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[ CAS No. 202931-88-2 ] {[proInfo.proName]}

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Chemical Structure| 202931-88-2
Chemical Structure| 202931-88-2
Structure of 202931-88-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 202931-88-2 ]

CAS No. :202931-88-2 MDL No. :MFCD10696346
Formula : C4H5N3O Boiling Point : -
Linear Structure Formula :- InChI Key :VFAQDMYUCHBIJL-UHFFFAOYSA-N
M.W : 111.10 Pubchem ID :21187507
Synonyms :

Calculated chemistry of [ 202931-88-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 26.67
TPSA : 47.78 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) : -7.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.73
Log Po/w (XLOGP3) : -0.52
Log Po/w (WLOGP) : -0.37
Log Po/w (MLOGP) : -1.08
Log Po/w (SILICOS-IT) : 0.11
Consensus Log Po/w : -0.22

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.6
Solubility : 28.1 mg/ml ; 0.253 mol/l
Class : Very soluble
Log S (Ali) : -0.01
Solubility : 107.0 mg/ml ; 0.966 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.31
Solubility : 54.2 mg/ml ; 0.488 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56

Safety of [ 202931-88-2 ]

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 [ 202931-88-2 ]

* 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 [ 202931-88-2 ]
  • Downstream synthetic route of [ 202931-88-2 ]

[ 202931-88-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 16681-65-5 ]
  • [ 68-12-2 ]
  • [ 202931-88-2 ]
YieldReaction ConditionsOperation in experiment
30%
Stage #1: With n-butyllithium In tetrahydrofuran at -78 - -60℃; for 0.5 h;
Stage #2: at 20℃; for 1 h;
To a solution of 1-methyl-1 H-1 ,2,3-triazole (Preparation 32, 0.1 g, 1.2 mmol) in tetrahydrofuran (THF, 10 ml) at -780C was added dropwise 1.6 M n-butyl lithium (0.9 ml, 1.4 mmol), maintaining the temperature below -6O0C. The reaction was stirred at - 780C for 30 minutes, then dimethylformamide (0.14 ml, 1.8 mmol) was added. The reaction was warmed to room temperature and stirred for 1 hour. The reaction was quenched with water and extracted with ethyl acetate (3 x 10\\ ml). The combined organic extracts were washed with water (3 x 10 ml), dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with 95:5 to 100:0 dichloromethane:methanol, to afford the title compound as a yellow oil (0.04 g, 30percent yield).1HNMR (CDCI3): 4.10 (s, 3H)1 7.88 (s, 1 H), 9.55 (s, 1 H)
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 6, p. 650 - 654
[2] Patent: WO2008/135826, 2008, A2, . Location in patent: Page/Page column 157; 158
[3] Patent: US2014/107094, 2014, A1, . Location in patent: Paragraph 0625; 0626
[4] Patent: US2015/105372, 2015, A1, . Location in patent: Paragraph 0304; 0305
[5] Patent: WO2015/57206, 2015, A1, . Location in patent: Page/Page column 74; 75
[6] Patent: KR2016/68948, 2016, A, . Location in patent: Paragraph 0402-0405
  • 2
  • [ 16681-65-5 ]
  • [ 202931-88-2 ]
YieldReaction ConditionsOperation in experiment
19% With n-butyllithium In N,N-dimethyl-formamide a
3-Methyl-3 H-1,2,3-triazole-4-carboxaldehyde
To a stirred solution of 1-methyl-1 H-1,2,3-triazole (0.500 g, 6.02 mmol) in anhydrous THF (20 ml), cooled to -70° C. under nitrogen, was added dropwise a 1.6 M solution of butyl lithium in hexanes (4.23 ml, 6.77 mmol).
The mixture was stirred at this temperature for 1 h, then anhydrous DMF (0.465 ml, 6.02 mmol) was added, and the mixture was allowed to warm to 0° C. over 30 min.
Saturated aqueous NH4Cl (25 ml) was then added and the mixture was extracted with ethyl acetate.
The organic layer was dried (Na2SO4) and evaporated in vacuo.
The residue was purified by flash chromatography (silica gel, 40percent EtOAc/hexane) to give 0.128 g (19percent) of the title compound as a yellow oil: 1H NMR (360 MHz, d6-DMSO) δ4.27 (3 H, s), 8.45 (1 H, s), 10.01 (1 H, s); MS (ES+) m/e 144[M+MeOH+H]+, 111[M]+.
Reference: [1] Patent: US6255305, 2001, B1,
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