Process for preparing pyrazoles

Patent metadata

Field	Value
Publication number	US-10513498-B2
Application number	US-201916292773-A
Country	US
Kind code	B2
Filing date	Mar 5, 2019
Priority date	Jul 31, 2014
Publication date	Dec 24, 2019
Grant date	Dec 24, 2019

Abstract

The present invention relates to a process for preparing a pyrazole compound of formula V, which comprises cyclizing a hydrazone substituted α,β-unsaturated carbonyl compound of formula IV by reacting it with a suitable reagent, e.g. a reducing agent, an organometallic reagent or a nucleophilic reagent. The compounds of formula V are versatile reaction tools for the preparation of pyrazole derived fine chemicals. The present invention also relates to pyrazole compounds of formulae Va, Vb, Vc, and VI.

First claim

The invention claimed is:

1. A compound of formula V or a salt, stereoisomer, tautomer or N-oxide thereof

wherein
R 2 is CH 3 , R 3 is H, R 4 is CH(CH 3 ) 2 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is CHFCH 3 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is 1-CN-cC 3 H 4 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is 1-C(O)NH 2 -cC 3 H 4 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 and R 5 together are CH 2 CH 2 CF 2 CH 2 CH 2 , and R 6 is H;
wherein
R 1 is CN or COOR c ; R c is H, C 1 -C 4 -alkyl or aryl-C 1 -C 4 -alkyl, or wherein R c together with the C(O)O group forms a salt [C(O)O] − NR 4 + , [C(O)O] − M a + or [C(O)O] − ½M ea 2+ , wherein M a is an alkali metal and M ea is an alkaline earth metal.

2. The compound of claim 1 , wherein said compound has formula Va or a salt, stereoisomer, tautomer or N-oxide thereof

wherein
R 2 is CH 3 , R 3 is H, R 4 is CH(CH 3 ) 2 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is CHFCH 3 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is 1-CN-cC 3 H 4 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is 1-C(O)NH 2 -cC 3 H 4 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 and R 5 together are CH 2 CH 2 CF 2 CH 2 CH 2 , and R 6 is H;
and wherein
R c is C 1 -C 4 -alkyl or aryl-C 1 -C 4 -alkyl, or wherein R c together with the C(O)O group forms a salt [C(O)O] − NR 4 + , [C(O)O] − M a + or [C(O)O] − ½M ea 2+ , wherein M a is an alkali metal and M ea is an alkaline earth metal.

3. The compound of claim 1 , wherein said compound has formula Vc or a salt, stereoisomer, tautomer or N-oxide thereof

wherein
R 2 is CH 3 , R 3 is H, R 4 is CH(CH 3 ) 2 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is CHFCH 3 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is 1-CN-cC 3 H 4 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is 1-C(O)NH 2 -cC 3 H 4 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 and R 5 together are CH 2 CH 2 CF 2 CH 2 CH 2 , and R 6 is H.

4. The compound of claim 1 , wherein said compound has formula Vb or a salt, stereoisomer, tautomer or N-oxide thereof

wherein
R 2 is CH 3 , R 3 is H, R 4 is CH(CH 3 ) 2 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is CHFCH 3 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is 1-CN-cC 3 H 4 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 is 1-C(O)NH 2 -cC 3 H 4 , R 5 is CH 3 and R 6 is H; or
R 2 is CH 3 , R 3 is H, R 4 and R 5 together are CH 2 CH 2 CF 2 CH 2 CH 2 , and R 6 is H.

5. A compound of formula IV or a salt, stereoisomer, tautomer or N-oxide thereof

wherein
R 1 is CN, C(O)OCH 3 , C(O)OCH 2 CH 3 , C(O)OC(CH 3 ) 3 , C(O)OCH 2 C 6 H 5 , or COOH;
R 2 is CH 3 , R 3 is H, and
R 4 is CH(CH 3 ) 2 , and R 5 is CH 3 ; or
R 4 is CHFCH 3 , and R 5 is CH 3 ; or
R 4 is 1-CN-cC 3 H 4 , and R 5 is CH 3 ; or
R 4 is 1-C(O)NH 2 -cC 3 H 4 , and R 5 is CH 3 ; or
R 4 and R 5 together are CH 2 CH 2 CF 2 CH 2 CH 2 .

Assignees

• Basf Se

Inventors

• Gockel Birgit
• Saelinger Daniel
• Soergel Sebastian
• Rack Michael

Classifications

• C07D405/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D403/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D231/14 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title