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[ CAS No. 53951-84-1 ] {[proInfo.proName]}

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Chemical Structure| 53951-84-1
Chemical Structure| 53951-84-1
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Product Details of [ 53951-84-1 ]

CAS No. :53951-84-1 MDL No. :MFCD03550859
Formula : C11H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CWRATHCADZOYAT-UHFFFAOYSA-N
M.W : 187.20 Pubchem ID :257955
Synonyms :

Calculated chemistry of [ 53951-84-1 ]      Expand+

Physicochemical Properties

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 : 0.0
Molar Refractivity : 53.02
TPSA : 39.19 ?2

Pharmacokinetics

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) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 2.25
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 1.63
Log Po/w (SILICOS-IT) : 2.3
Consensus Log Po/w : 2.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.81
Solubility : 0.287 mg/ml ; 0.00153 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.366 mg/ml ; 0.00195 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.78
Solubility : 0.0312 mg/ml ; 0.000167 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.36

Safety of [ 53951-84-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53951-84-1 ]

* 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.

  • Downstream synthetic route of [ 53951-84-1 ]

[ 53951-84-1 ] Synthesis Path-Downstream   1~10

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YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; at 0 - 80℃; The solution of quinoline-3-carboxylic acid (3 g, 17.32 mmol) in methanol (30 mL) was cooled on ice bath at 0C.Then thionyl chloride (1.264 mL, 17.32 mmol) was added and the reaction mixture was heated to 80C and maintained overnight. Reaction was monitored by TLC. After completion of reaction methanol was evaporated under reduced pressure and the resultant residue was basified with saturated sodium bicarbonate to make pH (7 to 8) to get white solid which was filtered and dried to get methyl quinoline-3- carboxylate (3.2 g, yield-99%) as a white solid; m/z-187.3.
97% With thionyl chloride; at 0℃; for 24h;Reflux; Inert atmosphere; To a precooled (0 C) solution of quinoline-3-carboxylic acid (1.50 g, 8.66 mmol) in MeOH (43 mL) under N2 atmosphere was added dropwise thionyl chloride (1.3 mL, 17 mmol). The resulting mixture was heated to reflux and stirred for 24 h, then allowed to cool to room temperature and concentrated in vacuo. The resulting residue was taken up in CH2Cl2 and quenched with sat. aq. NaHCO3. The layers were separated, and the aqueous phase was extracted with CH2Cl2 (3x). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the product as an off-white solid (1.58 g, 97% yield). See, Chen, Org. Biomol. Chem.2016, 14 (24), 5505-5510. 1H NMR (500 MHz, Chloroform-d) d 9.43 (s, 1H), 8.82 (d, J = 2.0 Hz, 1H), 8.16 (d, J = 8.5 Hz, 1H), 7.94- 7.86 (m, 1H), 7.81 (ddd, J = 8.4, 6.9, 1.4 Hz, 1H), 7.60 (t, J = 7.5 Hz, 1H), 3.99 (s, 3H); 13C NMR (126 MHz, CDCl3) d 165.78, 149.83, 149.57, 139.07, 132.08, 129.33, 129.20, 127.64, 126.95, 123.12, 77.16, 52.59; IR (ATR) vmax 3509, 2994, 1714, 1618, 1572, 1497, 1434, 1367, 1290, 1241, 1192, 1100 cm-1; AMM 188.0704 (ESI) m/z [calc for C11H10NO2 (M+H)+ 188.0712].
89% With thionyl chloride; at 0℃; for 30h;Reflux; Quinoline-3-carboxylic acid (8 g, 46.2 mmol) was dissolved in methanol (900 mL), after which thionyl chloride (5 mL, 68.5 mmol)was added at 0 oC. The solution was kept at reflux, under stirring (10 h), monitoring the reaction progress by TLC (dichloromethane/methanol 9:1). An additional amount of thionyl chloride (5 mL) was added and the solution was kept at reflux (20 h). After cooling at room temperature, the solvent was evaporated at reduced pressure. To the residue water (400 mL) and 1 M sodium hydroxide (until pH 8) were added; the mixture was extracted with dichloromethane (4 x 400 mL). The collected organic phases were dried over sodium sulfate; after filtration, the solvent was removed at reduced pressure, to afford title compound 4 (7.78 g, 89%), which was used directly in the next step without any further purification. The chemical and physical properties were in agreement with the reported ones.22
