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Chemical Structure| 24295-03-2
Chemical Structure| 24295-03-2
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Product Details of [ 24295-03-2 ]

CAS No. :24295-03-2 MDL No. :MFCD00005324
Formula : C5H5NOS Boiling Point : -
Linear Structure Formula :- InChI Key :MOMFXATYAINJML-UHFFFAOYSA-N
M.W : 127.16 Pubchem ID :520108
Synonyms :

Calculated chemistry of [ 24295-03-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 32.31
TPSA : 58.2 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.57
Log Po/w (XLOGP3) : 0.97
Log Po/w (WLOGP) : 1.35
Log Po/w (MLOGP) : -0.56
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 1.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.64
Solubility : 2.94 mg/ml ; 0.0231 mol/l
Class : Very soluble
Log S (Ali) : -1.78
Solubility : 2.11 mg/ml ; 0.0166 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.59
Solubility : 3.28 mg/ml ; 0.0258 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 24295-03-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H227-H302-H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24295-03-2 ]

* 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 [ 24295-03-2 ]
  • Downstream synthetic route of [ 24295-03-2 ]

[ 24295-03-2 ] Synthesis Path-Upstream   1~29

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Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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YieldReaction ConditionsOperation in experiment
87%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.833333 h;
Stage #2: at -78 - 20℃; for 0.533333 - 0.55 h;
To cooled (-78 °C) diethyl ether (30ml) was added n-butyllithium (13.2 ml of 2.5M solution in hexanes), followed by the dropwise addition of a solution of 2- bromothiazole (2. 7ml) in diethyl ether (35ml) over 20 minutes. The resulting mixture was stirred for 30 minutes AT-78 °C. Under rapid stirring, ethylacetate (5ml) was added over 2-3 minutes. The mixture was stirred for 30 minutes AT-78 °C, then allowed to warm to ambient and quenched with saturated sodium bicarbonate solution (50ml). More diethyl ether (50ml) and water (50ml) was added. The organic phase was separated, washed with water and brine, dried with magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (20percent ethyl acetate/petroleum ether) to afford the sub-title compound as a yellow oil (3.3g, 87percent) ; 1H NMR (4OOMHZ, CDC13) otilde; 2.7 (3H, s), 7.65 (1H, s), 8.0 (1H, s); MS (ES+) 128.1 (M+1).
Reference: [1] Patent: WO2004/87699, 2004, A2, . Location in patent: Page 82
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YieldReaction ConditionsOperation in experiment
95.2%
Stage #1: at -78℃; for 3 h;
Stage #2: for 3 h;
0.15mol containing a solution of 2-bromothiazole added dropwise to a solution containing 0.18mol butyllithium was added dropwise for about 2h, after the addition was completed, stirring was continued for 1h, maintained at low temperature (-78 deg.] C) reaction carried out under . 0.3mol ethyl acetate and then added to the solution dropwise addition was completed, stirring was continued for 3h, the reaction is complete, the organic phase extracted was allowed to stand, washed with distilled water, dried over anhydrous Na2SO4 was added, and then distilled under reduced pressure collecting bp89 ~ 91 / 1.6kPa fraction, 2-acetyl thiazole 18.16g. The yield was 95.2percent.
Reference: [1] Patent: CN105348216, 2016, A, . Location in patent: Paragraph 0050; 0051
[2] Journal of the Chemical Society [Section] C: Organic, 1969, p. 2270 - 2273
[3] Journal of Organic Chemistry, 1991, vol. 56, # 18, p. 5294 - 5301
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Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 4, p. 590 - 596
[2] Phosphorus and Sulfur and the Related Elements, 1985, vol. 24, p. 1 - 38
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  • [ 40982-30-7 ]
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Reference: [1] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
[2] Helvetica Chimica Acta, 1948, vol. 31, p. 1142,1156
[3] Tetrahedron Letters, 1993, vol. 34, # 5, p. 883 - 884
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Reference: [1] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
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Reference: [1] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
[2] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
[3] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
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Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 44, p. 6063 - 6066
