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[ CAS No. 5466-31-9 ] {[proInfo.proName]}

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Chemical Structure| 5466-31-9

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Quality Control of [ 5466-31-9 ]

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Product Details of [ 5466-31-9 ]

CAS No. :	5466-31-9	MDL No. :	MFCD00085413
Formula :	C₁₆H₁₀ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FTEWYGPKBUSJTI-UHFFFAOYSA-N
M.W :	283.71	Pubchem ID :	230596
Synonyms :

Safety of [ 5466-31-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P270-P273-P301+P312-P330-P501	UN#:
Hazard Statements:	H302-H413	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5466-31-9 ]

* 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 [ 5466-31-9 ]

[ 5466-31-9 ] Synthesis Path-Downstream 1~75

1
[ 5466-31-9 ]
[ 24698-70-2 ]

Reference： [1]Journal of Organic Chemistry,1953,vol. 18,p. 1209,1219

2
[ 5466-31-9 ]
[ 854864-03-2 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1810

3
[ 91-56-5 ]
[ 99-91-2 ]
[ 5466-31-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium hydroxide; In ethanol;Reflux;	General procedure: A mixture of isatin or 5-methoxyisatin (10 mmol), 33% potassiumhydroxide (10 mL) in ethanol (20 mL), and appropriate acetophenone derivative (10 mmol) was heated under reflux for 9e18 h. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water (50 mL) and extracted with ether (3 50 mL). The aqueous layer was neutralized with 1 M hydrochloric acid. The formed precipitate was filtered off, washed with water, dried, and crystallized from ethanol.
80%	With potassium hydroxide; In ethanol;Reflux;	satin (4a) or 5-methoxyisatin (4b) (10 mmol), 33% potassium hydroxide (10 mL), ethanol (20 mL), and appropriate acetophenone derivative (10 mmol) was mixed and heated under reux for 18-24 hr. The reaction mixture was concentrated under reduced pressure; the residue was diluted with water (50 mL) and extracted with diethylether (3 x 50 mL). The aqueous layer was neutralized with 1 M hydrochloric acid. The precipitated solid was ltered, washed with water, dried and crystallized from ethanol
51%	In ethanol;	General Method A 2-(4-chlorophenyl)quinoline-4-carboxylic acid (Intermediate 1) To a stirred solution of isatin (30.0 g, 204 mmol) in 500 mL ethanol, 4-chloroacetophenone (47.0 g, 244 mol) was added in one portion. Potassium hydroxide flakes (22.8 g, 408 mmol) were added in several portions and the reaction was heated to reflux for 14 hr. The reaction was diluted with 1 liter water and washed with ethyl acetate (3*300 mL). The aqueous layer was cooled in an ice-bath and acidified with glacial acetic acid. The precipitated product was filtered, washed with cold, dilute acetic acid and dried in vacuum to give analytically pure intermediate 1 (29.5 g, 51%). TLC: 30% EtOAc/Hexanes (Rf: 0.2) 1H NMR (400 MHz, DMSO-d6) δ8.59 (d, J=8.6 Hz, 1H), 8.37 (s, 1H), 8.23 (d, J=8.5 Hz, 2H), 8.11 (d, J=8.5 Hz, 1H), 7.82 (t, J=7.7 Hz, 1H), 7.68 (t, J=7.7 Hz, 1H), 7.57 (d, J=8.3 Hz, 2H). LC-MS (ESI+): m/z 284.5 [M+H]+.

