# US 10,246,427 B2 · Derivatives of 1,2,3-triazolyl cyclohexan-1-ol and its use

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- Number: US 10,246,427 B2
- Document ID: US10246427B2
- Status: Granted
- Kind: B2
- Application number: 15/580,040
- Filed: 2016-06-07
- Published: 2018-10-18
- Granted: 2019-04-02
- Earliest claimed: 2015-06-08
- Assignees: Uniwersytet Jagiellonski
- Applicants: Uniwersytet Jagiellonski
- Inventors: Przemyslaw Szafranski; Patryk Kasza; Marek Cegla
- Web page: https://patentgrep.com/patent/US10246427B2

## CPC

- C07D 249/04: 1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

1,2,3-triazolyl cyclohexanol derivatives have been disclosed and their use as ligands accelerating the copper(I)-catalyzed azide-alkyne cycloaddition and the zinc(II)-catalyzed azide-nitrile cycloaddition.

## Claims

### Claim 1

The compound of the general formula:
wherein:
substituents in the aliphatic ring are in cis- or trans-relative configuration, and
R1 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3)2, —NHCH3 —SH, or —SCH3
R2 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3)2, —NHCH3 —SH, or —SCH3
n is an integer from 0 to 3
R3 is an alkyl chain containing 1-3 carbon atoms,
R4 is an alkyl chain containing 1-3 carbon atoms,
or
substituents in the aliphatic ring are in cis- or trans-relative configuration, and
R1 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3)2, —NHCH3 —SH, or —SCH3
R2 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3)2, —NHCH3 —SH, or —SCH3
n is an integer from 0 to 3
and R3 and R4 together with the nitrogen atom form one of the systems presented below:
wherein R is the remaining part of the molecule described above.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein the structure is the following formula:
wherein R1 is hydrogen and R2 is a hydroxyl group in trans-position or R2 is hydrogen and R1—a hydroxyl group in any relative configuration, or R1 and R2 are hydrogen atoms.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein the structure is the following formula:
wherein R1 is hydrogen and R2 is a hydroxyl group in trans-position or R2 is hydrogen and R1—a hydroxyl group in any relative configuration, or R1 and R2 are hydrogen atoms.

### Claim 4 (depends on 1)

The compound according to claim 1, which is 2-{4-[(dimethylamine)methyl]-1,2,3-triazolyl}cyclohexan-1-ol.

### Claim 5

A method for accelerating a copper(I)-catalyzed azide—alkyne cycloaddition reaction comprising:
using a compound of the general formula:
wherein:
substituents in the aliphatic ring are in cis- or trans-relative configuration, and
R1 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3¬)2, —NHCH3 or —SCH3
R2 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3¬)2, —NHCH3 —SH, or —SCH3
n is an integer from 0 to 3
R3 is an alkyl chain containing 1-3 carbon atoms,
R4 is an alkyl chain containing 1-3 carbon atoms,
or
substituents in the aliphatic ring are in cis- or trans-relative configuration, and
R1 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3¬)2, —NHCH3 —SH, or —SCH3
R2 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3¬)2, —NHCH3 —SH, or —SCH3
n is an integer from 0 to 3
and R3 and R4 together with the nitrogen atom form one of the systems presented below:
wherein R is the remaining part of the molecule described above, as a ligand in the cycloaddition reaction.

### Claim 6

A method for accelerating a zinc(II)-catalyzed azide—nitrile cycloaddition reaction comprising:
using a compound of the general formula:
wherein:
substituents in the aliphatic ring are in cis- or trans-relative configuration, and
R1 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3¬)2, —NHCH3 —SH, or —SCH3
R2 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3¬)2, —NHCH3 —SH, or —SCH3
n is an integer from 0 to 3
R3 is an alkyl chain containing 1-3 carbon atoms,
R4 is an alkyl chain containing 1-3 carbon atoms,
or
substituents in the aliphatic ring are in cis- or trans-relative configuration, and
R1 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3¬)2, —NHCH3 —SH, or —SCH3
R2 is one of the following substituents: —H, ═O, —OH, —OCH3, —NH2, —N(CH3¬)2, —NHCH3 —SH, or —SCH3
n is an integer from 0 to 3
and R3 and R4 together with the nitrogen atom form one of the systems presented below:
wherein R is the remaining part of the molecule described above, as a ligand in the cycloaddition reaction.