1187-59-3

Usage

Safety Profile

Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C4H7NO/c1-3-4(6)5-2/h3H,1H2,2H3,(H,5,6)

Upstream product

• 6830-81-5 3-hydroxyl-N-methylpropanamide 
• 57-57-8 β-Propiolactone 
• 74-89-5 methylamine 
• 5450-85-1 2-acetoxy-propionic acid methylamide 
• 814-68-6 acryloyl chloride 
• 140-88-5 ethyl acrylate 
• 74-86-2 acetylene 
• 38188-92-0 β-Methoxypropionsaeure-monomethylamid 
• 2682-32-8 N-methyl-2-propynamide 
• 593-51-1 methylamine hydrochloride 
• 39198-51-1 N-methyl-endo-bicyclo<2.2.1>hept-5-ene-2-carboxamide 
• 50836-82-3 N-methylamide of β-methylaminopropionic acid 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 24685-31-2 methyl N-allyl-N-acrylamide 

Downstream Products

• 2680-03-7 N,N-Dimethylacrylamide 
• 207804-83-9 N-acryloyl-N-methyl-N'-p-tolylsulfonylurea 
• 1307612-93-6 C₁₃H₂₀N₂O₃ 
• 297734-22-6 C₁₀H₂₀N₂O 
• 50836-82-3 N-methylamide of β-methylaminopropionic acid 
• 1342826-49-6 3-(4-((6-(7-(4-(3-cyclopropylureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)piperazin-1-yl)-N-methylpropanamide 
• 1258852-55-9 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinyl]-N-methylpropanamide 
• 1001346-35-5 3-(2-methoxyethylamino)-N-methyl-propanamide 
• 1001346-14-0 3-(butan-2-ylamino)-N-methyl-propanamide 

Relevant academic research and scientific papers

Organocatalytic Trans Semireduction of Primary and Secondary Propiolamides: Substrate Scope and Mechanistic Studies

We report a chemoselective, phosphine-catalyzed semireduction of primary and secondary propiolamides. In the presence of stoichiometric pinacolborane and catalytic n-tributylphosphine, a variety of propiolamides were successfully converted to the corresponding acrylamides in excellent yield with (E)-stereoselectivity. The reaction condition is tolerant of various functional groups including alkene, alkyne, ketone, or ester. Deuterium labeling studies established that the hydride from activated pinacolborane is added to the α-carbon and the proton on the amide nitrogen is abstracted by the ?-carbon to furnish the (E)-acrylamides. DFT calculations revealed a clear energetic driving force for the (E)- over the (Z)-isomer. (Figure presented.).

Catalytic, transition-metal-free semireduction of propiolamide derivatives: Scope and mechanistic investigation

We report a transition-metal-free trans-selective semireduction of alkynes with pinacolborane and catalytic potassium tert-butoxide. A variety of 3-substituted primary and secondary propiolamides, including an analog of FK866, a potent nicotinamide mononucleotide adenyltransferase (NMNAT) inhibitor, are reduced to the corresponding (E)-3-substituted acrylamide derivatives in up to 99% yield with >99:1 E/Z selectivity. Mechanistic studies suggest that an activated Lewis acid-base complex transfers a hydride to the α-carbon followed by rapid protonation in a trans fashion.

Learning from Peptides to Access Functional Precision Polymer Sequences

Functional precision polymers based on monodisperse oligo(N-substituted acrylamide)s and oligo(2-substituted-α-hydroxy acid)s have been synthesized. The discrete sequences originate from a direct translation of side-chain functionality sequences of a peptide with well-studied properties. The peptide was previously selected to solubilize the photosensitizer meta-tetra(hydroxyphenyl)chlorin. The resulting peptidomimetic formulation additives preserve the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40 % higher payloads and 27-times faster initial drug release.

BIARYL AMIDES WITH MODIFIED SUGAR GROUPS FOR TREATMENT OF DISEASES ASSOCIATED WITH HEAT SHOCK PROTEIN PATHWAY

Provided are biaryl amides and coumarin-based compounds with modified sugar groups for treatment of diseases associated with heat shock protein pathway. The compounds having the following formulas, wherein variables are as defined herein. Formulae (I), (II), (III), (IV), and (V), Pharmaceutical compositions of the compounds are also provided. These biaryl amides and coumarin-based derivatives with modified sugar groups are useful for treatment and prevention of diseases and disorders, including neurological disorders, such as neurodegenerative diseases and nerve damaging disorders, for example, diabetic peripheral neuropathy.

