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[ CAS No. 96980-65-3 ] {[proInfo.proName]}

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Chemical Structure| 96980-65-3
Chemical Structure| 96980-65-3
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Quality Control of [ 96980-65-3 ]

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Product Details of [ 96980-65-3 ]

CAS No. :96980-65-3 MDL No. :MFCD00077473
Formula : C8H6ClF2NO Boiling Point : -
Linear Structure Formula :- InChI Key :TUPPVAAGWXKMRC-UHFFFAOYSA-N
M.W : 205.59 Pubchem ID :735854
Synonyms :

Calculated chemistry of [ 96980-65-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.47
TPSA : 29.1 Ų

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) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 2.0
Log Po/w (WLOGP) : 2.79
Log Po/w (MLOGP) : 2.68
Log Po/w (SILICOS-IT) : 2.74
Consensus Log Po/w : 2.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.52
Solubility : 0.623 mg/ml ; 0.00303 mol/l
Class : Soluble
Log S (Ali) : -2.24
Solubility : 1.19 mg/ml ; 0.00578 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.98
Solubility : 0.0214 mg/ml ; 0.000104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 96980-65-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 96980-65-3 ]

* 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 [ 96980-65-3 ]

[ 96980-65-3 ] Synthesis Path-Downstream   1~50

  • 2
  • [ 367-25-9 ]
  • [ 79-04-9 ]
  • [ 96980-65-3 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine In tetrahydrofuran at 0℃; for 10h;
89.31% With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; 4.1.20 2-Chloro-N-(4-methoxyphenyl)acetamide (10a) General procedure: To a solution of a4-methoxyaniline (6.16g, 0.050mol), Et3N (5.05g, 0.050mol) in DMF (40mL) was added chloroacely chloride (6.78g, 0.06mol) dissolved in DMF (15mL) under ice bath. The mixture was stirred at rt for 2h and poured into water and then filtered to get the compound compound 10a as yellow solid (9.61g, 96.25%).
78% at 20℃; Cooling; 3.1.1. Synthesis of 2-Chloro-N-(Substituted Phenyl) Acetamides(2a-c) General procedure: To the substituted aromatic amines (1a-c) (0.2 mol), cold chloroacetyl chloride (0.46 mol) was added with continuous stirring under anhydrous environment. The mixture was stirred for 4-6 hours at room temperature followed by the addition of sodium carbonate solution. The solid product separated out and filtered followed by washing with cold water. The solid product was dried and recrystallized from ethanol.
In 1,4-dioxane at 0 - 25℃; for 1h;
With triethylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; ethyl acetate 6.B B. B. Synthesis of 2-chloro-N-(2,4-difluorophenyl)acetamide To a cooled (0° C.) solution of 2,4-difluoroaniline, (1.5 g, 11.6 mmol) in DCM (50 mL) was added triethylamine (1.9 mL, 13.9 mmol) followed by 2-chloroacetyl chloride (1.0 mL, 12.8 mmol). The reaction was warmed to RT and stirred for 2 h. The reaction mixture was concentrated, redissolved in EtOAc (50 mL) and washed with brine (50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to yield 2.2 g of crude product which was further purified by flash column chromatography using 1:1 EtOAc:hexanes as the eluent. 2.0 g of 2-chloro-N-(2,4-difluorophenyl)acetamide, (yield: 84%) was isolated.
With sodium acetate In acetic acid
With potassium carbonate In acetone at 0 - 20℃; for 0.5h;
