This compound belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
External Descriptors
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1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No assay or kit protocols are provided for this small-molecule building block in the Product Data. Typical usage involves synthetic transformations (SNAr, cross-coupling) as detailed under Reaction Conditions and Synthetic Utility. For biochemical assays, prepare DMSO stock solutions and perform solubility/aggregation checks prior to testing.
Biological Roles
No biological function is assigned to this specific compound in the Product Data. It is supplied for research use only.
General context (biochemistry, literature):
Nicotinamide (vitamin B3) is a biological pyridine carboxamide; however, 2‑chloro‑N‑cyclopentylnicotinamide is a synthetic derivative without established endogenous role. Structural modifications at the 2‑position and on the amide nitrogen often alter physicochemical properties (basicity, H‑bonding, lipophilicity) and can be used to probe SAR in enzyme or receptor studies.
As a heteroaromatic amide, it can serve as a scaffold or intermediate in the synthesis of probes, ligands, or library members targeting NAD-related binding pockets or general heteroaromatic recognition sites, but any such use requires separate validation.
Practical note:
If used in biochemical assays, prepare DMSO stock solutions and maintain final DMSO ≤1–2% v/v in aqueous buffers to minimize nonspecific effects. Confirm solubility and absence of aggregation (e.g., by DLS or detergent supplementation) before interpreting assay data.
No clinical or therapeutic claims are made for this product.
Buffer Applications
This compound is a heteroaromatic carboxamide building block and is not a buffering agent. It does not have a defined acid/base pair suitable for classical buffer systems.
If solutions are required for assay or screening, use standard biological buffers (e.g., PBS, HEPES) and dissolve this compound first in a miscible co-solvent (DMSO or DMF), then dilute into the buffer with vigorous mixing to avoid precipitation.
Green Alternatives
While the molecule itself is a halopyridinyl amide (not directly replaceable), greener choices can be made in the transformations it undergoes.
Solvent choices (greener vs conventional):
For cross-coupling: 2‑MeTHF, CPME, or water/ethanol mixtures can often replace 1,4‑dioxane, toluene, or DMF. Cyrene or PolarClean may substitute for DMF/DMAc in some couplings.
For SNAr: Propylene carbonate or sulfolane/water can be evaluated as alternatives to DMSO/DMF, balancing rate and workup practicality.
Base and reagent selection:
Use inorganic carbonate/phosphate bases (K2CO3, K3PO4) in place of NaH/t‑BuOK where feasible to reduce hazard and improve EHS profile.
Employ air-stable Pd precatalysts and ligand systems that enable lower catalyst loadings and aqueous-compatible media (e.g., XPhos- or tBuBrettPhos-based systems).
Energy efficiency:
Microwave or flow platforms can shorten reaction times and reduce energy use for SNAr and couplings; consider room-temperature photoredox/Ni dual catalysis where applicable to avoid high heat.
Minimal chlorinated waste:
Prefer EtOAc/Heptane or 2‑MeTHF-based chromatography eluents; reserve DCM/CHCl3 only if necessary.
Quick comparison (general):
1,4-Dioxane vs 2‑MeTHF: similar coupling performance; 2‑MeTHF offers better EHS (biorenewable, lower toxicity) and easier aqueous separations.
DMF vs Cyrene: Cyrene is biorenewable and lower toxicity; viscosity and solubility differences may require temperature adjustment and co-solvent.
Pharmaceutical Uses
No pharmacopeial grade or excipient role is provided in the Product Data. The material is intended for research use only.
Typical role in pharmaceutical R&D (general):
As a halopyridinyl amide building block, it is suited for medicinal chemistry campaigns to access analogs of nicotinamide-derived scaffolds via SNAr or Pd-catalyzed diversification at C‑2, while retaining an N‑cycloalkyl amide motif.
Intermediate for preparation of heteroaryl ureas, sulfonamides, and biaryl derivatives when combined with isocyanates/sulfonyl chlorides or Suzuki partners, respectively.
Developability considerations (general):
Tertiary amides often display moderate polarity; verify permeability and metabolic stability in downstream ADME studies if used in lead optimization.
