Propellane derivates and synthesis

Patent metadata

Field	Value
Publication number	US-10654812-B2
Application number	US-201515123898-A
Country	US
Kind code	B2
Filing date	Mar 5, 2015
Priority date	Mar 7, 2014
Publication date	May 19, 2020
Grant date	May 19, 2020

Abstract

Disclosed herein are compounds of the general Formula (I), and methods of synthesizing substituted bicyclo[1.1.1 jpentanes. The synthetic methods described herein use a [1.1.1]propellane, a Group VIII transition metal compound, a hydride source and a reagent that can contribute a substituent to form a substituted bicyclo[1.1.1]pentane, such as a compound of the general Formula (I).

First claim

What is claimed is:

1. A compound having the structure of Formula (I):

wherein:
R 1 is —N 3 , —SCN, —NO, —C(═NOR 2 )(CN), —CH(═NOR 2 ), CH(CO 2 H)(NHBoc), —CH(CO 2 H)(NH 2 ), an optionally substituted cycloalkynyl, an optionally substituted heteroaryl(C 1-6 alkyl), an optionally substituted heterocyclyl(C 1-6 alkyl), an optionally substituted aminoalkyl or an optionally substituted haloalkoxy; and
R 2 is (C 1 to C 10 ) alkoxy, an optionally substituted C 1-30 alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted cycloalkynyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl, an optionally substituted aryl(alkyl), an optionally substituted heteroaryl(alkyl), an optionally substituted heterocyclyl(alkyl), an optionally substituted aminoalkyl or an optionally substituted alkylamino;
wherein an optionally substituted aminoalkyl is a NH 2 group connected, as a substituent, via a lower alkylene group; and
wherein the optionally substituted aminoalkyl is a straight-chained —CH 2 — tethering group, forming bonds to connect molecular fragments via its terminal carbon atoms and wherein the lower alkylene group can be substituted by replacing one or more hydrogen of the lower alkylene group or by substituting both hydrogens on the same carbon with a cycloalkyl group.

2. The compound of claim 1 , wherein the compound is

3. The compound of claim 1 , wherein R 1 is a substituted aminoalkyl.

4. The compound of claim 1 , wherein R 1 is an unsubstituted aminoalkyl.

5. The compound of claim 1 , wherein R 1 is H 2 N—(CH 2 )n-, wherein n is an integer in the range of 1 to 6.

6. The compound of claim 5 , wherein n is 1.

7. The compound of claim 5 , wherein n is 2.

8. The compound of claim 5 , wherein n is 3.

9. The compound of claim 5 , wherein n is 4.

10. The compound of claim 5 , wherein n is 5.

11. The compound of claim 1 , wherein the compound is

12. The compound of claim 1 , wherein the compound is

13. The compound of claim 1 , wherein the compound is

Assignees

• Kalyra Pharmaceuticals Inc
• Recurium Ip Holdings Llc

Inventors

• Bunker Kevin Duane

Classifications

• C07C209/26

  by reduction with hydrogen · CPC title

• C07C227/04

  Formation of amino groups in compounds containing carboxyl groups · CPC title

• C07C271/22

  to carbon atoms of hydrocarbon radicals substituted by carboxyl groups · CPC title

• C07C229/28

  the carbon skeleton being saturated and containing rings · CPC title

• C07D249/06 Primary

  with aryl radicals directly attached to ring atoms · CPC title