WO2007005455A2 - Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted heterocycles - Google Patents

Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted heterocycles Download PDF

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WO2007005455A2
WO2007005455A2 PCT/US2006/025144 US2006025144W WO2007005455A2 WO 2007005455 A2 WO2007005455 A2 WO 2007005455A2 US 2006025144 W US2006025144 W US 2006025144W WO 2007005455 A2 WO2007005455 A2 WO 2007005455A2
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optionally substituted
formula
alkyl
compound
heterocyclic ring
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PCT/US2006/025144
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French (fr)
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WO2007005455A3 (en
Inventor
Jaidev S. Goudar
Charles E. Hatch, Iii
Guozhi Wang
Craig A. Polsz
Russell Patera
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Bayer Cropscience Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings 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 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
    • C07D307/58—One oxygen atom, e.g. butenolide

Definitions

  • This invention is in the field of chemical processes; more specifically, an improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted heterocycles.
  • R 1 , R 2 , R 3 and R 4 are independently selected from halogen or alkyl, R 5 is an optionally substituted heterocyclic ring group and x is 2, 3, 4, 5 or 6; ; are useful insecticides and have been described in U.S. Patent 5,922,880 the disclosure of which is incorporated herein by reference. Disadvantages of processes to produce these compounds include less than optimal yields, less than optimal cycle times and high catalyst loadings.
  • R 3 , R 4 , R 5 and x are as defined above; are key intermediates in the process for preparing (disubstitutedpropenyl) phenylalkyl substituted heterocycles as described in U.S. Patent 5,922,880.
  • the present invention improves the process for preparing compounds of formula I.
  • overall yield, cycle times and catalyst loading are improved for the production of (disubstitutedpropenyl) phenylalkyl substituted heterocycles.
  • R 3 and R 4 are independently selected from halogen or alkyl
  • R 5 is an optionally substituted heterocyclic ring group, provided that R 5 is not an optionally substituted dihydrobenzofuran; and x is 2, 3, 4, 5 or 6;
  • R is as defined above;
  • R 6 and R 7 are independently selected from halogen, hydroxyl or
  • R 8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
  • R 5 , R 7 and x are as defined above;
  • R 3 and R 4 are as defined above;
  • the "about” range shall be not more than 10% of the absolute value of an end point or 10% of the range recited, whichever is less.
  • alkyl As used in this specification and unless otherwise indicated the substiruent terms "alkyl”, “alkenyl”, “alkoxy”, and “haloalkyl”, used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms, wherein “alkenyl” has at least one carbon to carbon double bond.
  • Halogen “halide” or “halo” refers to fluorine, bromine, iodine, or chlorine.
  • ambient temperature refers to a temperature in the range of about 20° C to about 30° C.
  • the present invention relates to a process for preparing a compound of formula I: I wherein
  • R 3 and R 4 are independently selected from halogen or alkyl; R 5 is an optionally substituted heterocyclic ring group, provided that
  • R 5 is not an optionally substituted dihydrobenzofuran; and x is 2, 3, 4, 5 or 6;
  • R 5 is as defined above;
  • R and R are independently selected from halogen, hydroxyl or -OSO 2 R 8 wherein R 8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6; in the presence of a base to form a compound of formula II:
  • R , R and x are as defined above;
  • R 3 and R 4 are as defined above;
  • the reacting of step a) can be conducted in the presence of a catalyst; at elevated temperature.
