ChemicalBook CAS DataBase List 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-3-en-1-yl)methyl]-N-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-N-(methoxymethyl)[1,1'-biphenyl]-2-sulfonamide

4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-3-en-1-yl)methyl]-N-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-N-(methoxymethyl)[1,1'-biphenyl]-2-sulfonamide synthesis

9synthesis methods

Product Name:4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-3-en-1-yl)methyl]-N-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-N-(methoxymethyl)[1,1'-biphenyl]-2-sulfonamide
CAS Number:1026355-73-6
Molecular formula:C34H44N4O6S
Molecular Weight:636.8

2-N-BUTYL-1,3-DIAZA-SPIRO[4,4]NON-1-EN-4-ONE HYDROCHLORIDE

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4'-(Bromomethyl)-N-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-N-(methoxymethyl)[1,1'-biphenyl]-2-sulfonamide

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4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-3-en-1-yl)methyl]-N-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-N-(methoxymethyl)[1,1'-biphenyl]-2-sulfonamide

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Yield:1026355-73-6 32 g

Reaction Conditions:

Stage #1: 2-butyl-1,3-diaza-spiro[4.4]non-1-en-4onewith sodium hydride in N,N-dimethyl-formamide;mineral oil at 0 - 20; for 0.333333 h;
Stage #2: 4'-(bromomethyl)-N-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-N-(methoxymethyl) [1,1'-biphenyl]-2-sulfonamide in N,N-dimethyl-formamide;mineral oil at 0 - 20;

Steps:

3.F Step F. 4’-[(2-Butyl-4-oxo-1,3-diazaspiro[4. 4]non-1-en-3-yl)methyl]-N-(4,5-dimethyl-3-isoxazolyl)-2’-(ethoxymethyl)-N-(methoxymethyl) [1,1’-biphenyl]-2-sulfonamide

Step F.
4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4. 4]non-1-en-3-yl)methyl]-N-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-N-(methoxymethyl) [1,1'-biphenyl]-2-sulfonamide
4'-(Bromomethyl)-N-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-N-(methoxymethyl) [1,1'-biphenyl]-2-sulfonamide] (entire sample) was used to alkylate 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one according to General Method 1.
The crude residue was chromatographed on silica gel using hexanes/ethyl acetate/triethylamine as eluant to provide 4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl-N-](4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-N- (methoxymethyl) [1,1'-biphenyl]-2-sulfonamide (32 g, 53% from Step B) as a slightly yellow oil.

References:

EP2732818,2017,B1 Location in patent:Paragraph 0174; 0149

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References

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References

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837408-81-8 Synthesis

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