Stage #1: 2,4-difluorophenylamine With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: chloroacetyl chloride In dichloromethane at 20℃; for 3h; Inert atmosphere; 3.2.2. Synthesis of Substituted Chloroacetamide I General procedure: Under nitrogen atmosphere, dry CH2Cl2 (30 mL), amine (0.02 mol), and Et3N (0.05 mol) wereadded to a three-necked round bottom ask and stirred for 0.5 h, then chloroacetyl chloride droppedslowly and reacted for 3 h at room temperature. Then, the solution was washed with 2 mol L1hydrochloric acid (30 mL), saturated aq NaHCO3 solution (30 mL), and brine (40 mL), successively,then dried over anhydrous Na2SO4 and filtered. After evaporating CH2Cl2 in vacuum, the obtainedcrude product was rened by recrystallization using ethyl acetate/petroleum ether.
With potassium carbonate at 20℃; Cooling with ice; 3.1.2. General procedure for synthesis of 2a-2k General procedure: We have previously reported preparation, purification and characterization of 2a-2k in our research papers [36,37]. Briefly, Chloroacetyl chloride (0.1mol) was added drop wise to a mixture of appropriate amines (0.05mol) and anhydrous potassium carbonate (K2CO3) (0.075mol) in dichloromethane or chloroform in an ice-cold condition. The reaction mixture was then stirred at room temperature. After completion of reaction, solvent was evaporated under reduced pressure, ice cold water was added to the obtained dry mass and the insoluble product was filtered and dried and purified by recrystallization with appropriate solvents.
With potassium carbonate In dichloromethane at 0℃;
In N,N-dimethyl-formamide at 20℃; for 0.5h;
With potassium carbonate In dichloromethane for 24h;
With potassium carbonate In dichloromethane at 20℃; for 24h;
With triethylamine In dichloromethane Cooling with ice;
In N,N-dimethyl-formamide at 20℃; for 0.5h; General procedure for synthesis of 2-chloro-Nphenylacetamidederivatives 3a-g General procedure: A mixture of aniline derivatives 1 (1 mmol) and 2-chloroacetyl chloride 2 (1 mmol) in DMF was stirred at room temperature for 30 min. At the end of the reaction (checked by TLC), the reaction mixture was diluted with cold water and poured into ice, and the obtained precipitate was filtered off. The residue was washed with cold water to obtain pure 2-chloro-N-phenylacetamide derivatives 3a-g.
With potassium carbonate In dichloromethane at 20℃; for 24h; 1.1.2 General procedure for synthesis of 2k-2y General procedure: The synthetic procedure for the synthesis of various acetamide have been described in our various reports. Briefly, aromatic or heteroaromatic amines were added to chloroacetyl chloride (1:1.5) under cold conditions along with a base in chloroform or dichloromethane for a day. On completion of reaction, the solvent was evaporated, and product was washed with water. Dried product was recrystallized using ethanol.
With potassium carbonate In dichloromethane at 0 - 20℃;
With sodium hydrogencarbonate In acetone at 20℃; for 1h;
In N,N-dimethyl-formamide at 20℃; for 0.5h; 4.1.2. Synthesis of 2-chloro-N-phenylacetamide derivatives (6) General procedure: A mixture of aniline derivatives (1 mmol) and chloroacetyl chloride (1.3 mmol) in DMF (5 ml) were stirred at room temperature for 30 min. The progress of the reaction was monitored by thin-layer chromatography (Hexane /EtOAc 60:40). After completion of the reaction, H2O was added and the precipitate was collected by filtration to give the desired compound in high yields.

