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[ CAS No. 117977-21-6 ] {[proInfo.proName]}

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Chemical Structure| 117977-21-6
Chemical Structure| 117977-21-6
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Product Details of [ 117977-21-6 ]

CAS No. :117977-21-6 MDL No. :MFCD08063845
Formula : C18H21N3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :BSXAHDOWMOSVAP-UHFFFAOYSA-N
M.W : 343.44 Pubchem ID :9949996
Synonyms :
Rabeprazole Related Compound E;Rabeprazole thioether;Rabeprazole impurity E
Chemical Name :2-[[[4-(3-Methoxypropoxy)-3-methylpyridine-2-yl ]methyl]thio]-1H-benzimidazole

Calculated chemistry of [ 117977-21-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.33
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 97.06
TPSA : 85.33 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.93
Log Po/w (XLOGP3) : 3.34
Log Po/w (WLOGP) : 3.82
Log Po/w (MLOGP) : 1.77
Log Po/w (SILICOS-IT) : 4.6
Consensus Log Po/w : 3.29

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.01
Solubility : 0.0337 mg/ml ; 0.0000982 mol/l
Class : Moderately soluble
Log S (Ali) : -4.81
Solubility : 0.00533 mg/ml ; 0.0000155 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.01
Solubility : 0.0000339 mg/ml ; 0.0000000986 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.05

Safety of [ 117977-21-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 117977-21-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 117977-21-6 ]

