[ CAS No. 88546-55-8 ] {[proInfo.proName]}

Name: 88546-55-8|5-Methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfonyl)-1H-benzo[d]imidazole|98%
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SKU: A400034
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Quality Control of [ 88546-55-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 88546-55-8 ]

Product Details of [ 88546-55-8 ]

CAS No. :	88546-55-8	MDL No. :	MFCD00869772
Formula :	C₁₇H₁₉N₃O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IXEQEYRTSRFZEO-UHFFFAOYSA-N
M.W :	361.42	Pubchem ID :	145900
Synonyms :	OMZ sulfone;OMP sulfone;OMEP sulfone;Omeprazole sulphone	Chemical Name :	5-Methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfonyl)-1H-benzo[d]imidazole

Safety of [ 88546-55-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 88546-55-8 ]

* 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 [ 88546-55-8 ]

[ 88546-55-8 ] Synthesis Path-Downstream 1~4

1
[ 73590-85-9 ]
[ 73590-58-6 ]
omeprazole sulphone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With oxone; sodium hydrogencarbonate;bis(acetylacetonate)oxovanadium; In methanol; water; at -2 - 0℃; for 5.5h;	A mixture of 3 grams 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl] thio]benzimidazole (MPB), 3 grams NaHCO3 and 20 ml aqueous methanol was cooled to -2° C. and 3.5 ml (5.69 mmol) Oxone.(R). was added. The mixture was stirred for 4 hours at 0° C. and a further 1 gram (mmol) Oxone.(R). was added and stirring continued for 1.5 hours. A solution of 0.8 gram sodium metabisulfite in 20 ml water was added dropwise over 5-10 minutes. After further stirring the resultant precipitate was filtered, washed successively with water and 50percent aqueous methanol and dried. [0064] Yield 2.7 grams, 84percent (purity 98.1percent), SOMP 0.15percent.
83.5%	With tert.-butylhydroperoxide;bis(acetylacetonate)oxovanadium; In water; isopropyl alcohol;	The above described processes of Example 1 and Example 2 were repeated while using the conditions given in Table I below, to give the following results:
74.6%	With tert.-butylhydroperoxide;bis(acetylacetonate)oxovanadium; In water; toluene;	The above described processes of Example 1 and Example 2 were repeated while using the conditions given in Table I below, to give the following results:

68.5 - 80.7%	With tert.-butylhydroperoxide;bis(acetylacetonate)oxovanadium; In toluene; at 5 - 22℃; for 3h;	15 mg (0.6percent molar) VO(acac)2) in 5 ml toluene were added to a suspension of 3 grams of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole (MPB) in 30 ml toluene at a temperature of about 5° C. 3.5 ml of tert-butyl hydroperoxide (TBHP) in toluene (3M, 115percent) were added dropwise, while the temperature was maintained between 5 and 7° C. Upon completing the addition of the TBHP, the temperature rose to 22° C. The reaction was allowed to proceed to completion (about 3 hours), after which the cooled product mixture was treated with aqueous sodium metabisulphite. The solid product was filtered off, washed with cooled ethyl acetate and dried in an oven (yield 80.7percent)
60%	With sodium hydrogencarbonate;bis(acetylacetonate)oxovanadium; In water; acetone; for 30.75h;	The above described reaction of Example 8 was repeated while using the conditions given in Table II below, to give the following results:
> 50%	With tert.-butylhydroperoxide;vanadium(V) oxide; SiO2; In methanol; water;	The above described processes of Example 1 and Example 2 were repeated while using the conditions given in Table I below, to give the following results:
> 50%	With tert.-butylhydroperoxide;sodium vanadate; In methanol; water;	The above described processes of Example 1 and Example 2 were repeated while using the conditions given in Table I below, to give the following results:
> 50%	With tert.-butylhydroperoxide;bis(acetylacetonate)oxovanadium; In methanol; water;	The above described processes of Example 1 and Example 2 were repeated while using the conditions given in Table I below, to give the following results:
50.7%	With tetrabutylammomium bromide; sodium hydrogencarbonate;bis(acetylacetonate)oxovanadium; In water; ethyl acetate; for 30.75h;	The above described reaction of Example 8 was repeated while using the conditions given in Table II below, to give the following results:

