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[ CAS No. 101494-95-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 101494-95-5
Chemical Structure| 101494-95-5
Chemical Structure| 101494-95-5
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Product Details of [ 101494-95-5 ]

CAS No. :101494-95-5 MDL No. :MFCD09954861
Formula : C8H5ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :JWLJDRWZFALRKE-UHFFFAOYSA-N
M.W : 180.59 Pubchem ID :135412869
Synonyms :

Calculated chemistry of [ 101494-95-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.57
TPSA : 46.01 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.15
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 1.65
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 1.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.212 mg/ml ; 0.00117 mol/l
Class : Soluble
Log S (Ali) : -2.75
Solubility : 0.322 mg/ml ; 0.00178 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.37
Solubility : 0.0774 mg/ml ; 0.000429 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 101494-95-5 ]

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 [ 101494-95-5 ]

* 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 [ 101494-95-5 ]
  • Downstream synthetic route of [ 101494-95-5 ]

[ 101494-95-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 491-36-1 ]
  • [ 7782-50-5 ]
  • [ 7705-08-0 ]
  • [ 64-19-7 ]
  • [ 16064-14-5 ]
  • [ 101494-95-5 ]
  • [ 6952-11-0 ]
Reference: [1] Scientia Sinica (English Edition), 1958, vol. 7, p. 1035,1038
[2] Huaxue Xuebao, 1956, vol. 22, p. 335,336[3] Scientia Sinica (English Edition), 1958, vol. 7, p. 1035,1036
  • 2
  • [ 6388-47-2 ]
  • [ 77287-34-4 ]
  • [ 101494-95-5 ]
YieldReaction ConditionsOperation in experiment
79% at 140℃; General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 °C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO4 and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl2*2H2O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 .x. 50 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 .x. 10 mL), the organic extracts were combined, dried over MgSO4 and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[2] Huaxue Xuebao, 1956, vol. 22, p. 335,336[3] Scientia Sinica (English Edition), 1958, vol. 7, p. 1035,1036
[4] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[5] Patent: WO2010/59627, 2010, A1, . Location in patent: Page/Page column 50
[6] Patent: US2010/273816, 2010, A1, . Location in patent: Page/Page column 36
  • 3
  • [ 67-56-1 ]
  • [ 18343-44-7 ]
  • [ 101494-95-5 ]
YieldReaction ConditionsOperation in experiment
68% at 130℃; for 2 h; Inert atmosphere; Microwave irradiation 2-Amino-3-chlorobenzamide (85 mg, 0.5 mmol), [Cp * Ir (2,2'-bpyO)(5.4 mg, 0.005 mmol, 1 molpercent),Cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.) And methanol (0.5 ml) were sequentially added to a dried 5 mL microwave reaction tube.The tube was nitrogen protected and placed in a single mode pressure microwave synthesizer (Discover CEM, USA). After the reaction mixture was reacted at 130 ° C for 2 hours, it was cooled to room temperature. Rotary evaporation to remove the solvent,Pure target compound was then obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 68percent
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337646, 2017, A, . Location in patent: Paragraph 0075; 0076; 0077; 0078
  • 4
  • [ 7477-63-6 ]
  • [ 101494-95-5 ]
Reference: [1] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
  • 5
  • [ 491-36-1 ]
  • [ 101494-95-5 ]
Reference: [1] Huaxue Xuebao, 1956, vol. 22, p. 335,336[2] Scientia Sinica (English Edition), 1958, vol. 7, p. 1035,1036
  • 6
  • [ 491-36-1 ]
  • [ 7782-50-5 ]
  • [ 7705-08-0 ]
  • [ 64-19-7 ]
  • [ 16064-14-5 ]
  • [ 101494-95-5 ]
  • [ 6952-11-0 ]
Reference: [1] Scientia Sinica (English Edition), 1958, vol. 7, p. 1035,1038
[2] Huaxue Xuebao, 1956, vol. 22, p. 335,336[3] Scientia Sinica (English Edition), 1958, vol. 7, p. 1035,1036
  • 7
  • [ 101494-95-5 ]
  • [ 7148-34-7 ]
Reference: [1] Patent: WO2010/59627, 2010, A1, . Location in patent: Page/Page column 50
[2] Patent: US2010/273816, 2010, A1, . Location in patent: Page/Page column 36-37
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