[ CAS No. 69065-98-1 ]

Name: 69065-98-1|Ethyl 2-((2-fluorophenyl)amino)-2-oxoacetate|95%
Brand: Ambeed
SKU: A992943
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Quality Control of [ 69065-98-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 69065-98-1 ]

SDS Specification

Alternatived Products of [ 69065-98-1 ]

Product Details of [ 69065-98-1 ]

CAS No. :	69065-98-1	MDL No. :	MFCD02859892
Formula :	C₁₀H₁₀FNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HCDBPTNQEKPGQP-UHFFFAOYSA-N
M.W :	211.19	Pubchem ID :	3412149
Synonyms :

Calculated chemistry of [ 69065-98-1 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.61
TPSA :	55.4 Å²

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) :	-6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.25
Log Po/w (XLOGP3) :	1.58
Log Po/w (WLOGP) :	1.56
Log Po/w (MLOGP) :	1.56
Log Po/w (SILICOS-IT) :	1.61
Consensus Log Po/w :	1.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.11
Solubility :	1.64 mg/ml ; 0.00775 mol/l
Class :	Soluble
Log S (Ali) :	-2.35
Solubility :	0.934 mg/ml ; 0.00442 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.17
Solubility :	0.144 mg/ml ; 0.000684 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.83

Safety of [ 69065-98-1 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P260-P264-P273-P301+P312-P305+P351+P338-P314	UN#:	3077
Hazard Statements:	H302-H319-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 69065-98-1 ]

* 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 [ 69065-98-1 ]

[ 69065-98-1 ] Synthesis Path-Downstream 1~27

1
[ 348-54-9 ]
[ 4755-77-5 ]
[ 69065-98-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine In chloroform at 10 - 20℃;
93%	In chloroform at 10 - 20℃;
90%	With sodium hydroxide In dichloromethane; water at 20℃; for 24h;

90%	With sodium hydroxide In dichloromethane at 20℃;
	With triethylamine In dichloromethane
	Stage #1: 2-Fluoroaniline With triethylamine In dichloromethane at 0 - 5℃; for 0.25h; Stage #2: Ethyl oxalyl chloride In dichloromethane at 0 - 20℃; for 16h;	2-((2-(tert-butyl)phenyl)amino)-2-oxoacetic acid (14) General procedure: A mixture of2-(tert-butyl)aniline(15.00 g, 100.52 mmol, 15.63 mL, 1.00eq), Et3N (11.19 g, 110.57 mmol, 15.33 mL, 1.10eq) and DCM (150.00 mL) was stirred at 0 - 5 °C for 15 minutes; ethyl 2-chloro-2-oxo-acetate (13.72 g, 100.52 mmol, 11.25 mL, 1.00eq) was added to the reaction mixture dropwise during 15 minutes. This mixture was stirred at 20 °C for 16 h. The mixture was quenched with water (100 mL). The mixture was extracted with EtOAc (200 mL * 2). The organic layers was combined, washed with 0.1 M HCl (150 mL) and water (100 mL). The organic phase was dried over Na2SO4, filtered and concentrated by vacuum to give ethyl 2-(2-tert-butylanilino)-2-oxo-acetate (25.00 g, crude) as a colorless oil. A mixture of ethyl 2-(2-tert-butylanilino)-2-oxo-acetate (25.00 g, 100.28 mmol, 1.00eq) and 1,4-dioxane (250.00 mL) was stirred at 20 °C for 5 minutes. A solution of LiOH·H2O (4.21 g, 100.28 mmol, 2.79 mL, 1.00eq) in Water (125.00 mL) was added to the mixtue. The reaction mixture was stirred at rt for 1.5 h. 400 mL water was added the reaction mixture ,the mixture was washed with 300 mL EtOAc. The aqueous layer was adjusted pH to 2 by HCl (12 M), then, extracted with EtOAc (300 mL * 2). The organic layers was combined, washed with 200 mL water. The organic layer was dried, filtered and the filtrate was concentrated by vacuum to give2-((2-(tert-butyl)phenyl)amino)-2-oxoacetic acid (14)(21.00 g, 94.92 mmol, 95% yield) as a white solid.
	With triethylamine In dichloromethane at 20℃;
	With triethylamine In dichloromethane at 20℃; for 1h;	4.1.3 General synthetic procedures for ethyl 2-oxo-2-(arylamino)acetates 8a-g General procedure: To a solution of substituted anilines (10mmol) and triethylamine (1mL, 10mmol) in DCM was added ethyl chlorooxoacetate (10mmol). The reaction mixture was stirred for 1h at room temperature. The reaction mixture was poured into water and extracted with DCM (50mL×3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield the crude product. The crude product was purified by column chromatography (n-hexane/EtOAc=1:2) on silica gel to afford pure products. For example
	With triethylamine In dichloromethane at 20℃; for 1h;