Reference： [1]Patent: US2004/138466,2004,A1 .Location in patent: Page 5
[2]Patent: JP2004/524303,2004,A .Location in patent: Page/Page column 12-13
[3]Patent: JP2004/524303,2004,A .Location in patent: Page/Page column 13
[4]Patent: US2004/138466,2004,A1 .Location in patent: Page 5
[5]Patent: US2004/138466,2004,A1 .Location in patent: Page 5
[6]Patent: US2004/138466,2004,A1 .Location in patent: Page 4-5
[7]Patent: US2004/138466,2004,A1 .Location in patent: Page 5
[8]Patent: JP2004/524303,2004,A .Location in patent: Page/Page column 13
[9]Patent: US2004/138466,2004,A1 .Location in patent: Page 5
[10]Patent: US2004/138466,2004,A1 .Location in patent: Page 5
[11]Patent: US2004/138466,2004,A1 .Location in patent: Page 5
[12]Patent: US2004/138466,2004,A1 .Location in patent: Page 5

2
[ 73590-85-9 ]
[ 119141-89-8 ]
omeprazole sulphone [ No CAS ]
[ 119141-88-7 ]

Yield	Reaction Conditions	Operation in experiment
		In a 100 ml flask, 7.5 gm diethyl (-)-D-tartrate and 5.16 gm titanium(IV) isopropoxide and 0.13 ml water were taken at room temperature, and the mixture was heated to 65 - 70 degrees for 1 hour. After cooling to room temperature, 10 gm 5-methoxy[(2-(4-methoxy)- 3,5-dimethyl-2-pyridinyl] methylsulfenyl]-lH-benzimidazole was added and heated until a clear solution was obtained. The mixture then stirred for 0.5 hours at heating and cooled to room temperature. 6.9 gm Cumene hydroperoxide was added slowly. After addition, the reaction was monitored by HPLC for the following with the results listed below:
		In a 100 ml flask, 7.5 gm diethyl (-)-D-tartrate, 20 ml methylene chloride, 5.16 gm titanium(IV) isopropoxide and 0.13 gm water were taken at room temperature, and the mixture was heated to 65 - 70 degrees for 1 hour. After cooling to room temperature, 10 gm PMT was added and heated until a clear solution was obtained. The mixture then <n="21"/>stirred for 0.5 hours at heating and cooled to room temperature. 6.9 gm Cumene hydroperoxide was added slowly. After addition, the reaction was monitored by HPLC for the following with the results listed below:
	With dihydrogen peroxide;Mn-complex of (R,R)-1,2-bis(3,5-di-tert-butyl-2-hydroxybenzylamino)cyclohexane; In water; acetonitrile; at -10℃; for 5h;Product distribution / selectivity;	5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-1 H-benzimidazole (4a) (0.987 g , 3 mmol) and manganese complex of (R,R)-1 ,2-bis(3,5-di-te/f-butyl-2-hydoxybenzyl- amino)cyclohexane (10c) (96 mg, 5 mol %) are dissolved in acetonitrile (45 ml). The reaction mixture is cooled to -100C and 30% aqueous H2O2 (13.8 ml, 45 mol equiv) is added dropwise over 3 hours period. The reaction mixture is stirred for additional 2 hours. HPLC analysis shows formation of 56% of sulfoxide (1a) with 67% ee (S-enriched) and 5% of sulfone.

