IP Library Granted Patent US 8,865,908
Granted Patent B2
US 8,865,908 · App. 12/847,152 · Granted Oct 21, 2014

Process for the preparation of a 2-pyridylethylcarboxamide derivative

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Quick Facts
Patent No.
US 8,865,908
App. No.
12/847,152
Granted
Oct 21, 2014
Kind
B2
Abstract

Process for the preparation of a N-[2-(2-pyridinyl)ethyl]carboxamide derivative of general formula (I) or a salt thereof Intermediate of general formula (II) Intermediate of general formula (III)

Claims (17)

1. A compound of formula (III)

wherein:

X is the same or different and is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkylamino, a di-C 1 -C 8 -alkylamino, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyloxy, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkynyloxy, a C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a (N—C 1 -C 8 -alkyl)oxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a (N—C 1 -C 8 -alkyl)-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkyloxycarbonyloxy, a C 1 -C 8 -alkylsulphenyl, a C 1 -C 8 -halogenoalkylsulphenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulphinyl, a C 1 -C 8 -halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulphonyl, a C 1 -C 8 -halogenoalkylsulphonyl having 1 to 5 halogen atoms, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, a (benzyloxyimino)-C 1 -C 6 -alkyl, a benzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyl or a phenylamino;

R 1 is a hydrogen atom, a C 1 -C 8 -alkyl, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms or a C 1 -C 8 -alkoxycarbonyl;

R 2 is a hydrogen atom or a cyclopropyl group;

p is an integer equal to 1, 2, 3 or 4;

A represents a phenyl group being optionally substituted by one or more substituents chosen independently of each other as being a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a C 1 -C 8 -alkyl, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkylamino, a di-C 1 -C 8 -alkylamino, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkoxy-C 2 -C 8 -alkenyl, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulphenyl, a C 1 -C 8 -halogenoalkylsulphenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulphinyl, a C 1 -C 8 -halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulphonyl, a C 1 -C 8 -halogenoalkylsulphonyl having 1 to 5 halogen atoms or a C 1 -C 8 -alkylsulfonamide;

R 3 represents a hydrogen atom or CO 2 Alk; and

Alk represents a C 1 -C 8 -alkyl group.

2. The compound according to claim 1 wherein p is 2.

3. The compound according to claim 1 wherein X is chosen, independently of the others, as being chlorine or CF 3 .

4. The compound according to claim 1 wherein the 2-pyridyl moiety is substituted by X in 3- and/or in 5-position.

5. The compound according to claim 1 wherein R 1 is a hydrogen atom, a methyl group, CF 3 , CHF 2 , CClF 2 or CCl 3 .

6. The compound according to claim 1 wherein R 2 is a hydrogen atom.

7. The compound according to claim 1 wherein A is substituted by one or two substituents.

8. The compound according to claim 1 wherein each substituent of A is chosen, independently of each other, as being chlorine or CF 3 .

9. The compound according to claim 1 wherein the A is substituted in ortho position.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Jul 4, 2023
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Reel/Frame 064198/0823 →
CHANGE OF ADDRESS Recorded Jun 12, 2023
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 064021/0344 →
NUNC PRO TUNC ASSIGNMENT Recorded Feb 3, 2016
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 037689/0656 →