Reference： [1]Chakraborty, Kajal; Devakumar, Chakravarthi; Tomar, Shiv M. S.; Kumar, Rajendra [Journal of Agricultural and Food Chemistry, 2003, vol. 51, # 4, p. 992 - 998]
[2]Chakraborty, Kajal; Devakumar [Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 5, p. 1868 - 1873]
[3]Yavari; Nasiri; Djahaniani [Polish Journal of Chemistry, 2004, vol. 78, # 10, p. 1871 - 1876]
[4]Yavari, Issa; Nasiri, Farough; Djahaniani, Hoorieh; Bijanzadeh, Hamid R. [Journal of Chemical Research, 2005, # 8, p. 537 - 539]
[5]Location in patent: body text Sengupta, Saumitra; Rao, G. Venkateshwar; Dubey [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 7, p. 901 - 905]
[6]Mou, Jianfeng; Wu, Songliang; Luo, Zhi; Guo, Fengying; He, Haiying; Wang, Jianhua; Lin, Fusen; Guo, Fengxun; Sun, Jianping; Shen, Liang; Zeng, Minggao; Wang, Chuan; Xu, Deming; Gu, Zhengxian; Tian, Xin; Zhang, Aiming; Xu, Hongjiang; Yang, Ling; Zhang, Xiquan; Li, Jian; Chen, Shuhui [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1874 - 1878]
[7]Winterton, Sarah E.; Capota, Emanuela; Wang, Xiaoyu; Chen, Hong; Mallipeddi, Prema L.; Williams, Noelle S.; Posner, Bruce A.; Nijhawan, Deepak; Ready, Joseph M. [Journal of Medicinal Chemistry, 2018, vol. 61, # 12, p. 5199 - 5221]
[8]Wang, Chao; Li, Yuelin; Liu, Tong; Wang, Zeyu; Zhang, Yujing; Bao, Kai; Wu, Yingliang; Guan, Qi; Zuo, Daiying; Zhang, Weige [Bioorganic Chemistry, 2020, vol. 104]
[9]Wang, Chao; Li, Yuelin; Liu, Zi; Wang, Zeyu; Liu, Zihan; Man, Shuai; Zhang, Yujing; Bao, Kai; Wu, Yingliang; Guan, Qi; Zuo, Daiying; Zhang, Weige [Journal of Enzyme Inhibition and Medicinal Chemistry, 2021, vol. 36, # 1, p. 549 - 560]

2
[ 66086-33-7 ]
[ 69065-98-1 ]
di-tert-butyl 4-ethoxy-1-(2-fluorophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triphenylphosphine In dichloromethane at 20℃; for 24h;

Reference： [1]Yavari; Nasiri; Djahaniani [Polish Journal of Chemistry, 2004, vol. 78, # 10, p. 1871 - 1876]

3
[ 762-42-5 ]
[ 69065-98-1 ]
dimethyl 4-ethoxy-1-(2-fluorophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triphenylphosphine In dichloromethane at 20℃; for 24h;

Reference： [1]Yavari; Nasiri; Djahaniani [Polish Journal of Chemistry, 2004, vol. 78, # 10, p. 1871 - 1876]