[ 117977-21-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 117976-90-6 ]
  • [ 60-24-2 ]
  • [ 7673-83-8 ]
  • 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyldisulfanylethanol [ No CAS ]
  • [ 117977-21-6 ]
  • 1-(1H-Benzoimidazol-2-yl)-2-(2-hydroxy-ethyldisulfanylmethyl)-4-(3-methoxy-propoxy)-3-methyl-pyridinium [ No CAS ]
  • 2
  • [ 103312-62-5 ]
  • [ 1589-49-7 ]
  • [ 117977-21-6 ]
  • 3
  • [ 117977-21-6 ]
  • 2-[(4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole [ No CAS ]
  • [ 117976-47-3 ]
  • 4
  • 2-chloromethyl-4-chloro-3-methylpyridine hydrochloride [ No CAS ]
  • [ 117977-21-6 ]
  • 5
  • 4-chloro-2-methanesulfonyloxymethyl-3-methylpyridine methanesulfonate [ No CAS ]
  • [ 117977-21-6 ]
  • 6
  • [ 37699-43-7 ]
  • [ 117977-21-6 ]
  • 7
  • [ 59886-90-7 ]
  • [ 117977-21-6 ]
  • 8
  • [ 134469-07-1 ]
  • [ 117977-21-6 ]
YieldReaction ConditionsOperation in experiment
98.8% In di-isopropyl ether;Purification / work up; (Reference Example 5-3) The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized with diisopropyl ether (200 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (4.94 g) (HPLC purity 99.1 %, yield 98.8%).
98.8% In di-isopropyl ether;Crystallization;Purification / work up; Reference Example 5-3; The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized using diisopropyl ether (200 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.94 g) (HPLC purity 99.1%, yield 98.8%).
97.0% In ethyl acetate;Purification / work up; (Reference Example 6-2) The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized with ethyl acetate (12 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.91 g) (HPLC purity 99.3%, yield 97.0%).
97.0 - 97.5% In Diethyl carbonate;Purification / work up; (Reference Example 5-8) The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized with diethyl carbonate (90 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.85 g) (HPLC purity 99.2%, yield 97.0%). The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized with diethyl carbonate (45 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (2.93 g) (HPLC purity 99.3%, yield 97.5%).
97.0 - 97.5% In Diethyl carbonate;Crystallization;Purification / work up; Reference Example 5-8; The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized using diethyl carbonate (90 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyrid in-2-yl}methylthio]-1H-benzimidazole (4.85 g) (HPLC purity 99.2%, yield 97.0%).; Reference Example 6-8 The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized using diethyl carbonate (45 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.93 g) (HPLC purity 99.3%, yield 97.5%).
96.0 - 97.0% In acetone;Purification / work up; (Reference Example 5-7) The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized with acetone (20 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.80 g) (HPLC purity 99.2%, yield 96.0%). The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized with acetone (9 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.91 g) (HPLC purity 99.3%, yield 97.0%).
96.0 - 97.0% In ethyl acetate;Crystallization;Purification / work up; Reference Example 5-1; 2-[{4-(3-Methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole-producing Step 2-Chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine (53.2 g (200 mmol)), denatured ethanol (320 ml), 2-benzimidazolethiol (30.2 g (201 mmol)), and sodium hydroxide (26.8 g (670 mmol)) were added together, and reaction was carried out for approximately 2 hours at 50 C. After it had been confirmed by TLC that the starting material had disappeared, vacuum concentration was carried out, and ethyl acetate (430 ml) and water (340 ml) were then added. After stirring and then leaving to stand, the aqueous layer was separated off. The organic layer was washed with a 10% sodium hydroxide aqueous solution (110 ml), and twice with water (110 ml), and then vacuum concentration was carried out, thus obtaining crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (69.0 g) (HPLC purity 98.7%, yield 101%). The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) was crystallized using ethyl acetate (25 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.80 g) (HPLC purity 99.2%, yield 96.0%).; Reference Example 6-2 The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized using ethyl acetate (12 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.91 g) (HPLC purity 99.3%, yield 97.0%).
96.0 - 97.0% In acetone;Crystallization;Purification / work up; Reference Example 5-7; The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized using acetone (20 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.80 g) (HPLC purity 99.2%, yield 96.0%).; Reference Example 6-7 The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized using acetone (9 ml), and then filtration was carried out, thus obtaining 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-yl }methylthio]-1H-benzimidazole (2.91 g) (HPLC purity 99.3%, yield 97.0%).
92.8 - 93.5% In acetonitrile;Purification / work up; (Reference Example 5-5) The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized with acetonitrile (40 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.64 g) (HPLC purity 99.1 %, yield 92.8%). The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized with acetonitrile (21 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.81 g) (HPLC purity 99.1 %, yield 93.5%).
92.8 - 93.5% In acetonitrile;Crystallization;Purification / work up; Reference Example 5-5; The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized using acetonitrile (40 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.64 g) (HPLC purity 99.1%, yield 92.8%).; Reference Example 6-5 The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized using acetonitrile (21 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.81 g) (HPLC purity 99.1%, yield 93.5%).
91.0 - 92.5% In isopropyl alcohol;Purification / work up; (Reference Example 5-6) The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized with isopropyl alcohol (20 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.55 g) (HPLC purity 99.1%, yield 91.0%). The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized with diisopropyl alcohol (9 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.78 g) (HPLC purity 99.4%, yield 92.5%).
91.2 - 94.5% In toluene;Purification / work up; The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized with toluene (15 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.84 g) (HPLC purity 99.1 %, yield 94.5%).(Reference Example 5-4) The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized with toluene (30 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.56 g) (HPLC purity 99.1%, yield 91.2%).
91.0% In isopropyl alcohol;Crystallization;Purification / work up; Reference Example 5-6; The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized using isopropyl alcohol (20 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.55 g) (HPLC purity 99.1%, yield 91.0%).
91.2 - 94.5% In toluene;Crystallization;Purification / work up; Reference Example 5-4; The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized using toluene (30 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.56 g) (HPLC purity 99.1%, yield 91.2%).; Reference Example 6-4 The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized using toluene (15 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.84 g) (HPLC purity 99.1%, yield 94.5%).
90.0 - 93.0% In tert-butyl methyl ether;Purification / work up; (Reference Example 5-2) The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized with tert-butyl(methyl) ether (30 m), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (4.50 g) (HPLC purity 99.2%), yield 90.0%). The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized with tert-butyl(methyl) ether (12 ml), and filtered to obtain 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1 H-benzimidazole (2.79 g) (HPLC purity 99.2%, yield 93.0%).
90.0 - 93.0% In tert-butyl methyl ether;Crystallization;Purification / work up; Reference Example 5-2; The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (5.00 g) obtained in Reference Example 5-1 was crystallized using tert-butyl(methyl) ether (30 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (4.50 g) (HPLC purity 99.2%, yield 90.0%).; Reference Example 6-3; The crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (3.00 g) obtained in Reference Example 6-1 was crystallized using tert-butyl(methyl) ether (12 ml), and then filtration was carried out, thus obtaining 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (2.79 g) (HPLC purity 99.2%, yield 93.0%).

