CN107954906A - A kind of synthetic method of arylsulfonyl tertiary amine compounds - Google Patents
A kind of synthetic method of arylsulfonyl tertiary amine compounds Download PDFInfo
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- CN107954906A CN107954906A CN201711189620.4A CN201711189620A CN107954906A CN 107954906 A CN107954906 A CN 107954906A CN 201711189620 A CN201711189620 A CN 201711189620A CN 107954906 A CN107954906 A CN 107954906A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B45/00—Formation or introduction of functional groups containing sulfur
- C07B45/04—Formation or introduction of functional groups containing sulfur of sulfonyl or sulfinyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
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Abstract
The present invention provides a kind of synthetic method of arylsulfonyl tertiary amine compounds, and in anhydrous aprotic solvent, under nitrogen protection, aryl sulfonyl chloride and two tertiary amines are with 1:1~1:20 molar ratio, it is purified to obtain when reaction 1 ~ 12 is small under the conditions of 50 ~ 150 DEG C.The formation of C S keys directly occurs by base sulfonic acid chloride and two tertiary amines in aprotic solvent for the present invention, while the fracture of C N keys occurs, and the method for one-step synthesis arylsulfonyl tertiary amine, its raw material is easy to get, and synthesis technique is simple, easy to operate, and cost is low, and yield is high.
Description
Technical field
The present invention relates to a kind of synthetic method of arylsulfonyl tertiary amine compounds, more particularly to one kind to pass through aryl sulphur
The method that acyl chlorides and two tertiary amines directly react synthesizing aryl sulphonyl tertiary amine, belongs to chemosynthesis technical field.
Background technology
Sulfamide compound has multiple biological activities, for example, clinically having as antimicrobial sulfonamide drug
Have a has a broad antifungal spectrum, property is stablized, using simplicity, it is cheap the advantages of, be the Common Antibiotics for being only second to antibiotic at present.
Further, since sulfonamides compound is also widely used in the multiple fields such as pesticide, material, thus its synthetic method is constantly opened
Issue.
Sulphonyl tertiary amine is a kind of compound that structure is more special in sulfonamides compound, its structural formula is as follows：
In formula, R1For any one of hydrogen, alkyl, aromatic radical, substituted aromatic base, vinyl, pi-allyl, alkynyl, propargyl
It is or several；Wherein R1The alkyl is C1-C20, such as methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, the tert-butyl group
Deng；The group that substituted aromatic base is substituted by halogen, nitro, alkoxy, benzyloxy, vinyl, alkynyl or alkyl, in aromatic rings
On position be contraposition, ortho position or meta, can be monosubstituted or polysubstituted.Het is heterocycle compound, including furans, pyrrole
The common heteroaromatic class compound such as pyridine, thiophene, quinoline and its derivative.R2, R3For in alkyl, aromatic radical, substituted aromatic base
Any one or more；Wherein alkyl is C1-C20, such as methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, the tert-butyl group
Deng；Substituted aromatic base is the aryl rings containing substituents such as halogen, nitro, alkoxy, benzyloxy, vinyl, alkynyl or alkyl.
The position of substituent on aromatic rings is contraposition, ortho position or meta, can be monosubstituted or polysubstituted.
Due to not having N-H keys, its property is also different with other sulfonamide.For example, tertiary sulfonamide will not be made with highly basic
With, thus structure is more stablized.In terms of biological property, sulphonyl tertiary amine is also the nuclear structure unit of multi-medicament, for example, again
It can drop（Mefruside）, also known as U.S. furan Seat, it is a kind of diuretics, for treating the medicine of various oedema and hypertension.Third sulphur
Relax（probenecid）It is using to control the medicine of hyperuricemia in gout interictal and chronic phase.Sulphonyl tertiary amine also may be used
Using the liver X receptor antagonist as on-steroidal（GENES ＆ DEVELOPMENT, 2000,14,2831-2838；J. Med.
Chem. 2010, 53, 3412）, the activator of orphan receptor（Bioorg. Med. Chem. Lett., 2014,24,
2182）Etc..In addition, sulphonyl tertiary amine is used also as antioxidant（United States Patent (USP) US5102934）, fluoropolymer resin high temperature process
During plasticizer.In synthesis chemistry, it is ortho-metalated that sulphonyl tertiary amine group can also be used as seeking group to be used for aryl
Reaction（Angew. Chem. Int. Ed., 2004,43,888）.