4
[ 762-21-0 ]
[ 69065-98-1 ]
diethyl 4-ethoxy-1-(2-fluorophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With triphenylphosphine In dichloromethane at 20℃; for 24h;

Reference： [1]Yavari; Nasiri; Djahaniani [Polish Journal of Chemistry, 2004, vol. 78, # 10, p. 1871 - 1876]

5
[ 7188-38-7 ]
[ 762-42-5 ]
[ 69065-98-1 ]
dimethyl 2-[(tert-butylimino)-methylene]-3-[(2-ethoxy-2-oxoacetyl)-2-fluoroanilino]-succinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In dichloromethane at 20℃;

Reference： [1]Yavari, Issa; Nasiri, Farough; Djahaniani, Hoorieh; Bijanzadeh, Hamid R. [Journal of Chemical Research, 2005, # 8, p. 537 - 539]

6
[ 7188-38-7 ]
[ 762-21-0 ]
[ 69065-98-1 ]
diethyl 2-[(tert-butylimino)-methylene]-3-[(2-ethoxy-2-oxoacetyl)-2-fluoroanilino]-succinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In dichloromethane at 20℃;

Reference： [1]Yavari, Issa; Nasiri, Farough; Djahaniani, Hoorieh; Bijanzadeh, Hamid R. [Journal of Chemical Research, 2005, # 8, p. 537 - 539]

7
[ 69065-98-1 ]
C₂₃H₂₅F₃N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium hydroxide / water 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 2 °C

Reference： [1]Sengupta, Saumitra; Rao, G. Venkateshwar; Dubey [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 7, p. 901 - 905]

8
[ 69065-98-1 ]
C₂₃H₂₃F₃N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 2 °C 3: Dess-Martin periodane / N,N-dimethyl-formamide / 0 - 20 °C

Reference： [1]Sengupta, Saumitra; Rao, G. Venkateshwar; Dubey [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 7, p. 901 - 905]

9
[ 69065-98-1 ]
[ 1338471-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: lithium hydroxide / water 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 2 °C 3: Dess-Martin periodane / N,N-dimethyl-formamide / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane; methoxybenzene / 0 °C

Reference： [1]Sengupta, Saumitra; Rao, G. Venkateshwar; Dubey [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 7, p. 901 - 905]

10
[ 69065-98-1 ]
[ 84944-15-0 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; water; at 20℃; for 1.5h;Alkaline conditions;	General procedure: A mixture of2-(tert-butyl)aniline(15.00 g, 100.52 mmol, 15.63 mL, 1.00eq), Et3N (11.19 g, 110.57 mmol, 15.33 mL, 1.10eq) and DCM (150.00 mL) was stirred at 0 - 5 C for 15 minutes; ethyl 2-chloro-2-oxo-acetate (13.72 g, 100.52 mmol, 11.25 mL, 1.00eq) was added to the reaction mixture dropwise during 15 minutes. This mixture was stirred at 20 C for 16 h. The mixture was quenched with water (100 mL). The mixture was extracted with EtOAc (200 mL * 2). The organic layers was combined, washed with 0.1 M HCl (150 mL) and water (100 mL). The organic phase was dried over Na2SO4, filtered and concentrated by vacuum to give ethyl 2-(2-tert-butylanilino)-2-oxo-acetate (25.00 g, crude) as a colorless oil. .A mixture of ethyl 2-(2-tert-butylanilino)-2-oxo-acetate (25.00 g, 100.28 mmol, 1.00eq) and 1,4-dioxane (250.00 mL) was stirred at 20 C for 5 minutes. A solution of LiOH·H2O (4.21 g, 100.28 mmol, 2.79 mL, 1.00eq) in Water (125.00 mL) was added to the mixtue. The reaction mixture was stirred at rt for 1.5 h. 400 mL water was added the reaction mixture ,the mixture was washed with 300 mL EtOAc. The aqueous layer was adjusted pH to 2 by HCl (12 M), then, extracted with EtOAc (300 mL * 2). The organic layers was combined, washed with 200 mL water. The organic layer was dried, filtered and the filtrate was concentrated by vacuum to give2-((2-(tert-butyl)phenyl)amino)-2-oxoacetic acid (14)(21.00 g, 94.92 mmol, 95% yield) as a white solid.

