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N-Methoxy-N-methylpyridine-4-carboxamide

  • CAS No. 100377-32-0

  • Cat. No. CS-0123032
  • Purity≥98%
  • MDL No.MFCD03837728

*For research and further manufacturing use only, not for direct human use.

N-Methoxy-N-methylpyridine-4-carboxamide|CS-0123032

Structure of 100377-32-0

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General Information

  • CAS No. 100377-32-0
  • Cat. No. CS-0123032
  • Purity ≥98%
  • MDL No. MFCD03837728
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀N₂O₂
  • Molecular Weight 166.18
  • Synonym(s) N-Methoxy-N-methylisonicotinamide
  • SMILES O=C(C1=CC=NC=C1)N(OC)C

Description

N-Methoxy-N-methylpyridine-4-carboxamide features a pyridine-4-carboxamide core with orthogonal N-methoxy and N-methyl groups, enabling selective reactivity in amidation and coupling processes. This bench-stable derivative delivers efficient amide bond formation under mild conditions, offering enhanced solubility and reduced side reactions compared to traditional acylating agents.

Application

N-Methoxy-N-methylpyridine-4-carboxamide serves as a versatile acyl transfer reagent in peptide synthesis and small molecule derivatization. Its pyridine-4-carboxamide core enables efficient coupling with carboxylic acids under mild conditions, while the N-methoxy-N-methyl group enhances electrophilicity and facilitates clean reaction progress. The compound exhibits good bench stability, ease of handling, and compatibility with diverse functional groups, making it a reliable choice for iterative synthetic sequences and API intermediate construction.

Synthesis

  • Route1

    References

    • Aventis Pharmaceuticals, Inc.; Hoechst Marion Roussel Deutschland GmbH Patent: EP1734037 A2, 2006 ; Location in patent: Page/Page column 17; 62 ;
  • Route2
    • Isonicotinic acid Nicotinic Acid  Impurity|CS-0229405
      55-22-1
    • null|null
      1117-97-1
    • ~54%
    • In-stock
      N-Methoxy-N-methylpyridine-4-carboxamide|CS-0123032
      100377-32-0

    References

    • ENVIVO PHARMACEUTICALS, INC. Patent: WO2009/158393 A1, 2009 ; Location in patent: Page/Page column 117 ;
  • Route3
    • Isonicotinic acid Nicotinic Acid  Impurity|CS-0229405
      55-22-1
    • In-stock
      N,O-Dimethylhydroxylamine hydrochloride|CS-D1361
      6638-79-5
    • null|null
      530-62-1
    • ~60%
    • In-stock
      N-Methoxy-N-methylpyridine-4-carboxamide|CS-0123032
      100377-32-0

    References

    • Aventis Pharmaceuticals Inc.; Aventis Pharma Deutschland GmbH Patent: US2005/261341 A1, 2005 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   42.43
  • LogP   0.715
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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