CN115557910A - Synthetic method of 6-azauracil - Google Patents
Synthetic method of 6-azauracil Download PDFInfo
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- CN115557910A CN115557910A CN202211377737.6A CN202211377737A CN115557910A CN 115557910 A CN115557910 A CN 115557910A CN 202211377737 A CN202211377737 A CN 202211377737A CN 115557910 A CN115557910 A CN 115557910A
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- azauracil
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- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical compound O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000010189 synthetic method Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- 239000007864 aqueous solution Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 22
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims abstract description 20
- YGQGQANLBGKOEN-UHFFFAOYSA-N Cl.NN.C(=O)N Chemical compound Cl.NN.C(=O)N YGQGQANLBGKOEN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 8
- 239000002244 precipitate Substances 0.000 claims description 34
- 239000000243 solution Substances 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 238000005406 washing Methods 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 10
- 239000012065 filter cake Substances 0.000 claims description 8
- -1 2- [2- (aminocarbonyl) hydrazono ] acetic acid compound Chemical class 0.000 claims description 6
- QZSYGBNBQHRGKK-UHFFFAOYSA-N 2-(carbamoylhydrazinylidene)acetic acid Chemical compound NC(=O)NN=CC(O)=O QZSYGBNBQHRGKK-UHFFFAOYSA-N 0.000 claims description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims 3
- 239000002994 raw material Substances 0.000 abstract description 8
- 208000012839 conversion disease Diseases 0.000 abstract description 5
- 230000035484 reaction time Effects 0.000 abstract description 5
- 150000002466 imines Chemical class 0.000 abstract description 4
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 2
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 2
- 102000002689 Toll-like receptor Human genes 0.000 description 2
- 108020000411 Toll-like receptor Proteins 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000004031 partial agonist Substances 0.000 description 2
- 150000003920 1,2,4-triazines Chemical class 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000001145 Metabolic Syndrome Diseases 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
- 230000008484 agonism Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 1
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having 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
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
- C07C281/10—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to an acyclic carbon atom or to a carbon atom of a ring other than a six-membered aromatic ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing 6-azauracil; the method comprises the following steps: in the first step, hydrazine formamide hydrochloride and glyoxylic acid aqueous solution are used as raw materials and react under alkaline conditions to generate imine, the reaction conditions are mild, the reaction conversion rate is high, and the raw materials are cheap; in the second step, microwave irradiation is adopted to close the ring, the conversion rate reaches 90% at normal temperature for half an hour, the reaction time is greatly shortened, and the reaction yield is improved. The method has the advantages of mild reaction conditions, safety, reliability and good process stability.
Description
Technical Field
The invention relates to the field of organic drug synthesis, in particular to a synthesis method of 6-azauracil (an important intermediate of etapirone).
Background
Etapirone, an anxiolytic, belongs to one of the 5-HT1A receptor partial agonists, as an effective 5-HT1A receptor partial agonist, has a great demand in relevant medical research and research trials and clinical treatment.
Furthermore 6-azauracil as 1,2, 4-triazine derivatives can be used for HIV inhibition therapy and prophylaxis of HI (CN 101035773); 6-azauracil derivatives are useful in the treatment of viral infections, immune or inflammatory diseases, in particular wherein the modulation or agonism of toll-like receptors (TLRs) is involved (EP 2712866A 1); the combined action of the 6-azauracil and the uracil derivative can inhibit the activity of 5SCD-1 enzyme, and reduce the side effect of the drug treatment of the metabolic syndrome to the maximum extent (WO 2010006962A 1); 6-azauracil and derivatives thereof in the manufacture of a medicament useful for inhibiting EGFR activity.
The existing synthesis conditions are mainly that hydrazine formamide hydrochloride reacts with chloral to generate Schiff base, the reaction conversion rate is not high (the yield of chemical paper volume73Issue6Pages1321-13312019 is only 58%), and the yield of a second closed loop is only 62% and the reaction time is long.
