Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-11-21
2003-12-09
Shah, Mukund J. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S467000, C564S134000, C564S167000, C564S256000, C564S258000, C564S265000, C560S039000
Reexamination Certificate
active
06660872
ABSTRACT:
This application is a 371 of PCT/EP00/04300, published May 12, 2000.
The present invention relates to novel processes for preparing methoxyimino-acetamides.
A process for preparing N-methyl-[2-(2-hydroxy)phenyl]-2-methoxyimino-acetamide has already been described (cf. EP 0 398 692 A2). However, the compounds prepared by this process are only obtainable in moderate yields.
It has now been found that according to process part 1) compounds of the formula (I)
in which
R
1
, R
2
, R
3
and R
4
are identical or different and independently of one another each represents hydrogen, halogen, cyano, nitro, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl,
R
5
represents substituted or unsubstituted alkyl,
R
6
represents hydrogen, substituted or unsubstituted alkyl,
are obtained when
A) according to process step 2), compounds of the formula (IV),
in which
R
1
, R
2
, R
3
and R
4
are as defined above,
are reacted, in the presence of an acid or an acidic ion exchanger, with an alcohol of the formula (V),
R
7
—OH (V)
in which
R
7
represents substituted or unsubstituted alkyl,
and with a carbonyl compound, which binds the hydroxylammonium chloride eliminated in the reaction forming an oxime, to give compounds of the formula (VI),
in which
R
1
, R
2
, R
3
, R
4
and R
7
are as defined above,
and the resulting compounds of the formula (VI) are either
a) according to process step 3), reacted with a hydroxylammonium salt, if appropriate in the presence of a diluent and if appropriate in the presence of an acid or an acid acceptor, to give compounds of the formula (VII),
in which
R
1
, R
2
, R
3
, R
4
and R
7
are as defined above,
and the resulting compounds of the formula (VII) are, according to process step 4), reacted with an alkylating agent of the formula (VIII),
R
5
—X (VIII)
in which
R
5
is as defined above and
X represents halogen, —O—CO—OR
5
— or —O—SO
2
—O—R
5
, where R
5
is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a base,
or
b) are, according to process step 5), reacted with an alkoxyamine of the formula (IX),
R
5
—O—NH
2
(IX)
in which
R
5
is as defined above,
— or an acid addition complex thereof—, if appropriate in the presence of a diluent and if appropriate in the presence of an acid or an acid acceptor,
or when
B) according to process step 6), compounds of the formula (IV),
in which
R
1
, R
2
, R
3
and R
4
are as defined above,
are reacted with an alkoxyamine of the formula (IX),
R
5
—O—NH
2
(IX)
in which
R
5
is as defined above,
— or an acid addition complex thereof—if appropriate in the presence of a diluent and if appropriate in the presence of an acid,
or when
C) according to process step 7), compounds of formula (IV),
in which
R
1
, R
2
, R
3
and R
4
are as defined above,
are reacted, in the presence of an acid or an acidic ion exchanger, with an alcohol of the formula (V),
R
7
—OH (V)
in which R
7
is as defined above,
if appropriate with addition of a hydroxylammonium salt, and the resulting compounds of the formula (VII),
in which
R
1
, R
2
, R
3
, R
4
and R
7
are as defined above,
are reacted according to process step 4),
or when
D) according to process step 8), compounds of the formula (X),
in which
R
1
, R
2
, R
3
, R
4
and R
5
are as defined above,
are reacted, in the presence of an acid or an acidic ion exchanger, with an alcohol of the formula (V),
R
7
—OH (V)
in which R
7
is as defined above, if appropriate in the presence of a carbonyl compound which binds the hydroxylammonium chloride eliminated in the reaction forming an oxime,
and the compounds of the formula (II) obtained according to proceses A)-D),
in which
R
1
, R
2
, R
3
, R
4
and R
5
are as defined above and
R
7
represents unsubstituted or substituted alkyl,
are, if appropriate without intermediate isolation of the compounds of the formula (II) (one-pot process),
reacted according to process step 1) with an alkylamine of the formula (III),
R
6
—NH
2
(III)
in which R
6
is as defined above, if appropriate in the presence of a diluent.
Moreover, it has been found that, according to process part 2), compounds of the formula (XI),
in which
Z represents unsubstituted or substituted cycloalkyl, aryl or heterocyclyl,
Q represents oxygen or sulphur,
Y represents halogen and
R
1
, R
2
, R
3
, R
4
, R
5
and R
7
are as defined above,
are obtained when compounds of the formula (I) are reacted according to the novel process part 1), and these compounds (I) are either
E) according to process step 9) reacted with pyrimidine derivatives of the formula (XII),
in which
T
1
and T
2
are identical or different and represent halogen or —SO
2
—R
8
, where R
8
is alkyl, aryl or benzyl, and
Y is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a base, and the resulting compounds of the formula (XIII),
in which
T
2
, Y, R
1
, R
2
, R
3
, R
4
, R
5
and R
7
are as defined above,
are reacted, according to process step 10), with a cyclic compound of the general formula (XIV),
Z—Q—H (XIV)
in which
Z and Q are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst,
or
F) are reacted according to process step 11) with compounds of the formula (XV),
in which
Z, Q, T
1
and Y are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a base.
Furthermore, it has been found that the Z-isomeric compounds of the formula (XI) are isomerized to E-isomeric compounds of the formula (XI) when Z isomers or E/Z isomer mixtures of the compounds of the formula (XI) are treated with acids, if appropriate in a diluent. The isomerization affords the E isomers in good yields.
Furthermore, it has been found that the Z-isomeric compounds of the formula (XIII) are isomerized to E-isomeric compounds of the formula (XIII) when Z isomers or E/Z isomer mixtures of the compounds of the formula (XIII) are treated with acids, if appropriate in a diluent. The isomerization affords the E isomers in good yields.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are, including in combination with heteroatoms, such as, for example, in alkoxy, alkylthio or alkylamino, in each case straight-chain or branched having in particular 4 carbon atoms.
Aryl denotes aromatic, mono- or polycyclic hydrocarbons rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Halogen generally denotes fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine. Heterocyclyl denotes saturated or unsaturated, and also aromatic, cyclic compounds in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen or sulphur. If appropriate, the cyclic compounds form a polycyclic ring system together with further carbocyclic or heterocyclic fused-on or bridged rings. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl denotes saturated carbocyclic compounds which may, if appropriate, form a polycyclic ring system with further carbocyclic, fused-on or bridged rings.
Halogenoalkyl denotes partially or fully halogenated alkyl. In the case of polyhalogenated halogenoalkyl, the halogen atoms can be identical or different. Preferred halogen atoms are fluorine and chlorine and in particular fluorine. If the halogenoalkyl also carries other substituents, the maximum number of halogen atoms possible is reduced to the remaining free valencies.
The compounds
Gallenkamp Bernd
Gayer Herbert
Gerdes Peter
Heinemann Ulrich
Hübsch Walter
Bayer Aktiengesellschaft
Harmuth Raymond J.
Henderson Richard E. L.
Shah Mukund J.
Tucker Zachary C.
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