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[ CAS No. 105434-90-0 ] {[proInfo.proName]}

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Chemical Structure| 105434-90-0
Chemical Structure| 105434-90-0
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Product Details of [ 105434-90-0 ]

CAS No. :105434-90-0 MDL No. :MFCD03468385
Formula : C6H9N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CPQKGGOPHDHAMN-UHFFFAOYSA-N
M.W : 155.16 Pubchem ID :4321844
Synonyms :

Calculated chemistry of [ 105434-90-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 39.08
TPSA : 81.0 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) : -6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.92
Log Po/w (XLOGP3) : 0.42
Log Po/w (WLOGP) : 0.18
Log Po/w (MLOGP) : -0.18
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.2
Solubility : 9.68 mg/ml ; 0.0624 mol/l
Class : Very soluble
Log S (Ali) : -1.69
Solubility : 3.18 mg/ml ; 0.0205 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.34
Solubility : 7.04 mg/ml ; 0.0454 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 105434-90-0 ]

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 [ 105434-90-0 ]

* 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 [ 105434-90-0 ]
  • Downstream synthetic route of [ 105434-90-0 ]

[ 105434-90-0 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 39846-84-9 ]
  • [ 105434-90-0 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogen In ethanol at 20℃; for 18 h; To a solution of 5-Nitro-lH-pyrazole-3-carboxylic acid ethyl ester (0.925 g, 0.500 mmol) in absolute ethanol (10 cm3) was added 10percent Pd/C (0.100 g). The mixture was stirred under an atmosphere of H2 at room temperature for 18 hours, filtered through Celite and the solvent removed under reduced pressure to give a green solid (0.70 g, 90percent). 1H (CD3OD): 6.0 (s, IH), 4.3 (q, 2H, J=7.1, CO2CH2CH3), 1.4 (t, 3H, J=7.1,CO2CH2CH3). m/z (ES+): 156 [M+H]+
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4207 - 4209
[2] Patent: WO2006/127595, 2006, A1, . Location in patent: Page/Page column 62
[3] Patent: WO2006/126695, 2006, A1, . Location in patent: Page/Page column 246-247
[4] Patent: US2007/32529, 2007, A1,
[5] Patent: US2009/36450, 2009, A1, . Location in patent: Page/Page column 21
  • 2
  • [ 95-92-1 ]
  • [ 75-05-8 ]
  • [ 105434-90-0 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 70℃; for 0.666667 h;
Stage #2: With hydrogenchloride; hydrazinecarboxylic acid methyl ester In ethanol; water at 30℃; for 20 h; Cooling with ice
Stage #3: With potassium carbonate In ethanol; water at 90℃; for 0.5 h;
To a solution of diethyl oxalate (10.0 g, 68.4 mM) in THF (10 mL), there were added 18-crown-6 (1.80 mg, 6.84 mM) and potassium tert-butoxide (1M THF solution, 71.6 mL, 71.6 mM), then acetonitrile (3.99 mL, 75.2 mM) was further added to the mixture at 0° C. and the resulting mixture was stirred for 10 minutes.
The temperature of this solution was raised up to 70° C. and it was stirred for 30 minutes at that temperature.
The resulting suspension was filtered and the solid was washed with diethyl ether.
The resulting solid was suspended in ethanol (100 mL), followed by the addition of water (20 mL), and then concentrated hydrochloric acid (3.0 mL) and methyl carbazinate (3.61 g, 39.7 mM) with ice-cooling and the stirring of the resulting mixture at room temperature for 20 hours.
After the completion of the stirring operation, potassium carbonate (2.74 g, 19.8 mM) was added to this suspension and the latter was stirred at 90° C. for 30 minutes.
This reaction liquid was concentrated under reduced pressure, the resulting concentrate was diluted with water and the mixture was extracted with ethyl acetate.
The resulting extracts were combined, dried over anhydrous sodium sulfate, the solvent was distilled off and then the resulting solid was sufficiently washed with diethyl ether to thus give the title compound (5.34 g, yield: 50percent).
1H-NMR (300 MHz, DMSO): δ 1.23 (t, 3H, J=6.9 Hz), 4.19 (q, 2H, J=6.9 Hz), 4.74-5.12 (br, 2H), 5.64-5.89 (br, 1H), 12.09-12.53 (br, 1H); MS (ESI) m/z 156 (M+H)+.
Reference: [1] Patent: US2011/294781, 2011, A1, . Location in patent: Page/Page column 44
  • 3
  • [ 6294-89-9 ]
  • [ 105434-90-0 ]
YieldReaction ConditionsOperation in experiment
39.3%
Stage #1: With hydrogenchloride In ethanol; water at 20℃; for 0.25 h;
Stage #2: at 20℃;
Stage #3: With potassium carbonate In methanol; water at 60℃; for 4 h; Heating / reflux
A 10 L three-necked flask is equipped with mechanical stirrer, reflux condenser and nitrogen inlet. To ethyl 3-cyano-2-oxopropionate sodium salt ("NaCOPE") (653.18 g; 4.0 mol), 585 mL of water, 3.6 L of ethanol and 350 mL of hydrochloric acid (12N; 4.2 mol) are added. The resulting suspension is stirred at RT for 15 min. Then, methyl hydrazino formiate (356.0 g; 3.95 mol) is added as a solid material. A slightly exothermic reaction occurs. After the mixture is stirred at RT for 6 h, another portion of methyl hydrazino formiate (12.0 g; 133.7 mmol) is added and the orange suspension is stirred at RT over night. Then potassium carbonate (K2CO3, 300.0 g; 2.17 mol) is added, followed by 250 mL of water. The internal temperature rises to 60° C. and a vigorous evolution of gas starts. The mixture is heated at reflux for four hours. After cooling to RT, the alcohol is evaporated to yield a red paste, which is taken up in 1 L of water and 3 L of ethyl acetate. The aqueous phase is extracted with another 500 mL portion of ethyl acetate. The organic extracts are washed with brine and dried over sodium sulfate (Na2SO4). After filtration the solvent is evaporated to yield 330 g of a brown paste. This crude product is mixed with 1 L of ether to give a light brown solid, which is separated from an orange liquid phase by filtration. The solid is dried under vacuum to yield 229.12 g (7). The liquid phase is evaporated; the residue is taken up in 250 mL of ether and cooled to -30° C. to yield another 15.09 g of 7. The total yield of 7 is 244.21 g (1.57 mol; 39.3percent). Physical characteristics are as follows: 1H-NMR (DMSO): δ (ppm) 1.26, 4.21, 5.0, 5.76, 12.12.
Reference: [1] Patent: US2008/32998, 2008, A1, . Location in patent: Page/Page column 20
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