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CAS No. : | 82241-22-3 | MDL No. : | MFCD01935745 |
Formula : | C14H17N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XYBLCORUTWKJOI-UHFFFAOYSA-N |
M.W : | 227.30 | Pubchem ID : | 702318 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 78.07 |
TPSA : | 28.16 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.05 cm/s |
Log Po/w (iLOGP) : | 2.4 |
Log Po/w (XLOGP3) : | 2.31 |
Log Po/w (WLOGP) : | 1.19 |
Log Po/w (MLOGP) : | 1.72 |
Log Po/w (SILICOS-IT) : | 2.58 |
Consensus Log Po/w : | 2.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.07 |
Solubility : | 0.192 mg/ml ; 0.000844 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.54 |
Solubility : | 0.656 mg/ml ; 0.00289 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.59 |
Solubility : | 0.00582 mg/ml ; 0.0000256 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.8 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
With triethylamine; In dichloromethane;Cooling with ice; | Step C: 2-Methyl-4-(4-methylsulfonylpiperazin-1-yl)quinoline2-Methyl-4-piperazin-1-yl-quinoline (227.3 mg, 1 mmol) was dissolved in anhydrous dichloromethane (7 ml), triethylamine was added (209 muIota, 1.5 mmol), followed by methanesulfonyl chloride (85 muIota, 1.1 mmol) which was added dropwise with ice-cooling. The mixture was diluted with dichloromethane and washed with 5% sodium bicarbonate solution. The wash solution was extracted with dichloromethane, the organic phases were combined and washed with 5% sodium bicarbonate solution, water and dried over magnesium sulfate. After evaporation of the solvent under reduced pressure 265 mg of a white foam were obtained (0.87 mmol, 87%) which was used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 2-ethoxy-ethanol; at 140℃; | Step B: 2-Methyl-4-piperazin-1-yl-quinoline4- Chloro-2-methylquinoline (1.8 g, 10 mmol) and anhydrous piperazine (5.25 g, 60 mmol) were dissolved in ethyleneglycol monoethylether (15 ml) and stirred at 140C overnight. The mixture was concentrated under reduced pressure, toluene was added (2 x 100 ml) and the solvent removed under reduced pressure. To the residue was was added 0.5 M NaOH (100 ml) and the mixture was extracted with a mixture of dichloromethane / diethylether / ethyl acetate (1 : 1 : 1 , 3 x 100 ml). The combined organic phases were washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure. 2.78 g of an off-white solid (8.5 mmol, 85%) were obtained that were used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine; In dichloromethane; for 0.25h; | Step A: (£)-1-[4-(2-Methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one2-Methyl-4-piperazin-1-yl-quinoline (1 13.7 mg, 0.5 mmol) was dissolved in anhydrous dichloromethane (1 ml), TEA (77 muIota, 0.5 mmol) followed by (£)-pent-2-enoyl chloride (65 mg, 0.55 mmol dissolved in 1 ml anhydrous dichloromethane) were added and the mixture was shaken for 15 minutes. The mixture was diluted with dichloromethane, washed with 5% sodium bicarbonate solution and water and the organic phase was evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1 % NH3 and acetonitrile) to yield 143 mg of a solid (0.44 mmol, 88%). MS (ES): m/z = 354.2 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Example 17: Synthesis of (£)-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]oct-2-en-1-one (A- 14)(£)-Oct-2-enoic acid (71.1 mg, 0.5 mmol) was dissolved in dichloromethane (1 ml) and a 2M solution of oxalyl chloride in dichloromethane was added (0.3 ml, 0.6 mmol). The solution was stirred at room temperature for one hour after which a drop of DMF was added. Stirring was continued for another hour, the mixture was evaporated to dryness under reduced pressure. The residue was dissolved in dichloromethane (1 ml), the resulting solution was added to a solution of <strong>[82241-22-3]2-methyl-4-piperazin-1-yl-quinoline</strong> (103 mg, 0.45 mmol) and triethylamine (90muIota, 0.64 mmol) in dichloromethane (1 ml). The resulting mixture was stirred at room temperature overnight, diluted with dichloromethane (1 ml), washed with water and 2M NaOH (2 ml each) and evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1 % ammonia and acetonitrile) to yield 121.3 mg of a solid (0.34 mmol, 77%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Step C: (£)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one (A-178) (£)-4-Hydroxypent-2-enoic acid (67 mg, 0.52 mmol) was dissolved in anhydrous DMF (2.5 ml), DCC (107.5, 0.52 mmol) and HOAt (106.7 mg, 0.79 mmol) were added and the mixture was stirred at room temperature for 15 minutes. 