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2011,vol. 50,p. 901 - 905
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 1874 - 1878

11
[ 69065-98-1 ]
C₂₉H₃₂F₅N₃O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 1,4-dioxane; water / 1.5 h / 20 °C / Alkaline conditions 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 25 °C 3.1: tetrahydrofuran; water / 1.5 h / 0 - 25 °C / Alkaline conditions 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h 4.2: 60 h / 25 °C

Reference： [1]Mou, Jianfeng; Wu, Songliang; Luo, Zhi; Guo, Fengying; He, Haiying; Wang, Jianhua; Lin, Fusen; Guo, Fengxun; Sun, Jianping; Shen, Liang; Zeng, Minggao; Wang, Chuan; Xu, Deming; Gu, Zhengxian; Tian, Xin; Zhang, Aiming; Xu, Hongjiang; Yang, Ling; Zhang, Xiquan; Li, Jian; Chen, Shuhui [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1874 - 1878]

12
[ 69065-98-1 ]
(S)-3-(1-(2-((2-fluorophenyl)amino)-2-oxoacetyl)piperidine-4-carboxamido)-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 1,4-dioxane; water / 1.5 h / 20 °C / Alkaline conditions 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 25 °C 3.1: tetrahydrofuran; water / 1.5 h / 0 - 25 °C / Alkaline conditions 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h 4.2: 60 h / 25 °C 5.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 24 h / 25 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 25 °C

13
[ 69065-98-1 ]
C₂₉H₃₀F₅N₃O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 1,4-dioxane; water / 1.5 h / 20 °C / Alkaline conditions 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 25 °C 3.1: tetrahydrofuran; water / 1.5 h / 0 - 25 °C / Alkaline conditions 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h 4.2: 60 h / 25 °C 5.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 24 h / 25 °C

14
[ 69065-98-1 ]
C₁₆H₁₉FN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,4-dioxane; water / 1.5 h / 20 °C / Alkaline conditions 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 25 °C

15
[ 69065-98-1 ]
C₁₄H₁₅FN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1,4-dioxane; water / 1.5 h / 20 °C / Alkaline conditions 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 25 °C 3: tetrahydrofuran; water / 1.5 h / 0 - 25 °C / Alkaline conditions

16
[ 55-81-2 ]
[ 69065-98-1 ]
N<SUP>1</SUP>-(2-fluorophenyl)-N<SUP>2</SUP>-(4-methoxyphenethyl)oxalamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.3 mg	In ethanol at 80℃;

Reference： [1]Winterton, Sarah E.; Capota, Emanuela; Wang, Xiaoyu; Chen, Hong; Mallipeddi, Prema L.; Williams, Noelle S.; Posner, Bruce A.; Nijhawan, Deepak; Ready, Joseph M. [Journal of Medicinal Chemistry, 2018, vol. 61, # 12, p. 5199 - 5221]

17
[ 348-54-9 ]
[ 762-21-0 ]
[ 69065-98-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With tert.-butylhydroperoxide; rose bengal In decane; acetonitrile at 20℃; for 48h; Irradiation;

Reference： [1]Arepally, Sagar; Katta, Narenderreddy; Murugan, Arumugavel; Ojha, Mamata; Sharada, Duddu S. [RSC Advances, 2020, vol. 10, # 21, p. 12599 - 12603]

18
[ 69065-98-1 ]
5-methyl-4-(2-fluorophenyl)-3-(4-(3-methylphenyl)piperazine-1-carbonyl)-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triphenylphosphine; tetrachloromethane / 16 h / Reflux 2.1: acetonitrile / Inert atmosphere 3.1: trimethylaluminum / dichloromethane; n-heptane / 0.25 h / 20 °C 3.2: 16 h / 20 °C / Inert atmosphere