  • the catalyst can be polyethylene glycol, triethylamine, pyridine, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof.
  • the catalyst can be present in a concentration of from about 0.1 % by weight to about 15% by weight.
  • the elevated temperature can be in the range of 30°C to 120°C.
  • the reaction of step b) can be conducted in the presence of a solvent; in the presence of a catalyst; at elevated temperature.
  • the solvent can be tetrahydrofuran, toluene, xylene, 1,2-dichloroethane, triethylamine, £>-dioxane, N 5 N- dimethylacetamide, N,N-dimethylformamide, glymes, methyl isobutyl ketone, dimethylsulfoxide or mixtures thereof.
  • the catalyst can be polyethylene glycol, potassium iodide, triethylamine, pyridine, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof.
  • the catalyst can be present in a concentration of from about 0.1 % by weight to about 20% by weight.
  • the elevated temperature can be in the range of 30°C to 70°C.
  • Another embodiment of the present invention is a compound of formula II:
  • R 5 is an optionally substituted heterocyclic ring group
  • R 5 is not an optionally substituted dihydrobenzofuran
  • R 7 is selected from halogen, hydroxyl or -OSO 2 R 8 wherein R 8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6.
  • the heterocyclic ring in the optionally substituted heterocyclic ring group is preferably selected from the group consisting of isoxazole, thiazole, 1,3,4- thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 1,2,3-triazole, 1,2,4- triazole, 1,2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazine, indole, benzofuran, thianaphthalene, indazole, benzimidazole, benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, piperidine, piperazine, tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, diox
  • the optional substitutent on the optionally substituted heterocyclic ring group is preferably selected from the group consisting of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, cycloalkyl, (alkyl)aminocarbonyl, [di(alkyl)amino]carbonyl, optionally substituted phenyl, optionally substituted benzyl, optionally substituted phenoxy,
  • R 5 is benzofuran wherein R 6 and R 7 are halogen ⁇
  • Example 1 In the first step (a) of Example 1, benzo[b]furan-7-ol, a compound of formula (A), is reacted with a 1,4-dihaloalkane, a compound of formula (B), for example 1 ,4-dihalobutane, in the presence of a base and a catalyst at elevated temperature to form a l-(benzo[2,3-b]furan-7-yloxy)-4-haloalkane, a compound of formula II, for example l-(benzo[2,3-b]furan-7-yloxy)-4-halobutane.
  • a compound of formula (A) is reacted with a 1,4-dihaloalkane, a compound of formula (B), for example 1 ,4-dihalobutane, in the presence of a base and a catalyst at elevated temperature to form a l-(benzo[2,3-b]furan-7-yloxy)-4-haloalkane,
  • step (b) of Example 1 2,6-dihalobenzene-l,4-diol, a compound of formula (C), is reacted with a l-(benzo[2,3-b]furan-7-yloxy)-4-haloalkane, a compound of formula II, for example l-(benzo[2,3-b]furan-7-yloxy)-4-halobutane, in the presence of a base, a solvent and a catalyst at elevated temperature to form a 3,5-dihalo-4-[4- (benzo[2,3-b]furan-7-yloxy)alkoxy]phenol, a compound of formula I, for example 3,5-dihalo-4-[4-(benzo[2,3-b]furan-7-yloxy)butoxy]phenol.
  • a compound of formula II for example l-(benzo[2,3-b]furan-7-yloxy)-4-halobutane
  • R 5 is a substituted wherein R 6 and R 7 are halogen ⁇ pyridine; Y is CF 3
  • step (b) of Example 2 2,6-dihalobenzene-l,4-diol, a compound of formula (C), is reacted with a 1 -(substituted pyridin-2-yloxy)-4-haloalkane, a compound of formula II, for example l-((5-trifluoromethyl)pyridin-2-yloxy)-4-halobutane, in the presence of a base, a solvent and a catalyst at elevated temperature to form a 3,5- dihalo-4- ⁇ 4-[substituted(2-pyridyloxy)]alkoxy ⁇ phenol, a compound of formula I, for example 3 ,5-dihalo-4- ⁇ 4- [5-(trifluoromethyl)(2-pyridyloxy)]butoxy ⁇ phenol.
  • a compound of formula II for example l-((5-trifluoromethyl)pyridin-2-yloxy)-4-halobutane

