[ CAS No. 87-13-8 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 87-13-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 87-13-8 ]

SDS Specification

Alternatived Products of [ 87-13-8 ]

Product Citations Expand+

Quinolone-3-amidoalkanol: A New Class of Potent and Broad-Spectrum Antimicrobial Agent

Dube, Phelelisiwe S. ; Angula, Klaudia T. ; Legoabe, Lesetja J. , et al. ACS Omega,2023,8(19):17086-17102. DOI: 10.1021/acsomega.3c01406 PubMed ID: 37214682

Abstract: Herein, we describe 39 novel

Purchased 98% after 30 min in the presence of human, rat, and mouse liver microsomes. Several compounds thus reported here are promising leads for the treatment of diseases caused by infectious agents.

from AmBeed: class="">403-19-0 ; class="">636-93-1 ; class="">5847-59-6 ; class="">87-13-8 ; class="">1548-61-4 ; class="">99-53-6 ; class="">402-49-3 ; class="">619-08-9 ; class="">18880-00-7 ; class="">111-41-1 ; class="">619-10-3 ; class="">766-80-3 ; class="">140-75-0 ; class="">823-78-9 ; class="">622-95-7 ; class="">402-23-3 ; class="span_more span_less">141776-91-2 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Investigation of quinolone‐tethered aminoguanidine as novel antibacterial agents

Klaudia T. Angula ; Lesetja J. Legoabe ; Audrey Jordaan , et al. Arch. Pharm.,2022,355(10):2200172. DOI: 10.1002/ardp.202200172 PubMed ID: 35674486

Abstract: A recent study identified quinolone-based thiosemicarbazone with an MIC90 value of 2?μM against Mycobacterium tuberculosis (Mtb). Herein, we report further optimization of the previous hit, which led to the discovery of quinolone-tethered aminoguanidine molecules with generally good antitubercular activity. Compounds 7f and 8e emerged as the hits of the series with submicromolar antitubercular activity, exhibiting MIC90 values of 0.49/0.90 and 0.49/0.60?μM, respectively, in the 7H9 CAS GLU Tx medium. This shows a fivefold increase in antitubercular activity compared to the previous study. Target compounds were also screened against ESKAPE (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter species) pathogens. However, the series generally exhibited poor antibacterial activities, with only compounds 8d and 8e demonstrating >50% growth inhibition of Staphylococcus aureus and Pseudomonas aeruginosa at 32?μg/ml. The compounds displayed selective antitubercular activity as they showed no cytotoxicity effects against two noncancerous human cell lines. In silico studies predict 7f to have good solubility, no inhibitory effect on cytochrome P450 isoenzymes, and to be a non-pan-assay interfering compound.

Keywords: tuberculosis ; ESKAPE pathogens ; aminoguanidine ; quinolones ; thiosemicarzone

Purchased from AmBeed: 99-92-3 ; 99-92-3 ; 87-13-8 ; 111-41-1 ; 109-85-3 ; 692764-08-2

Product Details of [ 87-13-8 ]

CAS No. :	87-13-8	MDL No. :	MFCD00009148
Formula :	C₁₀H₁₆O₅	Boiling Point :	No data available
Linear Structure Formula :	C₂H₅O₂CC(CHOC₂H₅)CO₂C₂H₅	InChI Key :	LTMHNWPUDSTBKD-UHFFFAOYSA-N
M.W :	216.23	Pubchem ID :	6871
Synonyms :

Calculated chemistry of [ 87-13-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.6
Num. rotatable bonds :	8
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.36
TPSA :	61.83 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.81
Log Po/w (XLOGP3) :	1.49
Log Po/w (WLOGP) :	1.03
Log Po/w (MLOGP) :	0.63
Log Po/w (SILICOS-IT) :	1.28
Consensus Log Po/w :	1.45

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.59
Solubility :	5.54 mg/ml ; 0.0256 mol/l
Class :	Very soluble
Log S (Ali) :	-2.4
Solubility :	0.869 mg/ml ; 0.00402 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.47
Solubility :	7.28 mg/ml ; 0.0337 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	5.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.69

Safety of [ 87-13-8 ]

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

Application In Synthesis of [ 87-13-8 ]

* 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.