89% With thionyl chloride; at 0℃; for 30h;Reflux; Quinoline-3-carboxylic acid (8 g, 46.2 mmol) was dissolved in methanol (900 mL); thionyl chloride (5 mL, 68.5 mmol) was added at 0 C. The solution was kept at reflux, under stirring (10 h), monitoring the reaction progress by TLC (dichloromethane/methanol 9:1). An additional amount of thionyl chloride (5 mL) was added and the solution was kept at reflux (20 h). After cooling at room temperature, the solvent was evaporated at reduced pressure. To the residue, water (400 ml) and 1M sodium hydroxide (until pH 8) were added; the mixture was extracted with dichloromethane (4*400 mL). The collected organic phases were dried over sodium sulfate; after filtration, the solvent was removed at reduced pressure, affording title compound 4 (7.78 g, 89%) directly used in the next step without any further purification.
75% With hydrogenchloride;Reflux; General procedure: To a suspension of the appropriate acid 17a-c (1 eq,) in MeOH (1.9 ml*mmol/eq) was added 1, 25 M HCl in MeOH solution (1.9 ml*mmol/eq). The solution was refluxed overnight, then cooled to room temperature and concentrated under vacuum. The residue was partitioned between sat. aq. NaHCO3 solution (30 ml) and EtOAc (3x35 ml). The combined organic extracts were washed with sat. aq. NaHCO3 solution (25 ml) and water (30 ml), dried over MgSO4 and concentrated under vacuum to give the pure title compounds.
74% With sulfuric acid;Reflux; Compound 3-Quinolinecarboxylic Acid (0801-131) (1.0 g, 5.78 mmol, 1.0 eq.)Dissolved in 30 ml of methanol,Then add sulfuric acid (0.5 ml),The reaction was refluxed overnight.After the reaction is completed, pH is adjusted to 8 by adding sodium bicarbonate solution.Dichloromethane extraction, liquid separation, the organic phase was dried over anhydrous sodium sulfate, spin-dry to give the product methyl 3-quinolinecarboxylate (800 mg,74%).
61% Quinoline-3-carboxylic acid (0.245 g, 1 .41 mmol) was charged in the flask with stir bar and thionyl chloride was added. The resulting mixture was allowed to stir at 80 C overnight. Upon completion, the reaction mixture was cooled to room temperature and concentrated in vacuo. MeOH was added to this crude mixture and was heated under reflux for 8 h. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and was washed with saturated aqueous NaHCO3. The aqueous layer was extracted with DCM twice, and the combined organic layers were dried with anhydrous Na2504. After removal of the solvents, the residue was purified by column chromatography on silica gel using EtOAc hexanes (1:6) as the eluentto give 4k (0.161 g, 61%). 1H NMR (600 MHz,CDCI3): O 9.46 (d, J= 2.1 Hz, 1H), 8.86 (d, J= 2.2 Hz, 1H), 8.17 (d, J= 8.5 Hz, 1H), 7.95 (d, J= 8.2 Hz, 1H), 7.84 (ddd, J= 8.5, 6.9, 1.4 Hz, 1H), 7.63 (ddd, J= 8.1, 6.9, 1.2 Hz, 1H), 4.03 (5, 3H). 1H NMR matches previously reported data8.
With thionyl chloride; at 0℃;Reflux; As depicted in Scheme 4-1, quinoline-3-carboxylic acid 3 was esterified with thionyl chloride in methanol to yield ester 4. Reduction of the pyridine ring of 4 with pyridine-borane complex in glacial acetic acid then delivered racemic THQ 5 whose methyl ester was saponified to yield ±-6. Alternatively, sulfonylation of ±-5 furnished compounds ±-7, which were also saponified with lithium hydroxide to afford the 3-carboxy target compounds ±-8. Further elaboration of the phenylsulfonyl group in ±-7c was accomplished by an SNAr reaction with 4- chloro-3,5-dimethylphenol followed by ester hydrolysis to afford compound ±-2, as shown in Scheme 4-2. In addition, the phenylsulfonyl moiety in ±-2 was replaced with a more flexible propylene group through a reductive amination-saponification sequence to yield ±-11.

