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[ CAS No. 72926-24-0 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 72926-24-0
Chemical Structure| 72926-24-0
Structure of 72926-24-0 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 72926-24-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 72926-24-0 ]

SDS Specification
Alternatived Products of [ 72926-24-0 ]

Product Details of [ 72926-24-0 ]

CAS No. :72926-24-0 MDL No. :MFCD00181155
Formula : C13H15N3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :JEFVYQYZCAVNTP-UHFFFAOYSA-N
M.W : 277.34 Pubchem ID :2930014
Synonyms :
K858
Chemical Name :N-(4-Acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide

Calculated chemistry of [ 72926-24-0 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.31
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 82.63
TPSA : 87.07 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) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 1.62
Log Po/w (WLOGP) : 0.99
Log Po/w (MLOGP) : 1.49
Log Po/w (SILICOS-IT) : 1.96
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.55
Solubility : 0.782 mg/ml ; 0.00282 mol/l
Class : Soluble
Log S (Ali) : -3.06
Solubility : 0.241 mg/ml ; 0.000869 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.53
Solubility : 0.0824 mg/ml ; 0.000297 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.71

Safety of [ 72926-24-0 ]

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 [ 72926-24-0 ]

* 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.

  • Downstream synthetic route of [ 72926-24-0 ]

[ 72926-24-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 2302-93-4 ]
  • [ 108-24-7 ]
  • [ 72926-24-0 ]
YieldReaction ConditionsOperation in experiment
72% Heating / reflux; Acetophenone=thiosemicarbazone (300 mg, 0.889 mmol) obtained above was dissolved in acetic anhydride (1.0 mL, 11 mmol). After being refluxing under heating, the solution was cooled to room temperature with vigorous stirring. To the reaction mixture was added diisopropyl ether (3 mL), and the deposited crystals were collected by filtration. After the collected crystals were suspended in diisopropyl ether and stirred for 3 hours, the crystals were collected by filtration and dried to obtain Compound 1 (195 mg, 72%).1H NMR (270 MHz, CDCl3) delta (ppm): 2.01 (s, 3H), 2.19 (s, 3H), 2.28 (s, 3H), 7.24-7.36 (br s, 5H), 11.63 (br s, 1H)
72% at 20℃;Heating / reflux; Acetophenone=thiosemicarbazone (300 mg, 0.889 mmol) obtained above was dissolved in acetic anhydride (1.0 mL, 11 mmol). After being refluxing under heating, the solution was cooled to room temperature with vigorous stirring. To the reaction mixture was added diisopropyl ether (3 mL), and the deposited crystals were collected by filtration. The collected crystals were suspended in diisopropyl ether and stirred for 3 hours, and then the crystals were collected by filtration and dried to give Compound 1 (195 mg, 72%). 1H NMR (270 MHz, CDCl3) delta (ppm): 2.01 (s, 3H), 2.19 (s, 3H), 2.28 (s, 3H), 7.24-7.36 (br s, 5H), 11.63 (br s, 1H).
Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1473 - 1477
[2]Patent: EP1454903,2004,A1 .Location in patent: Page 37
[3]Patent: EP1616866,2006,A1 .Location in patent: Page/Page column 65
[4]Heterocycles,1976,vol. 4,p. 1909 - 1912
  • 2
  • [ 72926-24-0 ]
  • [ 72926-06-8 ]
Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1473 - 1477
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3961 - 3963
  • 3
  • [ 72926-24-0 ]
  • 4-acetyl-2-acetylamino-5-methyl-5-phenyl-Δ2-1,3,4-thiadiazoline 1-oxide [ No CAS ]
Reference： [1]Journal of the Chemical Society. Chemical communications,1982,p. 901 - 902
  • 4
  • [ 72926-24-0 ]
  • [ 75-03-6 ]
  • C15H21N3OS [ No CAS ]
  • C15H19N3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
22%; 60% To a solution of 60% sodium hydride (110 mg, 2.70 mmol) in N,N-dimethylformamide (10.0 mL) was added Compound 1 (50.0 mg, 1.80 mmol) prepared in Example 1, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added ethyl iodide (0.22 mL, 2.70 mmol) and the reaction mixture was further stirred at room temperature for 12 hours. To the reaction mixture was added 5% aqueous ammonium chloride and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane = 1/1) to obtain Compound 8 (120 mg, 22%) and Compound 9 (330 mg, 60%).; Compound 8 1H NMR (270 MHz, CDCl3) delta (ppm): 1.19 (t, J = 7.0 Hz, 6H), 2.23 (s, 3H), 2.41 (s, 3H), 3.26 (q, J = 7.0 Hz, 4H), 7.21-7.45 (m, 5H); Compound 9 1H NMR (270 MHz, CDCl3) delta (ppm): 1.36 (t, J = 7.2 Hz , 3H), 2.24 (s, 6H), 2.37 (s, 3H), 3.91 (q, J = 7.2 Hz, 2H), 7.22-7.41 (m, 5H)
22%; 60% To a solution of 60% sodium hydride (110 mg, 2.70 mmol) in DMF (10.0 mL) was added Compound 1 (50.0 mg, 1.80 mmol) prepared in Reference Example 1, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added iodoethane (0.22 mL, 2.70 mmol) and the reaction mixture was further stirred at room temperature for 12 hours. To the reaction mixture was added 5% aqueous ammonium chloride and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane = 1/1) to give Compound 8 (120 mg, 22%) and Compound 9 (330 mg, 60%).Compound 8 1H NMR (270 MHz, CDCl3) delta (ppm): 1.19 (t, J = 7.0 Hz, 6H), 2.23 (s, 3H), 2.41 (s, 3H), 3.26 (q, J = 7.0 Hz, 4H), 7.21-7.45 (m, 5H).Compound 9 1H NMR (270 MHz, CDCl3) delta (ppm): 1.36 (t, J = 7.2 Hz , 3H), 2.24 (s, 6H), 2.37 (s, 3H), 3.91 (q, J = 7.2 Hz, 2H), 7.22-7.41 (m, 5H).
Reference： [1]Patent: EP1454903,2004,A1 .Location in patent: Page 39
[2]Patent: EP1616866,2006,A1 .Location in patent: Page/Page column 66
  • 5
  • [ 108-24-7 ]
  • [ 132121-93-8 ]
  • [ 72926-24-0 ]
YieldReaction ConditionsOperation in experiment
86% for 2h;Reflux; Compound 12 c (0.889mmol; 0.3g) in 14 acetic anhydride (11mmol; 1ml) was refluxed until a homogenous mixture appeared. Then, the solution was cooled to room temperature to obtain compound 15 1. Diethyl ether (120ml) was added to remove non-polar impurities to yield white crystals which were dried under vacuum (0.413g, 86%). 1H NMR (400MHz, DMSO-d6) delta: 2.01 (s, 3H, CH3), 2.19 (s, 3H, CH3), 2.28 (s, 3H, CH3), 7.24-7.25 (s, 1H, ArH), 7.25-7.35 (m, 4H, ArH), 11.63 (s, 1H, NH) ppm; 13C NMR (100MHz, DMSO-d6) delta: 22.4, 23.7, 26.6 (3CH3), 78.6, 124.4, 127.3, 128.4, 142.2, 143.8, 167.7 and 169.3 (2C=O) ppm.
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 156,p. 641 - 651

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