	With dihydrogen peroxide;Mn-complex of (S,S)-1,2-bis(2-hydroxybenzylamino)cyclohexane; In water; acetonitrile; at 0 - 20℃; for 3.5h;	5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-1 H- benzimidazole (4a) and a preformed salan (10b) - metal complex are dissolved in acetonitrile. The reaction temperature is adjusted and 30% aqueous H2O2 is added dropwise. The mixture is stirred for several hours. Then, it is poured portionwise into a cold (0 0C) 10% aqueous Na2SO3 and stirred for additional 15 min and extracted with dichloromethane. The organic phase is dried over Na2SO4 and concentrated yielding an oily residue which is analyzed by chiral and achiral HPLC.Typically, runs were carried out on 1 mmol scale of the starting material 4a in acetonitrile (1 mmol 4a in 10 mL MeCN). The amounts of added reagents, temperature and reaction time in particular examples are indicated in Table 4. Also the results are indicated in Table 4.
		Titanium tetraisopropoxide (66.7 mg, 0.235 mmol) and water (8.0 mg, the total amount of water is 8.47 mg, 0.47 mmol) were added to a solution of L1 (67.1 mg, 0.065 mmol) in toluene (20 mL) at 25 C. After stirring at that temperature for 1 h, pyrmetazol (165.0 mg, 0.5 mmol) was added. Then, the mixture was heated to 50 Cand maintained for 1 h. After the mixture was cooled to 25 C, N,N-diisopropylethylamine (16.8 mg, 0.13 mol) and cumene hydroperoxide (80% in cumene, 110.5 mg,0.65 mmol) were added subsequently. After stirring at 25 C for 1 h, a small sample of reaction mixture was taken for HPLC analysis for conversion and selectivity, and the product was isolated by preparative thin-layer chromatography (TLC; eluent: CH2Cl2/MeOH 25/1) for determination of the enantiomeric purity.
19%Chromat.	With iron(III)-acetylacetonate; 2,4-dichloro-6-[(E)-[[(1S)-1-(hydroxymethyl)-2,2-dimethylpropyl]imino]methyl]phenol; dihydrogen peroxide; p-N,N-dimethylaminobenzoic acid; In dichloromethane; water; at 15℃; for 1.5h;	General procedure: 79.3 mg (273 mumol) of S-dichloro chiral ligand and 32.2 mg (91.1 mumol) of iron(III) acetylacetonate were dissolved in 0.6 mL of ethyl acetate at 25° C., and stirred for more than 30 min. To the mixed solution were added 7.8 mg (45.5 mumol) of lithium 4-dimethylaminobenzoate and 0.3 mL of ethyl acetate, and the suspension was stirred for more than 30 min. 0.3 g (911 mumol) of sulfide A and 0.9 mL of ethyl acetate were added and the suspension was stirred for more than 30 min. After the mixture was cooled to ?5° C., 186 muL (1.82 mmol) of 30percent aqueous hydrogen peroxide solution was added dropwise for 2 min or more. After 4.5 hours, the reaction mixture was analyzed under HPLC analysis condition 1. sulfoxide A 88percent; sulfone A 11percent; sulfide A 0percent 98percent ee

Reference： [1]Patent: WO2009/66321,2009,A2 .Location in patent: Page/Page column 19
[2]Patent: WO2009/66321,2009,A2 .Location in patent: Page/Page column 19-20
[3]Patent: WO2010/43601,2010,A1 .Location in patent: Page/Page column 31
[4]Patent: WO2010/43601,2010,A1 .Location in patent: Page/Page column 30; 31
[5]Synthetic Communications,2015,vol. 45,p. 70 - 77
[6]Patent: US10307748,2019,B2 .Location in patent: Page/Page column 12; 13

3
[ 73590-85-9 ]
omeprazole sulphone [ No CAS ]
[ 119141-88-7 ]

