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[ CAS No. 125104-34-9 ] {[proInfo.proName]}

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Chemical Structure| 125104-34-9
Chemical Structure| 125104-34-9
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Product Details of [ 125104-34-9 ]

CAS No. :125104-34-9 MDL No. :MFCD14582033
Formula : C8H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :FLXVRBSKKVMMQQ-UHFFFAOYSA-N
M.W : 165.15 Pubchem ID :19744506
Synonyms :

Calculated chemistry of [ 125104-34-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.9
TPSA : 56.26 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) : -6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 0.5
Log Po/w (WLOGP) : 0.68
Log Po/w (MLOGP) : -0.28
Log Po/w (SILICOS-IT) : 1.35
Consensus Log Po/w : 0.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.35
Solubility : 7.36 mg/ml ; 0.0446 mol/l
Class : Very soluble
Log S (Ali) : -1.25
Solubility : 9.25 mg/ml ; 0.056 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.04
Solubility : 1.5 mg/ml ; 0.0091 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 125104-34-9 ]

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 [ 125104-34-9 ]

* 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 [ 125104-34-9 ]
  • Downstream synthetic route of [ 125104-34-9 ]

[ 125104-34-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 58481-17-7 ]
  • [ 125104-34-9 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With Dess-Martin periodane In dichloromethane at 20℃; for 2.5 h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 0.25 h;
Methyl 2-(hydroxymethyl)isonicotinate (8.36 g, 50 mmol) (from reference compound 38, step 1) was dissolved in dichloromethane (150 mL). Dess-Martin periodinane (25 g, 58.94 mmol) was added and the mixture stirred at room temperature for 2 h 30 min. Sodium sulfothioate (59.3 g, 375.00 mmol) was dissolved in satd NaHCO3 and added to the reaction mixture. The suspension was vigorously stirred at room temperature for 15 min, DCM was added and the phases were separated. The aqueous phase was extracted with DCM twice and the combined organic layers were dried over MgSO4 and evaporated. The residue was purified by automated flash chromatography on a Biotage.(R). KP-SIL 340 g column. Gradient heptanes/EtOAc 80:20 to 65:35 over 5 CV was used as mobile phase. Methyl 2-formylisonicotinate (7 g, 85percent) was isolated as an off-white solid. 1H NMR (400 MHz, cdcl3) δ 4.00 (s, 3H), 8.09 (dd, 1H), 8.49 (s, 1H), 8.95 (d, 1H), 10.15 (s, 1H). MS m/z 165 (M)+
85% With Dess-Martin periodane In dichloromethane at 20℃; for 2.5 h; Methyl 2-(hydroxymethyl)isonicotinate (8.36 g, 50 mmol) was dissolved in dichloromethane (150 ml_). Dess-Martin periodinane (25 g, 58.94 mmol) was added and the mixture stirred at room temperature for 2 h 30 min. Sodium sulfothioate (59.3 g, 375.00 mmol) was dissolved in satd NaHCO3 and added to the reaction mixture. The suspension was vigorously stirred at room temperature for 15 min, DCM was added and the phases were separated. The aqueous phase was extracted with DCM twice and the combined organic layers were dried over MgSO and evaporated. The residue was purified by automated flash chromatography on a Biotage.(R). KP-SIL 340g column. Gradient heptanes / EtOAc 80:20 to 65:35 over 5 CV was used as mobile phase. Methyl 2-formylisonicotinate (7 g, 85 percent) was isolated as an off-white solid. 1H NMR (400 MHz, cdcl3) δ 4.00 (s, 3H), 8.09 (dd, 1 H), 8.49 (s, 1 H), 8.95 (d, 1 H), 10.15 (s, 1 H). MS m/z 165 (M+H)+
72% With manganese(IV) oxide In dichloromethane at 20℃; A.
methyl 2-formylpyridine-4-carboxylate
To a solution of methyl 2-(hydroxymethyl)pyridine-4-carboxylate (30 g, 179.64 mmol) in DCM (1 L) was added MnO2 (93.77 g. 1.0778 mol) at r.t. and stirred overnight.
The reaction mixture was then filtered and concentrated to afford the title compound (21.3 g, 72percent).
[M+H] Calc'd for C8H7NO3, 166.
Found, 166.
Reference: [1] Patent: US2010/261755, 2010, A1, . Location in patent: Page/Page column 35
[2] Patent: WO2012/47156, 2012, A1, . Location in patent: Page/Page column 12-13
[3] Patent: US2014/275084, 2014, A1, . Location in patent: Paragraph 0574; 0575
  • 2
  • [ 25658-36-0 ]
  • [ 125104-34-9 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1998, vol. 63, # 2, p. 199 - 204
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2917 - 2921
  • 3
  • [ 2459-09-8 ]
  • [ 125104-34-9 ]
Reference: [1] Patent: WO2012/47156, 2012, A1,
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