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[ CAS No. 36404-90-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 36404-90-7
Chemical Structure| 36404-90-7
Chemical Structure| 36404-90-7
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Product Details of [ 36404-90-7 ]

CAS No. :36404-90-7 MDL No. :MFCD03095270
Formula : C6H4FNO Boiling Point : -
Linear Structure Formula :- InChI Key :OFBVGDCXXGXDKU-UHFFFAOYSA-N
M.W : 125.10 Pubchem ID :11434944
Synonyms :

Calculated chemistry of [ 36404-90-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.58
TPSA : 29.96 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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 0.75
Log Po/w (WLOGP) : 1.45
Log Po/w (MLOGP) : 0.22
Log Po/w (SILICOS-IT) : 1.94
Consensus Log Po/w : 1.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.52
Solubility : 3.82 mg/ml ; 0.0305 mol/l
Class : Very soluble
Log S (Ali) : -0.96
Solubility : 13.8 mg/ml ; 0.11 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.21
Solubility : 0.773 mg/ml ; 0.00618 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 36404-90-7 ]

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 [ 36404-90-7 ]

* 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 [ 36404-90-7 ]
  • Downstream synthetic route of [ 36404-90-7 ]

[ 36404-90-7 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 36404-90-7 ]
  • [ 68618-36-0 ]
Reference: [1] Patent: WO2012/83117, 2012, A1,
  • 2
  • [ 36404-90-7 ]
  • [ 271-73-8 ]
YieldReaction ConditionsOperation in experiment
90% With hydrazine hydrate In ethanol at 80℃; for 1 h; Formation of lH-pyrazolo[3,4-b]pyridine (42)Hydrazine hydrate (64percent, 0.29 L, 5.99 mol hydrazine, 3 eq) was added dropwise to a solution of 2-fluoropyridine-3-carboxylaldehyde (0.25 kg, 1.99 mol) in EtOH (600 mL) over lhr. During the addition, a thick suspension formed, which turned into a clear red solution towards the end of the addition. The reaction mixture was heated to 80 °C overnight. The reaction mixture was cooled to room temperature, quenched with H20/aqueous saturated NaHC03 (1/1 mixture, 600mL) and extracted with EtOAc (2x 800 mL, lx 500 mL). The combined organic layers were washed with brine (400 mL), dried over Na2S04 and concentrated in vacuo. The resulting solid was washed with heptanes (3x 800 mL), dried under reduced pressure and stripped twice with heptanes. The product (214 g, 90percent yield) was obtained as a light-yellow solid: NMR (CDC13, 300 MHz) δ 8.65-8.64 (m, 1 H); 8.14-8.10 (m, 2H); 7.17-7.12(m, 1 H) ppm.
Reference: [1] Patent: WO2012/83117, 2012, A1, . Location in patent: Page/Page column 126
  • 3
  • [ 2591-86-8 ]
  • [ 372-48-5 ]
  • [ 36404-90-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With trimethylsilylmethyllithium; diisopropylamine In tetrahydrofuran; hexane at -50℃; for 3 h;
Stage #2: at -50 - 20℃;
A solution of (trimethylsilylmethyl) lithium (22 mL, 13.8 weight percent in hexanes) was charged to a 100 mL 3-NECK round-bottom flask and cooled TO-50 °C. A solution of 2-fluoropyridine (2.0 g), THF (25 mL) and DIISOPROPYLAMINE (0.13 mL) was added at less than-50 °C in 1 minute. After 3 hours, 1-formylpiperidine (2.4 g) was added in 1 min at less THAN-50 °C. The mixture was allowed to warm to room temperature and stir overnight. The reaction mixture was quenched with acetic acid (3 mL) and water (7 mL). The aqueous layer was separated and washed with 3x25 mL MTBE. All organic layers were combined, dried over MGS04 and concentrated in vacuo to leave 3.79 g of brown oil. This oil was chromatographed through silica gel, eluting with 15 percent EtOAc in hexanes, to afford 2. 24 g of 92. 4percent pure 2-FLUORO-3-PYRIDINECARBOXALDEHYDE (90percent yield, corrected for assay).
Reference: [1] Patent: WO2004/92125, 2004, A2, . Location in patent: Page 7-8
[2] Journal of Organometallic Chemistry, 1991, vol. 406, # 1+2, p. 49 - 56
  • 4
  • [ 68-12-2 ]
  • [ 36404-90-7 ]
Reference: [1] Patent: WO2007/38215, 2007, A1, . Location in patent: Page/Page column 91-92
  • 5
  • [ 131747-55-2 ]
  • [ 36404-90-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 6
  • [ 119899-26-2 ]
  • [ 36404-90-7 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 7
  • [ 1603-40-3 ]
  • [ 36404-90-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[2] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 8
  • [ 2369-18-8 ]
  • [ 36404-90-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[2] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 9
  • [ 393-55-5 ]
  • [ 36404-90-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 10
  • [ 766-11-0 ]
  • [ 109-94-4 ]
  • [ 36404-90-7 ]
Reference: [1] Journal of Organometallic Chemistry, 1990, vol. 382, # 3, p. 319 - 332
  • 11
  • [ 36404-90-7 ]
  • [ 131747-55-2 ]
YieldReaction ConditionsOperation in experiment
63% at 20℃; for 1 h; Sodium borohydride 1.0 g (26 mmol) was added to an ethanol (14 mL) solution of 2-fluoronicotinaldehyde 1.6 mL (16 mmol), and the mixture was stirred at room temperature for 1 hour.
After the completion of the reaction, water was added to the reaction mixture, and followed by extraction with ethyl acetate.
The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered.
The filtrate was concentrated under reduced pressure to give the title compound 1.3 g (10 mmol, yield 63percent) as a colorless oil.
Reference: [1] Patent: EP3333163, 2018, A1, . Location in patent: Paragraph 1401; 1402
[2] Patent: WO2010/132999, 2010, A1, . Location in patent: Page/Page column 98
[3] Patent: WO2011/48082, 2011, A1, . Location in patent: Page/Page column 88
[4] Organic Letters, 2017, vol. 19, # 14, p. 3895 - 3898
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