Upstream synthesis route of [ 87-13-8 ]
Downstream synthetic route of [ 87-13-8 ]

[ 87-13-8 ] Synthesis Path-Upstream 1~7

1
[ 87-13-8 ]
[ 59713-58-5 ]

Reference： [1] Heterocyclic Communications, 2004, vol. 10, # 6, p. 407 - 410

2
[ 87-13-8 ]
[ 85386-14-7 ]

Reference： [1] Molecules, 2013, vol. 18, # 10, p. 11683 - 11704

3
[ 455-14-1 ]
[ 87-13-8 ]
[ 175203-85-7 ]

Reference： [1] Patent: US6093732, 2000, A,

4
[ 7732-18-5 ]
[ 87-13-8 ]
[ 343-67-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With NaOEt In ethanol	Example 15 ETHYL 2-TRIFLUOROMETHYL-4-HYDROXYPYRIMIDINE-5-CARBOXYLATE A solution of diethyl ethoxymethylenemalonate (35.0 g, 162 mmol), trifluoroacetaridine (18 g, 162 mmol) and NaOEt (11.0 g, 162 mmol) in EtOH (200 mL) was heated at reflux for 6 h. The reaction mixture was concentrated and H₂ O (48 naL) was added. The resulting solid was filtered, washed with Et₂ O (300 mL) and H₂ O (200 mL), and dried to give the title compound (21 g, 50percent yield); m.p.>220° C. (dec.); ¹ H NMR (DMSO-d₆) δ 8.38, 4.16 (q, 2H), 1.25 (q, 3H).

Reference： [1] Patent: US5935966, 1999, A,

5
[ 7732-18-5 ]
[ 354-37-0 ]
[ 87-13-8 ]
[ 343-67-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With NaOEt In ethanol	Example 33 ETHYL 2-TRIFLUOROMETHYL-4-HYDROXYPYRIMIDINE-5-CARBOXYLATE A solution of diethyl ethoxymethylenemalonate (35.0 g, 162 mmol), trifluoroacetamidine (18 g, 162 mmol) and NaOEt (11.0 g, 162 mmol) in EtOH (200 mL) was heated at reflux for 6 h. The reaction mixture was concentrated and H₂ O (48 mL) was added. The resulting solid was filtered, washed with Et₂ O (300 mL) and H₂ O (200 mL), and dried to give the title compound (21 g, 50percent yield); m.p. >220° C. (dec.); ¹ H-NMR (DMSO-d₆) δ 8.38, 4.16 (q, 2H), 1.25 (q, 3H).

Reference： [1] Patent: US5811428, 1998, A,

6
[ 354-37-0 ]
[ 87-13-8 ]
[ 343-67-9 ]

Reference： [1] Journal of medicinal chemistry, 2000, vol. 43, # 21, p. 3995 - 4004
[2] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1645 - 1648

7
[ 87-13-8 ]
[ 206258-97-1 ]

Reference： [1] Patent: US2013/210844, 2013, A1,
[2] Patent: WO2019/25341, 2019, A1,

[ 87-13-8 ] Synthesis Path-Downstream 1~18

1
[ 5552-83-0 ]
[ 87-13-8 ]
[ 113525-71-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 645 - 650
[2]Journal of Organic Chemistry,1954,vol. 19,p. 504,508

2
[ 538-28-3 ]
[ 87-13-8 ]
[ 93185-32-1 ]

Reference： [1]Patent: US2698326,1953,

3
[ 87-13-8 ]
[ 6296-99-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With ammonia; In ethanol; at 20℃; for 1.0h;	Ammonia was passed through ethanol (200 mL) for 30 minutes. Diethyl 2- (ethoxymethylene) malonate (21.6 g, 0.1 mol, 1.0 eq) was dissolved in an ammonia / ethanol solution and reacted at room temperature for 1 hour. After the reaction was detected by LC-MS and TLC, the reaction was concentrated. The crude product was purified by silica gel column chromatography (100-200 mesh silica gel, PE / EA = 5: 1) to obtain a white solid (18 g, yield: 96%)
	With ammonia; In ethanol; at 20℃; for 1.0h;	2-Ethoxymethylene-malonic acid diethyl ester (20 ml, 100 mmol) and a 10% soln. of ammonia in EtOH (37 ml, 220 mmol) are stirred at rt for 1 h. The mixture is evaporated and dried in HV to give 2-aminomethylene-malonic acid diethyl ester that is used without further purification.
	With ammonia; In ethanol;	a Diethyl aminomethylenemalonate To diethyl ethoxymethylenemalonate (50.13 g, 0.232 mmol), cooled to -20 C. under nitrogen, was added a 2.0 M solution of ammonia in ethanol (232 ml, 0.464 mmol) and the resulting solution was stirred at room temperature overnight. The solution was then evaporated in vacuo to give a quantitative yield of the title compound as a cream solid; 1H NMR (360 MHz, CDCl3) 5 1.28 (3H, t, J 7.1 Hz), 1.35 (3H, t, J 7.1 Hz), 4.19 (2H, q, J 7.1 Hz), 4.26 (2H, q, J 7.1 Hz), 5.68 (1H, br s), 8.11 (1H, dd), 8.69 (1H, br s).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3441 - 3444
[2]Patent: CN110041316,2019,A .Location in patent: Paragraph 0654; 0658-0660
[3]Journal of the American Chemical Society,1961,vol. 83,p. 4225 - 4228
[4]Gazzetta Chimica Italiana,1974,vol. 104,p. 715 - 729
[5]Journal of the Chemical Society. Perkin transactions II,1981,p. 561 - 570
[6]Australian Journal of Chemistry,1992,vol. 45,p. 1571 - 1576
[7]Patent: WO2009/21957,2009,A2 .Location in patent: Page/Page column 19
[8]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 608 - 613
[9]Patent: US6333336,2001,B1

