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[ CAS No. 90533-23-6 ] {[proInfo.proName]}

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Chemical Structure| 90533-23-6
Chemical Structure| 90533-23-6
Structure of 90533-23-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 90533-23-6 ]

CAS No. :90533-23-6 MDL No. :MFCD02664012
Formula : C9H7ClN2S Boiling Point : -
Linear Structure Formula :- InChI Key :QSEDBGULKWHVNE-UHFFFAOYSA-N
M.W : 210.68 Pubchem ID :675261
Synonyms :

Calculated chemistry of [ 90533-23-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.96
TPSA : 67.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 2.9
Log Po/w (WLOGP) : 3.05
Log Po/w (MLOGP) : 1.9
Log Po/w (SILICOS-IT) : 3.58
Consensus Log Po/w : 2.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.53
Solubility : 0.0617 mg/ml ; 0.000293 mol/l
Class : Soluble
Log S (Ali) : -3.97
Solubility : 0.0225 mg/ml ; 0.000107 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.08
Solubility : 0.0177 mg/ml ; 0.0000841 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 90533-23-6 ]

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 [ 90533-23-6 ]

* 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 [ 90533-23-6 ]
  • Downstream synthetic route of [ 90533-23-6 ]

[ 90533-23-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 17356-08-0 ]
  • [ 99-02-5 ]
  • [ 90533-23-6 ]
YieldReaction ConditionsOperation in experiment
65% at 100℃; for 8 h; General procedure: A mixture of thiourea (50 mmol), the corresponding acetophenone (25 mmol) and iodine (25 mmol) is stirred at 100 °C for 8 h.Then the reaction mixture is cooled, extracted with diethyl ether toremove excess of acetophenone, and then washed with aqueous sodium thiosulfate to remove excess iodine and later with cold water. The crude product is dissolved in hot water, filtered to remove sulphone, and the filtrate is basified with aqueous Na2CO3to yield the corresponding 2-amino-4-(substituted-phenyl)-1,3-thiazole. The crude product is purified by recrystallization from alcohol.
Reference: [1] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 7, p. 1014 - 1017
[2] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 305 - 313
[3] Arzneimittel-Forschung/Drug Research, 1986, vol. 36, # 9, p. 1391 - 1393
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 2, p. 692 - 702
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5428 - 5431
[6] Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 778 - 790
[7] Chemical Biology and Drug Design, 2018, vol. 91, # 3, p. 728 - 734
  • 2
  • [ 2039-85-2 ]
  • [ 17356-08-0 ]
  • [ 90533-23-6 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In water at 60℃; for 1 h;
Stage #2: for 1 h; Reflux
In a 25 mL reaction flask, add 3 mL of water and 30 μL of Tween,0.5mmol of m-chlorostyrene and 0.75mmol of DBH reacted at 60°C for 1h.After the reaction was completed, the water was swirled, 3 mL of ethanol was added, and 0.75 mmol of thiourea was added. The reaction was refluxed for 1 h. After the reaction was completed, ethanol was spin-dried, and ethyl acetate was added to dissolve the solution.The mixture was extracted with saturated brine, and the organic layer was concentrated. Column chromatography gave 85 mg of a white solid with a yield of 81percent.
Reference: [1] Patent: CN107501204, 2017, A, . Location in patent: Paragraph 0046; 0047; 0048; 0049
  • 3
  • [ 41011-01-2 ]
  • [ 17356-08-0 ]
  • [ 90533-23-6 ]
YieldReaction ConditionsOperation in experiment
93% for 1 h; Reflux Step 2: To a mixture of 2-bromo-1-(3-chlorophenyl)ethan-1-one (0.5 g, 2.1 mmol) and thiourea (0.2 g, 2.3 mmol) in anhydrous EtOH (5 mL) was heated at reflux for 1 h. After that, the solvent was removed in vacuo, and saturated aqueous NaHCO3 was added. The mixture was then extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 4-(3-chlorophenyl)thiazol-2-amine as a solid (0.4 g, 93percent).
23 g Reflux To a solution of 2-bromo-1-(3-chlorophenyl)ethanone (28 g) in ethanol (300 ml) was added thiourea (10.04 g). The reaction mixture was refluxed overnight. Solvent was removed, and the residue was triturated with diethyl ether to give the title compound (23 g) as a white solid. MS(ES+) m/z 211 (MH+).
Reference: [1] Patent: US2016/257690, 2016, A1, . Location in patent: Paragraph 0727
[2] Medicinal Chemistry Research, 2014, vol. 23, # 1, p. 259 - 268
[3] Patent: WO2012/100734, 2012, A1, . Location in patent: Page/Page column 20
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5293 - 5302
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3669 - 3674
[6] Patent: WO2017/9650, 2017, A1, . Location in patent: Page/Page column 103
[7] European Journal of Medicinal Chemistry, 2018, vol. 144, p. 179 - 200
[8] Tetrahedron, 2018, vol. 74, # 27, p. 3602 - 3607
  • 4
  • [ 17356-08-0 ]
  • [ 90533-23-6 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 88, p. 47368 - 47372
  • 5
  • [ 99-02-5 ]
  • [ 90533-23-6 ]
Reference: [1] Medicinal Chemistry Research, 2014, vol. 23, # 1, p. 259 - 268
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5293 - 5302
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3669 - 3674
[4] Patent: WO2012/100734, 2012, A1,
  • 6
  • [ 2039-85-2 ]
  • [ 90533-23-6 ]
Reference: [1] Tetrahedron, 2018, vol. 74, # 27, p. 3602 - 3607
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