions

Conditions	Yield
Inert atmosphere; Basic conditions;	92%

: 1003-03-8
Cyclopentamine

: 117976-89-3
rabeprazole

: 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylsulfinyl]-1H-benzimidazole, cyclopentylamine salt

Conditions

Conditions	Yield
In acetonitrile Product distribution / selectivity;	90.3%
In isopropyl alcohol Product distribution / selectivity;	88.9%
In ethyl acetate Product distribution / selectivity;	86.4%
In toluene at 55℃; Product distribution / selectivity;	80%

: 259183-87-4
2-[p-(chlorosulfonyl)phenoxy]-N-(2-pyridyl)acetamide

: 117976-89-3
rabeprazole

: 259183-27-2
2-(4-{[2-({[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)-N-(2-pyridyl)acetamide

Conditions

Conditions	Yield
Inert atmosphere; Basic conditions;	88%

: 33966-50-6
SEC-BUTYLAMINE

: 117976-89-3
rabeprazole

: 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methysulfinyl]-1H-benzimidazole, sec-butylamine salt

Conditions

Conditions	Yield
In acetonitrile Product distribution / selectivity;	87.1%
In ethyl acetate at 55℃; Product distribution / selectivity;	86.9%

: 75-31-0
isopropylamine

: 117976-89-3
rabeprazole

: 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-vl}methylsulfinyl]-1H-benzimidazole, isopropylamine salt

Conditions

Conditions	Yield
In acetonitrile Product distribution / selectivity;	83%
In acetonitrile at 55℃; Product distribution / selectivity;	82.7%
In ethyl acetate at 55℃; Product distribution / selectivity;	75.3%
In tetrahydrofuran Product distribution / selectivity;	75.6%

: 117976-89-3
rabeprazole

: 2-[(4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In methanol; chloroform at -10 - -5℃;	80%

: 519183-15-4
2-Carbamoylmethoxy-4-chlorosulfonylphenoxyacetamide

: 117976-89-3
rabeprazole

: 519183-09-6
2-(2-carbamoylmethoxy-4-{2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylmethylsulfinyl]benzimidazole-1-sulfonyl}phenoxy)acetamide

Conditions

Conditions	Yield
Inert atmosphere; Basic conditions;	79%
With triethylamine In dichloromethane

: 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride

: 117976-89-3
rabeprazole

: 935260-92-7
2-[([4-(3-methoxypropoxy)-3-methyl]pyridinyl)methyl]sulfinyl-1-[([4-(3-methoxypropoxy)-3-methyl]pyridinyl)methyl]-1H-benzimidazole

Conditions

Conditions	Yield
With sodium hydroxide In water at 25 - 75℃;	78%

: 125393-22-8
4-(4-morpholinyl)benzenesulfonyl chloride

: 117976-89-3
rabeprazole

: 259183-28-3
1-[4-(morpholin-4-yl)phenylsulfonyl]-2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole

Conditions

Conditions	Yield
Inert atmosphere; Basic conditions;	78%

: 259183-84-1
[2-(morpholin-4-yl)ethoxy]benzene-4-sulfonyl chloride

: 117976-89-3
rabeprazole

: 259183-29-4
1-[{2-(morpholin-4-yl)ethoxy}phenyl-4-sulfonyl]-2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole

Conditions

Conditions	Yield
Inert atmosphere; Basic conditions;	77%

: 40685-78-7
N-[4-(chlorosulfonyl)phenyl]urea

: 117976-89-3
rabeprazole

: 259183-25-0
N-(4-{[2-({[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenyl)urea

Conditions

Conditions	Yield
Inert atmosphere; Basic conditions;	74%

: 259183-90-9
N-(carbamoylmethyl)-2-[4-(chlorosulfonyl)phenoxy]acetamide

: 117976-89-3
rabeprazole

: 259183-47-6
N-(carbamoylmethyl)-2-(4-{[2-({[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl}sulfinyl)benzimidazol-1-yl]sulfonyl}phenoxy)acetamide

Conditions

Conditions	Yield
Inert atmosphere; Basic conditions;	72%

: 259183-85-2
[2-{2-(morpholin-4-yl)ethoxy}ethoxy]benzene-4-sulfonyl chloride

: 117976-89-3
rabeprazole

: 259183-43-2
1-[[2-{2-(morpholin-4-yl)ethoxy}ethoxy]phenyl-4-sulfonyl]-2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole

