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US 8,026,395 B1Granted
Process for the synthesis of anti-neoplasia agent VNP40101M
AssigneeNanotherapeutics, Inc.
InventorsXu Lin, Ivan King
Life of this patent
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Abstract
The present invention relates to simple, safe, high-yield methods of synthesizing VNP40101M, 1,2-bis(methylsulfonyl)-2-(2-chloroethyl)-2-(methylaminocarbonyl)hydrazine, an anti-neoplasia agent. One particularly preferred method uses methyl chloroformamide in a one-pot reaction at elevated temperatures to provide VNP40101M in high yield.
Claims11
A method for producing a compound of the formula:
- comprising subjecting a compound of the formula:
- to a chloroformylating reaction to produce a reactive intermediate of the formula
- which is subjected to a methylaminylating reaction to produce VNP40101M, said method optionally further purifying VNP40101M to a purity higher than 97% by subjecting said VNP40101M produced to at least one round of ethanol solubilization and crystallization.
A method for producing a compound of the formula:
- comprising subjecting a compound of the formula:
- to a reaction with ClCONHMe to produce VNP40101M, said method optionally further purifying VNP40101M to a purity higher than 97% by subjecting said VNP40101M produced to at least one round of ethanol solubilization and crystallization.
A method for producing a compound of the formula:
- comprising subjecting a compound of the formula:
- to a reaction with ClC(O)OR to produce a carbamate of the formula:
- which is subjected to a methylaminylating reaction containing methylamine and a Lewis acid to produce VNP40101M, said method optionally further purifying VNP40101M to a purity higher than 97% by subjecting said VNP40101M produced to at least one round of ethanol solubilization and crystallization.
Dependencies are inferred from the claim text.