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CAS No. : | 885519-72-2 | MDL No. : | MFCD07781390 |
Formula : | C9H7ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SBYBKVQDMAREOM-UHFFFAOYSA-N |
M.W : | 210.62 | Pubchem ID : | 24728139 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.38 |
TPSA : | 54.98 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) : | -6.14 cm/s |
Log Po/w (iLOGP) : | 0.64 |
Log Po/w (XLOGP3) : | 2.03 |
Log Po/w (WLOGP) : | 2.0 |
Log Po/w (MLOGP) : | 1.61 |
Log Po/w (SILICOS-IT) : | 2.47 |
Consensus Log Po/w : | 1.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.77 |
Solubility : | 0.359 mg/ml ; 0.0017 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.81 |
Solubility : | 0.324 mg/ml ; 0.00154 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.61 |
Solubility : | 0.0517 mg/ml ; 0.000245 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.76 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
45% | a) Methyl 6-chloro-l-(l-methylethyl)-l/f-indazole-4-carboxylateMethyl 6-chloro-lH-indazole-4-carboxylate (0.4 lOg, 1.947 mmol) was dissolved in DMF (10 mL) and placed into an ice bath and stirred for 15 min. Sodium hydride (0.101 g, 2.53 mmol) was added, the contents stirred for 15 min., and then 2-iodopropane (0.389 mL, 3.89 mmol) was added. The contents were stirred with warming to RT. After stirring at RT for 2h, a scoop of sodium carbonate and then 0.4 mL of methyl iodide were added. After stirring at RT for an additional lh, the reaction mixture was diluted with saturated NH4CI and then extracted with EtOAc (2x). The combined organic layers were washed with brine, dried over MgS04, filtered, and concentrated in vacuo. The crude residue was dissolved in a minimal amount of DCM and purified by silica gel chromatography (eluent: 3-20% ethyl acetate in hexanes). The title compound was the less polar of the two products separated from chromatography, and was collected as 0.22g (45% yield). ¾ NMR (400 MHz, DMSO-i/6) delta ppm 1.45 - 1.52 (m, 6 H), 3.93 - 3.99 (m, 3 H), 5.11 (quin, J=6.57 Hz, 1 H), 7.73 (d, J=1.77 Hz, 1 H), 8.30 (s, 1 H), 8.42 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | a) Methyl 6-chloro-l-cyclopentyl-l /-indazole-4-carboxylateMethyl 6-chloro-l-cyclopentyl- lH-indazole-4-carboxylate (2.1g, 9.97 mmol) was suspended in DMF(40 mL), placed into an ice bath, and stirred for 15 min. Next added sodium hydride (0.997 g, 24.93 mmol) slowly over 5 min (gas evolution) and stirred for 15 min. Bromocyclopentane (3.21 mL, 29.9 mmol) was added at once via syringe, and the mixture allowed to stir with warming to RT. After 15 min stirring at RT, the contents were stirred with heating at 45 C for 16h. The contents were cooled to RT, and then 0.5g sodium carbonate and 1 mL of iodomethane were added. The contents were stirred at RT for 3h, after which time the mixture was poured onto 400 mL of ice/water with stirring. After 5 min stirring, the contents were extracted with ether (2xl00mL). The combined organic layers were concentrated in vacuo. The crude product was purified by silica gel chromatography (eluent : gradient 3-25% EtOAc in hexanes) The first product off the column was determined to be the desired Nl -substituted isomer, and was collected after drying (vacuum pump, lh) as an orange solid (1.1 1 g, 39%). H NMR (400 MHz, DMSO-c 6) delta ppm 1.64 - 1.74 (m, 2 H), 1.82 - 1.93 (m, 2 H), 1.94 - 2.04 (m, 2 H), 2.09 - 2.19 (m, 2 H), 3.96 (s, 3 H), 5.27 (t, J=7.07 Hz, 1 H), 7.72 (d, J=1.77 Hz, 1H), 8.28 (s, 1 H), 8.40 (s, 1 H); LC-MS (ES) m/z = 278.7 [M+H]+ |
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