The most common preparation method of sulphonyl tertiary amine is reacted by sulfonic acid chloride and secondary amine.But some secondary amine are than corresponding uncle
Amine is expensive or is difficult to obtain.For example, dimethylamine is gas under normal conditions, it is unsuitable for being directly used in reaction.And phase therewith
The tetramethylethylenediamine answered is liquid, it is easy to is commercially available, thus is easy to weigh and shifts.In addition, sulphonyl tertiary amine
N- alkylations occur again to complete after sulfonamide can also be obtained by sulfonic acid chloride and a primary amine reaction.This method reaction
Step is more, is unsuitable for industrialized a large amount of preparations.
The content of the invention
The purpose of the present invention is for the prior art synthesis sulphonyl tertiary amine there are the problem of, there is provided one kind passes through arylsulfonyl
The method that chlorine and two tertiary amines directly react synthesizing aryl sulphonyl tertiary amine compounds.
The method of synthesizing aryl sulphonyl tertiary amine compounds of the present invention, under nitrogen protection, in anhydrous aprotic solvent, virtue
Base sulfonic acid chloride and two tertiary amines are with 1:1~1:20 molar ratio, when reaction 1 ~ 12 is small under the conditions of 50 ~ 150 DEG C, decompression boils off solvent,
Column chromatography for separation, obtains arylsulfonyl tertiary amines.
The structural formula of aryl sulfonyl chloride is：
In formula, R1For any one of hydrogen, alkyl, aromatic radical, substituted aromatic base, vinyl, pi-allyl, alkynyl, propargyl；
Wherein alkyl is C1-C20Alkyl, such as methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, the tert-butyl group；Substituted aromatic base is
The aryl rings that halogen, nitro, alkoxy, benzyloxy, vinyl, alkynyl or alkyl are substituted, position of the substituent on aromatic rings
It is set to contraposition, ortho position or meta；Can be monosubstituted or polysubstituted.
Het is heterocycle compound, including the heteroaromatic class compound such as furans, pyridine, thiophene, quinoline and its derivative.
The structural formula of two tertiary amines is：
In formula, R2, R3For any one of alkyl, aromatic radical, substituted aromatic base or several；Wherein alkyl is C1-C20Alkyl,
Such as methyl, ethyl, propyl group, isopropyl, normal-butyl, sec-butyl, the tert-butyl group；Substituted aromatic base is to contain halogen, nitro, alcoxyl
The aryl rings of the substituents such as base, benzyloxy, vinyl, alkynyl or alkyl；The position of substituent on aromatic rings is contraposition, neighbour
Position or meta, can be monosubstituted or polysubstituted.
Used anhydrous aprotic solvent is tetrahydrofuran, dichloromethane, acetonitrile, 1,4- dioxane, N, N- bis-
Methylformamide or dimethyl sulfoxide.
The synthesis type of arylsulfonyl tertiary amine compounds is as follows：
The characteristics of synthesizing aryl sulphonyl tertiary amine compounds of the present invention：Base sulfonic acid chloride is directly sent out with two tertiary amines in aprotic solvent
The formation of raw C-S keys, while the fracture of C-N keys occurs, the method for one-step synthesis arylsulfonyl tertiary amine, its raw material is easy to get, synthesis
Technique is simple, easy to operate, and cost is low, and yield is high.
Embodiment
It is described further below by synthesis of the specific embodiment to arylsulfonyl tertiary amine compounds of the present invention.