Ca.100%	With potassium hydroxide; In water; for 16h;Reflux; Inert atmosphere;	Isatin (1 g, 6.8 mmol, 1 equiv) was dissolved 33% w/v aqueous KOH solution. Acetophenone (6.8 mmol, 1 equiv) was added and the reaction mixture was gently heated to reflux. The reaction was refluxed for 16 h. After the reaction time, the mixture was cooled to rt then transferred to an Erlenmeyer flask and subsequently cooled to 0 C. Carefully, the reaction mixture was acidified with dropwise addition of cone. HCI and provided the carboxylic acid product as a yellow solid after collection by vacuum filtration. The carboxylic acid (1 g, 1 equiv) was dissolved in 50 ml of diethyl ether and cooled to 0 C. Lithium aluminum hydride (1.2 equiv) was added portion-wise at 0 C and the reaction mixture was allowed to warm to rt, while stirring, overnight. The Feiser work-up was used to isolate the reduced product after removal of the organic solvent by reduced pressure. The alcohol was used without further purification. The alcohol (1 equiv) was dissolved in 10 ml dimethyl sulfoxide (dried over molecular sieves). IBX (2 equiv) was added to the reaction mixture at rt and the reaction was allowed to stir overnight at rt. The reaction mixture was quenched with diH20. The aqueous layer was extracted three times with ethyl acetate and the combined organic layer was washed with 1 M NaOH, water and brine. The organic layer was then dried with sodium sulfate and the solvent was removed by reduced pressure. [00332] 2-(4-Chlorophenyl)-4-quinolinecarboxylic acid: [00333] A yellow solid was obtained in near quantitative yield (1 .9 g). Spectral data correspond to that reported.23 1H NMR (400 MHz, DMSO-cfe): δ 9.03 (dd, J = 8.2, 1.5 Hz, 1 H), 8.43 - 8.38 (app d of AA'BB', 2 H), 8.21 (dd, J = 8.8, 0.9 Hz, 1 H), 7.88 (ddd, J = 8.4, 6.9, 1.4 Hz, 1 H), 7.75 (ddd, J = 8.3, 6.9, 1.3 Hz, 1 H), 7.63 - 7.58 (app d of AA'BB', 2 H).
	With potassium hydroxide; In ethanol;Reflux;	General procedure: 10 mmol Isatin (1) was added into a stirred solutionof 33% potassium hydroxide (10 mL) and ethanol(20 mL). 10 mmol of appropriate acetophenone derivative(IIa-j) was mixed and heated under reflux for18-24 h. The reaction mixture was poured on crushedice and the pH was adjusted by the solution of 2 N HClto 6-7. The precipitated solid was filtered, washedwith water, dried and crystallized from ethanol whichwas then taken to the next step without any furtherpurification [29, 30].
		General procedure: To a solution of 33% KOH (aqueous, 6.8 mL) in MeOH (15 mL), isatin(A1, 1.00 g, 6.8 mmol) was reacted with 4′-methylacetophenone (B1,0.91 g, 6.8 mmol) at 100 for 24 h. After reaction, the solvent wasevaporated in vacuum, and the residue dissolved in water. Hydrochloricacid was used to adjust the pH to 2, and white solid was precipitated.Suction filtration was used to collect the white solid, which was thenvacuum dried to produce the intermediate C1 (1.20 g, yield 67%).

Reference： [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 977 - 984
[2]European Journal of Medicinal Chemistry,2020,vol. 186
[3]New Journal of Chemistry,2017,vol. 41,p. 12380 - 12383
[4]Bioorganic Chemistry,2019,vol. 82,p. 360 - 377
[5]Patent: US2016/214958,2016,A1
[6]Journal of Organic Chemistry,1953,vol. 18,p. 1209,1219
[7]Journal of Medicinal Chemistry,1997,vol. 40,p. 1794 - 1807
[8]Patent: WO2018/132905,2018,A1 .Location in patent: Paragraph 00218; 00258; 00330-00333
[9]Bioorganic Chemistry,2021,vol. 106
[10]Russian Journal of Bioorganic Chemistry,2021,vol. 47,p. 572 - 583
Bioorg. Khim.,
[11]Journal of Molecular Structure,2021,vol. 1244
[12]Bioorganic Chemistry,2022,vol. 118

4
[ 13200-60-7 ]
[ 5466-31-9 ]
[ 148887-65-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 977 - 984

5
[ 5466-31-9 ]
[ 15028-40-7 ]
N-[α-(methoxycarbonyl)benzyl]-2-(4-chlorophenyl)quinoline-4-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1794 - 1807

7
[ 5466-31-9 ]
[2-(4-Chloro-phenyl)-quinoline-4-carbothioyl]-methyl-amino}-acetic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 977 - 984

8
[ 5466-31-9 ]
[ 148887-78-9 ]

Reference： [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 977 - 984

9
[ 5466-31-9 ]
[ 6332-47-4 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1810
[2]Journal of the American Chemical Society,1946,vol. 68,p. 1810

10
[ 5466-31-9 ]
2-chloro-1-[2-(4-chloro-phenyl)-[4]quinolyl]-ethanone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1810

11
[ 5466-31-9 ]
[ 408326-15-8 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1810

12
[ 5466-31-9 ]
2-bromo-1-[2-(4-chloro-phenyl)-[4]quinolyl]-ethanol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1810

13
[ 5466-31-9 ]
[ 412041-86-2 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1810

14
[ 5466-31-9 ]
2,2-dibromo-1-[2-(4-chloro-phenyl)-[4]quinolyl]-ethanone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1810

