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[ CAS No. 64064-56-8 ] {[proInfo.proName]}

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Chemical Structure| 64064-56-8
Chemical Structure| 64064-56-8
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Product Details of [ 64064-56-8 ]

CAS No. :64064-56-8 MDL No. :MFCD09702465
Formula : C8H8ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MXEIFGRJRCYUDJ-UHFFFAOYSA-N
M.W : 185.61 Pubchem ID :13015359
Synonyms :

Calculated chemistry of [ 64064-56-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.33
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) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 2.68
Log Po/w (WLOGP) : 1.91
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 2.16
Consensus Log Po/w : 2.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.85
Solubility : 0.261 mg/ml ; 0.00141 mol/l
Class : Soluble
Log S (Ali) : -3.16
Solubility : 0.13 mg/ml ; 0.000699 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.12
Solubility : 0.14 mg/ml ; 0.000753 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.76

Safety of [ 64064-56-8 ]

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

Application In Synthesis of [ 64064-56-8 ]

* 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 [ 64064-56-8 ]
  • Downstream synthetic route of [ 64064-56-8 ]

[ 64064-56-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 64064-56-8 ]
  • [ 63071-10-3 ]
Reference: [1] Synthetic Communications, 2005, vol. 35, # 24, p. 3187 - 3190
[2] Patent: US2009/44345, 2009, A1,
  • 2
  • [ 5470-22-4 ]
  • [ 64-17-5 ]
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YieldReaction ConditionsOperation in experiment
89%
Stage #1: at 100℃; for 6 h;
Stage #2: at 20℃; for 20 h;
Step-1 : Ethyl-4-chloroypicolinate: A mixture of 4-chloropicolinic acid (20 g, 127 mmol) and thionyl chloride (200 mL) was heated to 100 °C and maintained for 6 h. The reaction was cooled to RT, and the excess of thionyl chloride was removed under vacuum. To the above obtained residue was then added ethanol (200 mL) at 0 °C drop-wise and the resulting mixture was stirred at RT for 20 h.The solvent was evaporated under vacuum and the residue was taken in ethyl acetate (1000 mL), washed with water (2x500 mL), saturated sodium bicarbonate solution (2x500 mL), brine (500 mL), dried (Na2S04) and filtered. The filtrate was evaporated to yield 21.0 g (89percent) the desired product as a semi solid. XHNMR (400 MHz, DMSO) δ 8.66 (d, = 5.0 Hz, 1Η), 8.13 (d, = 2.0Hz, 1Η), 7.49 (dd, = 5.0 &2.0HZ 1Η), 4.47 (q, = 7.0 Hz, 2Η), 1.46 (t, = 7.0 Hz, 3H); GC-MS (m/z) 185, 187 [(M)+, CI35' 37].
83.6%
Stage #1: at 100℃; for 6 h; Inert atmosphere
Stage #2: at 20℃; for 25.5 h; Cooling with ice
Stage #3: With sodium hydrogencarbonate In water
(Reference Example A-1) Ethyl 4-chloropyridine-2-carboxylate
A mixture of 4-chloropyridine-2-carboxylic acid (39.4g) and thionyl chloride (64 ml) was heated and stirred at 100 °C under a nitrogen atmosphere for 6 hr.
The reaction mixture was allowed to cool down to room temperature.
This was concentrated under reduced pressure and distilled azeotropically with toluene.
The resultant residue was gradually added to ethanol while stirring in an ice bath.
The reaction mixture was stirred at room temperature for 25.5 hr.
The reaction mixture was concentrated under reduced pressure.
To the residue was added a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate.
The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide the titled compound as a brown oil (38.8 g, 83.6 percent).
1H-NMR Spectrum (CDCl3) δ (ppm): 1.46 (3H, t, J = 7.2 Hz), 4.50 (2H, q, J = 7.2 Hz), 7.49 (1H, dd, J = 2.0, 5.2 Hz), 8.15 (1H, d, J = 2.0 Hz), 8.67 (1H, d, J = 5.2 Hz).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2669 - 2672
[2] Patent: WO2013/164769, 2013, A1, . Location in patent: Page/Page column 48
[3] Patent: EP2119706, 2009, A1, . Location in patent: Page/Page column 41
  • 3
  • [ 64-17-5 ]
  • [ 64064-56-8 ]
YieldReaction ConditionsOperation in experiment
83.6%
Stage #1: at 100℃; for 6 h;
Stage #2: at 0 - 20℃; for 25.5 h;
Stage #3: With sodium hydrogencarbonate In water; ethyl acetate
(Production Example 15) Ethyl 4-chloropyridine-2-carboxylate
A mixture of 4-chloropyridine-2-carboxylic acid (39.4g) and thionyl chloride (64 ml) was heated and stirred at 100 °C under a nitrogen atmosphere for 6 hr.
The reaction mixture was allowed to cool down to room temperature.
This was concentrated under reduced pressure and distilled azeotropically with toluene.
The resultant residue was gradually added to ethanol while stirring in an ice bath.
The reaction mixture was stirred at room temperature for 25.5 hr.
The reaction mixture was concentrated under reduced pressure.
To the residue was added a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate.
The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide the titled compound as a brown oil (38.8 g, 83.6 percent).
1H-NMR Spectrum (CDCl3) δ (ppm): 1.46 (3H, t, J = 7.2 Hz), 4.50 (2H, q, J = 7.2 Hz), 7.49 (1H, dd, J = 2.0, 5.2 Hz), 8.15 (1H, d, J = 2.0 Hz), 8.67 (1H, d, J = 5.2 Hz).
Reference: [1] Patent: EP1889836, 2008, A1, . Location in patent: Page/Page column 43
  • 4
  • [ 64-17-5 ]
  • [ 64064-56-8 ]
Reference: [1] Patent: WO2006/53227, 2006, A2, . Location in patent: Page/Page column 179
  • 5
  • [ 98-98-6 ]
  • [ 68-12-2 ]
  • [ 64064-56-8 ]
Reference: [1] Patent: US2009/44345, 2009, A1,
  • 6
  • [ 53750-66-6 ]
  • [ 64-17-5 ]
  • [ 64064-56-8 ]
Reference: [1] Patent: US2005/277652, 2005, A1, . Location in patent: Page/Page column 117-118
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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Acyl Group Substitution • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols Convert Acyl Chlorides into Esters • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcoholysis of Anhydrides • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • Amines Convert Esters into Amides • An Alkane are Prepared from an Haloalkane • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Chichibabin Reaction • Chloroalkane Synthesis with SOCI2 • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Complex Metal Hydride Reductions • Convert Esters into Aldehydes Using a Milder Reducing Agent • Convert Haloalkanes into Alcohols by SN2 • Decarboxylation of 3-Ketoacids Yields Ketones • Deprotection of Cbz-Amino Acids • Ester Cleavage • Ester Hydrolysis • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Grignard Reagents Transform Esters into Alcohols • Halogenation of Alkenes • Hantzsch Pyridine Synthesis • Hiyama Cross-Coupling Reaction • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Preparation of Amines • Pyridines React with Grignard or Organolithium Reagents • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • Transesterification
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