Propargyl alcohol → 2,3-Dichloro-N-[3-methoxy-5-(2-propyn-1-yloxy)-2-pyrazinyl]benzenesulphonamide

HRID 1444075Notes

Reaction equation

HRID 1444075 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]([C:22]1[C:27]([O:28][CH3:29])=[N:26][C:25](Cl)=[CH:24][N:23]=1)COCCO[Si](C)(C)C)(=[O:11])=[O:10].[CH2:31]([OH:34])[C:32]#[CH:33].[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:22]1[C:27]([O:28][CH3:29])=[N:26][C:25]([O:34][CH2:31][C:32]#[CH:33])=[CH:24][N:23]=1)(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 866028002,3-dichloro-N-(5-chloro-3-methoxy-2-pyrazinyl)-N-({2-[(trimethylsilyl)oxy]ethoxy}methyl)benzenesulphonamide

Product 1

HCID 102873522,3-Dichloro-N-[3-methoxy-5-(2-propyn-1-yloxy)-2-pyrazinyl]benzenesulphonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Procedure as for Example 115 using 2,3-dichloro-N-(5-chloro-3-methoxy-2-pyrazinyl)-N-({2-[(trimethylsilyl)oxy]ethoxy}methyl)benzenesulphonamide (Example 115a) (0.25 g), propargyl alcohol (0.025 mL) and sodium hydride (0.035 g of a 60% dispersion in oil) in N,N-dimethylformamide (5 mL). Yield 0.05 g.

Sources & evidence

ORD record
ord-04041adc49034716b305d5cd78eca9c6
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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