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[ CAS No. 16499-61-9 ] {[proInfo.proName]}

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Chemical Structure| 16499-61-9
Chemical Structure| 16499-61-9
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Product Details of [ 16499-61-9 ]

CAS No. :16499-61-9 MDL No. :MFCD07776652
Formula : C8H4ClFN2 Boiling Point : -
Linear Structure Formula :- InChI Key :XIKGISGZFBCGDW-UHFFFAOYSA-N
M.W : 182.58 Pubchem ID :13059457
Synonyms :

Calculated chemistry of [ 16499-61-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.51
TPSA : 25.78 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) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 2.6
Log Po/w (WLOGP) : 2.84
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 2.99
Consensus Log Po/w : 2.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.108 mg/ml ; 0.000593 mol/l
Class : Soluble
Log S (Ali) : -2.79
Solubility : 0.296 mg/ml ; 0.00162 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.22
Solubility : 0.0109 mg/ml ; 0.0000598 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 16499-61-9 ]

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 [ 16499-61-9 ]

* 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 [ 16499-61-9 ]
  • Downstream synthetic route of [ 16499-61-9 ]

[ 16499-61-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 16499-56-2 ]
  • [ 16499-61-9 ]
YieldReaction ConditionsOperation in experiment
65% for 2 h; Heating A mixture of compound 3 (1.64 g, 0.01 mol) in phosphorus oxychloride (0.05 mol, 7.5 mL) andphosphorous pentachloride (0.03 mol, 6 g) was heated on a water bath for 2 hr. The reaction mixturewas cooled and poured slowly onto crushed ice. The resulted precipitate was filtered off, washed withwater, dried, and purified by column chromatography with hexanes/ethyl acetate to afford the desiredproduct. Yield 65percent; mp: 140–142 °C; 1H-NMR (DMSO-d6, 300 MHz) δ 8.12 (s, 1H, ArH), 7.47 (dd, 1H,J = 7.9 Hz and 2.8 Hz, ArH), 7.53 (dd, 1H, J = 8.6 Hz and 5.1 Hz, ArH), 7.62 (s, 1H, ArH); C8H4ClFN2(182): MS (ESI) m/z 183 [M + 1]
Reference: [1] Molecules, 2017, vol. 22, # 2,
[2] Patent: US5955464, 1999, A,
[3] Organic Letters, 2010, vol. 12, # 3, p. 552 - 555
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4885 - 4888
[5] Bioorganic Chemistry, 2018, vol. 80, p. 433 - 443
  • 2
  • [ 16499-56-2 ]
  • [ 16499-61-9 ]
YieldReaction ConditionsOperation in experiment
0.75 g at 100℃; for 16 h; The crude product 172-2(0.82g, 5 mmol) is mixed with thionyl dichloride (12.0 g,0.1 mol) and catalytic amount of anhydrous DMF (0.5 mL), then heated at about 100 °C for16 hours. After the reaction is complete, the mixture is cooled and excess thionyl dichlorideis removed by rotary evaporation. Dichloromethane (10 mL) is added to dissolve the solid,and then petroleum ether (5OmL) is added to solution. The mixture is filtrated, washed with ether and petroleum ether, dried and purified by silica gel chromatography (PE:AE=1 :1) to afford compound 172-3 as a white solid (0.75 g, yield: 82percent).
Reference: [1] Patent: WO2011/11522, 2011, A2, . Location in patent: Page/Page column 56
[2] Patent: WO2012/79079, 2012, A1, . Location in patent: Page/Page column 60-61; 62
[3] Patent: WO2014/145512, 2014, A2, . Location in patent: Page/Page column 36; 37
  • 3
  • [ 446-08-2 ]
  • [ 16499-61-9 ]
Reference: [1] Patent: WO2011/11522, 2011, A2,
[2] Patent: WO2012/79079, 2012, A1,
[3] Patent: WO2014/145512, 2014, A2,
[4] Molecules, 2017, vol. 22, # 2,
  • 4
  • [ 63069-49-8 ]
  • [ 16499-61-9 ]
Reference: [1] Molecules, 2017, vol. 22, # 2,
  • 5
  • [ 319-24-4 ]
  • [ 16499-61-9 ]
Reference: [1] Bioorganic Chemistry, 2018, vol. 80, p. 433 - 443
  • 6
  • [ 16499-61-9 ]
  • [ 140-75-0 ]
  • [ 1262888-28-7 ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine In N,N-dimethyl-formamide for 4 h; Reflux General procedure: Compound 4 (1.84 g, 0.01 mol) was mixed with (1.06 g, 0.01 mol) of trimethylamine and (0.01 mol)of the appropriate aromatic amine in 5 mL of dimethylformamide (DMF). The mixture was refluxedfor 4 h, cooled, and poured on crushed ice. The crystals were collected and crystallized from ethylalcohol. The melting points for all synthesized compounds were above 300 °C.
Reference: [1] Molecules, 2017, vol. 22, # 2,
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