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[ CAS No. 142266-66-8 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 142266-66-8
Chemical Structure| 142266-66-8
Chemical Structure| 142266-66-8
Structure of 142266-66-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 142266-66-8 ]

CAS No. :142266-66-8 MDL No. :MFCD02932725
Formula : C8H7Cl2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QJUGBRJQIHDUNF-UHFFFAOYSA-N
M.W : 220.05 Pubchem ID :612963
Synonyms :

Calculated chemistry of [ 142266-66-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.15
TPSA : 50.19 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) : -5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 2.7
Log Po/w (MLOGP) : 0.71
Log Po/w (SILICOS-IT) : 2.93
Consensus Log Po/w : 2.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.2
Solubility : 0.139 mg/ml ; 0.000631 mol/l
Class : Soluble
Log S (Ali) : -3.44
Solubility : 0.0802 mg/ml ; 0.000365 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.41
Solubility : 0.085 mg/ml ; 0.000386 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 142266-66-8 ]

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 [ 142266-66-8 ]

* 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.

  • Downstream synthetic route of [ 142266-66-8 ]

[ 142266-66-8 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 175204-44-1 ]
  • [ 142266-66-8 ]
YieldReaction ConditionsOperation in experiment
96% With sulfuric acid; sodium nitrite
  • 2
  • [ 769-28-8 ]
  • [ 142266-66-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 94 percent / sulfuryl chloride / CCl4 / 6 h / Heating 2: 76 percent / POCl3 / Heating 3: 91 percent / aq. H2SO4 / Heating 4: 96 percent / H2SO4; aq. NaNO2
  • 3
  • [ 23819-92-3 ]
  • [ 142266-66-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 76 percent / POCl3 / Heating 2: 91 percent / aq. H2SO4 / Heating 3: 96 percent / H2SO4; aq. NaNO2
  • 4
  • [ 91591-63-8 ]
  • 2,5-dichloro-4,6-dimethylnicotinic acid [ No CAS ]
  • 5
  • [ 111-49-9 ]
  • [ 142266-66-8 ]
  • [ 2417330-56-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 85 - 140℃; for 96h; Sealed tube; 2.1 Step 1: 2-(azepan-1-yl)-5-chloro-4,6-dimethylnicotinic acid To a solution of 2,6-dichloro-4,6- dimethylnicotinic acid (0.50 g, 2.3 mmol) in DMF (5 mL) was added hexamethyleneimine (0.56 g, 5.7 mmol) and K2CO3 (1.0 g, 7.2 mmol). The mixture was heated at 85C for 3 days in a sealed tube, then additional hexamethyleneimine (0.50 g) and K2CO3 (1.0 g) were added. The mixture was heated at 140°C in a sealed tube for 24 hours, then cooled to rt and diluted with EtOAc. The organic layer was washed with 5% aqueous AcOH, water, brine, and then dried over MgSO4 and concentrated. The resulting residue was purified by silica gel chromatography (0-75% EtOAc/hexanes) to give the title compound.
With potassium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 140℃; for 16h; Sealed tube; 201.1 Step 1: 2-(azepan-l-yl)-5-chloro-4.6-dimethylnicotinic acid To a solution of 2,5-dichloro-4,6- dimethylnicotinic acid (0.50 g, 2.3 mmol) in DMF (5 mL) was added DIPEA (2.0 mL, 11 mmol), K2CO3 (2.0 g) and hexamethyleneimine (1.1 g, 11 mmol). The reaction vial was sealed and heated at l40°C for 16 hours. Then the reaction mixture was cooled to rt and diluted in EtOAc. The organic layer was washed with 5% AcOH in water, brine, dried over MgSOr. filtered and concentrated to give a residue that was purified via silica gel chromatography (0-75% (1662) EtO Ac/hexanes) to give the title compound.
  • 6
  • [ 111-49-9 ]
  • [ 142266-66-8 ]
  • [ 2417330-55-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; potassium carbonate / N,N-dimethyl-formamide / 16 h / 140 °C / Sealed tube 2: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 16 h / 80 °C
  • 7
  • [ 142266-66-8 ]
  • [ 2417330-76-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thionyl chloride / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 20 h / 25 - 220 °C / Microwave irradiation
  • 8
  • [ 142266-66-8 ]
  • [ 2417330-77-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 20 h / 25 - 220 °C / Microwave irradiation 3.1: palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO); caesium carbonate / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere
  • 9
  • [ 142266-66-8 ]
  • [ 2417330-74-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: thionyl chloride / 1 h / 20 °C / Inert atmosphere 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 20 h / 25 - 220 °C / Microwave irradiation 3.1: palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO); caesium carbonate / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 1 h / 25 °C
  • 10
  • [ 74-89-5 ]
  • [ 142266-66-8 ]
  • [ 2417330-75-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,5-dichloro-4,6-dimethylnicotinic acid With thionyl chloride at 20℃; for 1h; Inert atmosphere; Stage #2: methylamine In tetrahydrofuran; water at 20℃; 214.1 Step 1 : 2.5-dichloro-N.4.6-trimethylnicotinamide A mixture of 2,5-dichloro-4,6- dimethylnicotinic acid (150 mg, 0.68 mmol) in SOCh (2.0 mL, 27 mmol) was stirred at room temperature for 1 hour under a nitrogen atmosphere. The mixture was evaporated under reduced pressure, and the resulting residue was dissolved in THF (2 mL). The solution was added dropwise into a solution of methanamine (2.0 mL, 0.68 mmol) in water at room temperature. The resultant mixture was purified by prep-TLC (petroleum ether: ethyl acetate 1 : 1) to give the title compound.
  • 11
  • [ 111-49-9 ]
  • [ 142266-66-8 ]
  • [ 2417373-19-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 96 h / 85 - 140 °C / Sealed tube 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 17 h / 50 °C
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