  • 10
  • [ 117977-21-6 ]
  • [ 117976-90-6 ]
YieldReaction ConditionsOperation in experiment
2-[[[4-(3-methoxy-propoxy)-3-methyl-2-pyridinyl]methyl]-thio]-1H-benzimidazole (10g) was suspended in 200ml of purified water, sodium hydroxide (about 2g) and pyridine (4ml). To this was slowly added about 75g of approximately 3.8% sodium hypochlorite solution in 2 hours. The reaction mass was maintained at 5-8 C for 4 hours. After completion of the reaction, excess sodium hypochlorite was decomposed using 5% aqueous sodium thiosulphate solution. The pH was adjusted to between 8.0 to 9.0 using 10% ammonium acetate solution. After pH adjustment the compound was isolated from the water layer by adding ethyl acetate followed by extraction. Concentrating the organic layer under vacuum yielded a residue to which isopropyl acetate was added and stirred for about 1 hour, yielding the desired product. The product was purified by dissolving in a mixture of acetone and triethylamine. Rabeprazole base so obtained was dissolved in ethyl acetate and methanol ammonia mixture to which methanolic sodium hydroxide was added and distilled off to a thick residue at low temperature. This was again redissolved in ethyl acetate and rabeprazole sodium salt was isolated in n-heptane/n-hexane and dried.
With sodium hydroxide; sodium hypochlorite; In pyridine; water; at 5 - 10℃; for 4h; Example 3 Preparation of 2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridinyl]methyi]- sulfinyl]-lH-benzimidazole sodium (Rabeprazole Sodium) 2-[[ [4 -(3 -methoxy-propoxy)-3 -methyl-2-pyridinyl]methyl] -thio]-1 H benzimidazole (25 g) was suspended in 500 ml of Purified Water, Sodium hydroxide (5 g) and Pyridine (12.5 ml). To this was slowly added about 160 g of Sodium hypochlorite solution having a chlorine content of 3.2 % at 5-10 C in 2 hours. The reaction mass was maintained at 5 - 8 C for 2 hours. After completion of the reaction, excess Sodium hypochlorite was decomposed using 5% aqueous Sodium thiosulphate solution. The reaction mass was then saturated with 150 g of Sodium chloride and extracted with 250 ml of dichloromethane twice. The organic layer was then dried over anhydrous Sodium sulphate. Concentrating the organic layer under vacuum yielded a residue to which 125 ml of Ethyl acetate was added and heated to 45 - 50 C for dissolution. This solution was slowly added to 500 ml of n-Heptane under stirring and stirred for 2 hours. EPO <DP n="11"/>The solids were filtered under nitrogen atmosphere, washed with n-Heptane and dried in an oven at 45-50 C to give 20 g of Rabeprazole sodium.
Stage 1 : Preparation of Rabeprazole Preparation of Solution A: Dissolved 1 1 .5g of sodium hydroxide in 200ml water at 20-30C and added it to a solution of lOOg of 2[[[(4-(3-methoxypropoxy)-2-methyl- 2-pyridinyl]methyl]sulfanyl-lH-benzimidazole in 500ml of methanol at 25-30C to obtain solution A. Preparation of solution B: Dissolved 7.25g of sodium hydroxide in 100ml of water at 25-30C and added to 650g of sodium hypochlorite (4%) to obtain solution B. The solution of A and B prepared above were cooled to -5 to 0C. The temperature of plug flow reactor was set to -2 to -5C. The plug flows were fed simultaneously with solution A at flow rate 31ml/minutes and solution B at flow rate 30ml/minutes at -2 to -5C. After the completion of reaction, the resulting reaction mass was continuously quenched with an aqueous solution of sodium thiosulphate (8.0g sodium thiosulphate in 20ml water) followed by addition of dichloromethane. The layers were separated and the pH of aqueous layer was adjusted to 8.8 - 9.2 by addition of acetic acid at 10-15C. The reaction mass was extracted with 200ml of dichloromethane The organic layer was treated with a solution of 1 1.64g sodium hydroxide in 600ml water at 25-30C and stirred. The aqueous layer was washed with dichloromethane. To the resulting aqueous layer 200ml of acetonitrile was added at 25-30C.The reaction mass was then cooled to 0-5Cand pH of the reaction mass was adjusted to 8.5-8.7 using 30%aqueousacetic acid solution. The reaction mass was then stirred at 0-5C for 10-12 hours. The solid obtained was filtered and suck dried. Stage 2: Preparation of Rabeprazole sodium The wet material obtained from stage- 1 was charged to a solution of 11.01 g sodium hydroxide in 500ml water at 25-30C. The reaction mass was then stirred for about 1 hour and washed with dichloromethane. The aqueous layer was then spray dried to obtain the title compound. HPLC purity: 99.9% Sulphone impurity: 0.02%
Oxidation reaction: In a third preparation tank into a clean reaction 93.3kg of purified water, stirring speed 35Hz, input 4.67kg of sodium hydroxide, dissolved, was added a 10% sodium hypochlorite solution 144.2kg was stirred uniformly, and sodium hydroxide - sodium hypochlorite solution, standby .Preparation of the reaction into methylene chloride in a clean tank fourth 247.3kg, temperature 20 ~ 25 , was added with stirring on speed step 40Hz prepared <strong>[117977-21-6]rabeprazole sulfide</strong> and dissolved with stirring, cooling to at -5 ~ 5 , prepared above was added aqueous sodium hydroxide - sodium hypochlorite, about 1 hour, with a timing when the reaction was stirred for 1 hour, the residual liquid phase monitoring <strong>[117977-21-6]rabeprazole sulfide</strong> not greater than 0.5%, completion of the reaction, 27% aqueous sodium thiosulfate solution was added 10.9 kg, with 50% aqueous acetic acid adjusted to pH 9.0 to 10.0 (about 23.3 kg of use), separated, the aqueous phase was washed with 37.1kg of methylene chloride was added once and the combined organic phases purified 140.0kg of water was added with 30% NaOH solution of sodium pH was adjusted to 13.0 to 14.0 (by about 25.1kg), stratified, 46.7 kg purified water, the organic phase was extracted once, and the combined aqueous phase was 185.7kg methylene chloride, and washed with 50% aqueous acetic acid adjusted to pH 9.0 ~ 10.0 (about 23.3 kg of use), separated and the aqueous phase was extracted with 31.0kg of methylene chloride, the organic phases were combined, dried over anhydrous sodium sulfate is added 28.00kg 30 minutes, filtered, 61.9kg washed with dichloromethane, and the combined organic phases temperature 25 ~ 30 , vacuum degree -0.08 ~ -0.1Mpa distilled off under reduced pressureDichloromethane until no outflow, 147.5kg of acetonitrile was added with stirring crystallization, crystal growing was cooled to 0-5 deg.] C for 2 hours.Centrifugation, washed, and dried, to give oxazole Bella Ray.Table 2 gives the amount of raw materials and the oxidation reaction.The reaction to the sodium salt: In a clean reaction vessel after the fifth methanol was added 52.5kg, 20 ~ 25 oxazole 20.00 kg, 2.30kg of sodium hydroxide was added, stirred for 1 hour, 0.90kg activated carbon, stirred for 1 hour, the temperature remains unchanged, the liquid pressure filtration to filter decarburization crystallizer temperature was raised to 50 ~ 55 , the filtrate was evaporated under reduced pressure to crystallizer effluent free of methanol, was added 9.5kg of toluene was distilled under reduced pressure to continue 50-55 solvent-free effluent, ethyl acetate was added 9.9kg and 19.2kg dissolved in toluene, a solution of n-heptane crystallization 136.6kg, for about 15 minutes n-heptane addition was completed, cooled to 20-25 crystal growing one hour, centrifuged, washed, and dried, to give a compound of rabeprazole sodium Form.Table 3 gives the sodium salt as starting material and the amount of the reaction.