Disclosure of Invention
The invention aims to provide a method for synthesizing 6-azauracil, so as to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme: a method for synthesizing 6-azauracil comprises the following steps:
the first step is as follows: mixing 10mol and 1eq of hydrazine formamide hydrochloride and 10mol and 1eq of DIEA, dissolving in water, adding 10mol and 1eq of 50% glyoxylic acid aqueous solution into the mixed solution under stirring at room temperature, after the addition is finished, continuously stirring the reaction solution for 6-10h, finishing the reaction, cooling the reaction solution to 0-5 ℃, generating a large amount of precipitate, filtering and collecting the formed precipitate, washing with water, and drying to obtain 1.2g of a light yellow solid 2- [2- (aminocarbonyl) hydrazono ] acetic acid compound with the yield of 89% and the purity of 98.9%;
the second step is that: dissolving 10mol and 1eq of 2- [2- (aminocarbonyl) hydrazono ] acetic acid in 20mL of ethylene glycol, adding 12mol and 1.2eq of potassium hydroxide under stirring at room temperature, finishing the addition, irradiating the reaction solution at 25-35 ℃ for 30min under the microwave power of 200W for reaction, cooling the reaction solution to 0 ℃ after the reaction is finished, generating a large amount of precipitate, filtering the precipitate, dissolving the precipitate in 20mL of water, adjusting the pH value to 2-3 by using 1M of HCl aqueous solution, stirring the aqueous solution at room temperature for 30min, cooling the solution to 0-5 ℃ by using ice salt, generating a large amount of precipitate, filtering, washing a filter cake by using water, and drying in vacuum to obtain 1.0g of light yellow solid 6-azauracil with the yield of 90% and the purity of 99.0%;
the specific synthesis reaction formula is as follows:
preferably, in the first step: mixing 10mol and 1eq of hydrazine formamide hydrochloride and 10mol and 1eq of DIEA, dissolving in water, adding 10mol and 1eq of 50% glyoxylic acid aqueous solution into the mixed solution under stirring at room temperature, after the addition is finished, continuing stirring the reaction solution for 8 hours, finishing the reaction, cooling the reaction solution to 3 ℃, generating a large amount of precipitate, filtering and collecting the formed precipitate, washing with water, and drying to obtain 1.2g of 2- [2- (aminocarbonyl) hydrazono ] acetic acid compound which is a light yellow solid with the yield of 89% and the purity of 98.9%.
Preferably, in the second step, 10mol and 1eq of 2- [2- (aminocarbonyl) hydrazono ] acetic acid is dissolved in 20mL of ethylene glycol, 12mol and 1.2eq of potassium hydroxide are added under stirring at room temperature, after the addition of the potassium hydroxide is finished, the reaction solution is irradiated at 30-33 ℃ for 30min under the microwave power of 200W, after the reaction is finished, the reaction solution is cooled to 0 ℃, a large amount of precipitate is generated, the precipitate is filtered, dissolved in 20mL of water, the pH value of the solution is adjusted to 2-3 by using 1M of HCl aqueous solution, after the aqueous solution is stirred at room temperature for 30min, the solution is cooled to 3 ℃ by using ice salt, a large amount of precipitate is generated, the solution is filtered, a filter cake is washed by using water and dried in vacuum, and light yellow solid 6-azauracil 1.0g with the yield of 90% and the purity of 99.0% is obtained.
Preferably, in the second step, during the suction filtration, directly adding a washing solution to the filter cake and then performing suction filtration, wherein the way of adding the washing solution is continuous addition while performing suction filtration.
Compared with the prior art, the invention has the beneficial effects that:
the method has mild reaction conditions, safety, reliability and good process stability, and in the first step, hydrazine formamide hydrochloride and glyoxylic acid aqueous solution are used as raw materials to react under alkaline conditions to generate imine, so that the method has mild reaction conditions, high reaction conversion rate and cheap raw materials; in the second step, microwave irradiation is adopted, the conversion rate reaches 90% at normal temperature for half an hour, the reaction time is greatly shortened, and the reaction yield is improved.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A method for synthesizing 6-azauracil comprises the following steps:
the first step is as follows: mixing 10mol and 1eq of hydrazine formamide hydrochloride and 10mol and 1eq of DIEA, dissolving in water, adding 10mol and 1eq of 50% glyoxylic acid aqueous solution into the mixed solution under stirring at room temperature, after the addition is finished, continuing stirring the reaction solution for 8 hours, finishing the reaction, cooling the reaction solution to 0 ℃, generating a large amount of precipitate, filtering and collecting the formed precipitate, washing with water, and drying to obtain 1.2g of a light yellow solid 2- [2- (aminocarbonyl) hydrazono ] acetic acid compound with the yield of 89% and the purity of 98.9%;
the second step: dissolving 10mol and 1eq of 2- [2- (aminocarbonyl) hydrazono ] acetic acid in 20mL of ethylene glycol, stirring at room temperature, adding 12mol and 1.2eq of potassium hydroxide, finishing the addition, irradiating the reaction liquid at 28 ℃ for 30min under the microwave power of 200W to react, cooling the reaction liquid to 0 ℃ after the reaction is finished, generating a large amount of precipitate, filtering the precipitate, dissolving the precipitate in 20mL of water, adjusting the pH value to 2 by using 1M of HCl aqueous solution, stirring the aqueous solution at room temperature for 30min, cooling the solution to 2 ℃ by using ice salt, generating a large amount of precipitate, filtering, washing a filter cake by using water, and drying in vacuum to obtain 1.0g of faint yellow solid 6-azauracil with the yield of 90% and the purity of 99.0%;
the specific synthetic reaction formula is as follows:
the method has mild reaction conditions, safety, reliability and good process stability, and in the first step, the hydrazine formamide hydrochloride and the glyoxylic acid aqueous solution are used as raw materials and react under alkaline conditions to generate the imine, so the method has mild reaction conditions, high reaction conversion rate and cheap raw materials; in the second step, microwave irradiation is adopted, the conversion rate reaches 90% at normal temperature for half an hour, the reaction time is greatly shortened, and the reaction yield is improved.