Residual palladium or nickel from coupling steps should be controlled per ICH Q3D if material moves beyond discovery.
No therapeutic or clinical claims are made for this product.
Physical Properties
Item-specific specifications are not provided in the Product Data; consult the CoA/Spec Sheet for definitive values.
Item-specific specs:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Melting/Boiling point, density, refractive index, UV cutoff, residual solvents, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (non-spec) information to aid planning:
Approx. formula and MW (computed from name): C11H13ClN2O, ~224.69 g/mol.
Physical state expectation: neutral heteroaromatic carboxamide; likely a low-melting solid or high-boiling liquid depending on crystal packing (literature/analog-based; verify on receipt).
Solubility tendencies: amides typically show good solubility in polar aprotic solvents (DMSO, DMF, NMP) and moderate solubility in MeCN/EtOAc/CH2Cl2; limited solubility in water (literature/analog-based guidance).
Practical notes (general):
For analytical prep, begin with DMSO or DMF stock solutions (10–100 mM), then dilute into reaction medium or assay buffer containing co-solvent if required.
Verify hygroscopicity and thermal behavior experimentally (DSC/TGA) when process development requires precise handling windows.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general, for planning):
Research grade: suitable for synthetic R&D and discovery chemistry; analytical limits (metals, water, residual solvents) vary by lot—confirm on CoA when catalysis or moisture-sensitive chemistry is planned.
High-purity/building-block grade: typically supports medicinal chemistry SAR campaigns, parallel synthesis, and library production. If low-UV or LC/MS compatibility is critical, request UV and LC impurity profiles.
Catalyst-sensitive applications: When using in Pd-catalyzed couplings or photocatalysis, verify trace-metal content and halide assay on the CoA. Drying (vacuum/40–60 °C) and Karl Fischer may be warranted prior to use.
Stabilizers/antioxidants:
None are listed in the Product Data. If a stabilizer is present in a specific lot, it will appear on the CoA/SDS and may impact certain reactions (e.g., base-promoted SNAr). Remove, if necessary, by chromatographic purification or recrystallization.
Documentation:
For regulated workflows or lead optimization, request batch-specific CoA, NMR/HRMS, HPLC purity trace, and water content. Ensure identity by orthogonal methods (1H/13C NMR, HRMS, and, if needed, microanalysis).
Reaction and Applications
As a 2‑chloropyridinyl tertiary carboxamide, this building block supports multiple heteroaryl functionalization strategies in discovery and process chemistry.
Nucleophilic aromatic substitution (SNAr):
The 2‑chloro substituent is activated by the adjacent ring nitrogen; displacement by amines, alkoxides, thiolates, or amide enolates proceeds under heat in polar aprotic solvents (DMSO/DMF). Secondary amines and thiols are particularly effective nucleophiles.
Suzuki–Miyaura: install diverse (hetero)aryl groups at C‑2 from boron partners using Pd(0/II) with dialkylbiaryl phosphines (e.g., SPhos/XPhos) and K3PO4 or Cs2CO3 base.
Buchwald–Hartwig amination: couple N‑nucleophiles to replace chloride, accessing 2‑aminopyridine derivatives.
Carbonylation (Pd-catalyzed): convert the aryl chloride into 2‑carboxamide/ester motifs under CO pressure (or CO surrogates) without disturbing the existing amide.
Directed C–H functionalization (amide as directing group):
The tertiary amide can serve as a weak directing group for ortho‑C–H activation on appended aryls after C‑2 functionalization, or for site-selective acylation/metalation adjacent to the carbonyl (literature examples; reaction design dependent).
Orthogonal manipulations:
Amide transformations: N‑dealkylation/hydrolysis under forcing conditions to revert to 2‑chloro‑nicotinic acid or amide variants; activation to imidazolides for urea formation.
Pyridine N‑oxidation: provides N‑oxide for further rearrangements (e.g., Boekelheide) enabling C‑3 functionalization.
Use case context:
Particularly valuable for SAR around nicotinamide isosteres, introducing functionality at C‑2 while preserving an N‑cycloalkyl amide motif.
