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[ CAS No. 5805-53-8 ] {[proInfo.proName]}

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Chemical Structure| 5805-53-8
Chemical Structure| 5805-53-8
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Product Details of [ 5805-53-8 ]

CAS No. :5805-53-8 MDL No. :MFCD03413579
Formula : C9H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LKUBWDNDGBVKFK-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :576526
Synonyms :

Calculated chemistry of [ 5805-53-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.37
TPSA : 54.98 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 1.35
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.06 mg/ml ; 0.00603 mol/l
Class : Soluble
Log S (Ali) : -2.2
Solubility : 1.11 mg/ml ; 0.00631 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.98
Solubility : 0.183 mg/ml ; 0.00104 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 5805-53-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5805-53-8 ]

* 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 [ 5805-53-8 ]
  • Downstream synthetic route of [ 5805-53-8 ]

[ 5805-53-8 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 67-56-1 ]
  • [ 3584-65-4 ]
  • [ 5805-53-8 ]
YieldReaction ConditionsOperation in experiment
83% for 14 h; Reflux Na2C03 (0.64 g, 6.07 mmoi) was added to a solution of (17) (1.9 g, 6.07 mmol) in 20 mL MeOH. The reaction mixture was heated to reflux for 14 h and then cooled to RT. IN HCl was added to the solution and the reaction mixture was stirred for 0.5 hour. The mixture was extracted with EA. The organic phase was washed with brine, dried over Na2S04 and evaporated to give the title compound (0.89 g, yield -MS (M+l): 177 calc. for C9H8N202 176.
Reference: [1] Patent: WO2011/143365, 2011, A1, . Location in patent: Page/Page column 138
[2] Patent: WO2008/33739, 2008, A2, . Location in patent: Page/Page column 31
  • 2
  • [ 67-56-1 ]
  • [ 4856-97-7 ]
  • [ 5805-53-8 ]
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 27, p. 6382 - 6394
[2] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10776 - 10782
  • 3
  • [ 18370-95-1 ]
  • [ 95-54-5 ]
  • [ 5805-53-8 ]
Reference: [1] Synthetic Communications, 1984, vol. 14, # 10, p. 947 - 954
  • 4
  • [ 95-54-5 ]
  • [ 5805-53-8 ]
Reference: [1] Patent: WO2011/143365, 2011, A1,
  • 5
  • [ 67-56-1 ]
  • [ 3878-19-1 ]
  • [ 51-17-2 ]
  • [ 2849-93-6 ]
  • [ 5805-53-8 ]
  • [ 6965-02-2 ]
  • [ 6595-08-0 ]
Reference: [1] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 10, p. 1431 - 1437
  • 6
  • [ 5805-53-8 ]
  • [ 20572-01-4 ]
Reference: [1] Patent: WO2011/143365, 2011, A1,
  • 7
  • [ 5805-53-8 ]
  • [ 74-88-4 ]
  • [ 2849-92-5 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 4 h;
To a solution of lH-benzoimidazole-2-carboxylic acid methyl ester (18) (177 mg, 1.0 mmol) in dry DMF (5 mL) was added sodium hydride (applied as 60percent> dispersion in oil, 62 mg, 1.5 mmol)) at 0°C under N2 atmosphere. After 0.5 h, iodomethane (284 mg, 2.0 mmol) was added slowly. The reaction mixture was stirred at RT for 4 h. The reaction was diluted with brine at 0°C and extracted with EtOAc (3 x 20 mL). The combined organics were washed with water (2 x 15 mL), brine (20 mL), dried over sodium sulfate and filtered. The filtrate was concentrated and purified by flash column chromatography to provide the title compound (81) (180 mg, 90percent yield) as a light yellow solid.ESI-MS (M+l): 191 calc. for C10H10
Reference: [1] Patent: WO2011/143365, 2011, A1, . Location in patent: Page/Page column 170-171
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