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6231 - 6235
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Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 28, p. 2901 - 2904
[2] Journal of Organic Chemistry, 1988, vol. 53, # 8, p. 1748 - 1761
[3] Journal of Organic Chemistry, 1988, vol. 53, # 8, p. 1748 - 1761
[4] Tetrahedron Letters, 1986, vol. 27, # 30, p. 3547 - 3550
[5] Phosphorus and Sulfur and the Related Elements, 1985, vol. 24, p. 1 - 38
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  • [ 15679-09-1 ]
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Reference: [1] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
[2] Helvetica Chimica Acta, 1948, vol. 31, p. 1142,1156
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  • [ 134271-24-2 ]
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Reference: [1] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
[2] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
[3] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
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  • [ 40982-30-7 ]
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Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 19, p. 6495 - 6497
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Reference: [1] Helvetica Chimica Acta, 1957, vol. 40, p. 554,558
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Reference: [1] Tetrahedron, 1991, vol. 47, # 16, p. 2851 - 2860
  • 20
  • [ 288-47-1 ]
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Reference: [1] Bulletin de la Societe Chimique de France, 1953, p. 702,705
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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  • [ 867253-51-8 ]
Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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YieldReaction ConditionsOperation in experiment
88% With trimethylphenylammonium tribromide In tetrahydrofuran; dichloromethane Step A
A solution of 1-thiazol-2-ylethanone (2.00 g; 15.7 mmol) in anhydrous THF (8 ml) was added to a solution of 97percent phenyltrimethylammonium tribromide (6.08 g; 15.7 mmol) in anhydrous THF (32 ml).
The reaction mixture was heated at 35° C. for 3 hours and then left to stand overnight.
After filtering off the solid, the solution was concentrated under vacuum to give a residue which was dissolved in CH2Cl2 and purified by chromatography (eluent: 20/80 ethyl acetate/petroleum ether) to give 2-bromo-1-thiazol-2-ylethanone (2.85 g; 88percent yield) as an oil which solidifies.
1H-NMR (CDCl3) δ: 8.03 (d, 1H, JHH=2.8 Hz, -S-CH=CH-N=); 7.75 (d, 1H, JHH=2.8 Hz, -S-CH=CH*-N=); 4.70 (s, 2H, CH2).
50% With N-Bromosuccinimide In ethyl acetate at 40℃; 10 mmol 2-acetylthiazole added to a 100 mL round bottom flaskAnd 11mmol of N-bromosuccinimide (NBS),Dissolve 35mL of ethyl acetate and add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction was warmed to 40°C and reacted. After TLC tracks the reaction,The reaction solution was filtered to remove Amberlyst 15 ion exchange resin, and the filtrate was spin-dried.Column chromatography (eluent: petroleum ether/dichloromethane) gave a yellow solid in 50percent yield.
310 mg at 20℃; for 35 h; (i) To a solution of 1-(thiazol-2-yl)ethan-1-one (0.25 g, 1.97 mmol) in AcOH (5 mL), pyridinium bromide perbromide (0.82 g, 2.57mmol) was added and allowed the mixture to stir at room temperature for 35 hours. After TLCshowed completion, diluted the mixture with EtOAc (20 mL) and washed with water (3 x 10mL). The organic layer was dried over Na2SO4 and concentrated to obtain crude 2-bromo-1-(thiazol-2-yl)ethan-1-one (310 mg, crude), which was used in next step without furtherpurification.
Reference: [1] Patent: US6468979, 2002, B1,
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1093 - 1102
[3] Patent: CN107629022, 2018, A, . Location in patent: Paragraph 0534; 0535; 0536; 0537
[4] Helvetica Chimica Acta, 1948, vol. 31, p. 1142,1156
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4374 - 4377
[6] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 4, p. 959 - 964
[7] Patent: WO2014/143768, 2014, A1, . Location in patent: Page/Page column 94
[8] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5354 - 5367
[9] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 14 - 35
[10] PLoS ONE, 2016, vol. 11, # 5,
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Reference: [1] Patent: WO2006/44823, 2006, A2, . Location in patent: Page/Page column 133-134
[2] Organic Process Research and Development, 2014, vol. 18, # 6, p. 788 - 792
[3] Patent: EP1535910, 2005, A1,
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