Embodiment 1, N, the synthesis of N- dimethyl -4- methyl benzenesulfonamides
With the two neck bottles of the dried 50ml of flame, displacement nitrogen three times, will be dissolved in acetonitrile with syringe（3ml）To methylbenzene
Sulfonic acid chloride（190mg, 1mmol）Get in reaction bulb after cooling, after heating makes acetonitrile solution flow back, by N, N, N, N- tetramethyls
Ethylenediamine（139mg, 1.2mmol）It is dissolved in the anhydrous acetonitrile of 3ml, is slowly added drop-wise to syringe and fills p-methyl benzene sulfonic chloride
Reaction bulb in, then under acetonitrile reflux state, when reaction 1 is small, remove heating, decompression boils off solvent, and rapid column chromatography divides
From obtaining product 183mg, yield 92%.Its synthesis type is as follows：
Spectroscopic data：1H NMR (600 MHz, CDCl3) δ (ppm): 7.66 (d, J = 8.2 Hz, 2H), 7.33
(d, J = 8.0 Hz, 2H), 2.68 (s, 6H), 2.43 (s, 3H); 13C NMR (151 MHz, CDCl3) δ
(ppm):143.4, 132.4, 129.6, 127.8, 37.9, 21.5。
Embodiment 2, N, the synthesis of N- diethyl p-methylphenyl sulphonylamines
With the two neck bottles of the dried 50ml of flame, displacement nitrogen three times, will be dissolved in acetonitrile with syringe（3ml）To methylbenzene
Sulfonic acid chloride（190mg, 1mmol）Get in reaction bulb after cooling, after heating makes acetonitrile solution flow back, by N, N, N, N- tetraethyls
Ethylenediamine（206mg, 1.2mmol）It is dissolved in the anhydrous acetonitrile of 3ml, is slowly added drop-wise to syringe and fills p-methyl benzene sulfonic chloride
Reaction bulb in, then under acetonitrile reflux state, when reaction 1 is small, remove heating, decompression boils off solvent, and rapid column chromatography divides
From obtaining product 197mg, yield 87%.Its synthesis type is as follows：
Spectroscopic data：1H NMR (600 MHz, CDCl3) δ (ppm): 7.68 (d, J = 8.2 Hz, 2H), 7.27
(d, J = 8.0 Hz, 2H), 3.21 (q, J = 7.2 Hz, 4H), 2.41 (s, 3H), 1.11 (t, J = 7.1
Hz, 6H); 13C NMR (151 MHz, CDCl3) δ(ppm):142.9,137.4,129.6,127.0,42.0,
21.4, 14.1。
Embodiment 3, N, the synthesis of N- dipropyl base p-methylphenyl sulphonylamines
With the two neck bottles of the dried 50ml of flame, displacement nitrogen three times, will be dissolved in acetonitrile with syringe（3ml）To methylbenzene
Sulfonic acid chloride（190mg, 1mmol）Get in reaction bulb after cooling, it is after heating makes acetonitrile solution flow back, N, N, N, N- tetra- is different
Butyl ethylenediamine（273mg, 1.2mmol）It is dissolved in the anhydrous acetonitrile of 3ml, is slowly added drop-wise to and is filled to methylbenzene with syringe
In the reaction bulb of sulfonic acid chloride, then under acetonitrile reflux state, when reaction 1 is small, heating is removed, decompression boils off solvent, quick column
Chromatography obtains product 216mg, yield 85%.Its synthesis type is as follows：
Spectroscopic data：1H NMR (600 MHz, CDCl3) δ (ppm): 7.68 (d, J = 8.3 Hz, 2H), 7.27
(d, J = 16.4 Hz, 2H), 3.05 (dd, J = 8.5, 6.9 Hz, 4H), 2.41 (s, 3H), 1.59 –
1.49 (m, 4H), 0.86 (t, J = 7.4 Hz, 6H); 13C NMR (151 MHz, CDCl3) δ (ppm):
142.8, 137.2, 129.5 127.1, 50.0, 22.0, 21.4, 11.2。
Embodiment 4, N, the synthesis of N- diisobutyl p-methylphenyl sulphonylamines
