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[ CAS No. 217314-47-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 217314-47-1
Chemical Structure| 217314-47-1
Chemical Structure| 217314-47-1
Structure of 217314-47-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 217314-47-1 ]

CAS No. :217314-47-1 MDL No. :MFCD09263221
Formula : C9H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OWMZQNZFHGAVCN-UHFFFAOYSA-N
M.W : 181.19 Pubchem ID :11830046
Synonyms :

Calculated chemistry of [ 217314-47-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.62
TPSA : 61.55 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.07
Log Po/w (MLOGP) : 1.06
Log Po/w (SILICOS-IT) : 0.99
Consensus Log Po/w : 1.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.68 mg/ml ; 0.00927 mol/l
Class : Soluble
Log S (Ali) : -2.37
Solubility : 0.774 mg/ml ; 0.00427 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.24
Solubility : 1.04 mg/ml ; 0.00573 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 217314-47-1 ]

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 [ 217314-47-1 ]

* 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 [ 217314-47-1 ]
  • Downstream synthetic route of [ 217314-47-1 ]

[ 217314-47-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 78238-13-8 ]
  • [ 217314-47-1 ]
YieldReaction ConditionsOperation in experiment
73% With ammonium formate In methanol Methyl 3-methoxy-5-aminobenzoate (2):
2 g (9.5 mmol) methyl 3-methoxy-5-nitrobenzoate (7) were dissolved in 50 mL methanol by heating, then 0.3 g Pd/C (10percent) were added under a stream of nitrogen, followed by 2.99 g (47.5 mmol) ammonium formate.
The mixture was refluxed for 3 h, then stirred overnight at r.t..
The clear layer above the catalyst was decanted off portionwise and filtered through a syringe filter.
The catalyst that remained in the flask was washed twice with methanol during this procedure.
After concentration, 1.69 g of a brown solid were obtained, which were purified by column chromatography (hexanes/ethyl acetate, 7:3).
Drying under vacuum afforded 1.25 g (73percent) of a colorless solid. 1H NMR (CDCl3) δ7.00-6.97 (m, 2H), 6.42 (t, J1=2.2 Hz, J2=2.2 Hz), 3.89 (s, 3H, OCH3), 3.80 (s, 3H, OCH3), 3.78 (sb, 2H); 13C NMR (CDCl3) δ167.13 160.71, 147.49, 131.95, 109.01, 105.71, 104.36, 55.19, 51.880.box.ESI-MS m/z 314 [MH]+.
Reference: [1] Patent: WO2004/56366, 2004, A1, . Location in patent: Page/Page column 15
[2] Patent: US2004/116654, 2004, A1,
[3] Patent: WO2008/9750, 2008, A2, . Location in patent: Page/Page column 38-39
[4] Patent: WO2003/106405, 2003, A1, . Location in patent: Page 204-208
  • 2
  • [ 67-56-1 ]
  • [ 74165-74-5 ]
  • [ 217314-47-1 ]
YieldReaction ConditionsOperation in experiment
79% at 0 - 20℃; for 2 h; Thionyl chloride (26 mL; 359 mmol) was added dropwise to a solution of 3-amino-5- methoxybenzoic acid (1 Og; 59.82 mmol) in MeOH (150 mL) at 0°C. The reaction mixture was stirred for 2 hours at room temperature. The precipitate was filtered off, washed with DIPE and dried under vacuo at 50°C to give 8.6 g (79percent) of intermediate 1 19 (a white solid) .
46 g
Stage #1: at 0 - 20℃; for 72 h;
Stage #2: With sodium hydrogencarbonate In diethyl ether; dichloromethane; water
To a stirred suspension of 3-amino-5-methoxyben- zoic acid (47 g, 281 mmol) in MeOH (1 L) at 0° C. was added thionyl chloride (123 mE, 1687 mmol) dropwise. The reaction was warmed to it and stirred for 72 h. The resulting solid was isolated by filtration, washing with diisopropyl ether, affording the product as the HC1 salt. The filtrate was evaporated, the residue triturated with MeOH/ether, filtered and washed with ether. The combined solid was suspended in DCM (500 mE) and basified with sat. aq. NaHCO3 solution (300 mE) with vigorous stirring. The organic phase was separated, washed with brine (200 mE), dried (MgSO4), filtered and evaporated under reduced pressure to give a solid. The solid was triturated with ether/isohexane to afford the sub-title compound (46 g) as a solid.‘H NMR (400 MHz, DMSO-d6) ö: 6.83 (dd, 1H),6.63 (dd, 1H), 6.37 (t, 1H), 5.42 (s, 2H), 3.79 (s, 3H), 3.70 (s, 3H). LCMS mlz 182 (M+H) (ES)
Reference: [1] Patent: WO2011/135376, 2011, A1, . Location in patent: Page/Page column 245; 246
[2] Patent: US2017/291917, 2017, A1, . Location in patent: Paragraph 0452; 0453; 0454
  • 3
  • [ 217314-43-7 ]
  • [ 217314-47-1 ]
Reference: [1] Synthesis, 1998, # 11, p. 1599 - 1603
  • 4
  • [ 217314-45-9 ]
  • [ 217314-47-1 ]
Reference: [1] Synthesis, 1998, # 11, p. 1599 - 1603
  • 5
  • [ 217314-42-6 ]
  • [ 217314-47-1 ]
Reference: [1] Synthesis, 1998, # 11, p. 1599 - 1603
  • 6
  • [ 217314-47-1 ]
  • [ 1261566-52-2 ]
Reference: [1] Patent: WO2011/135376, 2011, A1, . Location in patent: Page/Page column 246
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