4
[ 4774-10-1 ]
[ 87-13-8 ]
[ 132973-00-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643

5
ammonium hydroxide [ No CAS ]
[ 87-13-8 ]
[ 6296-99-7 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1897,vol. 297,p. 77

6
[ 87-13-8 ]
[ 60481-51-8 ]
[ 374924-92-2 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3730 - 3745

7
[ 76369-62-5 ]
[ 87-13-8 ]
[ 6296-99-7 ]

Reference： [1]Australian Journal of Chemistry,2004,vol. 57,p. 685 - 688

8
[ 5369-19-7 ]
[ 87-13-8 ]
[ 82121-12-8 ]

Yield	Reaction Conditions	Operation in experiment
47%	In diphenylether; at 60 - 250℃; for 2.75h;	A mixture of <strong>[5369-19-7]3-tert-butylaniline</strong> (5.30 g, 35.5 mmol) and diethyl ethoxymethylenemalonate (10.2 g, 47.30 mmol) were heated at 60 0C for 15 min. then 1 hour at 120 0C. After the generated ethanol was evaporated in vacuo, the crude oil was added dropwise to boiling diphenylether (150 ml) at 200-2500C and the mixture was stirred at 25O0C for 90 min. After cooling to room temperature, the mixture was diluted with hexane (ca. 200 ml) and the precipitate solid was collected to give (4.55 g, 47 percent) of the title compound as a slightly yellow solid. The compound was used for the next step without the determination of NMR, MS for hard solids.

Reference： [1]Patent: WO2008/7211,2008,A1 .Location in patent: Page/Page column 49

9
[ 87-13-8 ]
[ 59702-07-7 ]
[ 1068150-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 100℃;	A mixture of <strong>[59702-07-7]1-<strong>[59702-07-7]methylpiperazin-2-one</strong></strong> (183 g, 1.6 mol) and diethyl ethoxymethylenemalonate (346 g, 1.6 mol) in toluene (12 L) was heated at 100 °C overnight. The resultant mixture was concentrated under vacuum. The residue was dissolved in anhydrous THF (8 L), brought to reflux under an atmosphere of nitrogen, and treated with a solution of lithium bis (trimethylsilyl)amide in THF (1 M, 1.05 eq). The reaction mixture was allowed to cool to room temperature and concentrated under vacuum. The residue was partitioned between methylene chloride and dilute aqueous HCI. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was triturated with ethyl acetate, cooled to -20 °C, and the solid precipitated was filtered to provide the title compound. 1H NMR (400 MHz, DMSO-d6) 8 8.50 (s, 1H), 7.33 (s, 1H), 4.18 (q, J = 7.1 Hz, 2H), 4.11 (t, J = 5.5 Hz, 2H), 3.59 (t, J = 5.5 Hz, 2H), 2.92 (s, 3H), 1.24 (t, J = 7.1 Hz, 3H). ES MS M+l = 239

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4581 - 4583
[2]Patent: WO2005/110414,2005,A2 .Location in patent: Page/Page column 71

