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[ CAS No. 75711-00-1 ] {[proInfo.proName]}

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Chemical Structure| 75711-00-1
Chemical Structure| 75711-00-1
Structure of 75711-00-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 75711-00-1 ]

CAS No. :75711-00-1 MDL No. :MFCD06658397
Formula : C6H5ClN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :XXGPBLSIXOYNEM-UHFFFAOYSA-N
M.W : 188.57 Pubchem ID :23456152
Synonyms :

Calculated chemistry of [ 75711-00-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.56
TPSA : 67.94 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) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 1.61
Log Po/w (WLOGP) : 1.65
Log Po/w (MLOGP) : 0.47
Log Po/w (SILICOS-IT) : -0.13
Consensus Log Po/w : 0.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.26
Solubility : 1.03 mg/ml ; 0.00548 mol/l
Class : Soluble
Log S (Ali) : -2.65
Solubility : 0.423 mg/ml ; 0.00225 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.15
Solubility : 1.33 mg/ml ; 0.00705 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.33

Safety of [ 75711-00-1 ]

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 [ 75711-00-1 ]

* 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 [ 75711-00-1 ]
  • Downstream synthetic route of [ 75711-00-1 ]

[ 75711-00-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 75711-00-1 ]
  • [ 75711-01-2 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With water; tin(ll) chloride In ethyl acetate at 20℃; for 1 h;
Stage #2: With sodium hydroxide In water; ethyl acetate
To a stirred solution of 2-chloro-3-(methyloxy)-5-nitropyridine (3.00 g, 15.90 mmol) in EtOAc (75 ml) was added SnCl2 dihydrate (21.54 g, 95.00 mmol) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with aqueous NaOH and extracted with EtOAc (5.x.75 ml). The collected organic layers were washed with water (3.x.75 ml), dried (Na2SO4), filtered and evaporated under reduced pressure to give the title compound D46 (2.34 g, 14.80 mmol, 93percent yield) as a brown solid.UPLC: rt=0.43 min, peaks observed: 159 (M+1, 100percent) and 161 (M+1, 33percent). C6H7ClN2O requires 158.1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.29 (d, 1H), 6.71 (d, 1H), 5.50 (bs, 2H), 3.77 (s, 3H).
78%
Stage #1: With hydrogenchloride; tin(ll) chloride In water at 5 - 80℃; for 1.25 h;
Stage #2: With sodium hydroxide In water
2-chloro-3-methoxy-5-nitropyridine (2.8 g, 14.9 mmol) was dissolved in concentrated HCl (30 mL) at 5 0C, tin chloride (10.0 g) was added and stirred at 5 0C for 15 min and then heated at 80 0C for 1 h. The reaction mixture was cooled and neutralized with 20 percent NaOH until pH 8, extracted with EtOAc, washed with water and dried with sodium sulfate and evaporated to obtain a brown solid (1.83 g, 78 percent).
Reference: [1] Patent: US2009/22670, 2009, A1, . Location in patent: Page/Page column 22
[2] Patent: WO2006/112828, 2006, A1, . Location in patent: Page/Page column 91
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