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CAS No. : | 190271-88-6 | MDL No. : | MFCD07368888 |
Formula : | C7H5ClN2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IPSMDDVNXJKYRH-UHFFFAOYSA-N |
M.W : | 216.58 | Pubchem ID : | 18922458 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 49.35 |
TPSA : | 85.01 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.56 cm/s |
Log Po/w (iLOGP) : | 1.33 |
Log Po/w (XLOGP3) : | 1.5 |
Log Po/w (WLOGP) : | 1.43 |
Log Po/w (MLOGP) : | -0.1 |
Log Po/w (SILICOS-IT) : | -0.25 |
Consensus Log Po/w : | 0.78 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.25 |
Solubility : | 1.23 mg/ml ; 0.00566 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.89 |
Solubility : | 0.277 mg/ml ; 0.00128 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.11 |
Solubility : | 1.7 mg/ml ; 0.00783 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.11 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
99% | With thionyl chloride In DMF (N,N-dimethyl-formamide)Heating / reflux | The third step of Scheme 4: To a 25 mL thionyl chloride suspension of 5-nitro-2-hydroxynicotinic acid methyl ester (4.62 g, 23.3 mmole) was added 1 mL DMF and the mixture heated to reflux until the reaction was complete as judged by TLC. The thionyl chloride was evaporated under reduced pressure and azeotroped twice with toluene. The resulting yellow semi-solid was cooled in an ice bath and treated with 50 mL MeOH. It was stirred for 20 minutes and then poured into 200 mL water, extracted with EtOAc (2*150 mL) and the combined organics washed with dilute aqueous NaOH, water, brine and dried over MgSO4. 5.03 g (99percent) of 2-chloro-5-nitronicotinic acid methyl ester was obtained as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-D) 8 ppm 4.04 (s, 3H) 8.94 (d, J=2.78 Hz, 1H) 9.33 (d, J=2.78 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: at 100℃; for 3 h; Stage #2: at 0℃; |
2-Hydroxy-5-nitronicotinic acid (29 g; 0.16 moles) was added portionwise to phosphorus oxychloride (90 ml) with stirring. The temperature was raised to 100 0C and heating continued for 3 hours before cooling to room temperature. The bulk of the solvent was removed before adding to ice-cold methanol (100 ml). The mixture was basified to pH 9 with saturated sodium bicarbonate solution and extracted with dichloromethane. The organic phase was dried (sodium sulphate), filtered and evaporated before purification by dry flash chromatography on silica gel. Methyl 2- chloro-5-nitronicotinate was eluted with 67percent ethyl acetate in heptane (31 g, 90percent). |
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