ChemicalBook CAS DataBase List Dronedarone

Dronedarone synthesis

4synthesis methods

Product Name:Dronedarone
CAS Number:141626-36-0
Molecular formula:C31H44N2O5S
Molecular Weight:556.76

Dronedarone is an antiarrhythmic, acting as a multichannel blocker. Dronedarone inhibits multiple outward potassium currents and reduces inward rapid Na current and L-type Ca channels.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

Process for the preparation of dronedarone; Gutman, Arie L.; Nisnevich, Gennady; Yudovitch, Lev; Assignee ISP Investments Inc., USA 2003; Patent Information; May 15, 2003; WO 2003040120 A1

1912-32-9 Synthesis

1912-32-9
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Methanesulfonamide, N-[3-[4-(3-aminopropoxy)benzoyl]-2-butyl-5-benzofuranyl]-

1026754-33-5
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141626-36-0
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$50.00/10mM (in 1mL DMSO)

Yield:141626-36-0 79%

Reaction Conditions:

with pyridine in butan-1-ol at 70; for 14 h;

Steps:

2
0.8 g of N- [2-butyl-3 - { 4- [(3 -amino)propoxy] benzoyl } - 1 -benzofuran-5- yl]methanesulfonamide (II) is dissolved in 5 ml of n-butanol. 0.15 g of pyridine is added and the mixture is heated to 70 °C at this temperature 0.68 g of butyl-methanesulfohate (III) dissolved in 1 ml of n-butanol is added during 15 minutes and the mixture is kept at 70 °C for 14 hours. [The methanesulfonate is prepared according to the procedure described in J. of Steroid Biochemistry and Molecular Biology 80 (2002) 429-440.] The reaction mixture is evaporated and 20 ml of dichloromethane and 10 ml of water is added. The phases are separated. The organic phase is washed with 10ml of NaHC0₃ of 5 %. The organic phase is evaporated. The product is purified by on silica gel (ethyl acetate/hexane; 1 :3 v/v ).Yield: 0.79 g (79 %). Purity: 100 % (HPLC).The product is identical with the compound prepared in example 1.

References:

SANOFI;FRIESZ, Antal;PáRKáNYI, Zsolt;DOMBRáDY, Zsolt WO2012/131409, 2012, A1 Location in patent:Page/Page column 14-15