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[ CAS No. 1658-42-0 ] {[proInfo.proName]}

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Chemical Structure| 1658-42-0
Chemical Structure| 1658-42-0
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Product Details of [ 1658-42-0 ]

CAS No. :1658-42-0 MDL No. :MFCD00006358
Formula : C8H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ORAKNQSHWMHCEY-UHFFFAOYSA-N
M.W :151.16 Pubchem ID :74264
Synonyms :

Calculated chemistry of [ 1658-42-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.1
TPSA : 39.19 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) : -6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 0.33
Log Po/w (WLOGP) : 0.8
Log Po/w (MLOGP) : 0.39
Log Po/w (SILICOS-IT) : 1.51
Consensus Log Po/w : 0.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.19
Solubility : 9.74 mg/ml ; 0.0645 mol/l
Class : Very soluble
Log S (Ali) : -0.72
Solubility : 29.0 mg/ml ; 0.192 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.491 mg/ml ; 0.00325 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 1658-42-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1658-42-0 ]

* 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 [ 1658-42-0 ]
  • Downstream synthetic route of [ 1658-42-0 ]

[ 1658-42-0 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 1658-42-0 ]
  • [ 154410-82-9 ]
YieldReaction ConditionsOperation in experiment
97% With acetic acid; sodium nitrite In water at 0 - 20℃; for 1.66667 h; To a solution of pyridin-2-yl-acetic acid methyl ester (8.9 ml, 0.66 mmol) in AcOH (16 mL) at 0 °C with stirring, an aqueous solution of sodium nitrite (4.67 g, 0.66 mmol in 14 mL) was added portion wise. After addition was completed stirring was continued for 40 min at room temperature. Water (30 mL) was added and the mixture was stirred for additional 1 h. The mixture was concentrated to remove most of the AcOH and basidified to pH 8-9 with Na2CO3 aq. extracted with EtOAc (3x). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. Drying in a vacuum oven affords Hydroxyimino-pyridin-2-yl-acetic acid methyl ester (11.6 g, 97percent) as an off-white solid, m/z 181.6 [M + I]+
Reference: [1] Patent: WO2009/70485, 2009, A1, . Location in patent: Page/Page column 131
[2] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1253 - 1260
[3] Zhurnal Obshchei Khimii, 1935, vol. 5, p. 1699,1703[4] Chem. Zentralbl., 1935, vol. 106, # II, p. 3240
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8049 - 8065
  • 2
  • [ 67-56-1 ]
  • [ 16179-97-8 ]
  • [ 1658-42-0 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: at 0 - 20℃; Inert atmosphere
Stage #2: With sodium hydrogencarbonate In water
S2 was prepared analogously to a published procedure.13 2.00 g S1 (11.5 mmol, 1.00 equiv.) and 14 mL MeOH were added to a round-bottom flask. The solution was cooled to 0 °C, and 2.90 mL TMSCl (23.0 mmol, 2.00 equiv.) were added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The solvent was then removed in vacuo, ant the remaining solid was treated slowly with sat. aq. NaHCO3 (40 mL). The aqueous solution was extracted with CH2Cl2 (4 x 40 mL), and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed in vacuo. The crude product (S2) was isolated as a clear oil (1.73 g, 11.47 mmol, quant.). The spectral data of the compound were compared with the published ones.13
95% at 0℃; for 1 h; To a solution of 2-(pyridin-2-yl)acetic acid hydrochloride salt MMMMMM (50.0 g, 288.0 mmol, 1.0 equiv.) in methanol (500 mL, 0.5M) at 0 °C was added thionyl chloride (31.5 mL, 432.0 mmol, 1.5 equiv.) dropwise. The reaction was stirred at 0 °C for 60 minutes or until the reaction was determined to be complete by LCMS or TLC. The reaction was carefully quenched with sodium carbonate and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting product (NNNNNN, 41.5 g, 275.0 mmol, 95percent) was used in the next step without further purification.