Abstract

An improved process is described for preparing (disubstitutedpropenyl) phenylalkyl substituted heterocycles. This improved process is focused on steps to produce key intermediates, namely compounds of formula (I): where R3, R4, R5 and x are defined herein.

Description

Improved Process for Preparing (Disubstitutedpropenyl) Phenylalkyl
Substituted Heterocycles
This application claims the benefit of U.S. Provisional Application No. 60/695,821, filed June 30, 2005.
Field of the Invention:
This invention is in the field of chemical processes; more specifically, an improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted heterocycles.
Backgound:
(Disubstitutedpropenyl) phenylalkyl substituted heterocycles, such as:
Figure imgf000002_0001
wherein R1, R2, R3 and R4 are independently selected from halogen or alkyl, R5 is an optionally substituted heterocyclic ring group and x is 2, 3, 4, 5 or 6; ; are useful insecticides and have been described in U.S. Patent 5,922,880 the disclosure of which is incorporated herein by reference. Disadvantages of processes to produce these compounds include less than optimal yields, less than optimal cycle times and high catalyst loadings. Compounds represented by formula I:
Figure imgf000002_0002
wherein R3, R4, R5 and x are as defined above; are key intermediates in the process for preparing (disubstitutedpropenyl) phenylalkyl substituted heterocycles as described in U.S. Patent 5,922,880.
Summary of the Invention
The present invention improves the process for preparing compounds of formula I. As a result of the present invention, overall yield, cycle times and catalyst loading are improved for the production of (disubstitutedpropenyl) phenylalkyl substituted heterocycles. Specifically, it has now been found that a compound of formula I:
Figure imgf000003_0001
wherein R3 and R4 are independently selected from halogen or alkyl;
R5 is an optionally substituted heterocyclic ring group, provided that R5 is not an optionally substituted dihydrobenzofuran; and x is 2, 3, 4, 5 or 6;
can be prepared in excellent yield and purity by a process comprising:
a) reacting a compound of formula (A):
HO-R3 Formula (AJ
wherein R is as defined above;
with a compound of formula (B): R6^(CH2)X \R7
Formula (B) wherein R6 and R7 are independently selected from halogen, hydroxyl or
-OSO2R8 wherein R8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
in the presence of a base to form a compound of formula II:
R7- ^K^ Formula II
wherein
R5, R7 and x are as defined above; and
reacting a compound of formula (CJ:
Figure imgf000004_0001
wherein R3 and R4 are as defined above;
with a compound of formula II in the presence of a base to form a compound of formula I. Definitions
The modifier "about" is used herein to indicate that certain preferred operating ranges, such as ranges for molar ratios for reactants, material amounts, and temperature, are not fixedly determined. The meaning will often be apparent to one of ordinary skill. For example, a recitation of a temperature range of about 120° C to about 135° C in reference to, for example, an organic chemical reaction would be interpreted to include other like temperatures that can be expected to favor a useful reaction rate for the reaction, such as 105° C or 150° C. Where guidance from the experience of those of ordinary skill is lacking, guidance from the context is lacking, and where a more specific rule is not recited below, the "about" range shall be not more than 10% of the absolute value of an end point or 10% of the range recited, whichever is less.
As used in this specification and unless otherwise indicated the substiruent terms "alkyl", "alkenyl", "alkoxy", and "haloalkyl", used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms, wherein "alkenyl" has at least one carbon to carbon double bond. "Halogen", "halide" or "halo" refers to fluorine, bromine, iodine, or chlorine. The term "ambient temperature" refers to a temperature in the range of about 20° C to about 30° C.
Certain solvents, catalysts, and the like are known by their acronyms. These include the acronyms "DMAC" meaning N,N-dimethylacetamide, "DMF" meaning N5N- dimethylformamide, "THF" meaning tetrahydrofuran. The term "glymes" refers to a class of solvents comprised of monoglyme, diglyme, triglyme, tetraglyme, and polyglyme.
Detailed Description of the Invention
The present invention relates to a process for preparing a compound of formula I:
Figure imgf000006_0001
I wherein
R3 and R4 are independently selected from halogen or alkyl; R5 is an optionally substituted heterocyclic ring group, provided that
R5 is not an optionally substituted dihydrobenzofuran; and x is 2, 3, 4, 5 or 6;
said process comprising:
a) reacting a compound of formula (A):
HO-R5
Formula (A)
wherein R5 is as defined above;
with a compound of formula (B):
R«^(CH2)χ \ R
Formula (B) wherein
R and R are independently selected from halogen, hydroxyl or -OSO2R8 wherein R8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6; in the presence of a base to form a compound of formula II:
Formula II
wherein R , R and x are as defined above; and
b) reacting a compound of formula (CJ:
Figure imgf000007_0001
Formula (C)
wherein R3 and R4 are as defined above;
