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US4105656A
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Process for preparing 3-n-monosubstituted amino-4-substituted-5-pyrazolones
Assignee: Fujifilm Holdings Corp
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Filing: 1977-01-31
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Granted: 1978-08-08
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Expires: 1997-01-31
Abstract
Abstract A process for preparing a 3-N-mono-substituted amino-4-substituted-5-pyrazolone which comprises replacing the hydrogen atom of the NH group at the 3-position of a 3-mono-substituted-5-pyrazolone with a protective group, halogenating the resulting compound to introduce a halogen atom into the 4-position, reacting the resulting compound with a 5- or 6-member heterocyclic compound containing two or more nitrogen atoms to replace the halogen atom at the 4-position with a nitrogen containing heterocyclic group, and hydrolyzing the resulting compound to remove the protective group.
Inventors
- 👤 Kotaro Nakamura
- 👤 Seiji Ichijima
- 👤 Nobuo Furutachi
- 👤 Yosio Kosuge
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 06:15
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/44; C07D231/52; G; G03; G03C; G03C7/00; G03C7/30; G03C7/32; G03C7/36; G03C7/38; G03C7/384
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
336 words
A process for preparing a 3-N-mono-substituted amino-4-substituted-5-pyrazolone represented by the formula (VI) ##STR7## wherein R 1 represents a hydrogen atom or has up to 35 carbon atoms and represents a straight or branched alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, a cycloalkenyl group, an aryl group, a heterocyclic group, an acyl group, a thioacyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a carbamoyl group or a thiocarbamoyl group; R 2 represents a hydrogen atom or has up to 35 carbon atoms and represents an alkyl group, an aryl group or a heterocyclic group; and Q represents a group of nonmetallic atoms necessary to form a 5-membered or 6-membered heterocyclic ring containing two or more nitrogen atoms; which comprises replacing the hydrogen atom of the N-H group in the 3-position of a compound represented by the formula (I) ##STR8## wherein R 1 and R 2 are as described above; with a protective group to prepare a compound represented by the formula (II) ##STR9## wherein R 1 and R 2 are as described above, and R 3 has up to 35 carbon atoms and represents a formyl group, an alkyl carbonyl group, an aryl carbonyl group, an alkyl sulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a sulfamoyl group or a thiocarbamoyl group; halogenating the resulting compound represented by the formula (II) to prepare a compound represented by the formula (III) ##STR10## wherein R 1 , R 2 and R 3 are as described above, and X represents a halogen atom; reacting the resulting compound represented by the formula (III) with a nitrogen-containing heterocyclic compound represented by the formula (IV) ##STR11## wherein Q is as described above; to prepared a compound represented by the formula (V) ##STR12## wherein R 1 , R 2 , R 3 and Q are as described above; and converting the resulting compound of the represented by the formula (V) into a compound represented by said formula (VI).
Claim 2
Dependent Claim
336 words
A process for preparing a 3-N-mono-substituted amino-4-substituted-5-pyrazolone represented by the formula (VI) ##STR7## wherein R 1 represents a hydrogen atom or has up to 35 carbon atoms and represents a straight or branched alkyl group, an alkenyl group, a cycloalkyl group, an aralkyl group, a cycloalkenyl group, an aryl group, a heterocyclic group, an acyl group, a thioacyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a carbamoyl group or a thiocarbamoyl group; R 2 represents a hydrogen atom or has up to 35 carbon atoms and represents an alkyl group, an aryl group or a heterocyclic group; and Q represents a group of nonmetallic atoms necessary to form a 5-membered or 6-membered heterocyclic ring containing two or more nitrogen atoms; which comprises replacing the hydrogen atom of the N-H group in the 3-position of a compound represented by the formula (I) ##STR8## wherein R 1 and R 2 are as described above; with a protective group to prepare a compound represented by the formula (II) ##STR9## wherein R 1 and R 2 are as described above, and R 3 has up to 35 carbon atoms and represents a formyl group, an alkyl carbonyl group, an aryl carbonyl group, an alkyl sulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a sulfamoyl group or a thiocarbamoyl group; halogenating the resulting compound represented by the formula (II) to prepare a compound represented by the formula (III) ##STR10## wherein R 1 , R 2 and R 3 are as described above, and X represents a halogen atom; reacting the resulting compound represented by the formula (III) with a nitrogen-containing heterocyclic compound represented by the formula (IV) ##STR11## wherein Q is as described above; to prepared a compound represented by the formula (V) ##STR12## wherein R 1 , R 2 , R 3 and Q are as described above; and converting the resulting compound of the represented by the formula (V) into a compound represented by said formula (VI).
