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[ CAS No. 41731-52-6 ] {[proInfo.proName]}

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Chemical Structure| 41731-52-6
Chemical Structure| 41731-52-6
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Product Details of [ 41731-52-6 ]

CAS No. :41731-52-6 MDL No. :MFCD11045348
Formula : C6H6ClNO2S Boiling Point : -
Linear Structure Formula :- InChI Key :GILVNZWYCBUGMT-UHFFFAOYSA-N
M.W :191.64 Pubchem ID :13106141
Synonyms :

Calculated chemistry of [ 41731-52-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.21
TPSA : 67.43 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) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 2.47
Log Po/w (WLOGP) : 1.97
Log Po/w (MLOGP) : 0.64
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.363 mg/ml ; 0.00189 mol/l
Class : Soluble
Log S (Ali) : -3.53
Solubility : 0.0565 mg/ml ; 0.000295 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.39
Solubility : 0.774 mg/ml ; 0.00404 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.73

Safety of [ 41731-52-6 ]

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 [ 41731-52-6 ]

* 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 [ 41731-52-6 ]
  • Downstream synthetic route of [ 41731-52-6 ]

[ 41731-52-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 41731-52-6 ]
  • [ 5198-87-8 ]
YieldReaction ConditionsOperation in experiment
56%
Stage #1: With water; potassium hydroxide In ethanol at 0 - 20℃;
Stage #2: With hydrogenchloride In water at 20℃; for 72 h;
14.0 g (73.1 mmol) of 2-chlorothiazole-4-carboxylic acid ethyl ester were slowly added to a solution of 1 1.0 g (0.17 mol, 85percent purity) of potassium hydroxide in ethanol/water (1 :3, 200 ml) at 0 0C. The reaction mixture was stirred at room temperature for 16 h, diluted with water and washed twice with diethyl ether. The aqueous layer was acidified (pH = 5.5) with cone. HCI and stirred at room temperature for three days. The formed precipitate was collected by filtration and dried at 40 0C under vaccum to yield 7.0 g (56percent, 95percent purity) of the title compound as a brown solid.
Reference: [1] Patent: WO2011/3796, 2011, A1, . Location in patent: Page/Page column 126; 127
[2] Helvetica Chimica Acta, 1944, vol. 27, p. 1432,1433
[3] Patent: US5498630, 1996, A,
[4] Patent: WO2007/146066, 2007, A2, . Location in patent: Page/Page column 152
  • 2
  • [ 5398-36-7 ]
  • [ 41731-52-6 ]
YieldReaction ConditionsOperation in experiment
74% With hydrogenchloride; copper(l) chloride; sodium nitrite In water at 20℃; for 2.16667 h; Cooling with salt-ice The free based 2-amino-thiazole-4-carboxylic acid ethyl ester (306 mg, 1.78 mmol) and CuCl (238 mg, 2.4 mmol) were suspended in conc. HC1 (8 ml) and the mixture cooled on a salt/ice bath. A pre-cooled solution of NaNO2 (166 mg, 2.4 mmol) in water (2ml) was added over a period of 10 min. The mixture was allowed to warm to room temperature over 1 h and was stirred for a further 1 h. Water was added and the aqueous layer extracted with EtOAc (3 x 10 ml). The combined EtOAc layers were washed with brine, dried (Na2SO4), filtered and the solvent removed in vacuo to give the title compound. Yield: 251 mg, 74percent ; LC/MS tr 1.06 min; MS (ES+) m/z 192,194 (M+H) ; 1H NMR (250 MHz, CDC13) 5 1.41 (t, 3H), 4.43 (q, 2H), 8.08 (s, 1H).
40% With tert.-butylnitrite; copper dichloride In tetrahydrofuran; acetonitrile at 23 - 65℃; At 23° C., a solution of ethyl 2-aminothlazole-4-formate (1.0 g, 6.35 mmol) in acetonitrile (10 mL) and tetrahydrofuran (10 mL) is added to a solution (10 mL) of t-butyl nitrite (1.3 mL, 9.52 mmol) and cuprous chloride (1.0 g, 7.6 mmol) in acetonitrile (10 mL) and tetrahydrofuran (10 mL). The reaction mixture is required to be heated at 65° C. until complete consumption of the starting materials as shown by thin-layer chromatography (40percent ethyl acetate-hexane). Then, the mixture is cooled to room temperature and partitioned between water and ethyl acetate. The organic layer is concentrated under vacuum and purified by flash silica gel column chromatography eluted with 20percent ethyl acetate-hexane to give ethyl 2-chloro-thiazole-4-formate (compound (2-2)) (0.49 g, 40percent).
Reference: [1] Patent: WO2005/80367, 2005, A1, . Location in patent: Page/Page column 109
[2] Organic Letters, 2013, vol. 15, # 20, p. 5390 - 5393
[3] Patent: US2013/178470, 2013, A1, . Location in patent: Paragraph 0106
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 5764 - 5768
[5] Helvetica Chimica Acta, 1944, vol. 27, p. 1432,1433
[6] Patent: WO2007/146066, 2007, A2, . Location in patent: Page/Page column 152
[7] Patent: EP2039686, 2009, A1, . Location in patent: Page/Page column 25-26
[8] Patent: WO2005/68432, 2005, A1, . Location in patent: Page/Page column 187-188
[9] Patent: WO2004/58702, 2004, A2, . Location in patent: Page 33; 25
[10] Patent: US2010/87448, 2010, A1, . Location in patent: Page/Page column 17
[11] Patent: WO2011/109799, 2011, A1, . Location in patent: Page/Page column 219-220
  • 3
  • [ 70-23-5 ]
  • [ 41731-52-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 5764 - 5768
  • 4
  • [ 1001-26-9 ]
  • [ 41731-52-6 ]
Reference: [1] Patent: US2013/178470, 2013, A1,
  • 5
  • [ 41731-52-6 ]
  • [ 57260-71-6 ]
  • [ 867065-53-0 ]
Reference: [1] Patent: WO2007/14290, 2007, A2, . Location in patent: Page/Page column 91
  • 6
  • [ 41731-52-6 ]
  • [ 153027-86-2 ]
Reference: [1] Patent: US5395845, 1995, A,
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