10
[ 87-13-8 ]
[ 60481-51-8 ]
[ 376593-74-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ethanol; for 3h;Heating / reflux;	A suspension of <strong>[60481-51-8]3,4-dimethylphenylhydrazine hydrochloride</strong> (2.0 g; 0.012 mol.) and potassium carbonate (3.2 g; 0.023 mol.) in anhydrous ethanol (40.0 mL) was treated dropwise with diethyl(ethoxymethylene)malonate (2.5 g; 0.012 mol.) and the mixture stirred and heated under reflux for 3 h. After cooling the mixture was evaporated and the residue suspended in water and acid;ified to pH 2 followed by extraction with ethyl acetate. After drying and evaporation the resulting intermediate 1-(3,4-dimethyl-phenyl)-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid; ethyl ester was dissolved in methanol (10.0 mL) and 10percent aqueous sodium hydroxide (10.0 mL) and stirred at room temperature for 3 h and then heated under reflux to effect hydrolysis. The solution was cooled and acid;ified to pH 4 with 3M aqu. hydrochloric acid; and stirred at room temperature for 2 h to effect decarboxylation. The mixture was extracted with ethyl acetate, dried and evaporated to give the title compound (87percent) as a yellow solid. 1H NMR (300 MHz, CDCl3) delta 7.61 (d, J=2.3 Hz, 1H), 7.55 (dd, J=8.2 and 2.3 Hz, 1H), 7.48 (t, J=1.3 Hz, 1H), 1.16 (d, J=8.2 Hz, 1H), 3.50 (d, J=1.3 Hz, 2H)

Reference： [1]Patent: US2004/19190,2004,A1 .Location in patent: Page 44

11
[ 87-13-8 ]
[ 59702-07-7 ]
[ 701208-31-3 ]

Yield	Reaction Conditions	Operation in experiment
		Step 4: Ethyl 8-hydroxy-2-methyl-l-oxo-l,2,3,4-tetrahydropyrrolo[l,2-alpha]-pyrazine-7-carboxylate; -A mixture of l-<strong>[59702-07-7]methylpiperazin-2-one</strong> (183 g, 1.6mol) and diethyl ethoxymethylenemalonate (346 g, 1.6 mol) in toluene (12 L) was heated at 100 0C overnight. The resultant mixture was concentrated under vacuum. The residue was dissolved in anhydrous THF (8 L), brought to reflux under an atmosphere of nitrogen, and treated with a solution of lithium bis(trimethylsilyl)amide in THF (I M, 1.05 eq). The reaction mixture was allowed to cool to room temperature and concentrated under vacuum. The residue was partitioned between methylene chloride and dilute aqueous HCl. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was triturated with ethyl acetate, cooled to -20 0C, and the solid precipitated was filtered to provide the title compound. lH NMR (400 MHz,DMSO-d6) delta 8.50 (s, IH), 7.33 (s, IH), 4.18 (q, J= 7.1 Hz, 2H), 4.11 (t, J= 5.5 Hz, 2H), 3.59 (t, J= 5.5Hz, 2H), 2.92 (s, 3H), 1.24 (t, J= 7.1 Hz, 3H). ES MS M+l = 239.
		A mixture of l-<strong>[59702-07-7]methylpiperazin-2-one</strong> (183 g, 1-6mol) and diethyl ethoxymethylenemalonate (346 g, 1.6 mol) in toluene (12 L) was heated at 100 °C ovemight. The resultant mixture was concentrated under vacuum. The residue was dissolved in anhydrous THF (8 L), brought to reflux under an atmosphere of nitrogen, and treated with a solution of lithium bis (trimethylsilyl) amide in THF (1 M, 1.05 eq). The reaction mixture was allowed to cool to rt and concentrated under vacuum. The residue was partitioned between methylene chloride and dilute aqueous HC1. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was triturated with ethyl acetate, cooled to-20 °C, and the solid precipitated was filtered to provide the title compound. 1H NMR (400 MHz, DMSO-d6) S 8.50 (s, 1H), 7.33 (s, 1H), 4.18 (q, J = 7.1 Hz, 2H), 4.11 (t, J = 5.5 Hz, 2H), 3.59 (t, J = 5.5 Hz, 2H), 2.92 (s, 3H), 1.24 (t, J = 7.1 Hz, 3H). ES MS M+1 = 239

Reference： [1]Patent: WO2007/50510,2007,A2 .Location in patent: Page/Page column 30
[2]Patent: WO2005/41664,2005,A1 .Location in patent: Page/Page column 95-96

12
[ 39745-40-9 ]
[ 87-13-8 ]
diethyl 2-(((2-chloro-6-methyl-3-pyridinyl)amino)methylene)-malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.9 g (95%)	In dichloromethane;	Preparation 42 Diethyl 2-(((2-Chloro-6-methyl-3-pyridinyl)amino)methylene) malonate [BT.2] A mixture of 2-chloro-6-methyl-3-pyridinylamine (8.5 g) and diethyl ethoxy-methylenemalonate (22.0 mL) is heated at 140° C. for 18 hours. The mixture is cooled to room temperature and the resulting solids are recrystallized from a mixture of heptane (400 mL) and CH2Cl2 (2 mL) to obtain 17.9 g (95percent) of the title compound as a pale red solid. Physical characteristics: MS (ESI+) m/z 313 (M+H).

