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[ CAS No. 816-27-3 ] {[proInfo.proName]}

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Chemical Structure| 816-27-3
Chemical Structure| 816-27-3
Structure of 816-27-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 816-27-3 ]

CAS No. :816-27-3 MDL No. :MFCD06797654
Formula : C6H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DSHWMBCJDOGPTB-UHFFFAOYSA-N
M.W : 145.16 Pubchem ID :10920638
Synonyms :

Calculated chemistry of [ 816-27-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.92
TPSA : 59.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 1.22
Log Po/w (WLOGP) : 0.56
Log Po/w (MLOGP) : 0.25
Log Po/w (SILICOS-IT) : 0.51
Consensus Log Po/w : 0.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.18
Solubility : 9.62 mg/ml ; 0.0663 mol/l
Class : Very soluble
Log S (Ali) : -2.06
Solubility : 1.25 mg/ml ; 0.00863 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.96
Solubility : 15.8 mg/ml ; 0.109 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.5

Safety of [ 816-27-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 816-27-3 ]

* 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 [ 816-27-3 ]
  • Downstream synthetic route of [ 816-27-3 ]

[ 816-27-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 816-27-3 ]
  • [ 4931-36-6 ]
  • [ 62135-58-4 ]
YieldReaction ConditionsOperation in experiment
30% With potassium hydroxide In ethanol at 20℃; for 16 h; Step 1Ethyl F 1 ,2,4ltriazo loll ,5-alpyridine-2-carboxylate To solution of ethyl 2-ethoxy-2-iminoacete (1.91 g, 13.2 mmol) in ethanol (66.1 mL) was added1,2-diaminopyridinium iodide (2.35 g, 9.91 mmol) followed by potassium hydroxide (556 mg,9.91 mmol) and stirred at r.t. for 16 h. Water was then added, the mixture extracted with EtOAc, the organic layer was separated, and concentrated in vacuo. Purification by chromatography (silica, 60 100 percent ethyl acetate in hexanes) gave ethyl [1,2,4]triazolo[1,5-a]pyridine-2- carboxylate (570 mg, 30 percent). 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.67 (dt, J=6.9, 1.2Hz, 1 H), 7.86 (dt,J=9.1, 1.2 Hz, 1 H), 7.62 (m, 1 H), 7.17 (td,J=7.0, 1.3 Hz, 1 H), 4.56 (q, J=7.2 Hz, 2 H), 1.48 (t, J=7.1 Hz, 3 H).
Reference: [1] Patent: WO2014/64134, 2014, A1, . Location in patent: Page/Page column 39
  • 2
  • [ 816-27-3 ]
  • [ 4931-36-6 ]
  • [ 107972-62-3 ]
  • [ 62135-58-4 ]
Reference: [1] Tetrahedron, 1986, vol. 42, # 10, p. 2625 - 2634
  • 3
  • [ 64-17-5 ]
  • [ 623-49-4 ]
  • [ 816-27-3 ]
YieldReaction ConditionsOperation in experiment
52.9%
Stage #1: With hydrogenchloride In dichloromethane; water at -5 - 0℃; Inert atmosphere
Stage #2: With triethylamine In dichloromethane; water at 0℃; for 1 h; Inert atmosphere
To a solution of ethyl carbonocyanidate (40 g, 404 mmol) in DCM (200 mL) stirred under nitrogen at 0 °C was added a solution of HCI (45 wt. percent, 27.3 mL, 404 mmol) in EtOH dropwise over 15 min. The reaction mixture was stirred at 0 °C for 3 hr and allowed to stand overnight at -5 °C to -3 °C. To the resulting mixture was added DCM (250 mL) at 0 °C. TEA (113 mL, 807 mmol) in DCM (50 mL) was added dropwise over 30 min at 0 °C. The mixture was stirred for 30 min at 0 °C, and water (100 mL) was added at 0 °C. The resulting mixture was stirred for 5 min. The organic layer was separated, dried over sodium sulfate, and evaporated. Diethyl ether (50 mL) was added to the residue and the solid was filtered. The filtrate was dried to afford ethyl 2-ethoxy-2-iminoacetate as a pale yellow liquid (31.0 g, 214 mmol, 52.9 percent yield). NMR (400 MHz, CDC) δ 8.78 (s, 1H), 4.36-4.28 (m, 4H), 1.40-1.35 (m, 6H).
Reference: [1] Synthesis, 1997, # 3, p. 301 - 304
[2] Patent: WO2018/154520, 2018, A1, . Location in patent: Page/Page column 92
[3] Helvetica Chimica Acta, 1989, vol. 72, p. 825 - 837
[4] Helvetica Chimica Acta, 1989, vol. 72, p. 825 - 837
[5] Patent: WO2009/155121, 2009, A2, . Location in patent: Page/Page column 106
  • 4
  • [ 623-49-4 ]
  • [ 816-27-3 ]
Reference: [1] Patent: US4331665, 1982, A,
[2] Patent: US4390534, 1983, A,
[3] Patent: US4425340, 1984, A,
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