US 6,211,381 B1Granted

Thiazole compounds

AssigneeNovartis Crop Protection, Inc.

InventorsHenry Szczepanski, Thomas Göbel, Ottmar Franz Hüter, Anthony Cornelius O'Sullivan, Marcel Senn, Thomas Rapold, Peter Maienfisch, Thomas Pitterna

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Abstract

The invention relates to a process for preparing a compound of formula (I), in which X is CH or N, Y is NO2 or CN, Z is CHR3, O, NR3 or S, R1 and R2 are either each, independently of the other, hydrogen or unsubstituted or R4-substituted alkyl or together a two- or three-membered alkylene bridge or a two- or three-membered alkylene bridge in which one member is replaced by a hetero member selected from the group, consisting of NR5, O and S, R3 is H or unsubstituted or R4-substituted alkyl, R4 is an unsubstituted or substituted aryl or heteroaryl group, and R5 is H or alkyl, which comprises a) reacting a compound of formula (II) with a chlorinating agent or b1) initially reacting a compound of formula (IV) with a compound of formula (V) and b2) further reacting the compound of formula (II) obtainable thereby, with or without intermediate isolation, with a chlorinating agent, to intermediates used in this process, to the use of these intermediates and to a process for the preparation of these intermediates.

Claims1

Dependent claims

A compound of the formula IV

in free form or in the form of a salt,
in which
n is 0, 1 or 2,
X1 is a leaving group,
R4 is an unsubstituted or substituted aryl or heteroaryl group,
R6 is unsubstituted or R8-substituted alkyl, unsubstituted or R8-substituted alkenyl, unsubstituted or R8-substituted alkynyl, cycloalkyl, unsubstituted or substituted aryl, heteroaryl, SR7, (alkylene)SH or (alkylene)SR7,
R7 is unsubstituted or R4-substituted alkyl, unsubstituted or R4-substituted alkenyl, unsubstituted or R4-substituted alkynyl, cycloalkyl, unsubstituted or substituted aryl, heteroaryl or a group of the formula
in which
X is CH or N,
Y is NO2 or CN,
Z is CHR3, O, NR3 or S,
R1 and R2 are either each, independently of the other, hydrogen, or unsubstituted or R4-substituted alkyl or together a two- or three-membered alkylene bridge or a two- or three-membered alkylene bridge in which one member is replaced by a hetero member selected from the group consisting of NR5, O and S, and
R5 is H or alkyl, and
R8 is an unsubstituted or substituted aryl or heteroaryl group, —COOH, COOM, wherein M is an alkali metal, or —COO-C1-C8-alkyl.

11 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/077,569Filed 1 Jun 1998
Priority: CH 3412/951 Dec 1995
Granted: 3 Apr 2001
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 277/32
Having two or three double bonds between ring members or between ring members and non-ring members: with hetero atoms or with carbon atoms having…
C07D 277/36
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,…:…
C07D 417/06
Containing two hetero rings: linked by a carbon chain containing only aliphatic carbon atoms
C07D
Heterocyclic compounds