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[ CAS No. 177995-39-0 ] {[proInfo.proName]}

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Chemical Structure| 177995-39-0
Chemical Structure| 177995-39-0
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Product Details of [ 177995-39-0 ]

CAS No. :177995-39-0 MDL No. :MFCD09788587
Formula : C7H5BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :CNLHHYURQCSYLB-UHFFFAOYSA-N
M.W : 213.03 Pubchem ID :10608621
Synonyms :

Calculated chemistry of [ 177995-39-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.11
TPSA : 52.05 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) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 2.05
Log Po/w (WLOGP) : 2.18
Log Po/w (MLOGP) : 1.95
Log Po/w (SILICOS-IT) : 1.86
Consensus Log Po/w : 1.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.187 mg/ml ; 0.000875 mol/l
Class : Soluble
Log S (Ali) : -2.77
Solubility : 0.361 mg/ml ; 0.00169 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.41
Solubility : 0.0821 mg/ml ; 0.000385 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.57

Safety of [ 177995-39-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 177995-39-0 ]

* 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.

  • Upstream synthesis route of [ 177995-39-0 ]
  • Downstream synthetic route of [ 177995-39-0 ]

[ 177995-39-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 546-88-3 ]
  • [ 105942-08-3 ]
  • [ 177995-39-0 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide for 0.5 h;
Stage #2: at 20℃; for 2 h;
Step A: 6-Bromobenzo[d]isoxazol-3-amine: N-hydroxyacetamide (1.13 g, 15.0 mmol) was dissolved in DMF (20 mL). To this was added KOt-Bu (1.68 g, 15.0 mmol) and the reaction was stirred for 30 minutes before addition of 4-bromo-2-fluorobenzonitrile (2.0 g, 10.0 mmol). The reaction mixture was left at ambient temperature for 2 hours, then diluted with ethyl acetate (50 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate The combined organics were washed with water, dried, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with ethyl acetate/hexanes (1:4), ethyl acetate/hexanes (1:3) to give the desired product (1.35 g, 63percent). MS (APCI) m/z 215.2, 217.1 (M+1).
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 17, p. 2885 - 2886
[2] Patent: US2007/49603, 2007, A1, . Location in patent: Page/Page column 61-62
[3] Patent: WO2010/51042, 2010, A1, . Location in patent: Page/Page column 135
[4] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00502
[5] Patent: US2014/357651, 2014, A1, . Location in patent: Paragraph 0485
[6] Patent: US9174994, 2015, B2, . Location in patent: Page/Page column 118
  • 2
  • [ 105942-08-3 ]
  • [ 177995-39-0 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 48, p. 8777 - 8779
[2] Journal of Organic Chemistry, 2000, vol. 65, # 10, p. 2924 - 2932
  • 3
  • [ 546-88-3 ]
  • [ 179897-89-3 ]
  • [ 177995-39-0 ]
Reference: [1] Patent: US9174994, 2015, B2, . Location in patent: Page/Page column 117
  • 4
  • [ 105942-08-3 ]
  • [ 177995-39-0 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 3, p. 780 - 785
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