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[ CAS No. 401815-98-3 ] {[proInfo.proName]}

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Chemical Structure| 401815-98-3
Chemical Structure| 401815-98-3
Structure of 401815-98-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 401815-98-3 ]

CAS No. :401815-98-3 MDL No. :MFCD04112534
Formula : C5H5BFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WXGBZJJAGLSBPR-UHFFFAOYSA-N
M.W : 140.91 Pubchem ID :2783396
Synonyms :

Calculated chemistry of [ 401815-98-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 34.02
TPSA : 53.35 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) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.19
Log Po/w (WLOGP) : -0.68
Log Po/w (MLOGP) : -0.93
Log Po/w (SILICOS-IT) : -0.72
Consensus Log Po/w : -0.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.21
Solubility : 8.66 mg/ml ; 0.0615 mol/l
Class : Very soluble
Log S (Ali) : -0.87
Solubility : 19.1 mg/ml ; 0.135 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.17
Solubility : 9.57 mg/ml ; 0.0679 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 401815-98-3 ]

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

Application In Synthesis of [ 401815-98-3 ]

* 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 [ 401815-98-3 ]
  • Downstream synthetic route of [ 401815-98-3 ]

[ 401815-98-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 401815-98-3 ]
  • [ 22282-69-5 ]
YieldReaction ConditionsOperation in experiment
99% at 100℃; for 10 h; A 25 mL reaction flask was charged with trifluoromethylhydrazine (0.05 mmol)2-fluoropyridine-4-boronic acid (0.5 mmol)Potassium tert-butoxide (1.0 mmol)And polyethylene glycol-400 (2.0 g).The mixture was reacted at 100 ° C until the reaction was complete. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The product was separated by column chromatography to yield 99percent yield.
Reference: [1] Patent: CN103936538, 2017, B, . Location in patent: Paragraph 0073; 0077; 0078
  • 2
  • [ 5419-55-6 ]
  • [ 128071-98-7 ]
  • [ 401815-98-3 ]
YieldReaction ConditionsOperation in experiment
91% With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1 h; Inert atmosphere [00178] Step 1 : To a solution of anhydrous toluene and tetrahydrofuran ("THF") (4:1, 250 mL) were added 4-bromo-2-fluoropyridine 1 (30.0 g, 0.17 mol) and triisopropyl borate (38.4 g, 0.20 mol). The mixture was cooled to -78 °C under a nitrogen atmosphere. Then, n- butyllithium (80 mL, 0.20 mol) (2.5 M in hexanes) was added dropwise over 30 minutes, followed by stirring at the same temperature for an additional 30 minutes. The mixture was finally warmed up to -20 °C over 1 hour. Thin layer chromatography ("TLC") (petroleum ether ("PE"):ethyl acetate ("EtOAc") = 1 :1) indicated that the starting material was consumed. The reaction mixture was acidified to a pH of 2 with 3N HCl (50 mL) and then stirred at room temperature for 15 minutes. The mixture was partitioned between EtOAc (150 mL) and water (150 mL). The organic layer was isolated, washed with water, brine, dried over anhydrous MgS04, then filtered and evaporated to provide (2-fluoropyridin-4-yl)boronic acid (22.0 g, 91percent) as a solid.
Reference: [1] Patent: WO2015/103137, 2015, A1, . Location in patent: Paragraph 00178
[2] Patent: US7087755, 2006, B1, . Location in patent: Page/Page column 6
[3] Patent: US2004/122237, 2004, A1, . Location in patent: Page 201
  • 3
  • [ 5419-55-6 ]
  • [ 22282-70-8 ]
  • [ 401815-98-3 ]
Reference: [1] Patent: US2004/122237, 2004, A1, . Location in patent: Page 232-233; 387
  • 4
  • [ 128071-98-7 ]
  • [ 401815-98-3 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 22, p. 4369 - 4373
  • 5
  • [ 688-74-4 ]
  • [ 22282-70-8 ]
  • [ 401815-98-3 ]
Reference: [1] Patent: US2004/53942, 2004, A1,
  • 6
  • [ 1285513-32-7 ]
  • [ 401815-98-3 ]
  • [ 1285515-21-0 ]
YieldReaction ConditionsOperation in experiment
62.2% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water for 2 h; Reflux A solution of 6g (771 mg, 2.012 mmol), (2-fluoro-4-pyridinyl)boronic acid (425 mg, 3.02 mmol),bis(triphenylphosphine)palladium(II) chloride (70.6 mg, 0.101 mmol) and Na2CO3 (1066 mg,10.06 mmol) in DME (20 mL) and water (2 mL) was stirred at reflux for 2 hours. The mixturewas then diluted with EA (50 mL) and water (50 mL). The organic layer was separated and theaqueous layer was extracted with ethyl acetate (50 mL*2). The combined organic layer wasconcentrated and the crude was purified by silica gel eluting with 0-10percent MeOH/DCM (1percentammonia) to give the title compound 8i (500 mg, 1.252 mmol, 62.2 percent yield) as an off-white solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 17, p. 4034 - 4038
[2] Patent: WO2011/38572, 2011, A1, . Location in patent: Page/Page column 158; 159
  • 7
  • [ 401815-98-3 ]
  • [ 1453848-26-4 ]
Reference: [1] Patent: WO2013/130976, 2013, A1,
[2] Patent: US2017/22183, 2017, A1,
[3] Patent: US2017/22183, 2017, A1,
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