N-(7-fluoro-1,1,3-trimethyl -1 H-inden-4yl) amides and a process for preparing same

Patent metadata

Field	Value
Publication number	US-11208374-B2
Application number	US-201916665114-A
Country	US
Kind code	B2
Filing date	Oct 28, 2019
Priority date	Mar 17, 2016
Publication date	Dec 28, 2021
Grant date	Dec 28, 2021

Abstract

The present invention relates to N-(7-fluoro-1,1,3-trimethyl-1H-inden-4yl) amides and a process for preparing same. The novel amides are useful in a process for converting the unwanted S enantiomer form of a 4-aminoindane derivative to its useful raceme.

First claim

The invention claimed is:

1. A compound of Formula V,

wherein, R is: (i) C 1 -C 6 alkyl group or (ii) a C 6 -C 10 aryl group, wherein group (i) or group (ii) is optionally substituted with one or more of C 1 -C 6 alkyl groups and/or halogen atoms.

2. The compound of claim 1 , which is N-(7-fluoro-1,1,3-trimethyl 1H-inden-4yl)acetamide.

3. The compound of claim 1 prepared by a process starting from Formula (II), which is (S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-amine,

and the process comprising the steps of:
(a) acylating the (S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-amine to obtain an indaneamide derivative;
(b) oxidizing said indaneamide derivative to obtain 3-hydroxyl indaneamide derivative;
(c) dehydrating said 3-hydroxyl indaneamide derivative to obtain the compound of Formula V.

4. The compound of claim 3 which is N-(7-fluoro-1,1,3-trimethyl-1H-inden-4yl)acetamide.

5. A compound of Formula V,

wherein, R is: (i) a C 1 -C 6 alkyl selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl and hexyl; or (ii) a C 6 -C 10 aryl group selected from the group consisting of phenyl and napthyl groups, wherein group (i) or group (ii) is optionally substituted with one or more of C 1 -C 6 alkyl groups and/or halogen atoms.

Assignees

• Fmc Corp

Inventors

• Swamy Narayana
• Devarajan Chokalingam
• Datar Ravindra Vitthal

Classifications

• C07C2602/08

  the other ring being five-membered, e.g. indane · CPC title

• C07C233/24

  with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring · CPC title

• C07C233/15

  with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring · CPC title

• C07C231/12

  by reactions not involving the formation of carboxamide groups · CPC title

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title