15
H₂O [ No CAS ]
NaHCO₃ [ No CAS ]
[ 5466-31-9 ]
[ 543-27-1 ]
N-[α-(methoxycarbonyl)benzyl]-2-(4-chlorophenyl)quinoline-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In Et2O;	EXAMPLE 93 (R,S)-N-(α-(Methoxycarbonyl)benzyl]-2-(p-chlorophenyl)quinoline-4-carboxamide 2 g (7.0 mmol) of 2-(p-chlorophenyl)quinoline-4-carboxylic acid and 1.7 ml (15.4 mmol) of N-methylmorpholine were dissolved, under nitrogen athmosphere, in 50 ml of dry THF.. The solution was cooled to -20C and 0.91 ml (7.0 mmol) of isobutyl chloroformate were added.. After 20 minutes, 2.12 g (10.5 mmol) of methyl (R,S) phenylglycinate hydrochloride and 1.3 ml (11.9 mmol) of N-methylmorpholine, dissolved in 30 ml of dry THF, were added and the reation mixture was stirred at room temperature overnight.. 5 ml of H2O were added and the reaction mixture was evaporated in vacuoto dryness.. The residue was dissolved in Et2O, washed with a saturated solution of NaHCO3, separated, dried over Na2SO4and evaporated in vacuoto dryness.. The residual oil was flash chromatographed on 230-400 mesh silica gel, eluding with a mixture of hexane/isopropyl ether 7: 3 to afford 0.9 g of crude product, which was recrystallized three times with IPrO2/toluene to yield 0.5 g of the title compound. . C25H19ClN2O3 M.P. = 170-172 C

Reference： [1]Patent: EP940391,1999,A2

16
methyl (R,S) phenylglycinate hydrochloride [ No CAS ]
[ 5466-31-9 ]
[ 543-27-1 ]
N-[α-(methoxycarbonyl)benzyl]-2-(4-chlorophenyl)quinoline-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; water;	EXAMPLE 93 (R,S)-N-[α-(Methoxycarbonyl)benzyl]-2-(p-chlorophenyl)quinoline-4-carboxamide 2 g (7.0 mmol) of 2-(p-chlorophenyl)quinoline-4-carboxylic acid and 1.7 ml (15.4 mmol) of N-methylmorpholine were dissolved, under nitrogen athmosphere, in 50 ml of dry THF. The solution was cooled to -20 C. and 0.91 ml (7.0 mmol) of isobutyl chloroformate were added. After 20 minutes, 2.12 g (10.5 mmol) of methyl (R,S) phenylglycinate hydrochloride and 1.3 ml (11.9 mmol) of N-methylmorpholine, dissolved in 30 ml of dry THF, were added and the reaction mixture was stirred at room temperature overnight. 5 ml of H2O were added and the reaction mixture was evaporated in vacuo to dryness. The residue was dissolved in Et2O, washed with a saturated solution of NaHCO3, separated, dried over Na2SO4 and evaporated in vacuo to dryness. The residual oil was flash chromatographed on 230-400 mesh silica gel, eluding with a mixture of hexane/isopropyl ether 7:3 to afford 0.9 g of crude product, which was recrystallized three times with iPrO2/toluene to yield 0.5 g of the title compound.

Reference： [1]Patent: US2003/195204,2003,A1

17
methyl (R,S) phenylglycinate hydrochloride [ No CAS ]
[ 5466-31-9 ]
[ 7732-18-5 ]
[ 543-27-1 ]
N-[α-(methoxycarbonyl)benzyl]-2-(4-chlorophenyl)quinoline-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether;	EXAMPLE 93 (R,S)-N-[α-(Methoxycarbonyl)benzyl]-2-(p-chlorophenyl)quinoline-4-carboxamide 2 g (7.0 mmol) of 2-(p-chlorophenyl)quinoline-4-carboxylic acid and 1.7 ml (15.4 mmol) of N-methylmorpholine were dissolved, under nitrogen athmosphere, in 50 ml of dry THF. The solution was cooled to -20 C. and 0.91 ml (7.0 mmol) of isobutyl chloroformate were added. After 20 minutes, 2.12 g (10.5 mmol) of methyl (R,S) phenylglycinate hydrochloride and 1.3 ml (11.9 mmol) of N-methylmorpholine, dissolved in 30 ml of dry THF, were added and the reaction mixture was stirred at room temperature overnight. 5 ml of H2 O were added and the reaction mixture was evaporated in vacuo to dryness. The residue was dissolved in Et2 O, washed with a saturated solution of NaHCO3, separated, dried over Na2 SO4 and evaporated in vacuo to dryness. The residual oil was flash chromatographed on 230-400 mesh silica gel, eluding with a mixture of hexane/isopropyl ether 7:3 to afford 0.9 g of crude product, which was recrystallized three times with iPrO2 /toluene to yield 0.5 g of the title compound.

