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[ CAS No. 123-39-7 ] {[proInfo.proName]}

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Chemical Structure| 123-39-7
Chemical Structure| 123-39-7
Structure of 123-39-7 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Comins, Daniel L ; DOI: PubMed ID:

Abstract: A short and economical synthesis of various 2-methylaminopyidine amides (MAPA) from 2-bromopyridine has been developed using the catalytic Goldberg reaction. The effective catalyst was formed in situ by the reaction of CuI and 1,10-phenanthroline in a 1/1 ratio with a final loading of 0.5–3 mol%. The process affords high yields and can accommodate multigram-scale reactions. A modification of this method provides a new preparation of 2-N-substituted aminopyridines from various secondary N-alkyl(aryl)formamides and 2-bromopyridine. The intermediate aminopyridine formamide is cleaved in situ through methanolysis or hydrolysis to give 2-alkyl(aryl)aminopyridines in high yields.

Keywords: N-methyl-N-(2-pyridyl)formamide ; 2-methylaminopyridine amides ; 2-alkyl(aryl)aminopyridines ; Goldberg reaction ; copper-catalyzed reactions ; cross-coupling reactions ; 1,10-phenanthroline

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Product Details of [ 123-39-7 ]

CAS No. :123-39-7 MDL No. :MFCD00003280
Formula : C2H5NO Boiling Point : -
Linear Structure Formula :- InChI Key :ATHHXGZTWNVVOU-UHFFFAOYSA-N
M.W : 59.07 Pubchem ID :31254
Synonyms :

Calculated chemistry of [ 123-39-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 4
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 15.12
TPSA : 29.1 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.82
Log Po/w (XLOGP3) : -0.97
Log Po/w (WLOGP) : -0.64
Log Po/w (MLOGP) : -0.49
Log Po/w (SILICOS-IT) : -0.5
Consensus Log Po/w : -0.36

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.47
Solubility : 175.0 mg/ml ; 2.96 mol/l
Class : Highly soluble
Log S (Ali) : 0.84
Solubility : 413.0 mg/ml ; 6.99 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.09
Solubility : 48.0 mg/ml ; 0.813 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 123-39-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 123-39-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 123-39-7 ]
  • Downstream synthetic route of [ 123-39-7 ]

[ 123-39-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 5780-36-9 ]
  • [ 123-39-7 ]
  • [ 24445-35-0 ]
Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 10, p. 1595 - 1601
  • 2
  • [ 123-39-7 ]
  • [ 5470-18-8 ]
  • [ 4093-88-3 ]
Reference： [1] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 8, p. 1439 - 1445
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