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[ CAS No. 17289-20-2 ] {[proInfo.proName]}

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Chemical Structure| 17289-20-2
Chemical Structure| 17289-20-2
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Product Details of [ 17289-20-2 ]

CAS No. :17289-20-2 MDL No. :MFCD01567300
Formula : C6H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :AKDPLDCXQNEMCL-UHFFFAOYSA-N
M.W : 140.14 Pubchem ID :2736896
Synonyms :

Calculated chemistry of [ 17289-20-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.77
TPSA : 44.12 Ų

Pharmacokinetics

GI absorption : High
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) : -7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 0.2
Log Po/w (WLOGP) : 0.21
Log Po/w (MLOGP) : -0.43
Log Po/w (SILICOS-IT) : 0.16
Consensus Log Po/w : 0.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.07
Solubility : 11.8 mg/ml ; 0.0846 mol/l
Class : Very soluble
Log S (Ali) : -0.69
Solubility : 28.9 mg/ml ; 0.206 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.85
Solubility : 20.0 mg/ml ; 0.143 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.63

Safety of [ 17289-20-2 ]

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

Application In Synthesis of [ 17289-20-2 ]

* 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 [ 17289-20-2 ]
  • Downstream synthetic route of [ 17289-20-2 ]

[ 17289-20-2 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 67-56-1 ]
  • [ 19485-38-2 ]
  • [ 17289-19-9 ]
  • [ 17289-20-2 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 5, p. 923 - 926
  • 2
  • [ 13515-93-0 ]
  • [ 20353-93-9 ]
  • [ 17289-20-2 ]
  • [ 40637-81-8 ]
Reference: [1] Synthesis, 1994, # 3, p. 247 - 248
  • 3
  • [ 68892-07-9 ]
  • [ 17289-20-2 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 644,645
  • 4
  • [ 67-56-1 ]
  • [ 41806-40-0 ]
  • [ 17289-20-2 ]
Reference: [1] Synthesis, 1988, # 10, p. 767 - 771
  • 5
  • [ 19485-35-9 ]
  • [ 17289-20-2 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 5, p. 923 - 926
[2] Synthesis, 1988, # 10, p. 767 - 771
  • 6
  • [ 19485-38-2 ]
  • [ 17289-20-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 2, p. 557 - 558
[2] Synthesis, 1988, # 10, p. 767 - 771
  • 7
  • [ 186581-53-3 ]
  • [ 41806-40-0 ]
  • [ 17289-20-2 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 4922,4926
  • 8
  • [ 41806-40-0 ]
  • [ 17289-20-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 2, p. 557 - 558
  • 9
  • [ 67-56-1 ]
  • [ 41716-12-5 ]
  • [ 17289-20-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 2, p. 557 - 558
  • 10
  • [ 17289-20-2 ]
  • [ 38993-84-9 ]
Reference: [1] Synthesis, 1994, # 3, p. 247 - 248
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 2444,2447
[3] Journal of medicinal chemistry, 1998, vol. 41, # 26, p. 5265 - 5271
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 2444,2447
[5] Patent: US4292431, 1981, A,
  • 11
  • [ 17289-20-2 ]
  • [ 41806-40-0 ]
YieldReaction ConditionsOperation in experiment
75% With sulfuric acid; dimethyl sulfate In methanol; water; acetic anhydride EXAMPLE 1
Preparation of 1-methylimidazole-5-carboxylic acid
Over a period of 1 h 252 g (2 mol) of dimethyl sulfate was added dropwise to a solution of 112 g (1 mol) of imidazole-4(5)-carboxylic acid in 200 ml of acetic anhydride at a temperature of 110° C.
The mixture was heated under reflux for a further 3 h, then the volatile components were removed by distillation.
To characterize the 1-methylimidazole-5-carboxylic acid it was converted into its methyl ester, as follows.
The residue obtained as described above was refluxed with 300 ml of methanol and 150 ml of concentrated sulfuric acid for 2 h, then the excess methanol was distilled off.
The residue was diluted with 250 ml of water, neutralized with concentrated ammonia solution, and extracted with methylene chloride.
After the extract had been dried and freed from solvent in vacuo, 105.1 g of methyl 1-methylimidazole-5-carboxylate, m.p. 44°-46° C., was obtained, an overall yield of 75percent.
1 H-NMR (CDCl3): 3.86 ppm (s, 3H), 3.91 ppm (s, 3H), 7.58 ppm (s, 1H), 7.72 ppm (s, 1H).
13 C-NMR (CDCl3): 34.0 ppm, 51.4 ppm, 123.1 ppm, 137.6 ppm, 142.6 ppm, 160.8 ppm (all signals s).
Reference: [1] Patent: US4864030, 1989, A,
  • 12
  • [ 17289-20-2 ]
  • [ 41806-40-0 ]
Reference: [1] Heterocycles, 2001, vol. 55, # 3, p. 495 - 503
[2] Patent: US2004/122018, 2004, A1, . Location in patent: Page 349
  • 13
  • [ 17289-20-2 ]
  • [ 120781-02-4 ]
Reference: [1] Synthesis, 1988, # 10, p. 767 - 771
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 5086 - 5098
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 18, p. 4984 - 4995
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