Conditions

Conditions	Yield
Inert atmosphere; Basic conditions;	56%

: 18531-99-2
(S)-[1,1']-binaphthalenyl-2,2'-diol

: 117976-89-3
rabeprazole

: (S)-rabeprazole-(S)-(-)-BINOL complex

Conditions

Conditions	Yield
In cyclohexane; toluene at 3 - 52℃; for 1.25 - 1.75h;	55.6%

: 77-78-1
dimethyl sulfate

: 117976-89-3
rabeprazole

: N1-methyl rabeprazole

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃;

: 117976-89-3
rabeprazole

: 2-[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]-methylsulfinyl]-1H-benzimidazole hemicalcium

Conditions

Conditions	Yield
Stage #1: rabeprazole With sodium hydroxide In methanol at 15 - 20℃; for 0.25h; Stage #2: With calcium acetate In methanol at 20℃; for 14.5h;

: 635751-00-7
2-[(chlorocarbonyl)(methyl)amino]ethyl ethyl carbonate

: 117976-89-3
rabeprazole

: ethyl 2-[[[2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl](methyl)amino]ethyl carbonate

Conditions

Conditions	Yield
With triethylamine; dmap In tetrahydrofuran at 60℃; for 17h;
With dmap; triethylamine In tetrahydrofuran at 60℃; for 17h;	0.44 g

: 635751-44-9
2-[(chlorocarbonyl) (phenyl)amino]ethyl acetate

: 117976-89-3
rabeprazole

: 2-[[[2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl](phenyl)amino]ethyl acetate

Conditions

Conditions	Yield
With triethylamine; dmap In tetrahydrofuran at 60℃; for 16h;
With dmap; triethylamine In tetrahydrofuran at 60℃; for 16h;	0.93 g

Rabeprazole Specification

The Rabeprazole, with the CAS registry number 117976-89-3, has the systematic name of 2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-1H-benzimidazole. Its classification code are: Anti-Ulcer Agents; Enzyme Inhibitors; Gastrointestinal Agents. The molecular formula of this chemical is C₁₈H₂₁N₃O₃S.

The physical properties of Rabeprazole are as following: (1)ACD/LogP: 1.83; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.79; (4)ACD/LogD (pH 7.4): 1.82; (5)ACD/BCF (pH 5.5): 13.1; (6)ACD/BCF (pH 7.4): 14.29; (7)ACD/KOC (pH 5.5): 213.27; (8)ACD/KOC (pH 7.4): 232.59; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 85.45 Å²; (13)Index of Refraction: 1.654; (14)Molar Refractivity: 98.66 cm³; (15)Molar Volume: 268.9 cm³; (16)Polarizability: 39.11×10^-24cm³; (17)Surface Tension: 72.6 dyne/cm; (18)Density: 1.33 g/cm³; (19)Flash Point: 319.1 °C; (20)Enthalpy of Vaporization: 89.82 kJ/mol; (21)Boiling Point: 603.9 °C at 760 mmHg; (22)Vapour Pressure: 1.54E-14 mmHg at 25°C.

Preparation of Rabeprazole: Dissolve 2-[[[3-methyl-4-(3-methoxy-propoxy)-2-pyridyl]methyl]thio]-1H-benzimidazole in the methylene dichloride, and add m-chloroperoxybenzoic acid of dichloromethane. Then deal it with sodium hydroxide, methylene chloride, ammonia and acetone, the aim product is obtained.

Uses of Rabeprazole: It is a proton pump antagonist, and inhibits urease. It is used for the short-term treatment in healing and symptomatic relief of duodenal ulcers and erosive or ulcerative gastroesophageal reflux disease (GERD). It is used for maintaining healing and reducing relapse rates of heartburn symptoms in patients with GERD; It is also used in the treatment of daytime and nighttime heartburn and other symptoms associated with GERD; In addition, it is used for long-term treatment of pathological hypersecretory conditions as well.

You should be cautious while dealing with this chemical. It irritates eyes and skin. Therefore, you had better take the following instructions: Wear suitable gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(c2nc1ccccc1n2)Cc3nccc(OCCCOC)c3C
(2)InChI: InChI=1/C18H21N3O3S/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,(H,20,21)
(3)InChIKey: YREYEVIYCVEVJK-UHFFFAOYAY

Product Name

Rabeprazole

Synthetic route

Rabeprazole Specification

Related Products

Hot Products