with a compound of formula II in the presence of a base to form a compound of formula I.
The reacting of step a) can be conducted in the presence of a catalyst; at elevated temperature. The catalyst can be polyethylene glycol, triethylamine, pyridine, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof. The catalyst can be present in a concentration of from about 0.1 % by weight to about 15% by weight. The elevated temperature can be in the range of 30°C to 120°C. The reaction of step b) can be conducted in the presence of a solvent; in the presence of a catalyst; at elevated temperature. The solvent can be tetrahydrofuran, toluene, xylene, 1,2-dichloroethane, triethylamine, £>-dioxane, N5N- dimethylacetamide, N,N-dimethylformamide, glymes, methyl isobutyl ketone, dimethylsulfoxide or mixtures thereof. The catalyst can be polyethylene glycol, potassium iodide, triethylamine, pyridine, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof. The catalyst can be present in a concentration of from about 0.1 % by weight to about 20% by weight. The elevated temperature can be in the range of 30°C to 70°C. Another embodiment of the present invention is a compound of formula II:
R7- ^K^
Formula II wherein R5 is an optionally substituted heterocyclic ring group, provided that
R5 is not an optionally substituted dihydrobenzofuran; R7 is selected from halogen, hydroxyl or -OSO2R8 wherein R8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6.
The heterocyclic ring in the optionally substituted heterocyclic ring group is preferably selected from the group consisting of isoxazole, thiazole, 1,3,4- thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 1,2,3-triazole, 1,2,4- triazole, 1,2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazine, indole, benzofuran, thianaphthalene, indazole, benzimidazole, benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, piperidine, piperazine, tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, dioxane, dioxolane and benzodioxolane. The optional substitutent on the optionally substituted heterocyclic ring group is preferably selected from the group consisting of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, cycloalkyl, (alkyl)aminocarbonyl, [di(alkyl)amino]carbonyl, optionally substituted phenyl, optionally substituted benzyl, optionally substituted phenoxy, optionally substituted benzyloxy, and optionally substituted pyridyloxy, wherein the optional substitutent is selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy or haloalkoxy.
The following examples illustrate processes for preparing compounds of formula I.
Example 1
Figure imgf000009_0001
wherein R5 is benzofuran wherein R6 and R7 are halogen π
Figure imgf000009_0002
a) Base/Catalyst/30°C to 120°C/4-8 hours b) Base/Catalyst/Solvent/SCC to 70°C/6-12 hours
In the first step (a) of Example 1, benzo[b]furan-7-ol, a compound of formula (A), is reacted with a 1,4-dihaloalkane, a compound of formula (B), for example 1 ,4-dihalobutane, in the presence of a base and a catalyst at elevated temperature to form a l-(benzo[2,3-b]furan-7-yloxy)-4-haloalkane, a compound of formula II, for example l-(benzo[2,3-b]furan-7-yloxy)-4-halobutane. In step (b) of Example 1, 2,6-dihalobenzene-l,4-diol, a compound of formula (C), is reacted with a l-(benzo[2,3-b]furan-7-yloxy)-4-haloalkane, a compound of formula II, for example l-(benzo[2,3-b]furan-7-yloxy)-4-halobutane, in the presence of a base, a solvent and a catalyst at elevated temperature to form a 3,5-dihalo-4-[4- (benzo[2,3-b]furan-7-yloxy)alkoxy]phenol, a compound of formula I, for example 3,5-dihalo-4-[4-(benzo[2,3-b]furan-7-yloxy)butoxy]phenol.
Example 2
Figure imgf000010_0001
wherein R5 is a substituted wherein R6 and R7 are halogen π pyridine; Y is CF3
Figure imgf000010_0002
a) Base/Cataryst/30°C to 120°C/4-8 hours b) Base/Catalyst/Solvent/30°C to 70°C/6-12 hours
In the first step (a) of Example 2, substituted pyridin-2-ol, a compound of formula (A), for example 5-(trifluoromethyl)pyridin-2-ol, is reacted with a 1,4- dihaloalkane, a compound of formula (B), for example 1,4-dihalobutane, in the presence of a base and a catalyst at elevated temperature to form a 1 -(substituted pyridin-2-yloxy)-4-haloalkane, a compound of formula II, for example l-((5- trifiuoromethyl)pyridin-2-yloxy)-4-halobutane.
In step (b) of Example 2, 2,6-dihalobenzene-l,4-diol, a compound of formula (C), is reacted with a 1 -(substituted pyridin-2-yloxy)-4-haloalkane, a compound of formula II, for example l-((5-trifluoromethyl)pyridin-2-yloxy)-4-halobutane, in the presence of a base, a solvent and a catalyst at elevated temperature to form a 3,5- dihalo-4-{4-[substituted(2-pyridyloxy)]alkoxy}phenol, a compound of formula I, for example 3 ,5-dihalo-4- {4- [5-(trifluoromethyl)(2-pyridyloxy)]butoxy} phenol.
While this invention has been described with an emphasis upon preferred embodiments, it will be obvious to those of ordinary skill in the art that variations of the preferred embodiments may be used and that it is intended that the invention may be practiced otherwise than as specifically described herein. Accordingly this invention includes all modifications encompassed within the spirit and scope as defined by the following claims.

