1255150-40-3

Basic information

• Product Name: pyridine-3-carboxamide
• CAS NO: 1255150-40-3
• Molecular Formula: C6H6N2O
• Molecular Weight: 122
• Mol File: 1255150-40-3.mol
• Article Data: 259

Chemical Properties

• Appearance: /
• CAS DataBase Reference: pyridine-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: pyridine-3-carboxamide(1255150-40-3)
• EPA Substance Registry System: pyridine-3-carboxamide(1255150-40-3)

Safety Data

• Hazardous Substances Data: 1255150-40-3(Hazardous Substances Data)

Upstream product

• 59-67-6 nicotinic acid 
• 108-19-0 BIURET 
• 57-13-6 urea 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 3569-99-1 N-hydroxymethylnicotinamide 
• 2139-47-1 nifenazone 
• 53-84-9 NAD 
• 13502-54-0 1-(2',6'-Dichlorobenzyl)-1,4-dihydronicotinamide 
• 865-05-4 nicotinamide adenine dinucleotide 
• 7732-18-5 water 
• 2503-55-1 N-benzylnicotinamide 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 

Downstream Products

• 19293-85-7 1,1'-Tetramethylen-bis-<3-carbamoyl-pyridinium-bromid> 
• 63405-87-8 1-butyl-3-carbamoylpyridin-1-ium bromide 
• 19293-86-8 1,1'-Pentamethylen-bis-<3-carbamoyl-pyridinium-bromid> 
• 53164-28-6 1-benzyloxymethyl-3-carbamoyl-pyridinium; chloride 
• 40481-07-0 3-carbamoyl-1-heptyl-pyridinium; bromide 
• 63906-11-6 3-carbamoyl-1-tetradecylpyridinium chloride 
• 63906-10-5 N-hexadecyl-3-(aminocarbonyl)pyridinium chloride 
• 114330-59-5 3-carbamoyl-1-(4-trans-styryl-benzyl)-pyridinium; bromide 
• 109475-85-6 3-carbamoyl-1-[(3,4-dimethyl-phenylcarbamoyl)-methyl]-pyridinium; chloride 
• 6276-11-5 3-ethoxycarbonylaminopyridine 
• 14910-22-6 bis-nicotinoylamino-phenyl-methane 
• 5463-59-2 3-carbamoyl-1-propyl-pyridinium; iodide 
• 6945-03-5 nicotinic acid-(2,2,2-trichloro-1-hydroxy-ethylamide) 
• 2254-99-1 N-Dodecylnicotinamide chloride 

Relevant articles and documents

Thiocarbonyl to carbonyl group transformation with nitrosonium tetrafluoroborate

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Formation of nicotinamide from nicotinuric acid by peptidylglycine α- amidating monooxygenase (PAM): A possible alternative route from nicotinic acid (niacin) to NADP in mammals [7]

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Synthesis of primary Amides via Copper-Catalyzed Aerobic Decarboxylative ammoxidation of Phenylacetic Acids and α-Hydroxyphenylacetic acids with Ammonia in water

A Cu2O-catalyzed aerobic oxidative decarboxylative ammoxidation to primary benzamides from phenylacetic acids and a-hydroxyphenylacetic acids is developed. A variety of primary benzamides could be prepared smoothly, in good to excellent yields, by means of a one-pot domino protocol combining decarboxylation, dioxygen activation, oxidative C-H bond functionalization, and amidation reactions.

Nicotinamide riboside-amino acid conjugates that are stable to purine nucleoside phosphorylase

The nutraceutical Nicotinamide Riboside (NR), an efficacious biosynthetic precursor to NAD, is readily metabolized by the purine nucleoside phosphorylase (PNP). Access to the PNP-stable versions of NR is difficult because the glycosidic bond of NR is easily cleaved. Unlike NR, NRH, the reduced form of NR, offers sufficient chemical stability to allow the successful functionalisation of the ribosyl-moiety. Here, we report on a series of NRH and NR derived amino acid conjugates, generated in good to excellent yields and show that O5′-esterification prevents the PNP-catalyzed phosphorolysis of these NR prodrugs.

