29802-22-0

Basic information

• Product Name: H-PRO-NME2
• Synonyms: PROLINE-NME2;L-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDE;L-PROLINE DIMETHYLAMIDE;H-PRO-NME2;H-PYRD(2)-NME2;L-PROLINE-N,N-DIMETHYLAMIDE;L-N,N,-DIMETHYL-PROLINAMIDE;N,N-Dimethylpyrrolidine-2-carboxamide
• CAS NO: 29802-22-0
• Molecular Formula: C₇H₁₄N₂O
• Molecular Weight: 142.2
• Product Categories: Proline [Pro, P];Amino Acids and Derivatives
• Mol File: 29802-22-0.mol

Chemical Properties

• Boiling Point: 250.2 °C at 760 mmHg
• Flash Point: 105.1 °C
• Appearance: /
• Density: 1.017 g/cm³
• Vapor Pressure: 0.0219mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: -15°C
• PKA: 9.18±0.10(Predicted)
• CAS DataBase Reference: H-PRO-NME2(CAS DataBase Reference)
• NIST Chemistry Reference: H-PRO-NME2(29802-22-0)
• EPA Substance Registry System: H-PRO-NME2(29802-22-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• Hazardous Substances Data: 29802-22-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
H-PRO-NME2 is used as a reactant for the synthesis of fluoromethylsulfonylaminophenyl propanamides, which are TRPV1 antagonists. These compounds have potential applications in the treatment of various conditions, such as pain, inflammation, and neurodegenerative diseases, due to their ability to block the TRPV1 receptor, which plays a role in sensory perception and cellular processes.

InChI:InChI=1/C7H14N2O/c1-9(2)7(10)6-4-3-5-8-6/h6,8H,3-5H2,1-2H3/t6-/m0/s1

Upstream product

• 118916-60-2 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 
• 124-40-3 dimethyl amine 
• 42718-55-8 (S)-2-Dimethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 147-85-3 L-proline 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 149152-54-5 tert-butyl (2S)-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate 

Downstream Products

• 118376-10-6 1-(Methacryloyl)prolin-dimethylamid 
• 609367-19-3 (S)-1-{(R)-2-[(Benzyloxy-formyl-amino)-methyl]-hexanoyl}-pyrrolidine-2-carboxylic acid dimethylamide 
• 1111659-06-3 (S)-N,N-dimethyl-1-(thiophen-2-ylmethyl)pyrrolidine-2-carboxamide 
• 151265-11-1 (S)-1-benzyl-N,N-dimethylpyrrolidine-2-carboxamide 
• 1111658-99-1 (S)-1-(4-tert-butylbenzyl)-N,N-dimethylpyrrolidine-2-carboxamide 
• 1111659-00-7 (S)-1-(4-bromobenzyl)-N,N-dimethylpyrrolidine-2-carboxamide 
• 1111659-03-0 (S)-N,N-dimethyl-1-(2-methylbenzyl)pyrrolidine-2-carboxamide 
• 1111659-01-8 (S)-N,N-dimethyl-1-(4-(trifluoromethyl)benzyl)pyrrolidine-2-carboxamide 
• 29618-57-3 N,N-dimethyl-1-[(2S)pyrrolidin-2-yl]methanamine 
• 347888-01-1 1-(4-(5-hydroxy-2,3,4,5-tetrahydro-1-benzazepin-1-ylcarbonyl)-2-methylbenzylcarbamoyl)-L-proline-N,N-dimethylamide 
• 1092844-53-5 1-(4-(5,5-difluoro-2,3,4,5-tetrahydro-1-benzazepin-1-ylcarbonyl)-2-methylbenzylcarbamoyl)-L-proline-N,N-dimethylamide 
• 1092844-62-6 1-(2-methyl-4-(5-methyl-2,3,4,5-tetrahydro-1-benzazepin-1-ylcarbonyl)-benzylcarbamoyl)-L-proline-N,N-dimethylamide 
• 1092844-63-7 1-(2-methyl-4-(2,3,4,5-tetrahydro-1,5-benzoxazepin-5-ylcarbonyl)benzylcarbamoyl)-L-proline-N,N-dimethylamide 