Example 2
A method for synthesizing 6-azauracil comprises the following steps:
the first step is as follows: mixing 10mol and 1eq of hydrazine formamide hydrochloride and 10mol and 1eq of DIEA, dissolving in water, adding 10mol and 1eq of 50% glyoxylic acid aqueous solution into the mixed solution under stirring at room temperature, after the addition is finished, continuously stirring the reaction solution for 9 hours, finishing the reaction, cooling the reaction solution to 4 ℃, generating a large amount of precipitate, filtering and collecting the formed precipitate, washing with water, and drying to obtain 1.2g of a light yellow solid 2- [2- (aminocarbonyl) hydrazono ] acetic acid compound with the yield of 89% and the purity of 98.9%;
the second step is that: dissolving 10mol and 1eq of 2- [2- (aminocarbonyl) hydrazono ] acetic acid in 20mL of ethylene glycol, adding 12mol and 1.2eq of potassium hydroxide under stirring at room temperature, after the addition is finished, irradiating the reaction solution at 30 ℃ for 30min under the microwave power of 200W for reaction, after the reaction is finished, cooling the reaction solution to 0 ℃, generating a large amount of precipitate, filtering the precipitate, dissolving the precipitate in 20mL of water, adjusting the pH value to 3 by using a 1MHCl aqueous solution, stirring the aqueous solution at room temperature for 30min, cooling the solution to 4 ℃ by using ice salt, generating a large amount of precipitate, filtering, washing a filter cake by using water, and drying in vacuum to obtain 1.0g of light yellow solid 6-azauracil with the yield of 90% and the purity of 99.0%;
the specific synthetic reaction formula is as follows:
the method has mild reaction conditions, safety, reliability and good process stability, and in the first step, the hydrazine formamide hydrochloride and the glyoxylic acid aqueous solution are used as raw materials and react under alkaline conditions to generate the imine, so the method has mild reaction conditions, high reaction conversion rate and cheap raw materials; in the second step, microwave irradiation is adopted, the conversion rate reaches 90% at normal temperature for half an hour, the reaction time is greatly shortened, and the reaction yield is improved.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (4)
1. A method for synthesizing 6-azauracil is characterized in that: the method comprises the following steps:
the first step is as follows: mixing 10mol and 1eq of hydrazine formamide hydrochloride and 10mol and 1eq of DIEA, dissolving in water, adding 10mol and 1eq of 50% glyoxylic acid aqueous solution into the mixed solution under stirring at room temperature, after the addition is finished, continuously stirring the reaction solution for 6-10h, finishing the reaction, cooling the reaction solution to 0-5 ℃, generating a large amount of precipitate, filtering and collecting the formed precipitate, washing with water, and drying to obtain 1.2g of a light yellow solid 2- [2- (aminocarbonyl) hydrazono ] acetic acid compound with the yield of 89% and the purity of 98.9%;
the second step: dissolving 10mol and 1eq of 2- [2- (aminocarbonyl) hydrazono ] acetic acid in 20mL of ethylene glycol, adding 12mol and 1.2eq of potassium hydroxide under stirring at room temperature, finishing the addition, irradiating the reaction solution at 25-35 ℃ for 30min under the microwave power of 200W for reaction, cooling the reaction solution to 0 ℃ after the reaction is finished, generating a large amount of precipitate, filtering the precipitate, dissolving the precipitate in 20mL of water, adjusting the pH value to 2-3 by using 1M of HCl aqueous solution, stirring the aqueous solution at room temperature for 30min, cooling the solution to 0-5 ℃ by using ice salt, generating a large amount of precipitate, filtering, washing a filter cake by using water, and drying in vacuum to obtain 1.0g of light yellow solid 6-azauracil with the yield of 90% and the purity of 99.0%;
the specific synthesis reaction formula is as follows:
2. the method for synthesizing 6-azauracil according to claim 1, wherein: in the first step: mixing 10mol and 1eq of hydrazine formamide hydrochloride and 10mol and 1eq of DIEA, dissolving in water, adding 10mol and 1eq of 50% glyoxylic acid aqueous solution into the mixed solution under stirring at room temperature, after the addition is finished, continuing stirring the reaction solution for 8 hours, finishing the reaction, cooling the reaction solution to 3 ℃, generating a large amount of precipitate, filtering and collecting the formed precipitate, washing with water, and drying to obtain 1.2g of 2- [2- (aminocarbonyl) hydrazono ] acetic acid compound which is a light yellow solid with the yield of 89% and the purity of 98.9%.
