Method for the preparation of thiadiazoles

Patent metadata

Field	Value
Publication number	US-9296735-B2
Application number	US-201314402069-A
Country	US
Kind code	B2
Filing date	May 17, 2013
Priority date	May 18, 2012
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

The present invention relates to processes for preparing protected glyceraldehydes, such as (hydroxy)methanesulfonates. In addition, the invention relates to thiadiazoles, particularly 3-diooxolanyl-thiadiazoles.

First claim

What is claimed is:

1. A compound of the structure

Wherein R is alkyl, aryl or the two R groups together form cycloalkyl; and
R b is an optionally substituted substituent selected from aryl, alkyl, arylalkyl, and 5-6 membered heterocyclyl.

2. A compound of claim 1 wherein R is C 1-6 alkyl or together forms C 3-6 cycloalkyl; and R b is optionally substituted phenyl.

3. A process for the preparation of

wherein R is optionally substituted aryl or alkyl, or the two R groups together form cycloalkyl or spirocycloalkyl; and
R b is optionally substituted aryl, alkyl, optionally substituted arylalkyl or optionally substituted 5-6 membered heterocyclyl;
comprising
treating

 with NH 2 OH to form

chlorination of

 followed by treatment with MsCl to form

treatment of

 with thiocyanate to form

 and
treatment of

 with R b —SH.

4. The process of claim 3 , wherein R is C 1-3 alkyl, or the two R groups together form cyclohexyl; and R b is optionally substituted aryl.

5. The process of claim 4 , wherein each R is methyl and R b is 4-methylphenyl, wherein said process is for the formation of

Assignees

• Amgen Inc

Inventors

• Bercot Eric A
• Bio Matthew
• Chan Johann
• Colyer John
• Fang Yuanqing
• Mennen Steven
• Milburn Robert R
• Tedrow Jason
• Riahi Babak

Classifications

• C07D417/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D317/26 Primary

  Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom · CPC title

• C07D317/72

  spiro-condensed with carbocyclic rings · CPC title