- Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids
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Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.
- Ramachandran, P. Veeraraghavan,Hamann, Henry J.
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supporting information
p. 2938 - 2942
(2021/05/04)
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- COMPOUND, COMPOSITION AND USES THEREOF
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The disclosures herein provide compounds of formula I, formula II, formula III, formula IV, formula V, formula VI and formula VII or its pharmaceutical acceptable compositions and salts, as well as polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These compositions or salts may be formulated as pharmaceutical compositions. The pharmaceutical compositions may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of stomach and esophageal problems or its associated complications.
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Paragraph 00169
(2017/03/28)
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- SYSTEM PROVIDING CONTROLLED DELIVERY OF GASEOUS CO FOR CARBONYLATION REACTIONS
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A carbonylation system comprising at least one carbon monoxide producing chamber and at least one carbon monoxide consuming chamber forming an interconnected multi-chamber system, said interconnection allowing carbon monoxide to pass from the at least one carbon monoxide producing chamber to the at least one carbon monoxide consuming chamber, said at least one carbon monoxide producing chamber containing a reaction mixture comprising a carbon monoxide precursor and a catalyst, said at least one carbon monoxide consuming chamber being suitable for carbonylation reactions, said interconnected multi- chamber system being sealable from the surrounding atmosphere during carbonylation.
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Page/Page column 92; 93
(2012/06/30)
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- Ex situ generation of stoichiometric and substoichiometric 12CO and 13CO and its efficient incorporation in palladium catalyzed aminocarbonylations
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A new technique for the ex situ generation of carbon monoxide (CO) and its efficient incorporation in palladium catalyzed carbonylation reactions was achieved using a simple sealed two-chamber system. The ex situ generation of CO was derived by a palladium catalyzed decarbonylation of tertiary acid chlorides using a catalyst originating from Pd(dba)2 and P(tBu)3. Preliminary studies using pivaloyl chloride as the CO-precursor provided an alternative approach for the aminocarbonylation of 2-pyridyl tosylate derivatives using only 1.5 equiv of CO. Further design of the acid chloride CO-precursor led to the development of a new solid, stable, and easy to handle source of CO for chemical transformations. The synthesis of this CO-precursor also provided an entry point for the late installment of an isotopically carbon-labeled acid chloride for the subsequent release of gaseous [ 13C]CO. In combination with studies aimed toward application of CO as the limiting reagent, this method provided highly efficient palladium catalyzed aminocarbonylations with CO-incorporations up to 96%. The ex situ generated CO and the two-chamber system were tested in the synthesis of several compounds of pharmaceutical interest and all of them were labeled as their [ 13C]carbonyl counterparts in good to excellent yields based on limiting CO. Finally, palladium catalyzed decarbonylation at room temperature also allowed for a successful double carbonylation. This new protocol provides a facile and clean source of gaseous CO, which is safely handled and stored. Furthermore, since the CO is generated ex situ, excellent functional group tolerance is secured in the carbonylation chamber. Finally, CO is only generated and released in minute amounts, hence, eliminating the need for specialized equipment such as CO-detectors and equipment for running high pressure reactions.
- Hermange, Philippe,Lindhardt, Anders T.,Taaning, Rolf H.,Bjerglund, Klaus,Lupp, Daniel,Skrydstrup, Troels
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p. 6061 - 6071
(2011/06/19)
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- The use of formamidine protection for the derivatization of aminobenzoic acids
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(Chemical Equation Presented) N,N-Dimethylformamidine and novel N,N-diisopropylformamidine protecting groups were used to carry out a one-pot conversion of aminobenzoic acids into the corresponding amides. General conditions for an in situ transformation of aminobenzoic acids and their heterocyclic analogues into the corresponding formamidine-protected acid chlorides were developed. These chlorides were used in reactions with amines, including poorly reactive anilines. The protected amides were then smoothly deprotected by heating with ethylenediamine derivatives, resulting in a general procedure for the one-pot transformation of aminobenzoic acids into their amides. Our one-pot procedure was successfully applied to the preparation of several compounds of pharmaceutical interest.
- Zhichkin, Paul E.,Peterson, Lisa H.,Beer, Catherine M.,Rennells, W. Martin
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supporting information; experimental part
p. 8954 - 8959
(2009/04/11)
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- Pharmaceutical compositions containing tramadol for migraine
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A method for treating migraine is disclosed in which a composition consisting essentially of pharmacologically effective amounts of both an antiemetic compound and tramadol is administered to a patient in need thereof.
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- Pharmaceutical composition for the preparation of a stable powder containing an association of acetylsalicylic acid and metoclopramide as the active ingredients
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A novel pharmaceutical composition for the preparation of a stable powder containing an association of acetylsalicylic acid and metoclopramide as the active ingredients. The acetylsalicylic acid is in the form of a water soluble salt or complex and is in association with metoclopramide or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable hydrophilic polymer in an amount sufficient to stabilize the metoclopramide. This composition has remarkable stability in powder form and can be used to prepare sachets for the treatment of migraine.
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- The Interaction of Ammonium, Sulfonium, and Sulfide Analogues of Metoclopramide with the Dopamine D2 Receptor
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A series of permanently charged ammonium and sulfonium analogues of metoclopramide as well as a permanently uncharged sulfide analogue were synthesized and evaluated for their ability to inhibit apomorphine-induced responses on mouse striatal slices.Three of the four permanently charged analogues were found to inhibit apomorphine's effects, although at higher concentrations than either metoclopramide or its dimethyl analogue.In contrast, the sulfide analogue was inactive at concentrations up to 100 μM.These findings are consistent with earlier studies of chlorpromazine and sulpiride analogues and provide further evidence that dopamine antagonists bind in their charged molecular forms to anionic sites on the D2 receptor.Further, the results of this study in conjunction with those of our earlier sulpiride study would seem to indicate that differences in the biological profiles of metoclopramide, a type 1 benzamide useful as a gastric prokinetic agent, and sulpiride, a type 2 benzamide useful for its antipsychotic effects, are not due to any appreciable differences in the binding of the basic nitrogen atom of these molecules.
- Harrold, Marc W.,Sriburi, Anong,Matsumoto, Kazuhisa,Miller, Duane D.,Farooqui, Tahira,Uretsky, Norman
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p. 3166 - 3170
(2007/10/02)
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- Method of preparing metoclopramide
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2-Chloro-4-N-(β-diethylaminoethyl)aminocarbonyl-5-methoxy-benzamide of the formula, STR1 a process for their preparation and a process for preparing metoclopramide of the formula, STR2 using the above described 2-chloro-4-N-(β-diethylaminoethyl)aminocarbonyl-5-methoxybenzamide.
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- Hydroxamic acid derivative and method of preparing metoclopramide using same
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2-Chloro-4-N-(β-diethylaminoethyl)aminocarbonyl-5-methoxybenzhydroxamic acid of the formula, STR1 or its metal salt, a process for their preparation and a process for preparing metoclopramide of the formula, STR2 using the above described 2-chloro-4-N-(β-diethylaminoethyl)aminocarbonyl-5-methoxybenzhydroxamic acid or its metal salt.
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- Sulfonic acid esters
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A novel process for the amidation or esterification which comprises reacting a compound having a carboxy group with a compound having an amino or imino group which can be acylated or with a compound having a hydroxy group in the presence of a sulfonic acid ester of the formula: wherein R1 is an organic group and R2 O-- is a residue of a strongly acidic N-hydroxy compound as a condensation agent, and a novel sulfonic acid ester useful as such a condensation agent and a process for the preparation thereof.
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