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[ CAS No. 169205-95-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 169205-95-2
Chemical Structure| 169205-95-2
Chemical Structure| 169205-95-2
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Product Details of [ 169205-95-2 ]

CAS No. :169205-95-2 MDL No. :MFCD00973738
Formula : C7H6N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :GAIIIUMBUSZYDH-UHFFFAOYSA-N
M.W : 166.20 Pubchem ID :2764090
Synonyms :

Calculated chemistry of [ 169205-95-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.52
TPSA : 64.22 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) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.99
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 0.78
Log Po/w (SILICOS-IT) : 1.95
Consensus Log Po/w : 1.71

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.59
Solubility : 0.429 mg/ml ; 0.00258 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.24 mg/ml ; 0.00144 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.03
Solubility : 0.154 mg/ml ; 0.000929 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.46

Safety of [ 169205-95-2 ]

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

Application In Synthesis of [ 169205-95-2 ]

* 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 [ 169205-95-2 ]
  • Downstream synthetic route of [ 169205-95-2 ]

[ 169205-95-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 80-48-8 ]
  • [ 60832-72-6 ]
  • [ 169205-95-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
  • 2
  • [ 53052-06-5 ]
  • [ 74-88-4 ]
  • [ 169205-95-2 ]
YieldReaction ConditionsOperation in experiment
93.75% With potassium carbonate In ethyl acetate at 20℃; Step 2: Preparation of 2-(methylthio)oxazolo[4,5-b]pyridine To a stirred solution of oxazolo[4,5-b]pyridine-2-thiol (3.0g, 19.73 mmol) in ethyl acetate (30mL) was added potassium carbonate (3.81g, 27.62 mmol) and methyl iodide (3.08g, 21.71 mmol) and stirred at RT overnight. The reaction mixture was diluted with water (100ml), extracted with ethyl acetate (2x50mL), dried over sodium sulphate and concentrated to afford the title compound (3.0g, 93.75percent). 1HNMR (CDCI3, 300MHz): δ 8.46-8.44 (d, 1H), 7.71-7.68 (d, 1H), 7.20-7.15 (m, 1H), 2.81 (s, 3H). LCMS: m/z: 167.0(M+1) +.
93.75% With potassium carbonate In ethyl acetate at 20℃; To a stirred solution of oxazolo[4,5-b]pyridine-2- thiol (3.0 g, 19.73 mmol) in ethyl acetate (30 mL) was added potassium carbonate (3.81 g, 27.62 mmol) and methyl iodide (3.08 g, 21.71 mmol) and stirred at RT overnight. The reaction mixture was diluted with water (100 ml), extracted with ethyl acetate (2x50 mL), dried over sodium sulphate and concentrated to afford the title compound (3.0 g, 93 .75percent).10208] ‘HNMR (CDC13, 300 MHz): ö 8.46-8.44 (d, 1H),7.71-7.68 (d, 1H), 7.20-7.15 (m, 1H), 2.81 (s, 3H). LCMS:mlz: 167.0 (M+1)+.
Reference: [1] Patent: WO2015/104688, 2015, A1, . Location in patent: Page/Page column 36
[2] Patent: US2016/340366, 2016, A1, . Location in patent: Paragraph 0207; 0208
[3] Journal of Organic Chemistry, 1995, vol. 60, # 17, p. 5721 - 5725
[4] Ultrasonics Sonochemistry, 2010, vol. 17, # 5, p. 783 - 788
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 2075 - 2078
[6] Advanced Synthesis and Catalysis, 2017, vol. 359, # 11, p. 1837 - 1843
[7] European Journal of Medicinal Chemistry, 2005, vol. 40, # 1, p. 15 - 23
[8] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 1, p. 114 - 125
  • 3
  • [ 53052-06-5 ]
  • [ 74-88-4 ]
  • [ 169205-95-2 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In N,N-dimethyl-formamide for 2 h; 2-(Mβthv)thio)ri,31oxazolor4,5-biPyridine; A 250 mL RB flask, equipped with a magnetic stirring bar and nitrogen gas inlet, was charged with [1,3]oxazolo[4,5-b]pyridine-2(3H)-thione (5.00 g, 32.9 mmol), potassium carbonate (4.54 g, 32.8 mmol), and 80 mL of anhydrous DMF. Then iodomethane (2.45 mL, 5.57 g, 39.3 mmol) was added dropwise to the stirring reaction mixture under nitrogen. The mixture was stirring for 2 h, then diluted with 300 mL of water, and extracted with EtOAc (4x150 mL). The combined organic extract was washed with water (3x100 mL), then with brine (100 mL), dried over Na2SO4 and evaporated to give 4.53 g (83 percent) of 2- (methylthio)[1,3]oxazolo[4,5-b]pyridine as a tan solid. LCMS m/z (M+H): 167.1. 1H NMR (300 MHz, DMSO-d6): δ 8.44 (1H), 8.08 (1H), 7.35 (1H), 2.81 (3H).
Reference: [1] Patent: WO2006/51410, 2006, A1, . Location in patent: Page/Page column 45
[2] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
  • 4
  • [ 16867-03-1 ]
  • [ 169205-95-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2005, vol. 40, # 1, p. 15 - 23
[2] Journal of Organic Chemistry, 1995, vol. 60, # 17, p. 5721 - 5725
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 2075 - 2078
[4] Patent: WO2015/104688, 2015, A1,
[5] Patent: US2016/340366, 2016, A1,
[6] Advanced Synthesis and Catalysis, 2017, vol. 359, # 11, p. 1837 - 1843
  • 5
  • [ 80-48-8 ]
  • [ 169205-95-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
  • 6
  • [ 80-48-8 ]
  • [ 60832-72-6 ]
  • [ 169205-95-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
  • 7
  • [ 74-88-4 ]
  • [ 169205-95-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
  • 8
  • [ 186581-53-3 ]
  • [ 53052-06-5 ]
  • [ 169205-95-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
  • 9
  • [ 77-78-1 ]
  • [ 169205-95-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
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