(Meth) acrylamide N-substituted (by machine translation)

PROBLEM TO BE SOLVED: a (meth) acrylic acid and a starting material, high yield, high-purity (meth) and N-substituted carboxylic acid amide derivative norbonene alkylacrylamide industrial production method. SOLUTION: and (meth) acrylic acid aminopentadienoic cyclometallized Diels-Alder reaction product of, norbonene carboxylic acid derivative, and silica as a main catalyst in the presence of an inorganic material, and amide-amine compound, norbonene carboxylic acid amide derivative. Furthermore, the vapor phase of the norbonene vinylcarboxamide deriv. aminopentadienoic cyclometallized by thermal decomposition reaction by desorbing, (meth) acrylamide purpose compd. N-substituted. Selected drawing: no (by machine translation)

METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE

PROBLEM TO BE SOLVED: To provide an industrial method for efficiently producing a high-purity N-substituted (meth)acrylamide in a short time even under mild reaction conditions, which uses (meth)acrylic acid as a starting material and generates only water as a byproduct. SOLUTION: There is provided a method for producing an N-substituted (meth)acrylamide to obtain an objective compound, N-substituted (meth)acrylamide by the step of: reacting a (meth)acrylic and an amine compound to synthesize an aminopropionic acid derivative; then adding an inorganic material composed mainly of silica as a catalyst and performing amidation with the same amine compound to obtain an aminopropionic acid derivative; and subsequently eliminating an amine by the thermal decomposition reaction. COPYRIGHT: (C)2015,JPOandINPIT

METHOD OF PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE

PROBLEM TO BE SOLVED: To provide a method of producing N-substituted (meth)acrylamide of high purity under mild conditions. SOLUTION: This invention relates to a method of obtaining N-substituted (meth)acrylamide [3] by the detachment of an amine compound through the liquid-phase thermal decomposition of an aminopropionic acid amide derivative [1] in the presence of a catalyst mainly composed of silica, wherein R1-R5 are represented by H, a C1-32 alkyl group, and a hydroxyalkyl group. COPYRIGHT: (C)2016,JPOandINPIT

METHOD FOR PRODUCING N-SUBSTITUTED (METH)ACRYLAMIDE

PROBLEM TO BE SOLVED: To provide an industrial method for producing a high-purity alkoxy propionic acid amide derivative and N-substituted (meth)acrylamide in a high yield, which uses a (meth)acrylic acid as a starting material. SOLUTION: There is provided a method for producing an objective compound, N-substituted (meth)acrylamide by the step of: amidating an alkoxy propionic acid derivative, which is synthesized from a (meth)acrylic acid and alcohol and represented by the formula [1], with an amine compound; R3-NH-R4(R3 and R4 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms or may form a saturated 5- to 7-membered ring with a nitrogen atom supporting them) in the presence of an inorganic material composed mainly of silica as a catalyst to obtain an alkoxy propionic acid amide derivative; and eliminating alcohol by the liquid phase thermal decomposition reaction of the alkoxy propionic acid amide derivative. (R1 represents H or a methyl group; and R2 represents a linear or branched alkyl group having 1 to 6 carbon atoms or an alkenyl group.) COPYRIGHT: (C)2015,JPOandINPIT

The oxidative dealkylation of tertiary amides: Mechanistic aspects

N-(But-3-enyl)-N-methylbenzamide 14a undergoes microsomal oxidation by rat liver microsomes to yield both N-methyl- and N-(but-3-enyl)benzamides 18a and 19, the products of N-dealkylation. Cyclic products, that could be derived from a carbon-centered radical formed by hydrogen atom abstraction from the N-methyl group, were not observed. When generated independently, this carbon-centred radical underwent cyclisation, the 5-exo-trig mode being preferred to 6-endo-trig by a factor of 5. In contrast, N-(but-3-ynyl)-N-methylbenzamide 15 undergoes microsomal oxidation to yield the products of dealkylation 18a and 23 and also N-benzoylpiperidone 24. Dealkylation is preferred by factor of 3 and the piperidone accounts for ca. 45% of the reaction at the N-methyl group. Piperidone formation is consistent with the generation of a carbon-centred radical α- to the amide nitrogen atom during dealkylation and implies that cyclisation proceeds preferentially via the 6-endo-dig mode. Generated independently the radical undergoes cyclisation by both 5-exo-dig and 6-endo-dig modes, the former being favoured by a factor of 10. Similarly, N,N-dimethylacrylamide 26 and N-methyl-N-(3-pyridyl)acrylamide 27 undergo microsomal oxidation to form, via the 5-endo-trig cyclisation mode, 3-hydroxy-N-methyl-2-pyrrolidone 33 and 3-hydroxycotinine ? 34, respectively, confirming the intermediacy of a carbon-centred radical in the dealkylation process. Attempts to trap N-acyliminium ions during microsomal dealkylation failed. Thus, although N,N-dimethylaniline 35 reacts in the presence of NaCN to form N-cyanomethyl-N-methylaniline 37 (Nu=CN), N,N-dimethylbenzamide undergoes dealkylation without forming N-cyanomethyl-N-methylbenzamide. Similarly, microsomal reaction of N,N-dimethylaniline in the presence of NaBD4 gives rise to multiple incorporation of deuterium atoms into the methyl groups of the starting material, whereas N,N-dimethylbenzamide undergoes dealkylation but with no such deuterium incorporation into the starting material. Further, microsomal oxidation of N,N-dimethylsalicylamide 38 yields N-methylsalicylamide 40 with no evidence for the formation of N-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one 39, the potential product of intramolecular cyclisation of the phenolic oxygen atom onto the putative N-aroylmethylene iminium ion.

Indole derivatives as 5-HT1-like agonists for use in migraine

The present invention relates to 3,5-disubstituted indole compounds which are selective agonists which act on 5-hdroxytryptamine receptors useful in the treatment of migraine.