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CAS No. : | 189281-66-1 | MDL No. : | MFCD02180634 |
Formula : | C7H4Cl2FNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WADLLLSMEPLCNO-UHFFFAOYSA-N |
M.W : | 224.02 | Pubchem ID : | 2775354 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.49 |
TPSA : | 39.19 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.73 cm/s |
Log Po/w (iLOGP) : | 2.02 |
Log Po/w (XLOGP3) : | 2.73 |
Log Po/w (WLOGP) : | 2.73 |
Log Po/w (MLOGP) : | 1.94 |
Log Po/w (SILICOS-IT) : | 2.94 |
Consensus Log Po/w : | 2.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.16 |
Solubility : | 0.156 mg/ml ; 0.000694 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.21 |
Solubility : | 0.139 mg/ml ; 0.000621 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.62 |
Solubility : | 0.0537 mg/ml ; 0.00024 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.98 |
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: |
* 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 |
---|---|---|
93.8% | at 0 - 20℃; for 5 h; Inert atmosphere | [0199] To a solution of 2,6-dichloro-5-fluoronicotinic acid(16) (5 g, 23.8 mmol) in methanol (50 ml) was added thionylchlorideindropwise (5.66 g, 47.62mmol) at oo C. and2 dropsofDMF [ vigourous bubbling was observed]. The mixture wasstirred at room temperature for 3 h. To this methanol wasadded and stirred the reaction mixture for 2 h at RT. Thereaction mixture is concentrated under reduced pressure toand the mixture was poured in to ice cold water (20 mL) andextracted with dichloromethane (2x50 mL). The combinedorganic layer was washed with water, brine and solvent wasevaporated under reduced pressure to yield methyl 2,6-dichloro-5-fluoronicotinate (17) (5 g, 93.8percent). |
67% | With hydrogenchloride In water at 70℃; for 2 h; | [00668] Intermediate 73a: methyl 2,6-dichloro-5-fluoro-pyridine-3-carboxylate[00669] Conc. HCI (0.75mL, 11 .91 mmol) was slowly added to a stirring solution of 2,6-dichloro-5- fluoronicotinic acid (2.5g, 11 .91 mmol) in MeOH (1 5mL). The reaction mixture was heated to 70 °C and left to stir for 2 hours. The reaction mixture was allowed to cool before being quenched by the addition of water (2OmL) and extracted with EtOAc (3 x 2OmL). The organic fractions werecollected, dried (Na2504), filtered and reduced in vacuo to afford the desired product methyl 2,6- dichloro-5-fluoro-pyridine-3-carboxylate (1 .80g, 8.O3mmol, 67percent yield) as a yellow solid. MS Method 2: RT: 1 .69 mi 223.8m/z [M+H] |
6 g | Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1 h; Stage #2: at 20℃; for 1 h; |
At room temperature,In the presence of 2,6-dichloro-5-fluoronicotinic acid (5g) and one drop of DMF and DCM (20mL) the mixture was added with oxalyl chloride (5mL).The mixture was stirred at room temperature for 1 hour and then concentrated. The resulting wake base was re-dissolved in DCM (10 mL)And then added dropwise to a mixture of DCM (20 mL) and ΜeΟΗ (20 mL). The resulting mixture was stirred at room temperature for 1 hour and then concentrated to give the title compound (6 g) as an oil. |
22.2 g | at 20 - 60℃; for 24.5 h; | Concentrated sulfuric acid (5 ml) was added to a methanol (50 ml) solution containing 2,6-dichloro-5-fluoronicotinic acid (25.0 g), followed by stirring at 50°C to 60°C for 6 hours and 30 minutes. The resulting solution was left at rest at room temperature for 15 hours. Concentrated sulfuric acid (5 ml) was added, followed by stirring at 50°C to 60°C for 3 hours. The reaction mixture was cooled to room temperature, neutralized with a 2N sodium hydroxide aqueous solution under ice cooling, and basified with sodium hydrogen carbonate, following which ethyl acetate was added. The organic layer was collected, washed with water and then with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and colorless oily matter of methyl 2,6-dichloro-5-fluoronicotinate (22.2 g) was thus obtained. 1H-NMR (CDCl3, 400MHz) 8:8.02 (d, 1H, J = 7.3Hz), 3.98 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6 g | at 20℃; for 1 h; | To a mixture of 2 6-dichloro-5-fluoronicotinic acid (5 g) and one drop of DMF in DCM (20 mL) was added dropwise oxalyl chloride (5 mL) at RT. The mixture was stirred at RT for 1 hour and then concentrated. The resulting acyl chloride was again dissolved in DCM (10 mL) and then added dropwise to a mixture of DCM (20 mL) and MeOH (20 mL) . The resulting mixture was stirred at RT for another 1 hour and then concentrated to afford the title compound (6 g) as an oil. MS (ESI) C7H4Cl2FNO2requires 223 found 224 [M+H]+. |
6 g | at 20℃; for 1 h; | To a mixture of 2,6-dichloro-5-fluoronicotinic acid (5 g) and one drop of DMF in DCM (20 mL) was added dropwise oxalyl chloride (5 mL) at RT. The mixture was stirred at RT for 1 hour, andthen concentrated. The resulting acyl chloride was again dissolved in DCM (10 mL), and then added dropwise to a mixture of DCM (20 mL) and MeOH (20 mL). The resulting mixture was stirred at RT for another 1 hour, and then concentrated to afford the title compound (6 g) as oil. MS (ESI): C7H4C12FNO2 requires 223; found 224 [M+H]. |
6 g | at 20℃; for 1 h; | Description 110Methyl 2,6-dichloro-5-fluoronicotinate (DuO)To a mixture of 2,6-dichloro-5-fluoronicotinic acid (5 g) and one drop of DMF in DCM (20 mL), oxalyl chloride (5 mL) was added dropwise at RT. The mixture was stirred at RT for 1 hour, and then concentrated. The resulting acyl chloride was re-dissolved in DCM (10 mL), and then addeddropwise to a mixture of DCM (20 mL) and MeOH (20 mL). The resulting mixture was stirred atRT for another 1 hour, and then concentrated to afford the title compound (6 g) as pale yellow oil.MS (ESI): C711.4C12FN02 requires 223; found 224 IM+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | at 20℃; for 1 h; | [00670] Intermediate 73b: methyl 2-chloro-5-fluoro-6-methoxy-pyridine-3-carboxylate[00671] Sodium methoxide (1 .86mL, 11.91 mmol) was added to methyl 2,6-dichloro-5-fluoro-pyridine-3-carboxylate (1 .8g, 8.O3mmol) in Methanol (9mL) and the resultant mixture was left to stir for 1 hour. To the mixture was added EtOAc (20 mL) and water (20 mL), the layers were separated and the organ ics extracted using EtOAc (3 x 20 mL). Organic fractions were collected, dried (Na2SO4), filtered and reduced in vacuo to afford the desired product methyl 2-chloro-5-fluoro-6- methoxy-pyridine-3-carboxylate (1 .72g, 7.83mmol, 97percent yield) as an orange solid.1H NMR (CDCI3,400MHZ) Olppm: 7.92 (1H, d, J= 9.6 Hz), 4.09 (3H, 5), 3.92 (3H, 5). MS Method 2: RT: 1.71 mm, 220.0 mlz [M+H] |
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