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CAS No. : | 5622-34-4 | MDL No. : | MFCD07776794 |
Formula : | C11H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CFVILHFXMRQYSG-UHFFFAOYSA-N |
M.W : | 187.19 | Pubchem ID : | 11788709 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.09 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 53.29 |
TPSA : | 50.19 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) : | -6.26 cm/s |
Log Po/w (iLOGP) : | 1.33 |
Log Po/w (XLOGP3) : | 1.67 |
Log Po/w (WLOGP) : | 1.86 |
Log Po/w (MLOGP) : | 1.36 |
Log Po/w (SILICOS-IT) : | 2.15 |
Consensus Log Po/w : | 1.68 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.45 |
Solubility : | 0.665 mg/ml ; 0.00355 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.34 |
Solubility : | 0.859 mg/ml ; 0.00459 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.48 |
Solubility : | 0.062 mg/ml ; 0.000331 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.27 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P264-P270-P301+P310+P330-P405-P501 | UN#: | 2811 |
Hazard Statements: | H301 | Packing Group: | Ⅲ |
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 |
---|---|---|
51% | Stage #1: With sulfuric acid; iron(II) sulfate In nitrobenzene at 200℃; for 5 h; Stage #2: With sodium hydroxide In water; nitrobenzene |
N-((4-chloro-2-methylp yl)quinolin-6-yl)acetamidea) 2-(quinolin-6-yl)acetic acidA mixture of / aminophenylacetic acid (20 g, 0.132 mol), FeSC>4 (4.9 g, 0.032 mol), glycerol (51 g, 0.555 mol), PhN02 (10.5 g, 0.086 mol), and concentrated H2S04 (23 mL) was heated to 200 °C for 5 h. The reaction mixture was treated with 4 N aq. NaOH to adjust the pH to -10. The reaction mixture was filtered and the clear filtrate was acidified with AcOH to pH~5. The resultant precipitate was collected by filtration to afford the title compound (12.5 g, 51percent) as a brown solid. TLC: 20percent MeOH/CH2Cl2, Rf= 0.2.H NMR (300 MHz, DMSO-d6) 8 ppm 8.85 (m, 1H), 8.31 - 8.28 (m, 1H), 7.96 (d, J= 8.3 Hz, 1H), 7.82 (m, 1H), 7.67 - 7.64 (m, 1H), 7.50 - 7.49 (m, 1H), 3.78 (s, 2H). |
17.8% | Stage #1: With sulfuric acid; iron(II) sulfate In nitrobenzene for 5 h; Heating / reflux Stage #2: With sodium hydroxide In water; nitrobenzene |
A mixture of compound 1 (276 g, 1.8 mol), ferrous sulfate (63.6 g, 0.22 mol), glycerol (696 g, 7.56 mol), nitrobenzene (138 g, 1.12 mol) and cone, sulfuric acid (324 mL) was heated gently. After the first vigorous reaction, the mixture was refluxed for five hours and then was treated with aq. sodium hydroxide solution (2 N, 1320 mL), stirred with kieselguhr, and filtered. The filtrate was basified with aq. sodium hydroxide solution to pH 5~6, and a dark brown precipitate formed. The precipitate was filtered, washed with water, taken up with aq. sodium hydroxide solution (0.82 N, 3000 mL), then boiled with carbon (150 g). The mixture was filtered and the filtrate was treated with glacial acetic acid (240 mL), and the mixture was left standing overnight during which time dark-brown crystalline precipitate formed. The precipitate was collected and dried in vacuo to give crude compound 2 (60 g, 17.8percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: Reflux Stage #2: With sodium hydroxide In ethyl acetateCooling with ice |