Transition state structure of the solvolytic hydrolysis of NAD+

The transition state structure has been determined for the pH- independent solvolytic hydrolysis of NAD+. The structure is based on kinetic isotope effects (KIEs) measured for NAD+'s labeled in various positions of the ribose ring and in the leaving group nitrogen. The KIEs for reactions performed at 100°C in 50 mM NaOAc (pH 4.0) were as follows: 1-15N, 1.020 ± 0.007; 1'-14C, 1.016 ± 0.002; [1-15N,1'-14C], 1.034 ± 0.002; 1'- 3H, 1.194 ± 0.005; 2'-3H, 1.114 ± 0.004; 4'-3H, 0.0997 ± 0.001; 5'3H, 1.000 ± 0.003; 4'-18O, 0.988 ± 0.007. The transition state structure was determined using bond energy/bond order vibrational analysis to predict KIEs for trial transition state models. The structure that most closely matches the experimental KIEs defines the transition state. A structure interpolation method was developed to generate trial transition state structures and thereby systematically search reaction coordinate space. Structures are generated by interpolation between reference structures, reactant NAD+ and a hypothetical {ribo-oxocarbenium ion plus nicotinamide} structure. The point in reaction coordinate space where all the predicted KIEs matched the measured ones was considered to locate the transition state structure. This occurred when the residual bond order to the leaving group nicotinamide, n(LG,TS), was 0.02 (bond length = 2.65 A?) and the bond order to the approaching nucleophile, n(Nu,TS), was 0.005 (3.00 A?). Thus, bond-breaking and bond-making in this A(N)D(N) reaction are asynchronous, and the transition state has a highly oxocarbenium ion-like character.

Monomeric nickel hydroxide stabilized by a sterically demanding phosphorus-nitrogen PN3P-pincer ligand: synthesis, reactivity and catalysis

A terminal nickel hydroxide complex (PN3P)Ni(OH) (3) bearing the 2nd generation phosphorus-nitrogen PN3P-pincer ligand has been synthesized and structurally characterized. As a nucleophile, 3 reacts with CO to afford the hydroxycarbonyl complex 4, (PN3P)Ni(COOH). 3 can also activate CO2 and CS2 to produce nickel bicarbonate (PN3P)Ni(OCOOH) (5) and bimetallic dithiocarbonate [(PN3P)NiS]2CO (6) respectively, as well as to promote aryl isocyanate and isothiocyanate insertion into the Ni-OH bond to give the corresponding (PN3P)NiEC(O)NHAr complexes (E = O, 7; E = S, 8). In addition, 3 catalyzes the nitrile hydration to various amides with well-defined intermediates (PN3P)Ni-NHC(O)R (R = Me, 9; R = Ph, 10).

Spinel cobalt oxide catalyzed controlled hydration of aromatic nitriles

Selective hydration of aromatic nitriles to their respective amides has been achieved in the presence of spinel cobalt oxide, Co3O 4 as a heterogeneous catalyst. Higher yields of the products in shorter duration have been accomplished under hydrothermal condition compared to thermal refluxing.

A phosphine-free approach to primary amides by palladium-catalyzed aminocarbonylation of aryl and heteroaryl iodides using methoxylamine hydrochloride as an ammonia equivalent

The palladium-catalyzed synthesis of primary amides by aminocarbonylation of aryl and heteroaryl iodides under phosphine-free conditions is reported for the first time. Methoxylamine hydrochloride, acting as an ammonia equivalent, undergoes sequential carbonylation and demethoxylation under mild reaction conditions. The procedure does not require a phosphine ligand and takes place in short reaction times at low temperatures to provide the products in excellent yields. Georg Thieme Verlag Stuttgart · New York.

Semisynthetic Enzymes: Synthesis of a New Flavopapain with High Catalytic Efficiency

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Copper-catalyzed aerobic oxidative synthesis of primary amides from (aryl)methanamines

A copper-catalyzed aerobic oxidative method for the synthesis of primary aryl amides has been developed, and the direct oxygenation of (aryl)methanamines to primary aryl amides by molecular oxygen showed convenient, practical, and environment-friendly advantages. This method will find wide application in chemistry and biology. Georg Thieme Verlag Stuttgart · New York.

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Organophosphorous analogues and derivatives of nucleotides. II. N-phosphono-, methylphosphinomethyl-nicotinamide and analogues

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A covalent intermediate in CD38 is responsible for ADP-ribosylation and cyclization reactions

Human CD38 is an ectoenzyme expressed on the surface of B-cells that makes cyclic-ADP-ribose (cADPR) and ADP-ribose from NAD+ (nicotinamide diphosphate ribose, oxidized form). The compound cADPR is a potent second messenger for calcium release inside cells. Nicotinamide guanine dinucleotide (NGD+) is also cyclized by CD38 to form cGDPR (cyclic guanosine diphosphate ribose) and hydrolyzed to form GDPR (guanosine diphosphate ribose). Kinetic isotope effect studies in the presence of 20 mM nicotinamide gave 1'-3H and 1'-14C isotope effects of 1.02 ± 0.01 and 1.00 ± 0.01, respectively, for the cyclization reaction and 1.23 ± 0.01 and 1.02 ± 0.01, respectively, for the hydrolysis reaction. These values support a covalent intermediate. The existence of a covalent intermediate was established by reaction of ara-F-NMN+ (arabinosyl-2'-fluoro-2'-deoxynicotinamide mononucleotide) with the enzyme. This compound reacted to release 1 mol of nicotinamide/mole of CD38 monomer and to form an inactive covalent intermediate. Reaction with excess nicotinamide rescued catalytic activity with an apparent K(m) of 17 ± 5 mM and a V(max) of 0.023 ± 0.003 s-1. Proof of covalent labeling of the enzyme by this inhibitor was obtained by MS analysis. Treatment of CD38 with ara-F-NMN+ increased mass by 215 amu, consistent with formation of CD38-fluoro-sugar monophosphate. Tryptic digestion in urea, phosphatase treatment, and purification of peptides in combination with MALDI-PSD permitted identification of Glu226 as the amino acid nucleophile. This residue is highly conserved across all ADP-ribosyl (adenosine diphosphate ribosyl) cyclases. The covalent intermediate inherent to the catalytic mechanism of human CD38 provides chemical precedent for related NAD+ glycosyltransferases.

