# US 2008/0188656 A1 · Process for the Synthesis of 5- (Methyl-1H-Imidazol-1-Yl) -3- (Trifluoromethyl) -Benzeneamine

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- Number: US 2008/0188656 A1
- Document ID: US20080188656A1
- Status: Published application
- Kind: A1
- Application number: 11/915,671
- Filed: 2006-06-07
- Published: 2008-08-07
- Earliest claimed: 2005-06-09
- Assignees: Novartis AG
- Inventors: Wen-Chung Shieh; Joseph McKenna
- Web page: https://patentgrep.com/patent/US20080188656A1

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- C07D 401/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a new method of making compounds of formula (I): wherein R1 is mono- or polysubstituted aryl; R2 is hydrogen, lower alkyl or aryl; and R4 is hydrogen, lower alkyl or halogen.

## Claims

### Claim 1

A process for the preparation of compounds of formula (I)
comprising reacting the compound:
with R1—NH—R2, wherein
R1 is substituted or unsubstituted aryl;
R2 is hydrogen, lower alky or aryl;
R4 is hydrogen, lower alkyl or halogen; and
R3 is lower alkyl, phenyl, phenyl-lower alkyl or substituted phenyl,
and wherein the process is catalyzed by a base in an organic solvent.

### Claim 2

A process for the preparation of a compound of the formula (Ia)
comprising reacting the compound:
wherein R3 is lower alkyl, phenyl, phenyl-lower alkyl or substituted phenyl, with the compound 5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine of the structure (IVa):
and wherein the process is catalyzed by a base in an organic solvent.

### Claim 3

A process for the preparation of a compound of the formula (Ia)
comprising reacting the compound:
with 5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine (IVa) wherein the process is catalyzed by a base in an organic solvent.

### Claim 4 (depends on 1)

The process of claim 1, wherein the base is selected from the group consisting of metal hydride, bulky alkyl lithium, metal alkoxide, metal bis(trimethylsilyl)amide and lithium dialkylamide.

### Claim 5 (depends on 4)

The process of claim 4, wherein the metal is selected from the group consisting of lithium, sodium and potassium.

### Claim 6 (depends on 4)

The process of claim 4, wherein the base is potassium tert-butoxide.

### Claim 7 (depends on 1)

The process of claim 1, wherein the organic solvent is selected from the group of tetrahydrofuran, dimethylformamide, toluene and N-methylpyrrolidone.