Reference： [1]Patent: US2002/25960,2002,A1

13
[ 5369-19-7 ]
[ 87-13-8 ]
[ 82121-12-8 ]

Yield	Reaction Conditions	Operation in experiment
	In diphenylether;	A mixture of 3-t-butylaniline (67.6 g.) and diethyl ethoxymethylenemalonate was heated on the steam bath for 3 hours, the ethanol formed being collected by distillation. The resulting yellow oil was dissolved in diphenyl ether (200 ml.) and added during 0.5 hour to stirred diphenyl ether (800 ml.) at 250°-260°, the ethanol formed being collected by distillation. The mixture was stirred at 250°-260° for 0.5 hour, then allowed to cool to room temperature and diluted with an equal volume of petroleum ether (b.p. 60°-80°). The precipitate was collected by filtration to give the novel compound ethyl 7-t-butyl-4-hydroxyquinoline-3-carboxylate, m.p. 279°-281°.

Reference： [1]Patent: US4442109,1984,A

14
[ 87-13-8 ]
[ 371-40-4 ]
[ 391-78-6 ]

Yield	Reaction Conditions	Operation in experiment
32%		To a suspension solution of 6-fluoroquinolin-4-ol (3.67 g, 22.5 mmol) (synthesized in overall yield of 32percent starting from 4-fluoroaniline and diethyl ethoxymethylenemalonate according to a literature procedure (see Price et al., Organic Syntheses, Coll. Vol. 3, p. 272; Vol. 28, p. 38), triphenylphosphine (6.56 g, 25 mmol), and 3-bromo-1-propanol (2.3 mL, 25 mmol) in dry tetrahydrofuran (30 mL) was added diisopropyl azodicarboxylate (4.9 mL, 25 mmol) at 25° C. over 30 minutes under nitrogen and the reaction mixture was left stirring for one hour. Hydrobromic acid (2.8 mL of 48percent aqueous solution, 25 mmol) was added, resulting in precipitation of the titled compound. The product was collected by suction filtration and washed with THF, acetone and ether to give a light yellow crystalline solid (4.17 g, 51percent). 1H NMR (400 MHz, DMSO-d6): 2.45 (2H, m), 3.82 (2H, t, J=6.5 Hz), 4.61 (2H, t, J=5.7 Hz), 7.64 (1H, d, J=6.6 Hz), 8.40 (1H, dt, J=8.5, 2.7 Hz), 7.90 (m, 1H), 8.27 (1H, dd, J=9.4, 4.8 Hz), 9.24 (1H, d, J=6.6 Hz).
	With hydrogenchloride; sodium hydroxide; In diphenylether; hexane; water;	(a) 6-Fluoro-4-hydroxyquinoline A mixture of 216 ml of diethyl ethoxymethylenemalonate, 95 ml of 4-fluoroaniline, and 800 ml of diphenyl ether was stirred and slowly heated to 185° with distillation of the ethanol formed. The reaction mixture was then heated to 245° for 1.5 hr. The total amount of ethanol collected was 105 ml. The reaction mixture was allowed to cool to 60° at which time 250 ml of hexane was added. After it had stood overnight, the product was collected, washed with hexane and dried to give 223 g of solid mp 305°-309°. A mixture of the above solid, 600 ml of 3N sodium hydroxide, and 250 ml of water was stirred and heated under reflux for 2 hr. To the hot brown cloudy mixture was slowly added 600 ml of 3N hydrochloric acid to precipitate the product, 6-fluoro-4-hydroxyquinoline-3-carboxylic acid. This product was filtered from the cooled reaction mixture. This damp solid and 600 ml of diphenyl ether was slowly heated to 250° while water was allowed to distill out. The reaction mixture was held at this temperature for 20 min. and then allowed to cool to 100°. Then 500 ml of hexane was added, and the mixture was stirred for 1 hr. The product 6-fluoro-4-hydroxyquinoline, was collected and washed with hexane to give 144 g, mp 209°-212°.

