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[ CAS No. 290328-55-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 290328-55-1
Chemical Structure| 290328-55-1
Chemical Structure| 290328-55-1
Structure of 290328-55-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 290328-55-1 ]

CAS No. :290328-55-1 MDL No. :MFCD11043260
Formula : C6H13NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :XKWZLZLVNFUCBL-UHFFFAOYSA-N
M.W : 163.24 Pubchem ID :22275038
Synonyms :

Calculated chemistry of [ 290328-55-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.52
TPSA : 54.55 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) : -7.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : -0.27
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : -0.11
Log Po/w (SILICOS-IT) : 0.36
Consensus Log Po/w : 0.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.62
Solubility : 39.5 mg/ml ; 0.242 mol/l
Class : Very soluble
Log S (Ali) : -0.42
Solubility : 62.6 mg/ml ; 0.383 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.39
Solubility : 6.62 mg/ml ; 0.0406 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 290328-55-1 ]

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 [ 290328-55-1 ]

* 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 [ 290328-55-1 ]
  • Downstream synthetic route of [ 290328-55-1 ]

[ 290328-55-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 189205-49-0 ]
  • [ 290328-55-1 ]
YieldReaction ConditionsOperation in experiment
76% With hydrogenchloride In 1,4-dioxane; ethyl acetate for 3 h; (Step 4); tert-Butyl 4-(methylsulfonyl)piperidine-1-carboxylate (2.4 g, 9.0 mmol) obtained in Reference Example 12, Step 3 was dissolved in ethyl acetate (16 mL), and a 4.0 mol/L solution of hydrogen chloride in dioxane (12 mL) was added thereto, followed by stirring for 3 hours. The precipitated solid was filtered to obtain 4-(methylsulfonyl)piperidine (1.4 g, 76percent). 1H-NMR (DMSO-d6, 270 MHz) δ (ppm): 3.41-3.31 (m, 3H), 2. 97 (s, 3H), 2.97-2.82 (m, 2H), 2.18-2.13 (m, 2H), 1.92-1.73 (m, 2H)
Reference: [1] Patent: EP1642880, 2006, A1, . Location in patent: Page/Page column 112
[2] Patent: US2003/100567, 2003, A1,
  • 2
  • [ 1570494-48-2 ]
  • [ 290328-55-1 ]
  • [ 1570496-34-2 ]
YieldReaction ConditionsOperation in experiment
39% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; ruphos In toluene at 140℃; for 18 h; Inert atmosphere 2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl (580 mg, 1.25 mmol) and tris(dibenzylideneacetone)dipalladium (760 mg, 0.83 mmol) were added to a mixture of 5-(1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (2.00 g, 4.16 mmol), 4-(methylsulfonyl)piperidine (1.02 mg, 6.24 mmol), and t-BuONa (800 mg, 8.33 mmol) in toluene (80 ml), and the reaction mixture was degassed with argon for 3 min and then was heated to 140 °C for 18 h under an argon atmosphere. The mixture was then cooled to RT, diluted with EtOAc (100 ml), filtered through a pad of celite, washed with EtOAc (100 ml), and concentrated under reduced pressure. The residue was purified using a silica gel chromatography column (PE:EtOAc = 1:1 with pureEtOAc) to produce a crude product, which was treated with EtOAc and Et2O (vol/vol = 1:9, 30 ml). The resulting suspension was stirred at RT for 30 min and thenfiltered to produce 5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole as a whitesolid (905 mg, 39percent). 1H NMR (600 MHz, DMSO-d6): δ 8.22 (d, J = 8.8 Hz, 2 H),7.61 (d, J = 8.2 Hz, 2 H), 7.21 (t, J = 7.9 Hz, 1 H), 6.97 (bs, 1 H), 6.94 (dd, J = 8.3,2.4 Hz, 1 H), 6.64 (d, J = 7.5 Hz, 1 H), 5.48 (s, 2 H), 3.86 (bd, J = 13.4 Hz, 2 H), 3.28(m, 1 H), 2.94 (s, 3 H), 2.76 (m, 2 H), 2.57 (s, 3 H), 2.06 (bd, J = 13.4 Hz, 2 H), 1.68(ddd, J = 16.5, 12.5, 4.1 Hz, 2 H). 13C NMR (126 MHz, DMSO-d6): δ 169.0, 167.2,155.1, 150.7, 150.5, 147.9, 136.0, 129.6, 129.4, 124.9, 121.7, 119.9 (q, J = 258 Hz),117.8, 115.5, 115.2, 58.6, 52.3, 47.2, 37.4, 23.7, 11.7. 19F NMR (471 MHz,DMSO-d6): δ –56.6. HRMS (ESI+) m/z: [M + H]+ calculated for C25H26F3N6O4S,563.1683; found, 563.1675.
Reference: [1] Nature Medicine, 2018, vol. 24, # 7, p. 1036 - 1046
[2] Patent: WO2014/31936, 2014, A2, . Location in patent: Paragraph 0355
[3] Patent: US2015/239876, 2015, A1, . Location in patent: Paragraph 0236; 0240
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