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[ CAS No. 866319-00-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 866319-00-8
Chemical Structure| 866319-00-8
Chemical Structure| 866319-00-8
Structure of 866319-00-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 866319-00-8 ]

CAS No. :866319-00-8 MDL No. :MFCD06659678
Formula : C7H5FN2 Boiling Point : -
Linear Structure Formula :- InChI Key :BALBNSFYMXBWNM-UHFFFAOYSA-N
M.W : 136.13 Pubchem ID :20784462
Synonyms :

Calculated chemistry of [ 866319-00-8 ]

Physicochemical Properties

Num. heavy atoms : 10
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 : 36.05
TPSA : 28.68 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) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 1.41
Log Po/w (WLOGP) : 2.12
Log Po/w (MLOGP) : 1.42
Log Po/w (SILICOS-IT) : 2.5
Consensus Log Po/w : 1.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.24
Solubility : 0.786 mg/ml ; 0.00578 mol/l
Class : Soluble
Log S (Ali) : -1.62
Solubility : 3.29 mg/ml ; 0.0242 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.16
Solubility : 0.0944 mg/ml ; 0.000693 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 866319-00-8 ]

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

Application In Synthesis of [ 866319-00-8 ]

* 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 [ 866319-00-8 ]
  • Downstream synthetic route of [ 866319-00-8 ]

[ 866319-00-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 869557-43-7 ]
  • [ 75-07-0 ]
  • [ 866319-00-8 ]
YieldReaction ConditionsOperation in experiment
92% With 1,4-diaza-bicyclo[2.2.2]octane; tri-tert-butyl phosphine; tetrabutylammomium bromide; bis(dibenzylideneacetone)-palladium(0) In hexane; dimethyl sulfoxide; ethyl acetate at 20 - 76.5℃; for 6 h; Inert atmosphere; Sealed tube To a 500 mL pressure flask purged with nitrogen was charged 3-bromo-5-fluoropyridin-2-amine (Compound 2a) (20 g, 104.7 mmol, 1 equiv), DABCO (17.6 g, 157.0 mmol, 1.5 equiv), and tetrabutylammonium bromide (3.38 g, 10.5 mmol, 0.1 equiv). The flask was charged with dimethyl sulfoxide (anhydrous, 40 mL) and ethyl acetate (anhydrous, 120 mL) and the resulting mixture was sparged with nitrogen for 30 min. Bis(dibenzylideneacetone) palladium (0) (3.01 g, 5.24 mmol, 0.05 equiv), a 10percent w/wsolution of tri-tert-butylphosphine in hexane (21.2 g, 10.47 mmol, 0.1 equiv) and acetaldehyde (5.08 g, 115.2 mmol, 1.1 equiv) were charged and the flask was sealed. The mixture was stirred for 1 h at room temperature then heated on an oil bath at 76.5 °C for 5 h. The batch was cooled and sampled for HPLC analysis. After complete conversion to Compound 3b was observed (typically 100percent conversion after 5 h), the batch was quenched with water (40 mL). The aqueous phase was back extracted with ethyl acetate (40mL) and the combined organics were filtered through a celite pad to remove fine solids. The celite was rinsed with ethyl acetate (40 mL) and the resulting solution of crude product was charged with 5percent Na2C03 (60 mL) and sparged with nitrogen for 30 min while mixing. The resulting organic phase was washed with water (60 mL) and concentrated at
Reference: [1] Patent: WO2015/73481, 2015, A1, . Location in patent: Paragraph 0307
  • 2
  • [ 866319-01-9 ]
  • [ 866319-00-8 ]
YieldReaction ConditionsOperation in experiment
3.2 g With potassium <i>tert</i>-butylate In 1-methyl-pyrrolidin-2-one at 130℃; for 12 h; A mixture of 5-fluoro-3-(2-trimethylsilylethynyl)pyridin-2-amine (6.40 g, 30.72 mmol, 1.00 eq) and t-buOK (5.72 g, 51.00 mmol, 1.66 eq) in NMP (60.00 mL) was stirred at 130 C for 12 h. The reaction mixture was diluted with water 200 mL and extracted with ethyl acetate (100 mL*3). The combined organic layers were washed with brine (300 mL*2), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, Petroleum ether/ethyl acetate=10:1 to 5:1) to afford the title compound (3.20 g, 23.04 mmol, 74.99percent yield, 98percent purity) as a yellow solid.
Reference: [1] Patent: US2007/93480, 2007, A1, . Location in patent: Page/Page column 45; 64-65
[2] Patent: US2008/45561, 2008, A1, . Location in patent: Page/Page column 30
[3] Patent: WO2018/13867, 2018, A1, . Location in patent: Paragraph 415
  • 3
  • [ 868387-37-5 ]
  • [ 866319-00-8 ]
Reference: [1] Patent: WO2005/103050, 2005, A2, . Location in patent: Page/Page column 180-181
  • 4
  • [ 936344-74-0 ]
  • [ 866319-00-8 ]
  • [ 1211524-51-4 ]
Reference: [1] Patent: WO2008/4117, 2008, A1, . Location in patent: Page/Page column 106
  • 5
  • [ 823218-51-5 ]
  • [ 866319-00-8 ]
  • [ 1211524-51-4 ]
Reference: [1] Patent: WO2008/4117, 2008, A1,
  • 6
  • [ 21717-96-4 ]
  • [ 866319-00-8 ]
  • [ 1211524-51-4 ]
Reference: [1] Patent: WO2008/4117, 2008, A1,
  • 7
  • [ 183208-35-7 ]
  • [ 866319-00-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 23, p. 6396 - 6400
  • 8
  • [ 21717-96-4 ]
  • [ 866319-00-8 ]
Reference: [1] Patent: WO2015/73481, 2015, A1,
  • 9
  • [ 869557-43-7 ]
  • [ 866319-00-8 ]
Reference: [1] Patent: WO2018/13867, 2018, A1,
  • 10
  • [ 866319-01-9 ]
  • [ 866319-00-8 ]
  • [ 1211524-51-4 ]
Reference: [1] Patent: WO2008/4117, 2008, A1,
  • 11
  • [ 866319-00-8 ]
  • [ 1190321-96-0 ]
Reference: [1] Patent: WO2012/74769, 2012, A1,
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