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CAS No. : | 54664-55-0 | MDL No. : | MFCD11113078 |
Formula : | C8H8ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IGDLNAWHTASKKG-UHFFFAOYSA-N |
M.W : | 153.61 | Pubchem ID : | 12203327 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.38 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.87 |
TPSA : | 12.89 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) : | -5.7 cm/s |
Log Po/w (iLOGP) : | 1.97 |
Log Po/w (XLOGP3) : | 2.17 |
Log Po/w (WLOGP) : | 2.22 |
Log Po/w (MLOGP) : | 2.06 |
Log Po/w (SILICOS-IT) : | 3.25 |
Consensus Log Po/w : | 2.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.6 |
Solubility : | 0.383 mg/ml ; 0.00249 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.07 |
Solubility : | 1.3 mg/ml ; 0.00844 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.45 |
Solubility : | 0.054 mg/ml ; 0.000352 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.89 |
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 |
---|---|---|
93% | at 120℃; for 3 h; | 6,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with phosphoryl chloride (20 mL, 200 mmol). The reaction mixture was stirred at 120° C. for 3 h. The excess POCl3 was removed under reduced pressure. The residue was diluted in 80 mL of EtOAc and neutralized with Na2CO3 solution. After filtration, the aqueous layer was extracted with EtOAc twice. The combined organic extracts were dried, filtered and concentrated under reduced pressure to give the sub-title compound (2.6 g, 93percent). LCMS calc. for C8H9ClN (M+H)+: m/z=154.2. Found: 154.3 |
93% | at 120℃; for 3 h; | 6,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with POCl3 (20 mL). The reaction mixture was stirred at 120° C. for 3 h. The excess POCl3 was removed under reduced pressure. The residue was diluted in EtOAc (80 mL) and neutralized with aq. Na2CO3. After filtration, the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried, filtered and concentrated under reduced pressure to give the sub-title compound (2.6 g, 93percent). LCMS calc. for C8H9ClN (M+H)+: m/z=154.0. Found: 154.3. |
93% | at 120℃; for 3 h; | 6,7-Dihydro-5H-cyclopenta[Z>]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with POCh (20 mL). The reaction mixture was stirred at 120 °C for 3 h. The excess POCh was removed under reduced pressure. The residue was dissolved in EtOAc (80 mL) and neutralized with aq. Na2C03. After filtration, the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried, filtered and concentrated under reduced pressure to give the sub-title compound (2.6 g, 93percent). LCMS calc. for CsHoClN (M+H)+: m/z = 154.0. Found: 154.3. |
91% | Stage #1: With lithium chloride In acetonitrile at 20℃; for 0.166667 h; Stage #2: With trichlorophosphate In water; acetonitrile at 20 - 80℃; Stage #3: With sodium carbonate In water; acetonitrile at 20℃; for 0.666667 h; |
b- :1.) .Preparation of .mtermediate.b A solution of 49.5g intermediate a (0.366mol), 15.5g lithiumchloride (LiCl) (leq) and 495mL acetonitrile (lOmL/g) was prepared and stirred for 10 minutes at ambient temperature. 102mL phosphoroxychloride (POCI3) (3eq) was added dropwise to the reaction mixture. The reaction mixture was heated to 800C and stirred for one night. The reaction mixture was cooled to 450C and 75OmL H2O (15mL/g) was added dropwise, while keeping the temperature between 400C and 500C, over lhour. The reaction mixture was cooled to ambient temperature and stirred for 2 hours at ambient temperature. 213g Na2CO3 (5.5eq) was added and stirred for 30 minutes at ambient temperature. Further Na2CO3 was added and stirring for 10 minutes at ambient temperature. 75OmL dsopropylether (DIPE) (15mL/g) was added and 50OmL H2O (lOmL/g). The mixture was stirred for 10 minutes at ambient temperature. The reaction mixture was filtered over dicalite. The layers were separated. The organic layer was dried with MgSO4. MgSO4 was filtered off. The filtrate was concentrated under reduced pressure. Yield: 5 Ig (91percent) (brown oil) of intermediate b. |
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