Reference： [1]Patent: US5811553,1998,A

18
[ 104-88-1 ]
[ 127-17-3 ]
[ 62-53-3 ]
[ 5466-31-9 ]

Reference： [1]Journal of Fluorine Chemistry,2009,vol. 130,p. 406 - 409
[2]Journal of Heterocyclic Chemistry,2020
[3]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 611 - 614

19
[ 5466-31-9 ]
[ 1597-32-6 ]
[ 1208372-55-7 ]

Yield	Reaction Conditions	Operation in experiment
~ 18%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃;Cooling with ice;	To a stirred and ice-cooled solution of commercial 2-(4-chloro-phenyl)- quinoline-4-carboxylic acid (1.400 g, 4.9346 mmol) and 2-amino-6-fluoropyhdine (0.664 g, 5.9215 mmol) in dichloromethane (20 ml), triethylamine (3.495 g, -4.8 ml, 34.5422 mmol) is added, followed by portion-wise addition of 1 - propanephosphonic acid cyclic anhydride (12.561 g, 19.7384 mmol) and the mixture is allowed to attain room temperature spontaneously overnight. The resulting mixture is diluted with dichloromethane (-30 ml), washed with water and brine, dried (MgSO4), and evaporated to afford a brown gummy residue (1.860 g, 100% mass balance). This is purified by column chromatography eluting with 8% ethyl acetate in hexane, to obtain the title compound as a pale yellow solid (0.474 g, -18% yield). M.p. 200-2010C.
~ 18%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃;Cooling with ice;	To a stirred and ice-cooled solution of commercial 2-(4-chloro-phenyl)-quinoline-4-carboxylic acid (1.400 g, 4.9346 mmol) and <strong>[1597-32-6]2-amino-6-fluoropyridine</strong> (0.664 g, 5.9215 mmol) in dichloromethane (20 ml), triethylamine (3.495 g, 4.8 ml, 34.5422 mmol) is added, followed by portion-wise addition of 1-propanephosphonic acid cyclic anhydride (12.561 g, 19.7384 mmol) and the mixture is allowed to attain room temperature spontaneously overnight. The resulting mixture is diluted with dichloromethane (30 ml), washed with water and brine, dried (MgSO4), and evaporated to afford a brown gummy residue (1.860 g, 100% mass balance). This is purified by column chromatography eluting with 8% ethyl acetate in hexane, to obtain the title compound as a pale yellow solid (0.474 g, 18% yield). M.p. 200-201 C

Reference： [1]Patent: WO2010/20672,2010,A1 .Location in patent: Page/Page column 16-17
[2]Patent: US2011/207773,2011,A1 .Location in patent: Page/Page column 7

20
[ 5466-31-9 ]
[ 98-86-2 ]
[ 1415834-93-3 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 3527 - 3535

21
[ 5466-31-9 ]
[ 1415834-96-6 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 3527 - 3535

22
[ 5466-31-9 ]
[ 1415834-99-9 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 3527 - 3535

23
[ 5466-31-9 ]
[ 1415835-09-4 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 3527 - 3535

24
[ 5466-31-9 ]
[ 1415835-12-9 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 3527 - 3535

25
[ 5466-31-9 ]
[ 1415835-02-7 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 3527 - 3535

26
[ 5466-31-9 ]
[ 119-53-9 ]
[ 1415835-05-0 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 3527 - 3535

27
[ 5466-31-9 ]
[ 41979-39-9 ]
C₂₁H₁₇ClN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 6h;	General procedure: To a solution of piperidin-4-one hydrochloride (2, 3.24 g, 24 mmol) and triethylamine (4.86 g, 48 mmol) in DMF (40 mL) was added substituted quinoline-4-carboxylic acid (1, 20 mmol) followed by HATU (9.12 g, 24 mmol). The reaction mixture was stirred at room temperature for 6 h and then poured into ice-cold water (50 mL). The precipitate was filtered and dried to give the corresponding substituted 1-(quinoline-4-carbonyl)piperidin-4-one 3. This product was used directly in the next reaction step without further purification.

Reference： [1]Molecules,2015,vol. 20,p. 16221 - 16234

28
[ 5466-31-9 ]
C₂₇H₂₈ClN₃O₃ [ No CAS ]

Reference： [1]Molecules,2015,vol. 20,p. 16221 - 16234

29
[ 5466-31-9 ]
C₂₉H₃₂ClN₃O₃ [ No CAS ]

Reference： [1]Molecules,2015,vol. 20,p. 16221 - 16234

30
[ 5466-31-9 ]
(R)-(2-(4-chlorophenyl)quinolin-4-yl)(3-(morpholine-4-carbonyl)-[1,4'-bipiperidin]-1'-yl)methanone [ No CAS ]