Ag-grafted covalent imine network material for one-pot three-component coupling and hydration of nitriles to amides in aqueous medium

A nitrogen rich porous covalent imine network material (CIN-1) has been successfully employed for grafting silver nanoparticles (Ag NPs). The Ag NPs grafted CIN-1, Ag-CIN-1 has been characterized by elemental analysis, powder X-ray diffraction (XRD), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), UV-vis diffuse reflectance spectroscopy (DRS), thermogravimetric analysis (TGA) and EPR spectroscopic studies. Ag-CIN-1 acts as a truly heterogeneous catalyst in the hydration of nitriles to amides and the A3 coupling reactions between the alkyne, amine and aldehyde to produce propargylamines by using water as a green solvent. This journal is

Water-soluble superbulky (η6- p -cymene) ruthenium(ii) amine: An active catalyst in the oxidative homocoupling of arylboronic acids and the hydration of organonitriles

A phosphine free water-soluble superbulky amine-ruthenium-arene complex (2) encompassing 2,6-bis(diphenylmethyl)-4-methylaniline was synthesised in good yield. 2 was characterized by FT-IR, 1H NMR, and 13C NMR spectroscopies, TGA and elemental analyses. The structure of 2 was confirmed by a single-crystal X-ray diffraction study. The ruthenium centre in 2 adopts the pseudo-octahedral geometry due to the η6-p-cymene ring and bulky aniline ligand along with two chloro groups. Besides, complex 2 was efficaciously employed as a catalyst in the hydration of organonitriles to amides. This reaction proceeds efficiently for a wide range of substrates in an environmentally benign medium and is an economically reasonable synthetic route to amides in good yields. In addition, 2 acts as an excellent catalyst in the oxidative homocoupling of arylboronic acids in water. A range of arylboronic acids undergo a homocoupling reaction in the presence of catalyst 2 to yield symmetrical biaryls in reasonable to good yields.

Investigation of 1,3,5-triaza-7-phosphaadamantane-stabilized silver nanoparticles as catalysts for the hydration of benzonitriles and acetone cyanohydrin

A straightforward synthesis of water-soluble silver nanoparticles stabilized by PTA (1,3,5-triaza-7-phosphaadamantane, a water-soluble phosphine ligand) ligands was developed. The nanoparticles were thoroughly characterized by ultraviolet-visible spectroscopy, 31P nuclear magnetic resonance spectroscopy, transmission electron microscopy, and energy dispersive X-ray spectroscopy. The effectiveness of the Ag-PTA nanoparticles as catalysts for the hydration of nitriles to amides in water under mild conditions was explored using a series of substituted benzonitriles and cyanohydrins. In comparison to all previously investigated homogeneous catalysts, the Ag-PTA system excels at cyanohydrin hydration, including acetone cyanohydrin hydration. Cyanohydrins are in equilibrium with small amounts of cyanide, and experiments revealed that the Ag-PTA nanoparticles disassemble in the presence of cyanide. The catalyst solution, which is proposed to contain a soluble Ag(CN)n1-ncomplex (with n likely equal to 2), remained unpoisoned even in the presence of 10 equiv of cyanide. It is suggested that no cyanide poisoning occurs because the Ag(I) complex is labile. Overall, the Ag-PTA catalyst system (a) is not poisoned by cyanide, (b) catalyzes hydration reactions under mild conditions (in air and at relatively low temperatures), (c) is easily synthesized from cheap starting materials, and (d) can hydrate heteroaromatics in good yields. The recognition of the importance of labile metal cyanide bonding represents an important step forward in catalyst design for improving the catalytic hydration of acetone cyanohydrin. (Chemical Equation Presented).