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  • quinoline-3-carboxylic acid-(2-diethylamino-ethylamide) [ No CAS ]
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YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; 1,4-dioxane; methanol; for 10h;pH 4;Inert atmosphere; To a solution of methyl ester 4 (7.68 g, 41 mmol) in dry tetrahydrofuran (150 mL) and methanol (70 mL) sodium cyanoborohydride (10.8 g, 172 mmol) was added under a nitrogen atmosphere. The pH was adjusted to 4, by the addition of 4 M hydrogen chloride in dioxane and kept at this value over the course of the reaction (10 h), by the addition of the same hydrogen chloride solution. The reaction progress was monitored by TLC (dichloromethane/acetone 9:1) until the starting material disappeared. The reaction mixture was cooled in an ice bath, after which water (200 mL) and a saturated sodium hydrogen carbonate aqueous solution (until neutral pH) were added. The organic solvents were removed at reduced pressure. The aqueous phase was extracted with ethyl acetate (3 x 200 mL). The collected organic phases were dried over sodium sulfate and after the usual work-up an oily residue (8.84 g) was obtained; the residue was purified by silica gel column chromatography by elution with hexane/ethyl acetate (9:1) to give pure 5 (6.88 g, 88%). The chemical and physical properties were in agreement with the reported ones.22
88% With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; 1,4-dioxane; methanol; for 10h;pH 4;Inert atmosphere; To a solution of methyl ester 4 (7.68 g, 41 mmol) in dry tetrahydrofuran (150 mL) and methanol (70 mL) sodium cyanoborohydride (10.8 g, 172 mmol) was added, under nitrogen atmosphere. The pH was adjusted at 4, by addition of 4M hydrogen chloride in dioxane and kept at this value, in the course of the reaction (10 h), by addition of the same hydrogen chloride solution. The reaction progress was monitored by TLC (dichloromethane/acetone 9:1) until the starting material disappearance. The reaction mixture was cooled in an ice bath, water (200 ml) and a saturated sodium hydrogen carbonate aqueous solution (until neutral pH) were added. Organic solvents were removed at reduced pressure. The aqueous phase was extracted with ethyl acetate (3*200 mL). The collected organic phases are dried over sodium sulfate and after usual work-up an oily residue (8.84 g) was obtained; the residue was purified by silica gel column chromatography: by elution with hexane/ethyl acetate (9:1) pure 5 was recovered (6.88 g, 88%). The chemical-physical properties are in agreement with the reported ones (Alatorre-Santamaria, S.; Gotor-Fernandez, V.; Gotor, V. Tetrahedron: Asymmetry 2010, 21, 2307-2313).
65% With hydrogenchloride; sodium cyanoborohydride; In 1,4-dioxane; methanol; at 25℃; for 12h; Compound 16-b (1.00 g, 5.34 mmol, 1.00 eq) was dissolved in methanol (12.50 mL), and NaBH3CN (1.68 g, 26.70 mmol, 5.00 eq) and HCl/dioxane (4 M, 8.00 mL, 5.99 eq) were added thereto. The reaction solution was stirred at 25C for 12 hours. After the reaction was completed, the reaction solution was added with 50 mL of water, and adjusted to pH of 7 with saturated sodium hydrogen carbonate solution. The above solution was extracted with ethyl acetate (100 mL 3 3). The organic phases were combined, washed successively with brine (100 mL) and water (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was subjected to column chromatography (petroleum ether : ethyl acetate = 1:0?1:1) to give the product of compound 16-c (800.00 mg, yield: 65%) as a yellow oil. LCMS m/z = 192.0 [M+H]+.
49% With hydrogenchloride; methanol; sodium cyanoborohydride; In 1,4-dioxane; at 20℃; for 16h;pH 4 - 5; To a solution of Intermediate- 11 (3g, 16.03mmol) in MeOH (100mL), sodium cyanoborohydride (5.04 g, 80 mmol) and then a small amount of bromocresol green (pH indicator) was added. 4M HCl solution in dioxane (5 mL X 3) in 30 min interval was added drop-wise into reaction mixture to make pH acidic (4 to 5), till reaction mixture maintained a yellow color then reaction mixture was stirred at RT for 16 h. Reaction was monitored by TLC/LCMS. After completion of reaction, the reaction mixture was quenched with sodium bicarbonate and extracted with ethyl acetate (20X3 mL). The combined organic layer was dried and concentrated under reduced pressure. The crude compound was purified by flash chromatography by using (20 % ethyl acetate in hexane) to get methyl 1,2,3,4-tetrahydroquinoline-3-carboxylate (1.5 g, yield 49%) as yellow color oily mass; m/z- 191.7
With borane pyridine; acetic acid; at 20℃; [00343] As depicted in Scheme 4-1, quinoline-3-carboxylic acid 3 was esterified with thionyl chloride in methanol to yield ester 4. Reduction of the pyridine ring of 4 with pyridine-borane complex in glacial acetic acid then delivered racemic THQ 5 whose methyl ester was saponified to yield ±-6. Alternatively, sulfonylation of ±-5 furnished compounds ±-7, which were also saponified with lithium hydroxide to afford the 3-carboxy target compounds ±-8. Further elaboration of the phenylsulfonyl group in ±-7c was accomplished by an SNAr reaction with 4- chloro-3,5-dimethylphenol followed by ester hydrolysis to afford compound ±-2, as shown in Scheme 4-2. In addition, the phenylsulfonyl moiety in ±-2 was replaced with a more flexible propylene group through a reductive amination-saponification sequence to yield ±-11.

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  • 3-Methoxycarbonyl-1-methyl-quinolinium; bromide [ No CAS ]
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