Reference： [1]Molecules,2015,vol. 20,p. 16221 - 16234

31
[ 5466-31-9 ]
[ 136081-84-0 ]
1'-(2-(4-chlorophenyl)quinoline-4-carbonyl)spiro[chroman-2,4'-piperidin]-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of tert-butyl 4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate (1.6 g, 5 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (2.5 mL). The reaction mixture was stirred at room temperature for 2 h and the solvent was removed under reduced pressure to give crude spiro[chroman-2,4′-piperidin]-4-one 11. The resulting solid was used directly for the next step reaction without further purification. A mixture of substituted quinoline-4-carboxylic acid (1, 5 mmol), NEt3 (0.61 g, 6 mmol) and HATU (1.9 g, 5 mmol) in DMF (10 mL) was stirred at room temperature for 0.5 h, followed by the abovementioned spiro[chroman-2,4′-piperidin]-4-one 11. The reaction mixture was stirred overnight at room temperature after which time it was diluted with EtOAc (100 mL) and washed with water (60 mL × 2). The organic extract was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by chromatography to afford substituted 1′-(quinoline-4-carbonyl)spiro[chroman-2,4′-piperidin]-4-ones 12.

Reference： [1]Molecules,2015,vol. 20,p. 16221 - 16234

32
[ 5466-31-9 ]
methyl‐2‐(4‐chlorophenyl)quinoline‐4‐carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		Methyl 2-(4-chlorophenyl)quinoline-4-carboxylate (Intermediate 2) To a stirred solution of 1 (500 mg, 1.76 mmol) in MeOH (10 mL), conc. sulphuric acid (0.45 mL) was added. The reaction mixture was heated to reflux for 6 h. The reaction mixture was diluted with saturated NaHCO3 solution (20 mL) and extracted with EtOAc (2*20 mL). The combined organic extracts were washed with water (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide the crude material, which was purified by silica gel column chromatography (10% EtOAc/hexanes) to afford intermediate 2 (402 mg, 76%) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ8.73 (d, J=8.0 Hz, 1H), 8.35 (s, 1H), 8.26-8.14 (m, 3H), 7.78 (t, J=6.8 Hz, 1H), 7.63 (t, J=7.2 Hz, 1H), 7.50 (d, J=6.8 Hz, 2H), 4.07 (s, 3H). LC-MS (ESI+): m/z 298.3 [M+H]+.

Reference： [1]Patent: US2016/214958,2016,A1

33
[ 5466-31-9 ]
Methyl 6-benzamido-2-(2-(4-chlorophenyl)quinoline-4-carbonyl)hexanoate [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1

34
[ 5466-31-9 ]
6-Amino-1-(2-(4-chlorophenyl)quinolin-4-yl)hexan-1-one [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1

35
[ 5466-31-9 ]
6-amino-2-bromo-1-(2-(4-chlorophenyl)quinolin-4-yl)hexan-1-one hydrobromide [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1

36
[ 5466-31-9 ]
(2-(4-Chlorophenyl)quinolin-4-yl) (piperidin-2-yl)methanone [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1
[2]Patent: US2016/214958,2016,A1

37
[ 5466-31-9 ]
[ 5428-80-8 ]

Reference： [1]Patent: US2016/214958,2016,A1
[2]Patent: US2016/214958,2016,A1

38
[ 5466-31-9 ]
tert-Butyl 2-(2-phenylquinoline-4-carbonyl) piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1

39
[ 5466-31-9 ]
tert-Butyl 2-((2-(4-chlorophenyl) quinolin-4-yl) (hydroxy) methyl) piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1

40
[ 5466-31-9 ]
2-(4-chlorophenyl)quinolin-4-yl [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1
[2]Patent: US2016/214958,2016,A1
[3]Patent: US2016/214958,2016,A1

41
[ 5466-31-9 ]
tert-Butyl 2-((2-(4-chlorophenyl) quinolin-4-yl) (methoxy) methyl) piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1

42
[ 5466-31-9 ]
2-(4-Chlorophenyl)-4-(methoxy (piperidin-2-yl) methyl) quinoline hydrochloride [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1

43
[ 5466-31-9 ]
tert-Butyl 2-(2-(4-chlorophenyl) quinoline-4-carbonyl) pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/214958,2016,A1

44
[ 5466-31-9 ]
[ 530-62-1 ]
C₁₉H₁₂ClN₃O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2103 - 2108

45
[ 5466-31-9 ]
C₁₈H₁₃ClN₄O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2103 - 2108

46
[ 5466-31-9 ]
C₁₈H₁₃ClN₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2103 - 2108

47
[ 5466-31-9 ]
C₁₇H₁₁ClN₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2103 - 2108

48
[ 5466-31-9 ]
C₁₇H₁₃ClN₄OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2103 - 2108