With the two neck bottles of the dried 50ml of flame, displacement nitrogen three times, will be dissolved in acetonitrile with syringe（3ml）To methylbenzene
Sulfonic acid chloride（190mg, 1mmol）Get in reaction bulb after cooling, after heating makes acetonitrile solution flow back, by N, N, N, tetra- isobutyls of N-
Base ethylenediamine（321mg, 1.2mmol）It is dissolved in the anhydrous acetonitrile of 3ml, is slowly added drop-wise to and is filled to Methyl benzenesulfonyl with syringe
In the reaction bulb of chlorine, then under acetonitrile reflux state, when reaction 1 is small, heating is removed, decompression boils off solvent, rapid column chromatography
Separation, obtains product 237mg, yield 84%.Its synthesis type is as follows：
Spectroscopic data：1H NMR (600 MHz, CDCl3) δ (ppm): 7.67 (d, J = 8.2 Hz, 2H), 7.28
(d, J = 8.1 Hz, 2H), 2.83 (d, J = 7.5 Hz, 4H), 2.41 (s, 3H), 1.88 (dt, J =
13.6, 6.9 Hz, 2H), 0.88 (d, J = 6.7 Hz, 12H); 13C NMR (151 MHz, CDCl3) δ
(ppm): 142.8, 136.7, 129.4, 127.3, 57.3, 27.3, 21.4, 20.2。
The synthesis of embodiment 5,4- (4- trifluoromethoxies-benzenesulfonyl)-morpholine
With the two neck bottles of the dried 50ml of flame, displacement nitrogen three times, will be dissolved in acetonitrile with syringe（3ml）To methylbenzene
Sulfonic acid chloride（260mg, 1mmol）Get in reaction bulb after cooling, after heating makes acetonitrile solution flow back, by N, N, N, tetra- isobutyls of N-
Base ethylenediamine（240mg, 1.2mmol）It is dissolved in the anhydrous acetonitrile of 3ml, is slowly added drop-wise to and is filled to Methyl benzenesulfonyl with syringe
In the reaction bulb of chlorine, then under acetonitrile reflux state, 1 hour is reacted, removes heating, decompression boils off solvent, flash column
Analysis separation, obtains product 255mg, yield 82%.Its synthesis type is as follows：
Spectroscopic data：1H NMR (400 MHz, CDCl3) δ (ppm): 7.82 (d, J = 8.8 Hz, 2H), 7.39
(d, J = 8.8 Hz, 2H), 3.79 – 3.69 (m, 4H), 3.11 – 2.90 (m, 4H), 0.00 (s, 3H);13C NMR (151 MHz, CDCl3) δ (ppm): 152.5 (q, J = 1.7 Hz), 133.6, 129.9, 120.9
(d, J = 0.9 Hz), 119.3, 66.0, 45.9。
Embodiment 6, N, bis- (methylphenylamines of N-）The synthesis of p-methyl benzene sulfonic chloride
With the two neck bottles of the dried 50ml of flame, displacement nitrogen three times, will be dissolved in acetonitrile with syringe（3ml）To methylbenzene
Sulfonic acid chloride（190mg, 1mmol）Get in reaction bulb after cooling, after heating makes acetonitrile solution flow back, by N, N'- dimethyl-N,
N'- diphenyl-ethane -1,2- diamines (288mg, 1.2mmol）It is dissolved in the anhydrous acetonitrile of 3ml, is slowly added drop-wise to syringe
In the reaction bulb for filling p-methyl benzene sulfonic chloride, then under acetonitrile reflux state, when reaction 1 is small, heating is removed, decompression boils off
Solvent, rapid column chromatography separation, obtains product 237mg, yield 91%.Its synthesis type is as follows：
Spectroscopic data：1H NMR (600 MHz, CDCl3) δ (ppm): 7.42 (d, J = 8.0 Hz, 2H), 7.29
(t, J = 7.3 Hz, 2H), 7.27–7.21 (m, 3H), 7.09 (d, J = 7.3 Hz, 2H), 3.16 (s,
3H), 2.41 (s, 3H); 13C NMR (151 MHz, CDCl3) δ (ppm): 143.5, 141.6, 133.5,
129.3, 128.8, 127.9, 127.2, 126.6, 38.1, 21.5。
Embodiment 7, N, bis- (methylphenylamines of N-）The synthesis of quinoline -8- sulfonic acid chlorides
