ChemicalBook > CAS DataBase List > (S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide

(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide

Product Name
(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide
CAS No.
154127-42-1
Chemical Name
(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide
Synonyms
Brinzolamide Impurity 5;Brinzolamide Impurity I;sulfonamide 1,1-dioxide;Brinzolamide Intermediate 1;-4-Hydroxy-2-(3-methoxypropyl);BrinzolaMide Related CoMpound A;Brinzolamide (4S)-Hydroxy Analog;(4S)-1,1-dioxide-3,4-dihydro-4-hydroxy-2-;(4S)-1,1-dioxide-3,4-dihydro-4-hydroxy-2-###154127-42-1;(4S)-1,1-dioxide-3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-2...
CBNumber
CB21570474
Molecular Formula
C10H16N2O6S3
Formula Weight
356.44
MOL File
154127-42-1.mol
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(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide Property

Melting point:
112-115oC
Boiling point:
612.4±65.0 °C(Predicted)
Density 
1.575±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,Room Temperature
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
9.53±0.40(Predicted)
color 
White to Off-White
InChI
InChI=1S/C10H16N2O6S3/c1-18-4-2-3-12-6-8(13)7-5-9(20(11,14)15)19-10(7)21(12,16)17/h5,8,13H,2-4,6H2,1H3,(H2,11,14,15)/t8-/m1/s1
InChIKey
UHIWBQIWXWWDKT-MRVPVSSYSA-N
SMILES
S1(=O)(=O)C2SC(S(N)(=O)=O)=CC=2[C@H](O)CN1CCCOC
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
H946200
Product name
(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide1,1-Dioxide
Packaging
5g
Price
$400
Updated
2021/12/16
Biosynth Carbosynth
Product number
FD33569
Product name
(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2h-thieno(3,2-e)-1,2-thiazine-6-sulfonamide 1,1-dioxide
Packaging
100mg
Price
$80
Updated
2021/12/16
Biosynth Carbosynth
Product number
FD33569
Product name
(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2h-thieno(3,2-e)-1,2-thiazine-6-sulfonamide 1,1-dioxide
Packaging
250mg
Price
$120
Updated
2021/12/16
Biosynth Carbosynth
Product number
FD33569
Product name
(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2h-thieno(3,2-e)-1,2-thiazine-6-sulfonamide 1,1-dioxide
Packaging
500mg
Price
$200
Updated
2021/12/16
AK Scientific
Product number
J10894
Product name
BrinzolamideRelatedCompoundA
Packaging
25mg
Price
$298
Updated
2021/12/16
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(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide Chemical Properties,Usage,Production

Uses

(S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-Dioxide has been used as a reactant for the preparation of Brinzolamide (AL-4862) [B677600], a topical carbonic anhydrase inhibitor.

Synthesis

1245550-91-7

154127-42-1

The general procedure for the synthesis of (S)-3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide from the compound (CAS: 1245550-91-7) is as follows: the cyclization reaction of the compound (VI) can be carried out with a chiral reductant, e.g., (+)-diisopropylphenylborane (DIPCI) to obtain a single isomer of the target compound (VII) by stereoselective reduction. The procedure was as follows: compound (VI) (210 g, 0.484 mol) was suspended in tert-butyl methyl ether (15 v/v) and stirred under nitrogen protection. The suspension was cooled to -40 °C and (+)-diisopropylaminoborane (DIPCI) (762 g, 60-65% hexane solution, 1.063 mol) was slowly added through a cannula over 30 min. The temperature was raised to -30 °C during the reaction. The reaction mixture was maintained at -25 to -20 °C for 3.0 to 4.0 h. The reaction progress was monitored by TLC (mobile phase: ethyl acetate:hexane = 3:7). After completion of the reduction reaction, 1M aqueous sodium hydroxide solution (20 vol) was added through the addition funnel within 15-20 minutes. The reaction mixture was stirred at 25-30°C overnight and the completion of the reaction was monitored by TLC (mobile phase: ethyl acetate:hexane=1:1). Upon completion of the reaction, the aqueous and organic phases were separated, and the aqueous phase was extracted with tert-butyl methyl ether (4.0 v/v), followed by acidification to pH 1 with 5N hydrochloric acid solution, and extraction with ethyl acetate (3 x 6.0 v/v). The ethyl acetate extracts were combined, washed with saturated brine solution (2 x 2.5 volumes), dried over sodium sulfate and filtered. The organic layer was completely distilled under reduced pressure (at a temperature below 50°C) to give a light yellow syrupy crude product. The yield of compound (VII) was 112 g (65.2% yield). Alternatively, step (f) can be carried out using a non-chiral reducing agent such as sodium tetrahydroborane, subject to a subsequent optical splitting step to remove unwanted isomers.