Reaction Conditions
General literature guidance for functionalizing 2‑chloropyridines and related nicotinamides (adjust per substrate and scale):
SNAr at C‑2:
Typical: amine or thiolate (1.2–2.0 equiv), K2CO3 or Cs2CO3 (1.5–3.0 equiv), DMSO or DMF (0.1–0.5 M), 80–140 °C, 2–16 h. More activated nucleophiles (thiolates) react at lower temperatures.
For alkoxides: NaOtBu/ROH can be used; monitor for competing elimination or hydrolysis.
Suzuki–Miyaura coupling:
Aryl/heteroaryl boronic acid/ester (1.2–1.5 equiv), Pd(dba)2 (1–2 mol%) + SPhos/XPhos (2–4 mol%) or a precatalyst (e.g., XPhos Pd G3, 1–2 mol%), base K3PO4 or Cs2CO3 (2–3 equiv), 2‑MeTHF, dioxane, or toluene with 5–10% H2O, 80–110 °C, 4–16 h.
Buchwald–Hartwig amination:
Amine (1.2–1.5 equiv), Pd2(dba)3 (1–2 mol%) with tBuBrettPhos or RuPhos (3–4 mol%), NaOtBu or K3PO4, toluene or dioxane, 90–110 °C, 6–18 h.
Carbonylation (Pd-catalyzed):
CO (1–10 bar) or CO surrogate (e.g., Mo(CO)6), Pd catalyst (1–3 mol%), phosphine ligand, base (Et3N or inorganic), solvent DMF/MeOH or 2‑MeTHF/EtOH, 60–100 °C.
Practical tips:
The pyridine nitrogen can coordinate Pd; ligand choice and base strongly influence rates. Dialkylbiaryl phosphines often outperform simple phosphines for aryl chlorides.
Additive screening (H2O, phase-transfer agents) can materially improve coupling yields.
For silica chromatography, add 0.1–1% Et3N or use basic alumina to minimize pyridine tailing.
All values are general literature guidance, not product specifications.
Safety and Handling
Safety information specific to this item is not provided in the Product Data. Always consult the SDS for authoritative guidance.
GHS classification, H/P statements, pictograms, signal word: Not specified for this item; refer to SDS.
General hazard considerations for halopyridinyl amides (literature/general):
May cause skin/eye irritation and respiratory tract irritation; avoid dust/aerosol formation. Handle in a fume hood.
Combustible organic; keep away from ignition sources. No peroxide-formation hazard expected for this functional class.
Aryl chlorides and pyridines can be harmful if swallowed or inhaled; prevent exposure and practice good hygiene.
Incompatibilities and reactivity (general):
Strong bases or nucleophiles at elevated temperature can displace the 2‑chloro substituent (SNAr). Avoid contact with strong reducing metals in polar aprotic media during storage.
Strong oxidants may oxidize the pyridine ring to the N‑oxide.
Recommended PPE/practices (general):
Lab coat, safety glasses, nitrile gloves; use local exhaust ventilation.
For weighing/transfer, minimize dust; for solutions, cap tightly and label solvent and concentration.
First-aid overview (general):
Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical advice.
Inhalation: move to fresh air; assist breathing if needed; obtain medical attention.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Always defer to the product SDS and institutional EHS procedures.
Solvent Selection
This product is a heteroaromatic carboxamide building block rather than a solvent. Selection here refers to solvents suitable for dissolving and reacting it.
Good: DMSO, DMF, NMP, DMAc; often soluble at 10–100 mM.
Moderate: MeCN, EtOAc, CH2Cl2, 2‑MeTHF; solubility improves upon gentle heating.
Limited: Alcohols and water; consider co-solvents for aqueous workups or bioassays.
Choosing by application:
SNAr at C‑2: Polar aprotic solvents (DMSO/DMF) favor nucleophilic substitution; tolerate strong bases and elevated temperatures.
Cross-coupling (Suzuki/Buchwald–Hartwig): 1,4-dioxane, toluene, PhMe/H2O, 2‑MeTHF, or CPME with inorganic base (K3PO4, Cs2CO3). DMF/DMAc for more challenging couplings.
