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CAS No. : | 88912-26-9 | MDL No. : | MFCD00466640 |
Formula : | C6H3Cl2NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GFOVTTQVBDEYPP-UHFFFAOYSA-N |
M.W : | 192.00 | Pubchem ID : | 2736087 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.22 |
TPSA : | 50.19 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.07 cm/s |
Log Po/w (iLOGP) : | 1.18 |
Log Po/w (XLOGP3) : | 1.97 |
Log Po/w (WLOGP) : | 2.09 |
Log Po/w (MLOGP) : | 0.09 |
Log Po/w (SILICOS-IT) : | 2.04 |
Consensus Log Po/w : | 1.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.61 |
Solubility : | 0.472 mg/ml ; 0.00246 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.65 |
Solubility : | 0.43 mg/ml ; 0.00224 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.63 |
Solubility : | 0.446 mg/ml ; 0.00232 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.66 |
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: |
* 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 |
---|---|---|
87% | Stage #1: With n-butyllithium; N,N,N',N'',N'''-pentamethyldiethylenetriamine In tetrahydrofuran; hexane at -75℃; for 2 h; |
2,5-Dichloro-4-pyridinecarboxylic acid was prepared according to known procedures (see Eur. J. Org. Chem. 2001, 1371-1376), as follows: At -75 °C, 2,5-dichloropyridine (3.7 g, 25 mmol) was added to a solution of butyllithium (1.6M in hexane) (25 mmol) and N,N,N',N",N"- pentamethyldiethylenetriamine (5.3 mL, 4.3 g, 25 mmol) in tetrahydrofuran (50 mL). After 2 h at - 75 °C, the mixture was poured onto an excess of freshly crushed dry ice. Water (50 mL) was10 added, the aqueous phase decanted and washed with diethyl ether (3 x 20 mL) and neutralized with 5N HCl to pH 1. The precipitate was filtered and washed with water to give 2.7g of white solid as a pure product. The filtrate was extracted with ethyl acetate and the combined organic layers were evaporated to dryness. The residue was recrystallized from ethanol to give another batch of pure product. (The filtrate was evaporated to small volume and the precipitate was filtered and washed15 with water to give another batch of product); m.p. 227-229 °C (from ethanol); 4.2 g (87percent).[00294] 1H NMR (400MHz, DMSO-d6): a 14.43 (brs, 1H, exchangeable with D2O), 8.64 (s, 1 H), 7.87 (s, 1 H).[00295]2-(2,5-DicHoro-pyridke-4-carb.infin.yl)-3<(S)-1-hydroxymethyl-2-methyl-propylamino)- acrylic acid ethyl ester was synthesized using the same procedure described in example IA, (91 percent20 yield).[00296] 1H NMR (DMSO-d6, 400MHz): δ 10.94 (dd, J=9.6 and 13.8Hz, 1H, NH, exchangeable with D2O), 8.48 (s, 1H), 8.28 (d, J=14.3Hz,1H, it becomes singlet after D2O exchange), 7.51 (s, 1H), 5.07 (t, J=5.1Hz,1H, OH, exchangeable with D2O), 3.92 (q, J=7.0Hz, 2H), 3.62 (m, 2H), 3.40 (m, 1H), 1.95 (m, 1H), 0.94 (d, J=6.6Hz, 3H), 0.91 (d, J=6.6Hz, 3H), 0.89 (t, J=7.0Hz, 3H). MS:25 375, 377 (M+l). |
47% | Stage #1: With n-butyllithium; N,N,N',N'',N'''-pentamethyldiethylenetriamine In tetrahydrofuran at -78℃; for 2 h; Stage #2: at -78℃; |
2, 5-Dichloropyridine was added to a THF solution of n-BuLi and PMDTA and stirred for 2 hours at -780C before quenching with dry ice. The product was isolated by acid-base work-up in 47percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: for 12 h; Heating / reflux Stage #2: With sodium hydrogencarbonate In methanol; water |
To a methanolic solution of 2, 5-dichloro- isonicotinic acid was added H2SO4 (cone) (0.5 mL) and the solution was heated to reflux for 12 h. The mixture was cooled to room temperature, neutralized with aqueous NaHCO3, extracted into EtOAc and evaporated to afford the methyl ester (6-2) in 89percent yield. |
4.57 g | for 16 h; Reflux | To a solution of 2,5-dichloroisonicotinic acid (5.0 g, 18.47 mmol) in methanol (25 mL) was added cone. H2SO4 (0.2 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was concentrated and the residue was slowly poured onto ice and the precipitate obtained was filtered, washed with sat. NaHC03 and was extracted with CH2C12. The organic layer was separated, dried, filtered and concentrated to afford 4.57 g of the of the title product .1H NMR (300 MHz, DMSO d6): δ 8.69 (s, 1H), 7.92(s, 1H), 3.90 (s, 3H). |
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