Relevant articles and documents

Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts

The Br?nsted basicities pKaH (i.e., pKa of the conjugate acids) of 32 pyrrolidines and imidazolidinones, commonly used in organocatalytic reactions, have been determined photometrically in acetonitrile solution using CH acids as indicators. Most investigated pyrrolidines have basicities in the range 16 aH aH aH 12.6) and the 2-imidazoliummethyl-substituted pyrrolidine A21 (pKaH 11.1) are outside the typical range for pyrrolidines with basicities comparable to those of imidazolidinones. Kinetics of the reactions of these 32 organocatalysts with benzhydrylium ions (Ar2CH+) and structurally related quinone methides, common reference electrophiles for quantifying nucleophilic reactivities, have been measured photometrically. Most reactions followed second-order kinetics, first order in amine and first order in electrophile. More complex kinetics were observed for the reactions of imidazolidinones and several pyrrolidines carrying bulky 2-substituents, due to reversibility of the initial attack of the amines at the electrophiles followed by rate-determining deprotonation of the intermediate ammonium ions. In the presence of 2,4,6-collidine or 2,6-di-tert-butyl-4-methyl-pyridine, the deprotonation of the initial adducts became faster, which allowed the rate of the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log?k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale, which compares n-, -, and σ-nucleophiles. The nucleophilic reactivities of the title compounds correlate only poorly with their Br?nsted basicities.

Targeting the Src Homology 2 (SH2) Domain of Signal Transducer and Activator of Transcription 6 (STAT6) with Cell-Permeable, Phosphatase-Stable Phosphopeptide Mimics Potently Inhibits Tyr641 Phosphorylation and Transcriptional Activity

Signal transducer and activator of transcription 6 (STAT6) transmits signals from cytokines IL-4 and IL-13 and is activated in allergic airway disease. We are developing phosphopeptide mimetics targeting the SH2 domain of STAT6 to block recruitment to phosphotyrosine residues on IL-4 or IL-13 receptors and subsequent Tyr641 phosphorylation to inhibit the expression of genes contributing to asthma. Structure-affinity relationship studies showed that phosphopeptides based on Tyr631 from IL-4Rα bind with weak affinity to STAT6, whereas replacing the pY+3 residue with simple aryl and alkyl amides resulted in affinities in the mid to low nM range. A set of phosphatase-stable, cell-permeable prodrug analogues inhibited cytokine-stimulated STAT6 phosphorylation in both Beas-2B human airway cells and primary mouse T-lymphocytes at concentrations as low as 100 nM. IL-13-stimulated expression of CCL26 (eotaxin-3) was inhibited in a dose-dependent manner, demonstrating that targeting the SH2 domain blocks both phosphorylation and transcriptional activity of STAT6.

N →π* interactions of amides and thioamides: Implications for protein stability

Carbonyl-carbonyl interactions between adjacent backbone amides have been implicated in the conformational stability of proteins. By combining experimental and computational approaches, we show that relevant amidic carbonyl groups associate through an n→π

Synthesis, characterisation and in vitro cytotoxicity studies of a series of chiral platinum(II) complexes based on the 2-aminomethylpyrrolidine ligand: X-ray crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N-dimethyl-2(R)-aminomethylpyrrolidine)

A series of platinum(II) complexes were synthesised based on the enantiomerically pure amino acid proline. Novel synthetic pathways were developed, adapted from standard peptide chemistry, to produce the 2-aminomethylpyrrolidine (pyrr) ligand and its derivatives with differing arrangements of methyl substituents at the exocyclic amine sites. The crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N,N-dimethyl-2(R)-aminomethylpyrrolidine) is reported and the five-membered ligand ring has been shown to be in an envelope conformation. Cytotoxicity studies were carried out on the ovarian cancer A2780 tumour cell line and its cisplatin-resistant variant, A2780cisR. Remarkably good activity was seen for several of the drugs when compared to cisplatin despite the addition of substantial steric bulk to the amine groups, and there was a lack of cross-resistance with cisplatin seen for some compounds.

Structure-activity relationships of the peptide deformylase inhibitor BB-3497: Modification of the P2′ and P3′ side chains

Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to both the P2′ and P3′ side chains. Enzyme inhibition and antibacterial activity data revealed that a variety of substituents are tolerated at the P2′ and P3′ positions of the inhibitor backbone. The data from this study highlights the potential for modification at the P2′ and P3′ positions to optimise the physicochemical properties.

Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N-methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF IMMUNOMEDIATED INFLAMMATORY DISORDERS

Compositions and methods for the prevention and treatment of immunomediated inflammatory disorders, especially for those disorders associated with the respiratory tract, are provided. More particularly, a tryptase inhibitor, typically a hydroxyaroyl or hydroxyheteroaroyl substituted dipeptide, is administered. Also provided by this invention are pharmaceutical compositions, typically aerosol or topical, as well as aerosol devices for administering these compositions intranasally.