4-[(2-methylpropyl)amino]-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride (1:1)

Base Information

• Chemical Name: 4-[(2-methylpropyl)amino]-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride (1:1)
• CAS No.: 126453-94-9
• Molecular Formula: C₁₁H₁₈N₂O₄S₃*ClH
• Molecular Weight: 374.934
• Mol file: 126453-94-9.mol

Synonyms:4H-Thieno[2,3-b]thiopyran-2-sulfonamide,5,6-dihydro-4-[(2-methylpropyl)amino]-, 7,7-dioxide, monohydrochloride (9CI);4H-Thieno[2,3-b]thiopyran-2-sulfonamide,5,6-dihydro-4-[(2-methylpropyl)amino]-, 7,7-dioxide, monohydrochloride, (?à)-; L 660039; MK 927

Chemical Property of 4-[(2-methylpropyl)amino]-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride (1:1)

Chemical Property:

• Vapor Pressure: 1.81E-13mmHg at 25°C
• Boiling Point: 580.5°Cat760mmHg
• Flash Point: 304.9°C
• Density: g/cm³

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-[(2-methylpropyl)amino]-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride (1:1)

There total 8 articles about 4-[(2-methylpropyl)amino]-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride (1:1) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5,6-dihydro-4H-4-hydroxythieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (105951-30-2) → (S)-(+)-5,6-Dihydro-4-<(2-methylpropyl)amino>-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-Dioxide Monohydrochloride (MK-0417) (119271-78-2,126453-94-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / tetrahydrofuran

2: 1) borane-dimethylsulfide, 2) HCl

With hydrogenchloride; dimethylsulfide borane complex; triethylamine; In tetrahydrofuran;

DOI:10.1021/jm00132a003

Reference yield:

(R)-(+)-5,6-Dihydro-4H-thieno<2,3-b>thiopyran-4-ol 7,7-Dioxide (131352-46-0,137004-58-1) → (S)-(+)-5,6-Dihydro-4-<(2-methylpropyl)amino>-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-Dioxide Monohydrochloride (MK-0417) (119271-78-2,126453-94-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium acetylide / 1.) xylene/light mineral oil, THF, 20 deg C, 2 h; 2.) THF, 2 h

2: tetrahydrofuran / 14 h / 20 °C

With sodium acetylide; In tetrahydrofuran;

DOI:10.1021/jo00002a050

Reference yield:

5,6-dihydro-4-isobutyrylamino-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide → (S)-(+)-5,6-Dihydro-4-<(2-methylpropyl)amino>-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-Dioxide Monohydrochloride (MK-0417) (119271-78-2,126453-94-9)

Guidance literature:

With hydrogenchloride; dimethylsulfide borane complex; Yield given;

DOI:10.1021/jm00132a003

upstream raw materials:

(S)-(-)-5,6-Dihydro-N-(2-methylpropyl)-4H-thieno<2,3-b>thiopyran-4-amine 7,7-Dioxide

5,6-dihydro-4H-4-hydroxythieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

(R)-(+)-5,6-Dihydro-4H-thieno<2,3-b>thiopyran-4-ol 7,7-Dioxide

Toluene-4-sulfonic acid (R)-7,7-dioxo-4,5,6,7-tetrahydro-7λ⁶-thieno[2,3-b]thiopyran-4-yl ester

Refernces

• 1、 Baldwin,Ponticello,Anderson,Christy,Murcko,Randall,Schwam,Sugrue,Springer,Gautheron,Grove,Mallorga,Viader,McKeever,Navia. "Thienothiopyran-2-sulfonamides: Novel topically active carbonic anhydrase inhibitors for the treatment of glaucoma". . p. 2510 - 2513. Retrieved 2007/10/02.