# US 2017/0283394 A1 · Novel intermediate and process useful in the preparation of -(2-chlorophenyl)-methanone

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- Number: US 2017/0283394 A1
- Document ID: US20170283394A1
- Status: Published application
- Kind: A1
- Application number: 15/623,550
- Filed: 2017-06-15
- Published: 2017-10-05
- Earliest claimed: 2006-12-20
- Assignees: Eli Lilly and Company
- Applicants: Eli Lilly and Company
- Inventors: Michael Edward Kobierski; Michael E. Kopach; Pingyun Chen
- Web page: https://patentgrep.com/patent/US20170283394A1

## CPC

- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/06: Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 13/10: of the bladder
- A61P 17/00: Drugs for dermatological disorders
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 213/50: Ketonic radicals
- C07D 213/53: Nitrogen atoms
- 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 relates to novel compounds, (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone benzoate, and (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone toluate, which are useful intermediates for the preparation of the compound of Formula I: The present invention further relates to novel processes for preparing a crystalline compound, which is {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV.

## Claims

### Claim 1

A process for preparing a compound that is {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV, comprising:
crystallizing the product from a solvent mixture of isopropyl acetate and heptanes.

### Claim 2 (depends on 1)

The process of claim 1 further comprising reacting a salt of (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone with 1-azidomethyl-3,5-bistrifluoromethylbenzene in the presence of tert-butanol.

### Claim 3 (depends on 2)

The process of claim 2 wherein the salt of (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone is a benzoate salt or a toluate salt.

### Claim 4 (depends on 3)

The process of claim 3 wherein the salt of (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone is a benzoate salt.

### Claim 5

A compound selected from the group consisting of (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone benzoate and (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-ylvinyl)pyridin-3-yl]methanone toluate.

### Claim 6 (depends on 5)

The compound of claim 5 which is (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-ylvinyl)pyridin-3-yl]methanone benzoate.