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[ CAS No. 153800-11-4 ] {[proInfo.proName]}

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Chemical Structure| 153800-11-4
Chemical Structure| 153800-11-4
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Product Details of [ 153800-11-4 ]

CAS No. :153800-11-4 MDL No. :MFCD13189804
Formula : C6H4N2 Boiling Point : -
Linear Structure Formula :- InChI Key :GLEJGPDNIJWWQH-UHFFFAOYSA-N
M.W : 104.11 Pubchem ID :15639205
Synonyms :

Calculated chemistry of [ 153800-11-4 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.97
TPSA : 25.78 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) : -6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.35
Log Po/w (XLOGP3) : 0.09
Log Po/w (WLOGP) : 0.54
Log Po/w (MLOGP) : -0.23
Log Po/w (SILICOS-IT) : 1.51
Consensus Log Po/w : 0.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.1
Solubility : 8.32 mg/ml ; 0.08 mol/l
Class : Very soluble
Log S (Ali) : -0.19
Solubility : 67.8 mg/ml ; 0.652 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.66
Solubility : 2.26 mg/ml ; 0.0217 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.25

Safety of [ 153800-11-4 ]

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 [ 153800-11-4 ]

* 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 [ 153800-11-4 ]
  • Downstream synthetic route of [ 153800-11-4 ]

[ 153800-11-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 291763-66-1 ]
  • [ 153800-11-4 ]
YieldReaction ConditionsOperation in experiment
56.5% With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.05 h; To a solution of 9(3.Og, 17.O2rnrnoi) in iOmL THE was added IM of TBAF over 3 minutes. TLC analysis showed complete conversion of starting material to a major product. The reactionmixture was then concentrated in vacuo. The crude product was purified by silica gel column chromatography to give product 10(1.0g. yield: 56.5percent).LCMS: m/ 105 (M+H).
47% at 20℃; for 1.5 h; To a solution of 2-trimethylsilanylethynyl-pyrazine 1-48 (726 mg, 4.12 mmol) in Me0H (3mL) was added K2C03 (57 mg, 0.42 mmol) and the reaction mixture stirred at rt for 1 .5 h.After which time the reaction mixture was concentrated in vacuo and purified by columnchromatography (Biotage SP1, 25 g KP-Sil column eluting with isohexane to 30percent Et0Ac / isohexane) to afford the title compound as a yellow solid (204 mg, 2.0 mmol, 47percent).
Reference: [1] Patent: WO2017/117708, 2017, A1, . Location in patent: Page/Page column 18; 19
[2] Patent: WO2017/93544, 2017, A1, . Location in patent: Page/Page column 97; 98
[3] Carbohydrate Research, 2011, vol. 346, # 9, p. 1083 - 1092
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3033 - 3047
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3532 - 3548
  • 2
  • [ 904694-67-3 ]
  • [ 153800-11-4 ]
YieldReaction ConditionsOperation in experiment
50% With sodium hydroxide In toluene at 120℃; for 0.33 h; 1.94 g (11.96 mmol) of pyrazylacetylene and 502 mg (12.56 mmol) of NaOH (KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98 percent) were placed in a 100 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 60 mL of toluene was added thereto and the mixture was refluxed at 120°C for 0.33 hour. Toluene was added to the reaction mixture and the mixture was washed with a saturated aqueous ammonium chloride solution and dried over magnesium sulfate, followed by distilling off of the solvent under reduced pressure. Then, 20 mL of hexane was added to the crude reaction product and the mixture was cooled to give pyrazylethyne, i.e., the desired compound as a yellow solid. (0.63 g, yield: 50percent). 1H-NMR (300 MHz, CDCl3) δ: 8.71 (s, 1H), 8.56 (d, 1H), 8.52 (d, 1H), 3.35 (s, 1H) [MS] EI (m/z): 104 (M+), CI (m/z): 105 (MH+)
Reference: [1] Patent: EP1847545, 2007, A1, . Location in patent: Page/Page column 54
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