With the two neck bottles of the dried 50ml of flame, displacement nitrogen three times, will be dissolved in acetonitrile with syringe（3ml）Quinoline -8-
Sulfonic acid chloride（227mg, 1mmol）Get in reaction bulb after cooling, after heating makes acetonitrile solution flow back, by N, N'- dimethyl-N,
N'- diphenyl-ethane -1,2- diamines (（288mg, 1.2mmol）It is dissolved in the anhydrous acetonitrile of 3ml, is then slowly dripped with syringe
It is added in the reaction bulb for filling p-methyl benzene sulfonic chloride, then under acetonitrile reflux state, when reaction 1 is small, removes heating, depressurize
Solvent is boiled off, rapid column chromatography separation, obtains product 244mg, yield 82%.Its synthesis type is as follows：
Spectroscopic data：1H NMR (600 MHz, CDCl3) δ (ppm): 9.06 (dd, J = 4.2, 1.8 Hz, 1H),
8.31 (dd, J = 7.4, 1.4 Hz, 1H), 8.22 (dd, J = 8.3, 1.7 Hz, 1H), 7.97 (dd, J =
8.1, 1.3 Hz, 1H), 7.52 (dd, J = 8.3, 4.2 Hz, 1H), 7.51 – 7.48 (m, 2H), 7.17 –
7.11 (m, 2H), 7.11 – 7.04 (m, 3H), 3.69 (s, 3H); 13C NMR (151 MHz,CDCl3) δ
(ppm): 151.1, 144.2, 141.6, 137.3, 136.4, 133.5, 133.4, 128.8, 128.8, 126.5,
126.1, 125.4, 122.0, 40.0。
Claims (9)
1. a kind of synthetic method of arylsulfonyl tertiary amine compounds, be under nitrogen protection, in anhydrous aprotic solvent, aryl
Sulfonic acid chloride and two tertiary amines are with 1:1~1:20 molar ratio, when reaction 1 ~ 12 is small under the conditions of 50 ~ 150 DEG C, decompression boils off solvent, column
Chromatography, obtains arylsulfonyl tertiary amines.
A kind of 2. synthetic method of arylsulfonyl tertiary amine compounds as claimed in claim 1, it is characterised in that：The aryl sulphur
The structural formula of acyl chlorides is：
In formula, R1For any one of hydrogen, alkyl, aromatic radical, substituted aromatic base, vinyl, pi-allyl, alkynyl, propargyl.
A kind of 3. synthetic method of arylsulfonyl tertiary amine compounds as claimed in claim 2, it is characterised in that：The alkyl is
C1~C20Alkyl.
A kind of 4. synthetic method of arylsulfonyl tertiary amine compounds as claimed in claim 2, it is characterised in that：The substitution virtue
Perfume base is halogen, nitro, alkoxy, benzyloxy, vinyl, alkynyl or alkyl-substituted aryl rings, and substituent is on aromatic rings
Position be contraposition, ortho position or meta.
A kind of 5. synthetic method of arylsulfonyl tertiary amine compounds as claimed in claim 2, it is characterised in that：Het is furans,
Pyridine, thiophene, quinoline compound and its derivative.
A kind of 6. synthetic method of arylsulfonyl tertiary amine compounds as claimed in claim 1, it is characterised in that：The knot of two tertiary amines
Structure formula is：
In formula, R2, R3For any one of alkyl, aromatic radical, substituted aromatic base or several.
A kind of 7. synthetic method of arylsulfonyl tertiary amine compounds as claimed in claim 6, it is characterised in that：The alkyl is
C1~C20Alkyl.
A kind of 8. synthetic method of arylsulfonyl tertiary amine compounds as claimed in claim 6, it is characterised in that：The substitution virtue
Perfume base is the aryl rings containing halogen, nitro, alkoxy, benzyloxy, vinyl, alkynyl or alkyl substituent；On aromatic rings
The position of substituent be contraposition, ortho position or meta.