2-Methyl-4-piperazin-1-yl- quinoline (118.2 mg, 0.52 mmol) was added and stirring was continued for 90 minutes. The mixture was evaporated to dryness, taken up in a mixture of acetonitrile and methanol and filtered. The filtrate was evaporated to dryness again and purified by preparative HPLC (gradient of water containing 0.1 % TFA and acetonitrile). 1 10 mg were obtained (0.33 mmol, 65%). MS (ES): m/z = 326.1 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Step B: 2-Methyl-4-piperazin-1-yl-quinolineTo te/f-butyl 4-(2-methyl-4-quinolyl)piperazine-1-carboxylate (4.382 g, 13.38 mmol) was added 40 ml of a 1 : 1 mixture of dichloromethane and trifluoroacetic acid. The mixture was stirred at room temperature for 15 minutes. The mixture was evaporated to dryness under reduced pressure and the residue dissolved in dichloromethane. The solution was washed with 5% sodium bicarbonate solution and 3M NaOH was added until the aqueous phase remained basic. The phases were separated, the aqueous phase was extracted twice with dichloromethane, the combined organic phases were washed with saturated sodium carbonate solution, water, dried over magnesium sulfate and evaporated to dryness. 2.1 g of a solid were obtained (9.25 mmol, 69%). MS (APCI): m/z = 227.8 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a solution of 7a (450 mg, 1.50 mmol), 1-(4-chloroisoquinolin-1-yl)piperazine (446 mg, 1.80 mmol) and acetic acid (0.090 mL, 1.6 mmol) in 1,2-dichloroethane (8 mL) was added sodium triacetoxyborohydride (636 mg, 3.00 mmol) and the mixture was stirred at room temperature for 3 h. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with brine, dried and concentrated under reduced pressure. The residue purified by silica gel chromatography with chloroform/methanol (50:1, v/v) to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(4-chloroisoquinolin-1-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine (596 mg, 75%) as a white powder.The above compound (592 mg, 1.11 mmol) was dissolved in 1.1 mol/L hydrogen chloride in methanol (10 mL), and the mixture was stirred at room temperature for 5 days. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized with ethanol to give the title compound (318 mg, 52%) as a pale-yellow powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.2973 g | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 20℃; | To a solution of triphosgene (0.099 g, 0.33 mmol, 0.33 eq) in CH2Cl2 (10 mL), was slowly added 4-hydroxybiphenyl (0.1702 g, 1 mmol, 1 eq) and N,N-diisopropylethylamine (DIEA) (176 muL, 0.130 g, 1 mmol, 1 eq) as a solution in THF (10 mL). The reaction was stirred at room temperature for 30 min to generate the intermediate chloroformate. In a separate flask containing CH2Cl2 (10 mL), 2-methyl-4- piperazinoquinoline (0.3410 g, 1.5 mmol, 1.5 eq) was mixed with DIEA (263 muL, 0.195 g, 1.5 mmol, 1.5 eq). The mixture was stirred for 5 min at room temperature and then dropped into the flask containing the chloroformate. The reaction mixture was stirred at room temperature for another 30 min and partitioned between CH2Cl2 (50 mL) and saturated NH4Cl (50 mL). The organic layer was washed one more time with saturated NH4Cl (30 mL), dried over MgSO4 and filtered. The solvent was removed by rotary evaporation and the product was purified by silica gel column chromatography (1:1 ethyl acetate/hexanes) to afford JMN4 (0.2973 g, 0.702 mmol, 70%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With triethylamine; In dichloromethane; at 0 - 20℃; | A solution of 2-methyl-4-(piperazin-1-yl)quinolone (455 mg, 2.0 mmol) in DCM (20 mL) was cooled to 0 C. To the solution was added acryloyl chloride (217 mg, 2.4 mmol) followed by triethylamine (243 mg, 2.4 mmol). The solution was allowed to warm to room temperature and stirred overnight. The solution was washed with brine and the crude product was purified via basic alumina chromatography (100% ethyl acetate) to afford the product in 26% yield as a yellow oil (145 mg).1H NMR (400MHz, CDCl3): d 7.90-8.05 (m, 2H), 7.58-7.70 (ddd, J = 8.4, 6.8, 1.5 Hz, 1H), 7.40-7.50 (ddd, J = 8.2, 6.8, 1.3 Hz, 1H), 6.68-6.76 (s, 1H), 6.56-6.67 (dd, J = 16.8, 10.5 Hz, 1H), 6.30-6.40 (dd, J = 16.8, 2.0 Hz, 1H), 5.70-5.80 (dd, J = 10.5, 2.0 Hz, 1H), 3.70-4.06 (d, J = 54.7 Hz, 4H), 3.10-3.30 (t, J = 5.0 Hz, 4H), 2.62-2.72 (s, 3H).13C NMR (100MHz, CDCl3): d 165.5, 159.4, 156.2, 149.2, 129.26, 129.24, 128.3, 127.3, 124.9, 123.0, 121.6, 109.8, 52.3, 51.9, 45.8, 42.0, 25.6. HRMS (+ESI): Calculated: 282.17 (C17H19N3O). Observed: 282.1597. |
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