Claim 3
Dependent Claim
267 words
The process of claim 1, wherein the replacing of the hydrogen atom of the N-H group in the 3-position of the compound represented by the formula (I) is by acylating the compound represented by the formula (I) with an acylating agent or an alkoxycarbonylating agent in an amount of about 1 to about 20 molar equivalents to the compound represented by the formula (I) at a temperature of about 0° to about 150° C in the absence of a solvent or in the presence of an inert solvent; wherein the halogenating of the compound represented by the formula (II) is with a halogenating agent in a molar equivalent amount to the compound represented by the formula (II) at a temperature of about 0° to about 100° C in the presence of an inert solvent; wherein the reacting of the compound represented by the formula (III) is with said nitrogen-containing heterocyclic compound represented by the formula (IV) in a molar equivalent amount of about 1 to 20 times to the compound represented by the formula (III) at a temperature of about 10° to about 200° C in the absence of a solvent or in the presence of an inert solvent; and wherein the converting of the compound represented by the formula (V) to the compound represented by the formula (VI) is by hydrolysis in the presence of an alkali in an amount of about 1 to about 100 times on a molar basis to the compound represented by the formula (V) at a temperature of about 0° to about 100° C in the presence of an inert solvent.
Claim 4
Dependent Claim
95 words
The process of claim 1, wherein Q represents a group of non-metalic atoms necessary to form a 5- membered or 6- membered heterocyclic ring containing two or more nitrogen atoms selected from the group consisting of imidazole, 2-methylimidazole, 2-ethylimidazole, 2-chloroimidazole, 2-bromoimidazole, 2-(β-hydroxyethyl)imidazole, 2,4-dimethylimidazole, 2-methyl-4-ethylimidazole, 2,4,5-trimethylimidazole, 4-methylimidazole, 4-chloroimidazole, 4-acetylimidazole, 4-methoxyimidazole, 2-(β-phenoxyethyl)imidazole, 4-nitroimidazole, 4-cyanoimidazole, benzimidazole, 5-nitrobenzimidazole, 2-methylbenzimidazole, 5-bromobenzimidazole, 5-acetylaminobenzimidazole, 5-capronamidobenzimidazole, 1,2,3-triazole, 4,5-dimethyl-1,2,3-triazole, 1,2,4-triazole, 3,5-diethyl-1,2,4-triazole, 3,5-dichloro-1,2,4-triazole, 3,5-di-(β-methoxyethyl)-1,2,4-triazole, 3,5-dibenzyl-1,2,4-triazole, pyrazole, 3,5-dimethylpyrazole, 3-methyl-5-oxo-2-pyrazoline, 2-hydroxypyrimidine, 4-hydroxypyrimidine, 2-hydroxypyrazine, 2-hydroxypyridazine, indazole, 5-methylindazole, 5-acetylaminoindazole, 5-methoxyindazole, benzotriazole, 5-bromobenzotriazole, 5-nitrobenzotriazole, 5-methylbenzotriazole, 5-capronamidobenzotriazole, 5-benzyloxybenzotriazole, 5-octyloxybenzotriazole, 5-(3-methyl-2-benzothiazolinylidene)amino-benzotriazole, naphthotriazole, 1,2-dihydro-1-oxophthalazine, purine, xanthine, guanine, histidine, 4,5-dicarboxyimidazole, 4-carboxyimidazole, 5-hydroxy-1-phenyltetrazole or 5-methylthio-1-phenyltetrazole.
Claim 5
Dependent Claim
20 words
The process of claim 1, wherein said temperature of about 10° to about 200° C is 50° to 150° C.
Claim 6
Dependent Claim
22 words
The process of claim 1, wherein said 3-N-mono-substituted amino-4-substituted-5-pyrazolone represented by the formula (VI) is selected from the group consisting of ##STR13##
References Cited (Backward Citations)
US3935262A
Cited
US3956339A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-08-07 | 1982-02-06 | 1982-08-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-08-07 | 1986-02-06 | 1986-08-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-08-07 | 1990-02-06 | 1990-08-08 | $7700.00 | Window Closed / Lapsed |