Reagents for fluorosulfating alcohols or amines

Patent metadata

Field	Value
Publication number	US-10836717-B2
Application number	US-201816103824-A
Country	US
Kind code	B2
Filing date	Aug 14, 2018
Priority date	Aug 14, 2017
Publication date	Nov 17, 2020
Grant date	Nov 17, 2020

Abstract

Disclosed herein are compounds of formula Ar—N(SO 2 F) 2 , wherein Ar is selected from an optionally substituted aryl, an optionally substituted five-membered heteroaryl, or an optionally substituted six-membered heteroaryl. Also disclosed are methods of synthesizing the above compounds by reacting a compound of formula Ar—NH—R 9 with MN(SO 2 F) 2 .

First claim

What is claimed is:

1. A compound of Formula I:
Ar—N(SO 2 F) 2   (I)

wherein Ar is a moiety of Formula II:

wherein:
each of X 1, X 2, X 3, X 4, and X 5 is carbon;
each of R 1, R 2, R 4, and R 5 is independently selected from hydrogen, halide, an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted five-membered heteroaryl, or an optionally substituted six-membered heteroaryl, or a moiety of formula R 6 —C(═O)-NH- , wherein R 6 is selected from hydrogen, an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted five-membered heteroaryl, or an optionally substituted six-membered heteroaryl;
R 3 is selected from halide, an optionally substituted aryl, an optionally substituted five-membered heteroaryl, or an optionally substituted six-membered heteroaryl, or a moiety of formula R 6 —C(═O)—NH— , wherein R 6 is selected from hydrogen, an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted five-membered heteroaryl, or an optionally substituted six-membered heteroaryl.

2. The compound of claim 1 , wherein each of R 1, R 2, R 4, and R 5 is independently selected from hydrogen, halide, an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted five-membered heteroaryl, or an optionally substituted six-membered heteroaryl.

3. The compound of claim 1 , wherein R 3 is a moiety of formula R 6 —C(═O)—NH— .

4. The compound of claim 1 , wherein each of R 1, R 2, R 4, and R 5 is independently selected from hydrogen, fluoro, chloro, bromo, methyl, trifluoromethyl, ethyl, perfluoroethyl, n-propyl, i-propyl, n-butyl, sec-butyl, or tert-butyl.

5. The compound of claim 1 , wherein each of R 1, R 2, R 4, and R 5 is independently selected from hydrogen, chloro, methyl, trifluoromethyl, and ethyl.

6. The compound of claim 1 , wherein R 1, R 2, R 4, and R 5 are hydrogen.

7. The compound of claim 1 , wherein R 6 is independently selected from hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, or tert-butyl.

8. The compound of claim 1 , wherein R 6 is independently selected from methyl, ethyl, and n-propyl.

9. The compound of claim 1 , wherein R 6 is methyl.

10. The compound of claim 1 , wherein the compound is a compound of Formula III

Assignees

• Bioduro Llc
• Pfizer

Inventors

• Zhou Hua
• Mukherjee Paramita
• Liu Rongqiang
• Am Ende Christopher W
• Deng Tianjing

Classifications

• C07B45/00 Primary

  Formation or introduction of functional groups containing sulfur · CPC title

• C07D413/04

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

• C07D213/65

  attached in position 3 or 5 · CPC title

• C07D491/10

  Spiro-condensed systems · CPC title

• C07D239/88

  Oxygen atoms · CPC title