Nicotinamide biosynthesis by intestinal bacteria as influenced by

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A general palladium-catalyzed aminocarbonylation of phenols to primary benzamides via in situ generation of aryl nonaflates

Amides in mind! A novel palladium-catalyzed amino-carbonylation of in situ formed aryl nonaflates to give primary amides in moderate to excellent yields has been developed (see scheme). Copyright

Ru (III) Schiff-base complex anchored on nanosilica as an efficient and retrievable catalyst for hydration of nitriles

Transition metal catalyzed hydration of nitriles is an attractive methodology for amide synthesis, and hence recently attracted wide attention. It is one of the significant organic transformations as amides play a vital role in biological, pharmaceutical and industrial applications. In this work, we report the synthesis of a new solid supported Ru (III) Schiff base complex, Ru@imine-nanoSiO2 immobilized on nanosilica obtained from rice husk. The complex was characterized by FTIR, powder X-ray diffraction, BET surface area measurement, UV–vis, SEM–EDX, TEM, ESR, X-ray photoelectron spectroscopy and ICP-AES analysis. Using Ru@imine-nanoSiO2 as the catalyst, the hydration of nitriles in i-PrOH at 40?°C was studied which resulted in good isolated yields (60–99%). The catalyst can be recycled and reused up to 5th cycle without any loss in activity. The products were characterized by FTIR, GC–MS and 1H-NMR spectroscopy and compared with authentic samples.

Enzyme and process development for production of nicotinamide

Through screening a library of nitrile hydratases developed in-house, NHT-120 was selected to catalyze the hydration of 3-cyanopyridine for production of nicotinamide. After reaction optimization, a fed-batch method was used to alleviate the substrate inhibition. Under this approach, 200 g/L of 3-cyanopyridine could be converted to nicotinamide in 5.5 h, and no nicotinic acid was produced. Under a substrate to enzyme ratio of 100:1 (w/w), nicotinamide in the reaction solution could reach 230 g/L.

Aminocarbonylation of (Hetero)aryl bromides with ammonia and amines using a palladium/dalphos catalyst system

Variants of the DalPhos [2-aminophenylbisadamantyl)phosphine] ligand family were examined in a palladium-catalyzed carbonylative amination reaction using inexpensive carbon monoxide and ammonia as reagents. As a result of this survey, the Pyr-DalPhos ligand was identified as being effective for the selective aminocarbonylation of aryl bromides with ammonia, as well as primary and secondary alkylamines. A variety of primary aromatic, heteroaromatic and N-substituted benzamides were formed in moderate to good yields. As part of this study, a (Mor-DalPhos)Pd-benzoyl complex was prepared and crystallographically characterized, thereby showing the viability of the carbonyl insertion step. Copyright

A new homogeneous platinum containing catalyst for the hydrolysis of nitriles

[(Me2PO···H···OPMe2)PtH(PMe2OH) is an extremely active homogeneous catalyst for the hydration of nitriles to amides: a mechanism involving intramolecular attack by a phosphine oxide on a nitrile within the co-ordination sphere of the platinum atom is suggested.

A pre-steady state and steady state kinetic analysis of the N-ribosyl hydrolase activity of hCD157

hCD157 catalyzes the hydrolysis of nicotinamide riboside (NR) and nicotinic acid riboside (NAR). The release of nicotinamide or nicotinic acid from NR or NAR was confirmed by spectrophotometric, HPLC and NMR analyses. hCD157 is inactivated by a mechanism-based inhibitor, 2′-deoxy-2′-fluoro-nicotinamide arabinoside (fNR). Modification of the enzyme during the catalytic cycle by NR, NAR, or fNR increased the intrinsic protein fluorescence by approximately 50%. Pre-steady state and steady state data were used to derive a minimal kinetic scheme for the hydrolysis of NR. After initial complex formation a reversible step (360 and 30 s-1) is followed by a slow irreversible step (0.1 s-1) that defined the rate limiting step, or kcat. The calculated KMapp value for NR in the hydrolytic reaction is 6 nM. The values of the kinetic constants suggest that one biological function of cell-surface hCD157 is to bind and slowly hydrolyze NR, possibly converting it to a ligand-activated receptor. Differences in substrate preference between hCD157 and hCD38 were rationalized through a comparison of the crystal structures of the two proteins. This comparison identified several residues in hCD157 (F108 and F173) that can potentially hinder the binding of dinucleotide substrates (NAD+).

Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes

C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.

Mechanochemical Synthesis of Primary Amides

Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.

Amide bond formation in aqueous solution: Direct coupling of metal carboxylate salts with ammonium salts at room temperature

Herein, we report a green, expeditious, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary amine bases. The water-soluble coupling reagent EDC·HCl is a key component in the reaction. The reaction runs smoothly with unsubstituted/substituted ammonium salts and provides a clean product without column chromatography. Our reaction tolerates both carboxylate (which are unstable in other forms) and amine salts (which are unstable/volatile when present in free form). We believe that the reported method could be used as an alternative and suitable method at the laboratory and industrial scales. This journal is