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[ CAS No. 517920-69-3 ] {[proInfo.proName]}

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Chemical Structure| 517920-69-3
Chemical Structure| 517920-69-3
Structure of 517920-69-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 517920-69-3 ]

CAS No. :517920-69-3 MDL No. :MFCD03094270
Formula : C6H6BrFN2 Boiling Point : -
Linear Structure Formula :- InChI Key :OZKZRRLKJAXHQA-UHFFFAOYSA-N
M.W : 205.03 Pubchem ID :2773279
Synonyms :

Calculated chemistry of [ 517920-69-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.91
TPSA : 52.04 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) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.27
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 1.52
Consensus Log Po/w : 1.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.41
Solubility : 0.806 mg/ml ; 0.00393 mol/l
Class : Soluble
Log S (Ali) : -2.04
Solubility : 1.85 mg/ml ; 0.00902 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.82
Solubility : 0.312 mg/ml ; 0.00152 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 517920-69-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 517920-69-3 ]

* 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 [ 517920-69-3 ]
  • Downstream synthetic route of [ 517920-69-3 ]

[ 517920-69-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 517920-70-6 ]
  • [ 517920-69-3 ]
YieldReaction ConditionsOperation in experiment
99% With iron; ammonium chloride In tetrahydrofuran; water at 95℃; for 22 h; Intermediate 14; 5 -bromo-3 -fluorobenzene- 1 ,2 -diamine; To a solution of 4-bromo-2-fluoro-6-nitroaniline (0.5 g, 2.1 mmol) in THF (4.6 mL), EtOH (4.6 mL) and H20 (1.5 mL) was added iron powder (0.6 g, 10.6 mmol) and ammonium chloride (0.17 g, 3.2 mmol). The resulting mixture was stirred at 95 °C for 22 hours. The mixture was cooled to room temperature and filtered through diatomaceous earth. The solid was washed with EtOH until no further color came through the filter. The filtrate was concentrated and the residue was dissolved in EtOAc, washed with H20 and brine, dried over Na2S04, filtered and concentrated to give the title compound (0.43 g, 99percent) as a brown, waxy solid.
92% With tin(ll) chloride In ethanol at 70℃; 5.00 g (21.275 mmol) of 4-bromo-2fluoro-6-nitroaniline was dissolved in 190 ml ethanol, 19.20 g (85.100 mmol) of tin(II) chloride dihydrate was added and it was stirred overnight at 700C. After cooling, the mixture was concentrated in a rotary evaporator, water was added and it was made weakly alkaline with saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted three times with ethyl acetate, the combined organic phases were dried over sodium sulfate and concentrated in a rotary evaporator. The residue was dried under high vacuum. We obtained 4.18 g (92percent of theor.) of the target compound, which was reacted further without further purification.LC-MS (method 3): R, = 1.29 min; MS (EIpos): m/z = 205 [M+H]+. 1H-NMR (400 MHz, DMSO-D6): δ [ppm] = 4.52 (sbr, 2H), 5.10 (sbr, 2H), 6.49-6.52 (m, 2H).
1.69 g With iron; ammonium chloride In tetrahydrofuran; ethanol; water at 90℃; for 2 h; The 4 - bromo -2 - fluoro -6 - nitroaniline (1.5 g, 6.3 mmol), iron powder (1.8 g, 31.8 mmol) and ammonium chloride (5.1 g, 96.0 mmol) dissolved in ethanol (15 ml), tetrahydrofuran (15 ml) and water (5 ml) in the, and heated to 90 °C stirring 2 h. The reaction cooled to room temperature, filtered, the filtrate is concentrated, the crude product of the title compound obtained (1.69 g), without purification directly used for the next step reaction.
Reference: [1] Patent: WO2012/83170, 2012, A1, . Location in patent: Page/Page column 156-157
[2] Patent: WO2010/20363, 2010, A1, . Location in patent: Page/Page column 116-117
[3] Patent: CN108314680, 2018, A, . Location in patent: Paragraph 0472-0476
  • 2
  • [ 1193385-18-0 ]
  • [ 517920-69-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 24, p. 6390 - 6393
[2] Patent: WO2009/134750, 2009, A1, . Location in patent: Page/Page column 87-88
  • 3
  • [ 4845-50-5 ]
  • [ 517920-69-3 ]
  • [ 1210048-05-7 ]
YieldReaction ConditionsOperation in experiment
80% at 20℃; for 28 h; 4.00 g (19.509 mmol) of the compound from example 89A was dissolved in 100 ml ethanol and 2.42 g (19.509 mmol) of 2,3-dihydroxy-l,4-dioxane was added. The mixture was stirred for 4 h at room temperature and a further 2.42 g (19.509 mmol) of 2,3-dihydroxy-l,4-dioxane was added. After stirring for 24 h at room temperature, the mixture was concentrated in a rotary evaporator and the residue was purified by silica-gel chromatography (eluent: dichloromethane/methanol = 30:1). We obtained 3.60 g (80percent of theor.) of the target compound.LC-MS (method 1): R, = 1.79 min; MS (EIpos): m/z = 227 [M+H]+.1H-NMR (400 MHz, DMSO-D5): δ [ppm] = 8.06 (dd, IH), 8.24 (t, IH), 9.05 (d, IH), 9.07 (d, IH).
Reference: [1] Patent: WO2010/20363, 2010, A1, . Location in patent: Page/Page column 117
  • 4
  • [ 131543-46-9 ]
  • [ 517920-69-3 ]
  • [ 1210048-05-7 ]
Reference: [1] Patent: WO2010/52448, 2010, A2, . Location in patent: Page/Page column 70
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