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[ CAS No. 1034921-05-5 ] {[proInfo.proName]}

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Chemical Structure| 1034921-05-5
Chemical Structure| 1034921-05-5
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Product Details of [ 1034921-05-5 ]

CAS No. :1034921-05-5 MDL No. :MFCD16293406
Formula : C7H5ClFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KEROPLWMUGCPSB-UHFFFAOYSA-N
M.W : 189.57 Pubchem ID :59200355
Synonyms :

Calculated chemistry of [ 1034921-05-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
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 : 40.48
TPSA : 39.19 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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 2.08
Log Po/w (MLOGP) : 1.36
Log Po/w (SILICOS-IT) : 2.27
Consensus Log Po/w : 1.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.812 mg/ml ; 0.00428 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.17 mg/ml ; 0.00615 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.19 mg/ml ; 0.001 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 1034921-05-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1034921-05-5 ]

* 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 [ 1034921-05-5 ]
  • Downstream synthetic route of [ 1034921-05-5 ]

[ 1034921-05-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 1034921-05-5 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: at 95℃; for 120 h;
Stage #2: at 0 - 23℃;
Stage #3: With water; sodium carbonate In ethyl acetate
A. Synthesis of methyl 4-chloro-3-fluoropicolinate[00211] The title compound was prepared according to the procedure described in Org. Prep, and Proc. Int., 29 (1), 117-122 (1997). A suspension of lithium 3- fluoropicolinate (20.Og, 136 mmol) and sodium bromide (28.Og, 272 mmol, 2 eq) in thionyl chloride (99 mL, 1.36 umol, 10 eq) was heated to reflux (95°C) with an argon <n="71"/>flush. The reaction was refluxed for 2 days then thionyl chloride (50 mL, 680 mmol, 5 eq) was added again and the reaction was refluxed for 3 more days. The mixture was then evaporated and the residue cooled down to 00C. Methanol (300 mL) was cautiously added by portions and the mixture was stirred at 23°C overnight. The reaction was then partitioned into ethyl acetate/sat, aq sodium carbonate and the aqueous phase was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in boiling hexanes and the residual black tar was decanted. The filtrate was evaporated to give the title material (24.36g, 94percent) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.92 (3H, s), 8.01 (IH, t, J=5.1 Hz), 8.50 (IH, d, J=5.1 Hz). LC/MS (M+H)+: 190.
Reference: [1] Patent: WO2008/124757, 2008, A1, . Location in patent: Page/Page column 69-70
  • 2
  • [ 67-56-1 ]
  • [ 1034921-07-7 ]
  • [ 1034921-05-5 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: at 95℃; for 120 h;
Stage #2: at 0 - 23℃;
A.
Synthesis of methyl 4-chloro-3-fluoropicolinate
The title compound was prepared according to the procedure described in Org. Prep. and Proc. Int., 29 (1), 117-122 (1997).
A suspension of lithium 4-chloro-3-fluoropicolinate (20.0 g, 136 mmol) and sodium bromide (28.0 g, 272 mmol, 2 eq) in thionyl chloride (99 mL, 1.36 mmol, 10 eq) was heated to reflux (95° C.) with an argon flush.
The reaction was refluxed for 2 days then thionyl chloride (50 mL, 680 mmol, 5 eq) was added again and the reaction was refluxed for 3 more days.
The mixture was then evaporated and the residue cooled down to 0° C. Methanol (300 mL) was cautiously added by portions and the mixture was stirred at 23° C. overnight.
The reaction was then partitioned into ethyl acetate/sat.
aq sodium carbonate and the aqueous phase was extracted with ethyl acetate.
The combined organic layers were dried over magnesium sulfate, filtered and concentrated.
The residue was dissolved in boiling hexanes and the residual tar was decanted.
The filtrate was evaporated to give the title material (24.36 g, 94percent) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.92 (3H, s), 8.01 (1H, t, J=5.1 Hz), 8.50 (1H, d, J=5.1 Hz). LC/MS (M+H)+: 190.
Reference: [1] Patent: US2010/48581, 2010, A1, . Location in patent: Page/Page column 37
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