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[ CAS No. 71777-70-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 71777-70-3
Chemical Structure| 71777-70-3
Chemical Structure| 71777-70-3
Structure of 71777-70-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 71777-70-3 ]

CAS No. :71777-70-3 MDL No. :MFCD13181658
Formula : C10H13NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :LJXADWCGSBYCDC-UHFFFAOYSA-N
M.W : 195.22 Pubchem ID :49853411
Synonyms :

Calculated chemistry of [ 71777-70-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.62
TPSA : 48.42 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) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.54
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.66
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : 1.9
Consensus Log Po/w : 1.71

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.43 mg/ml ; 0.00735 mol/l
Class : Soluble
Log S (Ali) : -2.37
Solubility : 0.826 mg/ml ; 0.00423 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.04
Solubility : 0.177 mg/ml ; 0.000908 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.1

Safety of [ 71777-70-3 ]

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 [ 71777-70-3 ]

* 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 [ 71777-70-3 ]
  • Downstream synthetic route of [ 71777-70-3 ]

[ 71777-70-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 5470-22-4 ]
  • [ 64-17-5 ]
  • [ 71777-70-3 ]
YieldReaction ConditionsOperation in experiment
93% for 48 h; Heating / reflux A solution of 4-chloropicolinic acid (3.0 g, 19.04 mmol) in EtOH (100 mL) was mixed with H^SO4 (cone, 5 ml_) and was stirred at reflux for 48 hours. The reaction mixture was cooled to room temperature and neutralized with NaOH (1 N) to adjust pH = 8~9. The mixture was extract with dichloromethane (3x100 mL) and concentration to afforded ethyl 4-ethoxypicolinate (3.44 g, 93percent).
93%
Stage #1: for 48 h; Reflux
Stage #2: With sodium hydroxide In ethanol
A solution of 4-chloropicolinic acid (3.0 g, 19.04 mmol) in EtOH (100 mL) was mixed with H2SO4 (conc., 5 mL) and was stirred at reflux for 48 h. The reaction mixture was cooled to rt and neutralized with NaOH (1 N) to adjust pH=8-9. The mixture was extract with dichloromethane (3×100 mL) and concentration to afforded ethyl 4-ethoxypicolinate (3.44 g, 93percent).
69% at 85℃; for 16 h; Step-1 : Ethyl 4-ethoxypicolinate: A solution of 4-chloropicolinic acid (1.0 g, 6.35 mmol) and sulphuric acid (0.2 mL, 3.75 mmol) in ethanol (10 mL) was heated to 85°C and maintained for 16 h. Reaction mixture was cooled to RT and the solvent was evaporated under vacuum. The residue was taken into ethyl acetate (20 mL) and basified with aqueous saturated sodium bicarbonate (pH 10, 20 mL). The layers were separated and the organic layer was washed with brine (15 mL), dried (Na2S04) and filtered.The filtrate was concentrated under vacuum to afford l.Og (69percent) the title compound as brown oily mass HNMR (400 MHz, CDC13) δ 8.54 (d, = 5.5 Hz, 1Η), 7.65 (d, = 2.5 Hz, 1Η), 6.94 (dd, / = 5.5&2.5HZ, 1Η), 4.47 (q, / = 7.0Hz, 2Η), 4.15 (q, / = 7.0Hz, 2Η), 1.47-1.42 (m, 6H); GC-MS (m/z) 185(M)+.
Reference: [1] Patent: WO2007/16525, 2007, A2, . Location in patent: Page/Page column 54
[2] Patent: US2013/281396, 2013, A1, . Location in patent: Paragraph 0319-0320
[3] Patent: WO2013/164769, 2013, A1, . Location in patent: Page/Page column 46-47
  • 2
  • [ 19235-89-3 ]
  • [ 64-17-5 ]
  • [ 71777-70-3 ]
YieldReaction ConditionsOperation in experiment
34% at 80℃; for 48 h; A solution of 4-chloropicolinonitrile (5.5 g, 39.7 mmol) in saturated HCI/EtOH solution (80 mL) was stirred at 80 °C for 2 days. The solvent was removed under reduced pressure, saturated aqueous NaHCO.3 (200 mL) was added and the aqueous layer extracted with DCM (3 x 200 mL). The pooled organic extracts were dried (Na2S04) and concentrated to give the title compound as a white solid (2.6 g, 34percent). 1H NMR (400 MHz, CDCb) δ 8.52 (d, J = 5.6 Hz, 1 H), 7.63 (d, J = 2.4 Hz, 1 H), 6.93-6.91 (m, 1 H), 4.80-4.43 (m, 2H), 4.16-4.1 1 (m, 2H), 1.46-1 .41 (m, 6H). LCMS-C: RT 1 .35 min; m/z 196.1 [M+H]+
Reference: [1] Patent: WO2016/34673, 2016, A1, . Location in patent: Page/Page column 111
  • 3
  • [ 53750-66-6 ]
  • [ 64-17-5 ]
  • [ 71777-70-3 ]
Reference: [1] Organic Preparations and Procedures International, 1997, vol. 29, # 1, p. 117 - 122
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