Claims

What is claimed is:
1. A process for preparing a compound of formula I:
Figure imgf000012_0001
I wherein
R3 and R4 are independently selected from halogen or alkyl;
R5 is an optionally substituted heterocyclic ring group, provided that
R5 is not an optionally substituted dihydrobenzofuran; and x is 2, 3, 4, 5 or 6;
said process comprising:
a) reacting a compound of formula (A):
HO-R5 Formula (A)
wherein R5 is as defined above;
with a compound of formula (B):
R6^(CH2)χ \R7
Formula (B) wherein
R6 and R7 are independently selected from halogen, hydroxyl or -OSO2R8 wherein R8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
in the presence of a base to form a compound of formula II:
Figure imgf000013_0001
Formula II
wherein R5, R7 and x are as defined above; and
b) reacting a compound of formula (C):
Figure imgf000013_0002
Formula (Q
wherein R3 and R4 are as defined above;
with a compound of formula II in the presence of a base to form a compound of formula I.
2. The process of claim 1 wherein the reacting of step a) is conducted in the presence of a catalyst.
3. The process of claim 1 wherein the reacting of step a) is conducted at elevated temperature.
4. The process of claim 1 wherein the reacting of step b) is conducted in the presence of a solvent.
5. The process of claim 1 wherein the reacting of step b) is conducted in the presence of a catalyst.
6. The process of claim 1 wherein the reacting of step b) is conducted at elevated temperature.
7. The process of claim 1 wherein the heterocyclic ring in the optionally substituted heterocyclic ring group is selected from the group consisting of isoxazole, thiazole, 1,3,4-thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 1,2,3-triazole, 1 ,2,4-triazole, 1, 2,3, 4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazine, indole, benzofuran, thianaphthalene, indazole, benzimidazole, benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, piperidine, piperazine, tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, dioxane, dioxolane and benzodioxolane.
8. The process of claim 7 wherein the optional substituent on the optionally substituted heterocyclic ring group is selected from the group consisting of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfinyl, haloalkylsulfonyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, cycloalkyl, (alkyl)aminocarbonyl, [di(alkyl)amino]carbonyl, optionally substituted phenyl, optionally substituted benzyl, optionally substituted phenoxy, optionally substituted benzyloxy, and optionally substituted pyridyloxy, wherein the optional substitutent is selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy or haloalkoxy.
9. A compound of formula II : Formula II wherein
R5 is an optionally substituted heterocyclic ring group wherein the heterocyclic ring in the optionally substituted heterocyclic ring group is selected from the group consisting of isoxazole, thiazole, 1,3,4-thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazine, indole, benzofuran, thianaphthalene, indazole, benzimidazole, benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, piperidine, piperazine, tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, dioxane, dioxolane and benzodioxolane;
R7 is selected from halogen, hydroxyl or -OSO2R8 wherein R is alkyl or aryl; and x is 2, 3, 4, 5 or 6.
10. The compound of claim 9 wherein the optional substitutent on the optionally substituted heterocyclic ring group is selected from the group consisting of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfmyl, haloalkylsulfonyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, cycloalkyl, (alkyl)aminocarbonyl, [di(alkyl)amino]carbonyl, optionally substituted phenyl, optionally substituted benzyl, optionally substituted phenoxy, optionally substituted benzyloxy, and optionally substituted pyridyloxy, wherein the optional substitutent is selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy or haloalkoxy.
PCT/US2006/025144 2005-06-30 2006-06-28 Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted heterocycles WO2007005455A2 (en)

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WO2020219906A1 (en) * 2019-04-25 2020-10-29 Board Of Regents, The University Of Texas System Heterocyclic inhibitors of tyrosine kinase

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