Purification: Normal-phase silica with EtOAc/hexane or DCM/MeOH gradients; for basic pyridines, add 0.1–1% Et3N to suppress tailing.
Brief comparison (general guidance):
DMF vs DMSO: DMF easier to remove; DMSO often gives higher SNAr rates.
2‑MeTHF vs dioxane: 2‑MeTHF is a greener alternative with similar coupling performance and simpler phase separations.
Always confirm actual solubility and stability in your chosen solvent prior to scale-up.
Storage and Reconstitution
Storage (from Product Data): Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (literature/practice):
Keep tightly sealed in the original container, protected from light and moisture. Store under ambient, dry conditions; for long-term storage, consider desiccation or an inert-atmosphere cabinet.
Avoid prolonged exposure to strong bases or nucleophiles; the 2‑chloro group is susceptible to SNAr under basic conditions at elevated temperatures.
Reconstitution and solution handling:
Prepare concentrated stock solutions in DMSO, DMF, or MeCN (typical 10–100 mM). Filter if needed (0.2 μm PTFE) to remove particulates.
For reaction setups, dry solvents and use anhydrous technique if base- or moisture-sensitive reagents are present. For assay use, dilute DMSO stocks into buffer while mixing; maintain final DMSO ≤1–2% v/v to minimize matrix effects.
Solution stability should be verified experimentally (e.g., by LC/HPLC); if not in immediate use, store aliquots at 2–8 °C or −20 °C, protected from light, to minimize degradation. Avoid repeated freeze–thaw cycles by aliquoting.
Research use only: Not for human or veterinary use.
Structure and Identity
A heteroaromatic carboxamide featuring a 2-chloropyridinyl core and an N‑cyclopentyl substituent on the amide nitrogen; useful as a halopyridine building block for cross-coupling and SNAr chemistry.
Item-specific identifiers (from Product Data):
CAS: 57841-73-3
CID (PubChem): 803643
InChIKey: 322074 (as provided; format not the usual 27-character InChIKey)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature structural information (not product specifications):
A six-membered pyridine ring bearing: (i) a chlorine substituent at the 2-position (adjacent to ring N), and (ii) a carboxamide at the 3-position. The amide nitrogen is mono-substituted with a cyclopentyl group, rendering the amide tertiary (N‑alkylated). The ring nitrogen and 2‑chloro substituent together activate the ring toward nucleophilic aromatic substitution at C‑2.
Notes:
Any structural depictions or exact identifiers beyond those listed as Product Data should be confirmed against the product’s CoA/SDS prior to regulated use.
Synthetic Utility
Key features that make 2‑chloro‑N‑cyclopentylnicotinamide valuable in synthesis:
Electrophilic handle at C‑2:
The 2‑chloro substituent of the nicotinamide ring is predisposed to both SNAr and Pd-catalyzed cross-coupling, enabling rapid installation of amine, thio, alkoxy, (hetero)aryl, vinyl, or carbonylated substituents.
Built-in amide functionality:
Tertiary amide confers stability and H‑bonding characteristics; it can be retained as a pharmacophore or transformed (e.g., to ureas via activation, to amines through hydrolysis/N‑dealkylation under forcing conditions, or to imidates/imidazolides for coupling cascades).
Ring nitrogen reactivity:
Pyridine N‑oxidation opens routes to regioselective C‑3 functionalization (e.g., Boekelheide rearrangement) complementary to C‑2 derivatization.
Retrosynthetic value:
Serves as a convergent node: keep the amide constant while diversifying C‑2; or install the desired C‑2 functionality first (from 2‑chloro) and adjust the amide N‑substituent via transamidation or CDI-mediated exchange if needed.
Suzuki to introduce biaryl motifs for binding pocket exploration.
Buchwald–Hartwig to introduce anilines/alkylamines giving 2‑aminonicotinamide analogs.
Thiolation to give thioethers as synthetic linchpins for further oxidation to sulfoxides/sulfones.
Target Specificity
Not an antibody, protein, or biological targeting reagent. No target specificity, clone, isotype, or species reactivity applies to this chemical building block.
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