Nitrosation reagents and methods

Patent metadata

Field	Value
Publication number	US-12459909-B2
Application number	US-202117928519-A
Country	US
Kind code	B2
Filing date	Jun 17, 2021
Priority date	Jun 18, 2020
Publication date	Nov 4, 2025
Grant date	Nov 4, 2025

Abstract

Provided are compounds that can find use as nitrosation reagents. Provided are nitrosation methods that include reacting a substrate with one of the provided nitrosation reagents and thereby generating a nitrosation product. Provided are kits including a nitrosation reagent. Provided are compositions wherein the nitrosation reagent is enriched in the 15 N isotope.

First claim

The invention claimed is:

1 . A compound of formula (I):

wherein:
n is 0 to 4,
N′ is 14 N or 15 N, and
R 1 , R 2 , and each R 3 are each independently selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, heterocycle, substituted heterocycle, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halo, and hydroxyl.

2 . The compound of claim 1 , wherein n is 0.

3 . The compound of claim 1 , wherein n is 1 to 4.

4 . The compound of claim 1 , wherein R 1 and R 2 are each independently selected from H, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, and halo.

5 . The compound of claim 4 , wherein at least one of R 1 and R 2 is a non-hydrogen group.

6 . The compound of claim 4 , wherein R 1 and R 2 are each independently selected from H, methyl, phenyl, fluoro, and trifluoromethyl.

7 . The compound of claim 1 , wherein R 1 and R 2 are the same group.

8 . The compound of claim 7 , wherein R 1 and R 2 are both H, both methyl, both phenyl, or both fluoro.

9 . The compound of claim 1 , wherein R 1 and R 2 are different groups.

10 . The compound of claim 1 , wherein N′ is 14 N.

11 . The compound of claim 1 , wherein N′ is 15 N.

12 . A nitrosation method, comprising:
reacting a substrate with a nitrosation composition comprising a compound of claim 1 and thereby generating a nitrosation product.

13 . The method of claim 12 , wherein:
the substrate has the formula E-H or E − , E is selected from the group consisting of: —SR A , —OR A , —NR A R B , —PR A R B , —CR A R B R C , and —SiR A R B R C , R A , R B , and R C are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, heterocycle, substituted heterocycle, aryl, substituted aryl, heteroaryl, and substituted heteroaryl, at least one of R A , R B , and R C is a non-hydrogen group, and the reacting generates a product of formula E-NO.

14 . The method of claim 12 , wherein the substrate has the formula E-H, the reacting generates a product of formula E-NO, wherein E has the formula (II):

wherein:
Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently selected from CR′ and N, and
each R′ is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, heterocycle, substituted heterocycle, aryl, substituted aryl, heteroaryl, substituted heteroaryl.

15 . The method of claim 14 , wherein Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each CR′.

16 . The method of claim 14 , wherein each R′ is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl.

17 . The method of claim 13 , wherein E is —SR A .

18 . The method of claim 13 , wherein E is —OR A .

19 . The method of claim 13 , wherein E is —NR A R B .

20 . A kit, comprising:
a composition comprising a compound of formula (I)

wherein:
n is 0 to 4,
N′ is 14 N or 15 N, and
R 1 , R 2 , and each R 3 are each independently selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, heterocycle, substituted heterocycle, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halo, and hydroxyl; and
a container containing the composition.

Assignees

• Univ California

Inventors

• Baxter Ryan D
• Galloway Jordan

Classifications

• C07C243/06

  N-nitroso-amines · CPC title

• C07D277/30

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D233/80

  with hetero atoms or acyl radicals directly attached to ring nitrogen atoms · CPC title

• C07D209/38

  in positions 2 and 3, e.g. isatin · CPC title