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[ CAS No. 1427-06-1 ] {[proInfo.proName]}

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Chemical Structure| 1427-06-1
Chemical Structure| 1427-06-1
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Product Details of [ 1427-06-1 ]

CAS No. :1427-06-1 MDL No. :MFCD03095098
Formula : C7H6FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HLYBWNNPVXFCPZ-UHFFFAOYSA-N
M.W : 155.13 Pubchem ID :13758765
Synonyms :

Calculated chemistry of [ 1427-06-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.47
TPSA : 39.19 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) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 1.14
Log Po/w (WLOGP) : 1.43
Log Po/w (MLOGP) : 0.76
Log Po/w (SILICOS-IT) : 1.61
Consensus Log Po/w : 1.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.79
Solubility : 2.51 mg/ml ; 0.0162 mol/l
Class : Very soluble
Log S (Ali) : -1.56
Solubility : 4.3 mg/ml ; 0.0277 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.669 mg/ml ; 0.00432 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 1427-06-1 ]

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 [ 1427-06-1 ]

* 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 [ 1427-06-1 ]
  • Downstream synthetic route of [ 1427-06-1 ]

[ 1427-06-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 93-60-7 ]
  • [ 446-26-4 ]
  • [ 1427-06-1 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 3, p. 255 - 258
[2] Tetrahedron Letters, 1987, vol. 28, # 3, p. 255 - 258
  • 2
  • [ 403-45-2 ]
  • [ 74-88-4 ]
  • [ 1427-06-1 ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In N,N-dimethyl-formamide at 20℃; Step G:
6-fluoro-nicotinic acid methyl ester
A round bottom flask was charged with K2CO3 (191 g, 1380 mmol), 6-fluoronicotinic acid (77.8 g, 551 mmol) and dimethylformamide (551 mL).
Methyl iodide (51.5 mL, 827 mmol) was then added in one portion at room temperature and mixture stirred overnight at room temperature.
The reaction mixture was partitioned between ethyl acetate and water.
The organic layer was washed three times with water and once with brine, and then dried over Na2SO4.
Purification by silica gel flash chromatography (ethyl acetate/dichloromethane) gave 6-fluoro-nicotinic acid methyl ester (71.8 g, 84percent) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 3.96 (s, 3H) 7.01 (dd, J=8.58, 2.93 Hz, 1H) 8.41 (ddd, J=8.49, 7.61, 2.44 Hz, 1H) 8.89 (d, J=2.34 Hz, 1H); MS (M+1): 156.1.
78% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16 h; A mixture of 6-fluoro-nicotinic acid (2.07g, 14.7mmol), K2CO3 (4.48g, 32.4mmol) and MeI (3.2Og, 22.5mmol) in DMF (6OmL) was stirred for 16h at rt. After dilution with H2O (5OmL), the reaction mixture was extracted with EtOAc (5OmL) and the extract washed successively with saturated NaHCO3 solution (2OmL), brine (2 x 2OmL) and dried (MgSO4). Filtration and evaporation of the solvent gave the product as an orange solid (1.79g, 78percent). 1H (CDCl3) 8.53 (IH, s), 8.12 (IH, m), 6.77 (IH, dd), 3.67 (3H, s)
Reference: [1] Patent: US2012/165343, 2012, A1, . Location in patent: Page/Page column 67
[2] Patent: WO2007/135350, 2007, A1, . Location in patent: Page/Page column 69
  • 3
  • [ 403-45-2 ]
  • [ 18107-18-1 ]
  • [ 1427-06-1 ]
YieldReaction ConditionsOperation in experiment
47% at 20℃; for 0.5 h; Methyl 6-fluoronicotinate. To a solution of 6-fluoronicotinic acid (255 mg, 1.32 mmol) in methanol (5 mL) at room temperature was added (trimethylsilyl)diazomethane (4.0 mL, 2 M in diethyl ether, 8.0 mmol). The reaction mixture was stirred at room temperature for 30 min and concentrated. Methyl 6- fluoronicotinate (129 mg, 47percent) was used without further purification: 1H NMR (600 MHz, DMSOd6) δ 8.79 (d, J = 2.6 Hz, IH), 8.47 (td, J = 7.9, 2.6 Hz, IH), 7.35 (ddd, J = 8.5, 2.6, 0.6 Hz, IH), 3.88 (s, 3H); ESIMS calcd 156.0 (M+ + H), found 156.1 (M+ + H).
Reference: [1] Patent: WO2007/2248, 2007, A2, . Location in patent: Page/Page column 76
  • 4
  • [ 93-60-7 ]
  • [ 446-26-4 ]
  • [ 1427-06-1 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 3, p. 255 - 258
[2] Tetrahedron Letters, 1987, vol. 28, # 3, p. 255 - 258
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