49
[ 5466-31-9 ]
tert-butyl 2-(4-chlorophenyl)-α-(2R)-2-(5,6-dihydropyridinyl)-(αR)-4-quinolinemethanol-1(2H)-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/132905,2018,A1

50
[ 5466-31-9 ]
tert-butyl 2-(4-chlorophenyl)-α-(2R)-2-pyridinyl-(αR)-4-quinolinemethanol-1(2H)-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/132905,2018,A1

51
[ 5466-31-9 ]
C₂₆H₂₅ClN₂O₃ [ No CAS ]

Reference： [1]Patent: WO2018/132905,2018,A1

52
[ 5466-31-9 ]
tert-butyl 2-(4-chlorophenyl)-α-(2R)-2-(5,6-dihydropyridinyl)-(αS)-4-quinolinemethanol-1(2H)-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/132905,2018,A1

53
[ 5466-31-9 ]
2-(4-chlorophenyl)-α-(2R)-2-(5,6-dihydropyridinyl)-(αR)-4-quinolinemethanol [ No CAS ]

Reference： [1]Patent: WO2018/132905,2018,A1

54
[ 5466-31-9 ]
[ 148336-22-5 ]

Yield	Reaction Conditions	Operation in experiment
570 mg		Isatin (1 g, 6.8 mmol, 1 equiv) was dissolved 33% w/v aqueous KOH solution. Acetophenone (6.8 mmol, 1 equiv) was added and the reaction mixture was gently heated to reflux. The reaction was refluxed for 16 h. After the reaction time, the mixture was cooled to rt then transferred to an Erlenmeyer flask and subsequently cooled to 0 C. Carefully, the reaction mixture was acidified with dropwise addition of cone. HCI and provided the carboxylic acid product as a yellow solid after collection by vacuum filtration. The carboxylic acid (1 g, 1 equiv) was dissolved in 50 ml of diethyl ether and cooled to 0 C. Lithium aluminum hydride (1.2 equiv) was added portion-wise at 0 C and the reaction mixture was allowed to warm to rt, while stirring, overnight. The Feiser work-up was used to isolate the reduced product after removal of the organic solvent by reduced pressure. The alcohol was used without further purification. The alcohol (1 equiv) was dissolved in 10 ml dimethyl sulfoxide (dried over molecular sieves). IBX (2 equiv) was added to the reaction mixture at rt and the reaction was allowed to stir overnight at rt. The reaction mixture was quenched with diH20. The aqueous layer was extracted three times with ethyl acetate and the combined organic layer was washed with 1 M NaOH, water and brine. The organic layer was then dried with sodium sulfate and the solvent was removed by reduced pressure.

Reference： [1]Patent: WO2018/132905,2018,A1 .Location in patent: Paragraph 00218; 00258; 00330-00331; 00342-00343

55
[ 5466-31-9 ]
2-(4-chlorophenyl)quinoline-4-carbohydrazide [ No CAS ]

Reference： [1]Bioorganic Chemistry,2019,vol. 82,p. 360 - 377
[2]European Journal of Medicinal Chemistry,2020,vol. 186
[3]Bioorganic Chemistry,2021,vol. 106
[4]Journal of Molecular Structure,2021,vol. 1244

56
[ 64-17-5 ]
[ 5466-31-9 ]
[ 7147-98-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sulfuric acid;Reflux;	General procedure: A mixture of the appropriate 4-carboxylic acid 6a-f(10 mmol), absolute ethanol (20 mL) and concentrated sulfuric acid (2 mL) was heated under reuxed for 12-18 hr. Excess solvent was removed under reduced pressure; the residue was diluted with water, and then rendered alkaline with concentrated sodium bicarbonate solution. The formed precipitate was ltered off, washed with water and crystallized from ethanol
80%	With sulfuric acid; for 10h;Reflux;	General procedure: A mixture of the appropriate 4-carboxylic acid 1aef (10 mmol),absolute ethanol (20 mL), and concentrated sulfuric acid (2 mL)was refluxed for 10 h. The solution was concentrated under reduced pressure; the mixture was allowed to cool at room temperature,diluted with water then rendered alkaline with a sodium bicarbonate solution. The formed precipitate was filtered off, washed wiith water and crystallized from ethanol.
	With sulfuric acid; for 10h;Reflux;	General procedure: A mixture of the appropriate 4-carboxylic acid 1a-e (10 mmol), absolute ethanol (20 mL) and concentrated sulfuric acid (2 mL) was refluxed for 10 h. Excess ethanol was removed under reduced pressure; the mixture was allowed to cool, diluted with water then rendered alkaline with saturated sodium bicarbonate solution. The precipitate was filtered, washed with water and crystallized from ethanol.