Reference: [1] Tetrahedron, 2011, vol. 67, # 24, p. 4435 - 4441
[2] Patent: WO2017/87667, 2017, A1, . Location in patent: Paragraph 0069
[3] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10246 - 10253
[4] Journal of Organic Chemistry, 2001, vol. 66, # 20, p. 6595 - 6603
  • 3
  • [ 16179-97-8 ]
  • [ 1658-42-0 ]
YieldReaction ConditionsOperation in experiment
95% With thionyl chloride In methanol at 0℃; for 1 h; Step 1: To a solution of 2-(pyridin-2-yl)acetic acid hydrochloride salt MMMMMM (50.0 g, 288.0 mmol, 1.0 equiv.) in methanol (500 mL, 0.5M) at 0° C. was added thionyl chloride (31.5 mL, 432.0 mmol, 1.5 equiv.) dropwise. The reaction was stirred at 0° C. for 60 minutes or until the reaction was determined to be complete by LCMS or TLC. The reaction was carefully quenched with sodium carbonate and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting product (NNNNNN, 41.5 g, 275.0 mmol, 95percent) was used in the next step without further purification.
Reference: [1] Patent: US2015/329528, 2015, A1, . Location in patent: Paragraph 0099; 0100
  • 4
  • [ 694-59-7 ]
  • [ 77086-38-5 ]
  • [ 1658-42-0 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 12, p. 3336 - 3339
  • 5
  • [ 67-56-1 ]
  • [ 13115-43-0 ]
  • [ 1658-42-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 11, p. 2479 - 2484
[2] Patent: WO2015/112441, 2015, A1, . Location in patent: Page/Page column 60
[3] Patent: US2016/333021, 2016, A1, . Location in patent: Paragraph 0363
  • 6
  • [ 3731-51-9 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 1658-42-0 ]
Reference: [1] ACS Catalysis, 2018, vol. 8, # 1, p. 738 - 741
  • 7
  • [ 694-59-7 ]
  • [ 77086-38-5 ]
  • [ 1658-42-0 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 12, p. 3336 - 3339
[2] Organic Letters, 2014, vol. 16, # 12, p. 3336 - 3339
  • 8
  • [ 67-56-1 ]
  • [ 83308-31-0 ]
  • [ 1658-42-0 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 48, p. 15777 - 15783
  • 9
  • [ 1749-29-7 ]
  • [ 124-38-9 ]
  • [ 1658-42-0 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 1936
[2] Monatshefte fuer Chemie, 1950, vol. 81, p. 473,479
  • 10
  • [ 109-06-8 ]
  • [ 616-38-6 ]
  • [ 1658-42-0 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 41, p. 14391 - 14393
  • 11
  • [ 109-06-8 ]
  • [ 79-22-1 ]
  • [ 1658-42-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 37, p. 10975 - 10979[2] Angew. Chem., 2015, vol. 127, # 37, p. 11126 - 11130,5
  • 12
  • [ 586-98-1 ]
  • [ 1658-42-0 ]
Reference: [1] ChemMedChem, 2015, vol. 10, # 11, p. 1875 - 1883
  • 13
  • [ 6959-47-3 ]
  • [ 1658-42-0 ]
Reference: [1] ChemMedChem, 2015, vol. 10, # 11, p. 1875 - 1883
  • 14
  • [ 186581-53-3 ]
  • [ 16179-97-8 ]
  • [ 1658-42-0 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 48, p. 15777 - 15783
  • 15
  • [ 20093-35-0 ]
  • [ 1658-42-0 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9537 - 9549
  • 16
  • [ 61890-12-8 ]
  • [ 1658-42-0 ]
Reference: [1] Monatshefte fuer Chemie, 1947, vol. 77, p. 137,143, 144
[2] Zhurnal Obshchei Khimii, 1935, vol. 5, p. 1699,1703[3] Chem. Zentralbl., 1935, vol. 106, # II, p. 3240
  • 17
  • [ 67-56-1 ]
  • [ 85274-59-5 ]
  • [ 1658-42-0 ]
Reference: [1] Monatshefte fuer Chemie, 1947, vol. 77, p. 137,143, 144
[2] Zhurnal Obshchei Khimii, 1935, vol. 5, p. 1699,1703[3] Chem. Zentralbl., 1935, vol. 106, # II, p. 3240
  • 18
  • [ 1620-53-7 ]
  • [ 1658-42-0 ]
Reference: [1] Zhurnal Obshchei Khimii, 1935, vol. 5, p. 1699,1703[2] Chem. Zentralbl., 1935, vol. 106, # II, p. 3240
  • 19
  • [ 67-56-1 ]
  • [ 2739-97-1 ]
  • [ 1658-42-0 ]
Reference: [1] ChemMedChem, 2015, vol. 10, # 11, p. 1875 - 1883
  • 20
  • [ 1658-42-0 ]
  • [ 59942-87-9 ]
Reference: [1] Patent: WO2013/43521, 2013, A1, . Location in patent: Page/Page column 54
  • 21
  • [ 1658-42-0 ]
  • [ 60637-33-4 ]
Reference: [1] Patent: WO2013/43521, 2013, A1,
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