Sulfamoylating reagents
AssigneeMillennium Pharmaceuticals, Inc.
InventorsIan Armitage, Eric L. Elliott, Marianne Langston, Steven P. Langston, Quentin J. McCubbin, Hiro Mizutani, Matthew Stirling, Lei Zhu
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Abstract
The present invention provides sulfamoylating reagents of formula RuN−—S(O)2X+, wherein X is a cyclic tertiary amine or a nitrogen-containing heteroaryl and Ru is an amine protecting group or hydrogen.
Claims18
A compound of formula RuN−—S(O)2X+, wherein X is a cyclic tertiary amine which is triethylenediamine, diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicycle[4.3.0]non-5-ene, sparteine, N,N′-dimethylpiperazine, or N-ethylmorpholine and Ru is an amine protecting group or hydrogen.
A complex comprising a compound of formula RuN−—S(O)2X+ and the hydrochloride salt of X, wherein X is a cyclic tertiary amine which is triethylenediamine, diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicycle[4.3.0]non-5-ene, sparteine, N,N′-dimethylpiperazine, or N-ethylmorpholine and Ru is an amine protecting group or hydrogen.
A process for the formation of a compound of formula RuN−—S(O)2X+, wherein Ru is —C(O)OC(Rv)2(Rw), comprising:
- I-E) treating (Rw)(Rv)2C—OH with chlorosulfonylisocyanate;
- II-E) treating the reaction mixture formed in step I-E) with X;
- and
- III-E) isolating the sulfamoylating reagent RuN−—S(O)2X+ formed in step II-E);
- wherein
- X is a cyclic tertiary amine which is triethylenediamine, diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicycle[4.3.0]non-5-ene, sparteine, N,N′-dimethylpiperazine, or N-ethylmorpholine,
- each Rv is independently optionally substituted C1-10 aliphatic, optionally substituted aryl, or hydrogen;
- Rw is optionally substituted C1-10 aliphatic or optionally substituted aryl;
- or one Rv is optionally substituted C1-10 aliphatic;
- and the other Rv is taken together with Rw to form an optionally substituted C3-6 cycloaliphatic ring.
Dependencies are inferred from the claim text.