Reference： [1]Bioorganic Chemistry,2019,vol. 82,p. 360 - 377
[2]European Journal of Medicinal Chemistry,2020,vol. 186
[3]Bioorganic Chemistry,2021,vol. 106
[4]Journal of Molecular Structure,2021,vol. 1244

57
[ 5466-31-9 ]
4-allyl-5-(2-(4-chlorophenyl)quinolin-4-yl)-4H-1,2,4-triazole-3-thiol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 186
[2]Bioorganic Chemistry,2021,vol. 106
[3]Journal of Molecular Structure,2021,vol. 1244

58
[ 5466-31-9 ]
5-(2-(4-chlorophenyl)quinolin-4-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 186
[2]Bioorganic Chemistry,2021,vol. 106
[3]Journal of Molecular Structure,2021,vol. 1244

59
[ 5466-31-9 ]
N-(4-acetylphenyl)-2-((4-allyl-5-(2-(4-chlorophenyl)-quinolin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 186

60
[ 5466-31-9 ]
N-(4-acetylphenyl)-2-((5-(2-(4-chlorophenyl)quinolin-4-yl)-4-phenyl 4H-1,2,4-triazol-3-yl)thio)acetamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 186

61
[ 5466-31-9 ]
2-((4-allyl-5-(2-(4-chlorophenyl)quinolin-4-yl)-4H-1,2,4-triazol-3-yl)thio)-N-(4-(1-(hydroxyimino)ethyl)phenyl)acetamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 186

62
[ 5466-31-9 ]
2-((5-(2-(4-chlorophenyl)quinolin-4-yl)-4-phenyl-4H-1,2,4-triazol-3-yl)thio)-N-(4-(1-(hydroxyimino)ethyl)phenyl)acetamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 186

63
[ 1198001-03-4 ]
[ 5466-31-9 ]
2’-(tert-butyl)-1-(2-(4-chlorophenyl)quinoline-4-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20℃; for 12.5h;	According to the method of Example 1, the compound 2'-(tert-butyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazole]-7'( 6'H)-ketone.Under ice bath conditions, the 2'-(tert-butyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazole]-7'(6'H )-Ketone (400mg, 1.1mmol), HATU (458mg, 1.2mmol), triethylamine (0.2ml, 1.2mmol) were dissolved in 10mL DMF, stirred at 0 for 0.5h, then added <strong>[5466-31-9]2-(4-chlorophenyl)quinoline-4-carboxylic acid</strong> (1mmol, 285mg), react at room temperature for 12h; add the reaction solution to 50mL ice water, extract with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure, and pass the crude product through a silica gel column Chromatographic purification to obtain title compound I4.
78%	With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 12h;	General procedure: (A) Pyruvic aldehyde (2, 25 mmol) was added dropwise to asolution of 1 (30 mmol) in H2O (100 mL), and after stirring atroom temperature for 2 h, the mixture was extracted withCH2Cl2, dried with anhydrous Na2SO4, and concentrated invacuo to afford hydrazine 3. Then, a 40% aqueous solution ofglyoxal (25 mL) was added to a solution of 3 (62 mmol) inH2O (100 mL). The mixture was heated at reflux for 5 h andextracted with ethyl acetate. The organic phase was dried,filtered, and concentrated to give 4 as yellow solid. Tetrahydropyrrole(8 mmol) was added to a solution of 4 (24 mmol)in MeOH (45 mL), and after stirring at room temperature for2 h, 1-(N-Boc)-4-piperidone (28 mmol) was subsequentlyadded, with the mixture heated at reflux for 24 h. Themixture was concentrated in vacuo and purified via columnchromatography to give 5. The Boc-protecting group wasremoved using trifluoroacetic acid in CH2Cl2 to provide 6.Finally, appropriate quinoline-4-carboxylic acid derivatives(1 mmol) was added to the mixture of 6 (1.1 mmol), HATU(1.2 mmol), and triethylamine (0.2 mL) in DMF (10 mL). Themixture was stirred at room temperature overnight, andthen added to ice water. The resulting precipitate wasfiltered, dried, and purified by column chromatography togive target compounds 7a~7m and 7q~7u.