Yield	Reaction Conditions	Operation in experiment
		Titanium tetraisopropoxide (66.7 mg, 0.235 mmol) and water (8.0 mg, the total amount of water is 8.47 mg, 0.47 mmol) were added to a solution of L1 (67.1 mg, 0.065 mmol) in toluene (20 mL) at 25 C. After stirring at that temperature for 1 h, pyrmetazol (165.0 mg, 0.5 mmol) was added. Then, the mixture was heated to 50 Cand maintained for 1 h. After the mixture was cooled to 25 C, N,N-diisopropylethylamine (16.8 mg, 0.13 mol) and cumene hydroperoxide (80% in cumene, 110.5 mg,0.65 mmol) were added subsequently. After stirring at 25 C for 1 h, a small sample of reaction mixture was taken for HPLC analysis for conversion and selectivity, and the product was isolated by preparative thin-layer chromatography (TLC; eluent: CH2Cl2/MeOH 25/1) for determination of the enantiomeric purity.
10.2%Chromat.; 88.3%Chromat.	With lithium 4-dimethylaminobenzoate; iron(III)-acetylacetonate; 2,4-dichloro-6-[(E)-[[(1S)-1-(hydroxymethyl)-2,2-dimethylpropyl]imino]methyl]phenol; dihydrogen peroxide; In water; ethyl acetate; at -5℃; for 4.5h;	As described in Non-Patent Literature 1 and the like, when using titanium as a catalyst, there was a problem that it was necessary to increase the catalyst amount upon scaling up the reaction. Accordingly, experiments using 1 g, 20 g and 100 g of the starting sulfide A were conducted in a production method of the present invention. The reaction using 100 g is described below, but the reactions were similarly conducted using the corresponding amount of reagents in case of using 1 g or 20 g. (0149) 7.93 g (27.3 mmol) of S-dichloro chiral ligand, 8.04 g (22.77 mmol) of iron(III) acetylacetonate and 3.9 g (22.77 mmol) of lithium 4-dimethylaminobenzoate were suspended in 300 mL of ethyl acetate at room temperature, and stirred for more than 30 min. To the mixture were added 100 g (303.56 mmol) of sulfide A and 500 mL of ethyl acetate. After the mixture was cooled to ?5° C., 68.82 g (607.12 mmol) of 30percent aqueous hydrogen peroxide solution was added dropwise. After 8 hours, the reaction mixture was analyzed under HPLC analysis condition 3. (0150) The analysis results of the reactions in these various scales are shown in Table 5 below. [table-us-00005-en] Amount of Content (percent) Sulfide A Sulfoxide A Sulfone A Sulfide A percent ee 1 g 88.3 10.2 1.5 96.3 20 g 85.8 13.7 0.5 97.0 20 g 85.4 13.7 0.8 95.6 100 g 86.5 11.8 1.7 95.1 (0152) As described above, good reproducibility is observed in a production method of the present invention. It is understood that high yield and enantioselectivity can be maintained even in an increased scale, and it is not necessary to increase the amount of the catalyst.

Reference： [1]Synthetic Communications,2015,vol. 45,p. 70 - 77
[2]Patent: US10307748,2019,B2 .Location in patent: Page/Page column 12; 13; 14; 15; 17; 18

4
[ 73590-58-6 ]
[ 88546-55-8 ]

Yield	Reaction Conditions	Operation in experiment
	With glucose-6-phosphate dehydrogenase; glucose-6-phosphate; ferredoxin 8; ferredoxin-NADP<SUP>+</SUP> reductase B; recombinant CYP₂₆₇B₁ from Sorangium cellulosum So ce56; NADPH In dimethyl sulfoxide at 30℃; for 3h; Enzymatic reaction;	In Vitro Conversions. General procedure: A reconstituted in vitro system containing the corresponding P450 (0.5 mM), FdR_B (1.5 mM), and Fdx8 (10 mM), and acofactor regenerating system with glucose-6-phosphate (5 mM) and glucose-6-phosphate dehydrogenase (2 U/ml) in potassium phosphate buffer (20 mM, pH 7.4,1% glycerin) was used. The potential substrates, except olanzapine and omeprazole(both dissolved in dimethylsulfoxide),were dissolved in ethanol (10mM) and addedto an end concentration of 200 mM. The total volume of the reaction was 250 ml.The reaction was started by the addition of NADPH (800 mM) and carried out for3 hours at 30C. For substrates 1, 9, 11-15, and 18-21, 1M glycine buffer (pH 11)or acetate buffer (pH 4) was added after reaction to enable improved recovery of theanalytes. Therefore, the reaction was stopped by adding buffer (300 ml) ororganic solvent (500 ml). The extraction was performed twice with 500 ml of theappropriate solvent (see (Supplemental Table 0). A negative control withoutP450 was implemented for each substrate to verify the P450-dependent reaction.

Reference： [1]Kern, Fredy; Khatri, Yogan; Litzenburger, Martin; Bernhardt, Rita [Drug Metabolism and Disposition, 2016, vol. 44, # 4, p. 495 - 504]

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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 88546-55-8 ] {[proInfo.proName]}

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[ 88546-55-8 ] Synthesis Path-Downstream 1~4

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