A kind of 9. synthetic method of arylsulfonyl tertiary amine compounds as claimed in claim 1, it is characterised in that：It is described non-proton
Property solvent is tetrahydrofuran, dichloromethane, acetonitrile, 1,4- dioxane, N,N-dimethylformamide or dimethyl sulfoxide.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110204464A (en) * | 2019-06-10 | 2019-09-06 | 西北师范大学 | A kind of synthetic method of the tertiary sulfamide compound of aryl |
| CN110204465A (en) * | 2019-06-13 | 2019-09-06 | 西北师范大学 | Photocatalytic synthesis at high allyl amine compound method |
| CN110240533A (en) * | 2019-07-10 | 2019-09-17 | 河南科技大学 | The preparation method of N, N- dimethyl sulfonamide analog derivative |
| CN115850119A (en) * | 2022-11-26 | 2023-03-28 | 南昌大学 | Synthetic method of 2-chloro aromatic amine compound |
| WO2024054669A3 (en) * | 2022-09-08 | 2024-04-18 | Nanotech Pharma Inc. | Compounds and compositions for intracellular delivery of nucleic acid-based therapeutics and methods thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1432003A (en) * | 2000-06-05 | 2003-07-23 | Fmc有限公司 | Process to prepare sulfonamides |
| CN101981019A (en) * | 2008-03-26 | 2011-02-23 | 詹森药业有限公司 | Process for the preparation of benzo-fused heteroaryl sulfamates and crystalline form of n-( ( (2s) -6-chloro-2,3-dihydro-l,4-benzodioxin-2-yl) methyl-sulfamide |
| JP2012184225A (en) * | 2011-02-18 | 2012-09-27 | Otsuka Pharmaceut Co Ltd | Pharmaceutical composition |
| CN103608010A (en) * | 2010-08-02 | 2014-02-26 | 中央佛罗里达大学研究基金公司 | Substituted 2-hydroxy-4-(2-(phenylsulfonamido)acetamido)benzoic acid analogs as inhibitors of STAT proteins |
| EP2381783B1 (en) * | 2008-12-04 | 2015-09-02 | Enzo Life Sciences, Inc. | Labeling of target molecules, identification of organelles and other applications, novel compositions, methods and kits |
-
2017
- 2017-11-24 CN CN201711189620.4A patent/CN107954906B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1432003A (en) * | 2000-06-05 | 2003-07-23 | Fmc有限公司 | Process to prepare sulfonamides |
| CN101981019A (en) * | 2008-03-26 | 2011-02-23 | 詹森药业有限公司 | Process for the preparation of benzo-fused heteroaryl sulfamates and crystalline form of n-( ( (2s) -6-chloro-2,3-dihydro-l,4-benzodioxin-2-yl) methyl-sulfamide |
| EP2381783B1 (en) * | 2008-12-04 | 2015-09-02 | Enzo Life Sciences, Inc. | Labeling of target molecules, identification of organelles and other applications, novel compositions, methods and kits |
| CN103608010A (en) * | 2010-08-02 | 2014-02-26 | 中央佛罗里达大学研究基金公司 | Substituted 2-hydroxy-4-(2-(phenylsulfonamido)acetamido)benzoic acid analogs as inhibitors of STAT proteins |
| JP2012184225A (en) * | 2011-02-18 | 2012-09-27 | Otsuka Pharmaceut Co Ltd | Pharmaceutical composition |
Non-Patent Citations (6)
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110204464A (en) * | 2019-06-10 | 2019-09-06 | 西北师范大学 | A kind of synthetic method of the tertiary sulfamide compound of aryl |
| CN110204464B (en) * | 2019-06-10 | 2021-05-04 | 西北师范大学 | Synthesis method of aryl tertiary sulfonamide compound |
| CN110204465A (en) * | 2019-06-13 | 2019-09-06 | 西北师范大学 | Photocatalytic synthesis at high allyl amine compound method |
| CN110204465B (en) * | 2019-06-13 | 2021-05-11 | 西北师范大学 | Method for synthesizing homoallylamine compound by photocatalysis |
| CN110240533A (en) * | 2019-07-10 | 2019-09-17 | 河南科技大学 | The preparation method of N, N- dimethyl sulfonamide analog derivative |
| CN110240533B (en) * | 2019-07-10 | 2022-03-18 | 河南科技大学 | Preparation method of N, N-dimethyl sulfonamide derivative |
| WO2024054669A3 (en) * | 2022-09-08 | 2024-04-18 | Nanotech Pharma Inc. | Compounds and compositions for intracellular delivery of nucleic acid-based therapeutics and methods thereof |
| CN115850119A (en) * | 2022-11-26 | 2023-03-28 | 南昌大学 | Synthetic method of 2-chloro aromatic amine compound |
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