References

[1] Patent: WO2010/103115, 2010, A1. Location in patent: Page/Page column 15-16

(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide Suppliers

China 179 India 8 United Kingdom 1 United States 8 Global 196
Qingdao Kingway Pharmtech Co.,Ltd.
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0532-87118899 13918827946
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J & K SCIENTIFIC LTD.
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18210857532; 18210857532
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86-10-82849933
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Chemvon Biotechnology Co., Ltd
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021-50790412
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+86-21-50790419
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JinYan Chemicals(ShangHai) Co.,Ltd.
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13817811078
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Adamas Reagent, Ltd.
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XiaoGan ShenYuan ChemPharm co,ltd
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Wuhan Sunrise Technology Development Co., Ltd.
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Jinan Chenghui Shuangda biological Co., LTD
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0086-21-58956006
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View Lastest Price from (S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide manufacturers

Shanghai Joiny Pharmaceutical Co.,LTD
Product
(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide 154127-42-1
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2025-09-19
WUHAN FORTUNA CHEMICAL CO., LTD
Product
(S)-4-Hydroxy-2-(3-Methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonaMide 1,1-Dioxide 154127-42-1
Price
US $0.00/Kg/Bag
Min. Order
100g
Purity
98%-102%
Supply Ability
10KGS
Release date
2021-07-03
Wuhan Biocar Pharmacy CO.,Ltd.
Product
(S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide 154127-42-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
800kg
Release date
2025-03-12

154127-42-1, (S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxideRelated Search:

N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(2-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Bicalutamide (R)-Bicalutamide 3-(4-Fluobenzenesulfhydry)-2-hydroxyl-2-methylpropionic acid brinzolamide Brinzolamide Brinzolamide impurity Deshydroxy Bicalutamide BICALUTAMIDE-D4 Desfluoro Bicalutamide BrinzolaMide iMpurity N-Desethyl Brinzolamide Brinzolamide impurity BrinzolaMide IMpurity C 3,4-Dihydro-2-(3-methoxypropyl)-4-oxo-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide (S)-6-Chloro-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazin-4-ol 1,1-dioxide N-Ethyl-p-toluenesulfonamide

  • (S)-2-(3-Methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-4-ol-6-sulfonaMide-1,1- dioxide
  • BrinzolaMide Related CoMpound A
  • 4-hydroxy-2-(3-Methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonaMide 1,1-dioxide
  • (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno-[3,2-e][1,2]thiazine-6-sulfonamide 1,1-di
  • 2H-Thieno[3,2-e]-1,2-thiazine-6-sulfonaMide,3,4-dihydro-4-hydroxy-2-(3-Methoxypropyl)-, 1,1-dioxide, (4S)-
  • Brinzolamide Intermediate 1
  • -3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide
  • -4-Hydroxy-2-(3-methoxypropyl)
  • (S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno-[3,2-e][1,2]thiazine-6-sulfonamide 1,1
  • (4S)-1,1-dioxide-3,4-dihydro-4-hydroxy-2-
  • (4S)-1,1-dioxide-3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-Thieno[3,2-e]-1,2-thiazine-6-sulfonamide
  • (S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide
  • (S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide
  • (4S)-1,1-dioxide-3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-Thieno
  • (4S)-1,1-dioxide-3,4-dihydro-4-hydroxy-2-###154127-42-1
  • 2H-Thieno[3,2-e]-1,2-thiazine-6-sulfonamide,3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-, 1,1-dioxide
  • (S)-3,4-Dihydro-4-hydroxy-2-(3-Methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonaMide-1,1-dioxid
  • (S)-4-Hydroxy-2-(3-Methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonaMide 1,1-dioxide
  • Brinzolamide Impurity 5
  • Brinzolamide (4S)-Hydroxy Analog
  • (4S) -1, 1-dioxide-3, 4-dihydro-4-hydroxy-2 - (4S) -1, 1-dioxide-3, 4-dihydro-4-hydroxy-2 -
  • Brinzolamide Impurity I
  • sulfonamide 1,1-dioxide
  • (4S)-1,1-dioxide-3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-2...
  • (S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1
  • (4S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-Dioxide
  • (4R)-4-(Isopropylamino)-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-Dioxide
  • 2H-Thieno[3,2-e]-1,2-thiazine-6-sulfonamide, 3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-, 1,1-dioxide, (4S)- (9CI, ACI)
  • 3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-Thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide (4S)- (9CI ACI)
  • (4S)-4-Hydroxy-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide
  • (4S)-3,4-Dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-Dioxi
  • (4R)-4-(Isopropylamino)-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide
  • 154127-42-1
  • C10H16N2O6S3