Reference： [1]Patent: US2009/99220,2009,A1 .Location in patent: Page/Page column 8-9
[2]Patent: US4560692,1985,A

15
[ 41608-73-5 ]
[ 87-13-8 ]
C₁₆H₂₁NO₇S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1380 - 1385

16
[ 1124-16-9 ]
[ 87-13-8 ]
[ 19735-96-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2340 - 2343

17
ethyl 2-cyanoethanecarboximidate [ No CAS ]
[ 87-13-8 ]
[ 138007-24-6 ]
[ 1039037-34-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2963 - 2968

18
[ 10167-97-2 ]
[ 87-13-8 ]
diethyl 2-(((5-methoxypyridin-2-yl)amino)methylene)malonate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 1073 - 1084

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Technical Information

? Acyl Group Substitution ? Arndt-Eistert Homologation ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Heat of Combustion ? Hunsdiecker-Borodin Reaction ? Passerini Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Carboxylic Acids ? Reactions with Organometallic Reagents ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction

Historical Records

Pharmaceutical Intermediates of
[ 87-13-8 ]

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[ 380844-49-5 ]

7-(3-Chloropropoxy)-4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxyquinoline-3-carbonitrile

[ 846023-24-3 ]

2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide

[ 5317-33-9 ]

3-(4-Methylpiperazin-1-yl)propan-1-ol

[ 98446-49-2 ]

2,4-Dichloro-5-methoxyaniline

[ 94-05-3 ]

Ethyl (ethoxymethylene)cyanoacetate

Avanafil Intermediates

[ 20187-46-6 ]

Ethyl 4-amino-2-hydroxypyrimidine-5-carboxylate

[ 330785-84-7 ]

(S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylic acid

[ 330785-83-6 ]

(S)-Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate

[ 330785-81-4 ]

Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylate

[ 71-30-7 ]

6-Aminopyrimidin-2(1H)-one

Related Functional Groups of
[ 87-13-8 ]

Alkenyls

[ 3044-06-2 ]

Diethyl 2-(1-ethoxyethylidene)malonate

Similarity: 0.86

[ 3377-20-6 ]

Diethyl 2-methylenemalonate

Similarity: 0.81

[ 3788-94-1 ]

Ethyl 2-(ethoxymethylene)-3-oxobutanoate

Similarity: 0.80

[ 30982-08-2 ]

Methyl 2-(acetoxymethyl)acrylate

Similarity: 0.78

[ 10029-04-6 ]

Ethyl 2-(hydroxymethyl)acrylate

Similarity: 0.78

Aliphatic Chain Hydrocarbons

[ 3044-06-2 ]

Diethyl 2-(1-ethoxyethylidene)malonate

Similarity: 0.86

[ 3377-20-6 ]

Diethyl 2-methylenemalonate

Similarity: 0.81

[ 3788-94-1 ]

Ethyl 2-(ethoxymethylene)-3-oxobutanoate

Similarity: 0.80

[ 30982-08-2 ]

Methyl 2-(acetoxymethyl)acrylate

Similarity: 0.78

[ 10029-04-6 ]

Ethyl 2-(hydroxymethyl)acrylate

Similarity: 0.78

Esters

[ 3044-06-2 ]

Diethyl 2-(1-ethoxyethylidene)malonate

Similarity: 0.86

[ 3377-20-6 ]

Diethyl 2-methylenemalonate

Similarity: 0.81

[ 3788-94-1 ]

Ethyl 2-(ethoxymethylene)-3-oxobutanoate

Similarity: 0.80

[ 30982-08-2 ]

Methyl 2-(acetoxymethyl)acrylate

Similarity: 0.78

[ 10029-04-6 ]

Ethyl 2-(hydroxymethyl)acrylate

Similarity: 0.78

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
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

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[ CAS No. 87-13-8 ] {[proInfo.proName]}

Quality Control of [ 87-13-8 ]

Related Doc. of [ 87-13-8 ]

Product Citations Expand+

Product Details of [ 87-13-8 ]

Calculated chemistry of [ 87-13-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 87-13-8 ]

Application In Synthesis of [ 87-13-8 ]

[ 87-13-8 ] Synthesis Path-Upstream 1~7

[ 87-13-8 ] Synthesis Path-Downstream 1~18

Technical Information

Pharmaceutical Intermediates of [ 87-13-8 ]

Bosutinib Intermediates

Avanafil Intermediates

Related Functional Groups of [ 87-13-8 ]

Alkenyls

Aliphatic Chain Hydrocarbons

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 87-13-8 ]

Related Functional Groups of
[ 87-13-8 ]