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4-(4-Methoxyphenyl)-2-(methylthio)pyrimidine

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Related Parent Nucleus of
[ 117977-21-6 ]

Pyridines

Chemical Structure| 103577-40-8

[ 103577-40-8 ]

2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole

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Chemical Structure| 73590-85-9

[ 73590-85-9 ]

5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

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Chemical Structure| 171440-18-9

[ 171440-18-9 ]

Dexrabeprazole sodium

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Chemical Structure| 119141-89-8

[ 119141-89-8 ]

(R)-5-Methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole

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Chemical Structure| 102625-64-9

[ 102625-64-9 ]

5-(Difluoromethoxy)-2-(((3,4-dimethoxypyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole

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Benzimidazoles

Chemical Structure| 103577-40-8

[ 103577-40-8 ]

2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole

Similarity: 0.85

Chemical Structure| 73590-85-9

[ 73590-85-9 ]

5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

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Chemical Structure| 171440-18-9

[ 171440-18-9 ]

Dexrabeprazole sodium

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Chemical Structure| 119141-89-8

[ 119141-89-8 ]

(R)-5-Methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole

Similarity: 0.78

Chemical Structure| 102625-64-9

[ 102625-64-9 ]

5-(Difluoromethoxy)-2-(((3,4-dimethoxypyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole

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; ;