Reference： [1]Patent: CN111574530,2020,A .Location in patent: Paragraph 0116-0120
[2]European Journal of Medicinal Chemistry,2021,vol. 212

64
[ 5466-31-9 ]
2-(4-allyl-5-(2-(4-chlorophenyl)quinolin-4-yl)-4H-1,2,4-triazol-3-ylthio)-N-(4-((E)-3-(4-methoxyphenyl)acryloyl)phenyl)acetamide [ No CAS ]

Reference： [1]Bioorganic Chemistry,2021,vol. 106

65
[ 5466-31-9 ]
2-(5-(2-(4-chlorophenyl)quinolin-4-yl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)-N-(4-((E)-3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)acetamide [ No CAS ]

Reference： [1]Bioorganic Chemistry,2021,vol. 106

66
[ 5466-31-9 ]
2-(4-allyl-5-(2-(4-chlorophenyl)quinolin-4-yl)-4H-1,2,4-triazol-3-ylthio)-N-(4-((E)-3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)acetamide [ No CAS ]

Reference： [1]Bioorganic Chemistry,2021,vol. 106

67
[ 5466-31-9 ]
2-(5-(2-(4-chlorophenyl)quinolin-4-yl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)-N-(4-((E)-3-(4-chlorophenyl)acryloyl)phenyl)acetamide [ No CAS ]

Reference： [1]Bioorganic Chemistry,2021,vol. 106

68
[ 5466-31-9 ]
2-(4-allyl-5-(2-(4-chlorophenyl)quinolin-4-yl)-4H-1,2,4-triazol-3-ylthio)-N-(4-((E)-3-(4-chlorophenyl)acryloyl)phenyl)acetamide [ No CAS ]

Reference： [1]Bioorganic Chemistry,2021,vol. 106

69
[ 5466-31-9 ]
2-(5-(2-(4-chlorophenyl)quinolin-4-yl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)-N-(4-((E)-3-(4-methoxyphenyl)acryloyl)phenyl)acetamide [ No CAS ]

Reference： [1]Bioorganic Chemistry,2021,vol. 106

70
[ 17832-99-4 ]
[ 5466-31-9 ]
(2-oxobenzo[d]oxazol-3(2H)-yl)methyl-2-(4-chlorophenyl)quinoline-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 5℃; for 2h;	General procedure: To an ice-cold solution of the 2-aryl quinoline-4-carboxylic acid derivatives (3 mmol) in 10 mL DMF,3-(hydroxymethyl)benzo[d]oxazol-2(3H)-one (3mmol),dimethyl-aminopyridine (DMAP, 20 mg), and dicyclohexylcarbodiimde(DCC, 3.5 mmol) were added.The reaction mixture was stirred at 5C for 2 h andkept overnight at room temperature. The precipitateformed was separated by filtration. Ethyl acetate wasadded to the filtrate and was washed with cooled0.05 N HCl followed by saturated solution of NaHCO3and finally with brine. The organic layer wasdried over anhydrous Na2SO4 and evaporated underreduced pressure. The residue obtained was crystallisedtwice with ethanol to afford pure product.

Reference： [1]Russian Journal of Bioorganic Chemistry,2021,vol. 47,p. 572 - 583
Bioorg. Khim.,

71
[ 5466-31-9 ]
2-(5-(2-(4-chlorophenyl)quinolin-4-yl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)-N-(4-chloro phenyl)acetamide [ No CAS ]

Reference： [1]Journal of Molecular Structure,2021,vol. 1244

72
[ 5466-31-9 ]
2-(4-allyl-5-(2-(4-chlorophenyl)quinolin-4-yl)-4H-1,2,4-triazol-3-yl thio)-N-(4-chloro phenyl)acetamide [ No CAS ]

Reference： [1]Journal of Molecular Structure,2021,vol. 1244

73
[ 5466-31-9 ]
2-(5-(2-(4-chlorophenyl)quinolin-4-yl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)-N-(4-methoxyphenyl)acetamide [ No CAS ]

Reference： [1]Journal of Molecular Structure,2021,vol. 1244

74
[ 5466-31-9 ]
2-(4-allyl-5-(2-(4-chlorophenyl)quinolin-4-yl)-4H-1,2,4-triazol-3-ylthio)-N-(4-methoxyphenyl)acetamide [ No CAS ]

Reference： [1]Journal of Molecular Structure,2021,vol. 1244

75
[ 5466-31-9 ]
[ 103-67-3 ]
N-benzyl-2-(4-chlorophenyl)-N-methylquinoline-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;	General procedure: Intermediates C1 (50.0 mg, 0.190 mmol) and benzylamine (D1, 20.4mg, 0.190 mmol) were dissolved in 10 mL DCM. DCC (47.0 mg, 0.227mmol) and DMAP (4.0 mg) were added and the solution was reacted atroom temperature for overnight. After reaction, the solvent was evaporatedin vacuum, and the residue was purified by silica gel column chromatography (petroleum ether/EtOAc, 5:1), yielding E1 as a whitesolid (48.9 mg, yield 73%). The synthetic procedure for derivatives E2~ E27 was similar to that of E1.

Reference： [1]Bioorganic Chemistry,2022,vol. 118

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Code	Phrase
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Prevention
Code	Phrase
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H200	Unstable explosive
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H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere