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CAS No. : | 78350-50-2 | MDL No. : | MFCD00235172 |
Formula : | C3H3N3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YOXIXLVJYMCCIB-UHFFFAOYSA-N |
M.W : | 129.07 | Pubchem ID : | 547454 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 25.66 |
TPSA : | 102.24 Ų |
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) : | -7.22 cm/s |
Log Po/w (iLOGP) : | 0.44 |
Log Po/w (XLOGP3) : | -0.19 |
Log Po/w (WLOGP) : | -0.64 |
Log Po/w (MLOGP) : | -1.42 |
Log Po/w (SILICOS-IT) : | -0.57 |
Consensus Log Po/w : | -0.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.87 |
Solubility : | 17.6 mg/ml ; 0.136 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.5 |
Solubility : | 4.07 mg/ml ; 0.0315 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.16 |
Solubility : | 185.0 mg/ml ; 1.44 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.3 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: With phosphoric acid; sodium nitrite In ethanol; water at 10 - 15℃; for 12 h; Stage #2: With hydroxylamine hydrochloride; potassium hydroxide; sodium hydroxide In ethanol; water at 20 - 95℃; for 2 h; |
To a stirred suspension of ethyl cyanoacetate (28.3 g, 0.25 mol, 1 eq.) and sodium nitrite (17.3 g, 0.25 mol, 1.0 eq.) in a mixture of EtOH (17 mL) and water (200 mL) was added dropwise 85percent H3PO4 (10 mL) at 10-15 °C and stirred for 12 h. Afterwards the reaction mixture was treated with NaOH (4*10 g, 1 mol, 4 eq.) and KOH (2*14 g, 0.5 mol, 2.0 eq.). To the resulting solution NH2OH·HCl (69.5 g, 1.0 mol, 4.0 eq.) was slowly added at room temperature and heated upto 95 °C, stirred for 2 h, cooled to ambient temperature and quenched with conc. HCl to pH 1. Precipitation occurred on cooling to 0 °C for 12 h and the precipitate was collected by filtration and dried. The filtrate was extracted with diethyl ether (3x30 mL). The combined organic extracts were evaporated under reduced pressure. The residue was combined with the precipitate and recrystallized from hot water to give compound (4) (21.3 g, 0.165 mol, 66percent) as white solid.1H-NMR (300 MHz, DMSO-d6): δ=9.69 (br s, 1 H, H-1), 6.24 (s, 2H, H-5) ppm. 13C-NMR (75 MHz, DMSO-d6): δ = 162.5 (C-2), 157.1 (C-3), 144.9 (C-4) ppm. HRMS: (ESI): C3H3N3O3 [M], 129.0174 Da. calcd m/z 128.0096 [M-H]-, found m/z 128.0106 [M-H]-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With thionyl chloride In ethanol at 0℃; for 4 h; Heating / reflux | To a solution of 4-amino-1,2, 5- oxadiazole-3-carboxylic acid (0.25g, 1.9 mmol) in 2 mL OF ETOH was added SOC12 (0.2 mL) dropwise, under cooling with an ice-bath. The resulting mixture was refluxed for 4 hours and then concentrated. The oil was diluted with 50 mL OF H20 and extracted with diethyl ether (3X100 mL). The combined organic layer was dried over MgS04 and concentrated to give a white solid (0. 15g, 50percent). IH NMR (DMSO, 500 MHZ) B 6. 39 (s, 2H), 4.39 (q, 2H), 1. 35 (t, 3H). Mass Spec. FIA MS 158. 1 (M+1). |
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