3. The method of claim 1, wherein the synthesis of 6-azauracil comprises: in the second step, 10mol and 1eq of 2- [2- (aminocarbonyl) hydrazono ] acetic acid are dissolved in 20mL of ethylene glycol, 12mol and 1.2eq of potassium hydroxide are added under the condition of stirring at room temperature, the reaction solution is irradiated at 30-33 ℃ under the microwave power of 200W for 30min to react after the addition is finished, the reaction solution is cooled to 0 ℃, a large amount of precipitate is generated, the precipitate is filtered, dissolved in 20mL of water, the pH value is adjusted to 2-3 by using 1M of HCl aqueous solution, the aqueous solution is stirred at room temperature for 30min, the solution is cooled to 3 ℃ by using ice salt, a large amount of precipitate is generated, the solution is filtered, a filter cake is washed by using water and dried in vacuum, and 1.0g of light yellow solid 6-azauracil with the yield of 90% and the purity of 99.0% is obtained.
4. The method for synthesizing 6-azauracil according to claim 1, wherein: and in the second step, directly adding a washing liquid on the filter cake during suction filtration, and then performing suction filtration, wherein the way of adding the washing liquid is continuous addition while adding the washing liquid.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211377737.6A CN115557910A (en) | 2022-11-04 | 2022-11-04 | Synthetic method of 6-azauracil |
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| CN202211377737.6A CN115557910A (en) | 2022-11-04 | 2022-11-04 | Synthetic method of 6-azauracil |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3922273A (en) * | 1974-11-01 | 1975-11-25 | Deutsch Daniel Harold | Cyclization of glyoxylic acid semicarbazone |
| US3983114A (en) * | 1974-11-05 | 1976-09-28 | Nobel Hoechst Chimie | Method of preparation of 6-aza uracile and its O-disilyl derivative |
| CN1361769A (en) * | 1999-06-04 | 2002-07-31 | 拜尔公司 | Substituted 2-aryl-1,2,4-triazine-3,5-di(thi) one |
| CN108440505A (en) * | 2018-03-30 | 2018-08-24 | 中南大学 | The total synthesis method of eptapirone |
-
2022
- 2022-11-04 CN CN202211377737.6A patent/CN115557910A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3922273A (en) * | 1974-11-01 | 1975-11-25 | Deutsch Daniel Harold | Cyclization of glyoxylic acid semicarbazone |
| US3983114A (en) * | 1974-11-05 | 1976-09-28 | Nobel Hoechst Chimie | Method of preparation of 6-aza uracile and its O-disilyl derivative |
| CN1361769A (en) * | 1999-06-04 | 2002-07-31 | 拜尔公司 | Substituted 2-aryl-1,2,4-triazine-3,5-di(thi) one |
| CN108440505A (en) * | 2018-03-30 | 2018-08-24 | 中南大学 | The total synthesis method of eptapirone |
Non-Patent Citations (1)
| Title |
|---|
| WEI PENG，等: "An improved synthesis of the 5‑HT1A receptor agonist Eptapirone free base", 《CHEMICAL PAPERS》, pages 1321 - 1331 * |
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