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[ CAS No. 21908-08-7 ] {[proInfo.proName]}

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Chemical Structure| 21908-08-7
Chemical Structure| 21908-08-7
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Product Details of [ 21908-08-7 ]

CAS No. :21908-08-7 MDL No. :MFCD13659319
Formula : C9H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :UWXSUYORWIRRCH-UHFFFAOYSA-N
M.W : 179.17 Pubchem ID :19600808
Synonyms :

Calculated chemistry of [ 21908-08-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.71
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) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.5
Log Po/w (XLOGP3) : 0.87
Log Po/w (WLOGP) : 1.07
Log Po/w (MLOGP) : 0.04
Log Po/w (SILICOS-IT) : 1.69
Consensus Log Po/w : 1.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.58
Solubility : 4.75 mg/ml ; 0.0265 mol/l
Class : Very soluble
Log S (Ali) : -1.64
Solubility : 4.15 mg/ml ; 0.0231 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.45
Solubility : 0.631 mg/ml ; 0.00352 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 21908-08-7 ]

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 [ 21908-08-7 ]

* 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 [ 21908-08-7 ]
  • Downstream synthetic route of [ 21908-08-7 ]

[ 21908-08-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 41438-38-4 ]
  • [ 21908-08-7 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 3 h;
Stage #2: With acetic acid In tetrahydrofuran; water at 20℃; for 1.5 h;
To a solution of diethyl pyridine-2,4-dicarboxylate (20. Og, 89.6mmol) in anhydrous tetrahydrofuran (300mL) was added diisobutylaluminum hydride ((134.4mL,134.4mmol,lmol/L in toluene) dropwise at -78°C. After the addition was complete, the mixture was stirred at -78°C for 3 hr and then poured slowly into an ice-cold mixture of acetic acid (50mL) and water(250mL). The mixture was then warmed to room temperature and stirred for 1.5 hr. The pH of the mixture was adjusted to 8 with sodium (0173) hydrogencarbonate solution at 0°C and extracted with ethyl acetate (500mLx5). The combined organics layer was dried over anhydrous sodium sulfate and concentrated. The crude residue was purified by column chromatography on silica gel (Petroleum ether: ethyl acetate =40: 1-10: 1) to afford ethyl 2-formylisonicotinate (13.0g, yield 81percent). LCMS m/z 180
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 21, p. 9346 - 9361,16
[2] Patent: WO2016/130396, 2016, A1, . Location in patent: Paragraph 0090; 0093; 0094
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1388 - 1409
[4] Collection of Czechoslovak Chemical Communications, 1998, vol. 63, # 2, p. 199 - 204
  • 2
  • [ 207671-42-9 ]
  • [ 21908-08-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 21, p. 9346 - 9361,16
  • 3
  • [ 499-80-9 ]
  • [ 21908-08-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1388 - 1409
[2] Patent: WO2016/130396, 2016, A1,
  • 4
  • [ 21908-08-7 ]
  • [ 1227163-84-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 21, p. 9346 - 9361,16
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