Example 1. Preparation of 6-((5)-l-(6-(l-methyl-lH-pyrazol-4-yl)-[l,2,4]triazolo[3,4- δ][l,3,4]thiadiazol-3-yl)ethyl)quinoline (compound 1); [0064] As shown in step i of Scheme 1, concentrated sulfuric acid (206 mL, 3.868 mol) was added dropwise to a solution of 2-(quinolin-6-yl)acetic acid (compound 1001, 658.2 g, 3.516 mol, Okeanos Tech Co., Cat. No. OK-J-05024) in 6.5 liters of methanol. During the addition, a slight exotherm was observed. After the addition was complete, the reaction was stirred at reflux for 4 hours. After cooling, the volatiles were removed under reduced pressure, the resulting residue was diluted with 4 liters of ethyl acetate, cooled in an ice bath, treated with 2N NaOH (2.1 liters, 1.2 equiv.) until a pH of 4 was achieved, and then treated with saturated sodium bicarbonate until a pH of 8 was achieved. The layers were separated and the aqueous layer extracted twice with ethyl acetate. The combined organics were washed with saturated sodium bicarbonate, washed with water, washed with brine, dried over anhydrous MgSO4, filtered, and evaporated under reduced pressure to afford methyl 2-(quinolin-6-yl)acetate as a clear brown oil (compound 1002, 696.8 g, 98 percent yield): ESMS (M+l), 202.14; 1H NMR (300.0 MHz, DMSO-d6) δ 8.90 (IH, dd, J = 1.7, 4.2 Hz), 8.14 - 8.10 (IH, m), 8.08 (IH, d, J = 8.7 Hz), 7.72 (IH, d, J = 1.4 Hz), 7.65 (IH, dd, J = 2.0, 8.7 Hz), 7.40 (IH, dd, J = 4.2, 8.3 Hz), 3.83 (2H, s), 3.73 (3H, s). |
85% | at 20℃; for 6 h; | To a solution of 2-(quinolin-6-yl)acetic acid (2.0 g, 11 mmol) in methanol (40 mL) wasadded concentrated sulphuric acid (0.2 mL). The mixture was stirred at roomtemperature for 6 hours. The reaction mass was poured into water and the resulting solution was neutralised with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2504 and evaporated in vacuo to give methyl 2-(quinolin-6-yl)acetate (1.8 g, 85percent). LCMS: m/z202.25 [M+H]. |
76% | With thionyl chloride In methanol at 0℃; for 2 h; Reflux | 2-(quinolin-6-yl)acetic acid (12.0 g, 0.064 mol) was dissolved in dry MeOH (120 mL) and cooled to 0 °C. SOCl2 (7.0 mL, 0.096 mol) was added, and the reaction mixture was refluxed for 2 h. The reaction mixture was concentrated under reduced pressure and the resultant residue was dissolved in EtOAc, washed with water and brine, dried over anhydrous Na2SO/t, filtered, and concentrated under reduced pressure. The resultant residue was purified by columnchromatography (20 - 25percent EtOAc/petroleum ether) to afford the title compound (9.8 g, 76percent).TLC: 20percent MeOH/CH2Cl2, Rf= 0.6. lU NMR (300 MHz, DMSO-d6) δ ppm 8.86 (dd, J= 4.3, 1.6 Hz, 1H), 8.32 - 8.29 (m, 1H), 7.97 (d, J= 8.6 Hz, 1H), 7.84 (m, 1H), 7.66 (dd, J= 8.8, 2.0 Hz, 1H), 7.50 (dd, J= 8.2, 4.3 Hz, 1H), 3.90 (s, 2H), 3.63 (s, 3H). |
73.6% | for 3 h; Heating / reflux | To a stirred solution of quinolin-6-yl-acetic acid (10 g, 53.0 mmol) in 100 ml of methanol was added 2.5 ml of concentrated H2SO4 The mixture was then heated to reflux for 3 hours. The reaction mixture was concentrated to give a brown residue, which was diluted with 100 ml of dichloromethane, washed with sat. aq.NaHCO3 and brine, then the organic layer was dried over anhydrous Na2Sψ4 and concentrated to return title compound as a brown oil (7.9 g, 73.6percent). |
72.6% | Stage #1: at 0 - 5℃; for 2 h; Heating / reflux Stage #2: With sodium hydrogencarbonate In water; ethyl acetate |
To a suspension of compound 2 (60 g, 0.32 mol) in MeOH (600 mL) cooled to 0~5°C, SOCI2 (30 mL, 0.35 mol) was added dropwise. After the mixture was heated to reflux for 2 h, the mixture was evaporated under reduced pressure, and the residue was taken up with EtOAc (600 mL). The mixture was washed with aq. NaHCO3 and brine, dried over Na2SO4 and concentrated to give crude product, which was purified via a silica column chromatography (EtOAc: Petroleum ether = 1 :5) to give pure compound 3 (50 g, 72.6percent) as a yellow oil. 1H NMR (400 MHz, CDCI3): δ 8.898-8.878 (dd, 1 H), 8.130-8.055 (m, 2H), <n="31"/>7.718 (s, 1 H), 7.670-7.634 (dd, 1 H), 7.407-7.365 (q, 1 H), 4.207-4.135(q, 2 H), 3.799(s, 2H), 1.279-1.232 (t, 3H). |
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