Reference: [1]Wilde, Richard G.; Billheimer, Jeffrey T.; Germain, Sandie J.; Hausner, Elizabeth A.; Meunier, Paul C.; Munzer, Deborah A.; Stoltenborg, Janet K.; Gillies, Peter J.; Burcham, Deborah L.; Huang, Shiew-Mai; Klaczkiewicz, John D.; Ko, Soo S.; Wexler, Ruth R. [Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 9, p. 1493 - 1513]
[2]Guo, Xiaoke; Yang, Qian; Xu, Jing; Zhang, Li; Chu, Hongxi; Yu, Peng; Zhu, Yingying; Wei, Jinglian; Chen, Weilin; Zhang, Yaozhong; Zhang, Xiaojin; Sun, Haopeng; Tang, Yiqun; You, Qidong [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6466 - 6476]
[3]Singh, Jagseer; Chawla, Pooja A.; Bhatia, Rohit; Singh, Shamsher [Letters in Organic Chemistry, 2021, vol. 18, # 12, p. 957 - 968]
[4]Khanna, Smriti; Madan, Manjula; Vangoori, Akhila; Banerjee, Rahul; Thaimattam, Ram; Jafar Sadik Basha; Ramesh, Mullangi; Casturi, Seshagiri Rao; Pal, Manojit [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 14, p. 4820 - 4833]
[5]Current Patent Assignee: SUN PHARMACEUTICAL INDUSTRIES LIMITED - US2008/280900, 2008, A1
[6]Shruthi; Poojary, Boja; Kumar, Vasantha; Prathibha; Hussain, Mumtaz Mohammed; Revanasiddappa; Joshi, Himanshu [Russian Journal of Bioorganic Chemistry, 2015, vol. 41, # 2, p. 223 - 230][Bioorg. Khim., 2014]
[7]Ugale, Vinod G.; Bari, Sanjay B. [Archiv der Pharmazie, 2016, vol. 349, # 11, p. 864 - 880]
[8]Cai, Nan; Liu, Caixiu; Feng, Zhihui; Li, Xinghai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Ahmed, Wasim; Cui, Zining [Molecules, 2018, vol. 23, # 4]
[9]Jänsch, Niklas; Meyer-Almes, F. J.; Mrowka, Piotr; Ramaa, C. S.; Schweipert, Markus; Tilekar, Kalpana; Upadhyay, Neha [Bioorganic Chemistry, 2020, vol. 95]
[10]Aguilera, Renato J.; Choe, Jun-yong; Henze Macias, Luca; Hess, Jessica D.; Meyer-Almes, Franz-Josef; Mrowka, Piotr; Ramaa, C. S.; Schweipert, Markus; Tilekar, Kalpana; Upadhyay, Neha; Jänsch, Niklas [Bioorganic Chemistry, 2020, vol. 100]
[11]Sepehri, Nima; Mohammadi-Khanaposhtani, Maryam; Asemanipoor, Nafise; Hosseini, Samanesadat; Biglar, Mahmood; Larijani, Bagher; Mahdavi, Mohammad; Hamedifar, Haleh; Taslimi, Parham; Sadeghian, Nastaran; Gulcin, Ilhami [Archiv der Pharmazie, 2020, vol. 353, # 10]
[12]Aguilera, Renato J.; Choe, Jun-yong; Hess, Jessica D.; Iancu, Cristina V.; Macias, Lucasantiago Henze; Meyer-Almes, Franz-Josef; Mrowka, Piotr; Ramaa, C. S.; Tilekar, Kalpana; Upadhyay, Neha [European Journal of Medicinal Chemistry, 2020, vol. 202]
[13]Aguilera, Renato J.; Choe, Jun-yong; Hess, Jessica D.; Iancu, Cristina V.; Macias, Lucasantiago Henze; Meyer-Almes, Franz-Josef; Mrowka, Piotr; Ramaa, C. S.; Schweipert, Markus; Tilekar, Kalpana; Upadhyay, Neha [European Journal of Pharmaceutical Sciences, 2020, vol. 154]
[14]Chen, Shunhong; Dai, Ali; Guo, Shengxin; He, Feng; Luo, Dexia; Wu, Jian; Zhang, Renfeng [Journal of Agricultural and Food Chemistry, 2020, vol. 68, # 27, p. 7226 - 7234]
[15]Sedaghati, Saeb; Azizian, Homa; Montazer, Mohammad Nazari; Mohammadi-Khanaposhtani, Maryam; Asadi, Mehdi; Moradkhani, Fatemeh; Ardestani, Mehdi Shafiee; Asgari, Mohammad Sadegh; Yahya-Meymandi, Azadeh; Biglar, Mahmood; Larijani, Bagher; Sadat-Ebrahimi, Seyed Esmaeil; Foroumadi, Alireza; Amanlou, Massoud; Mahdavi, Mohammad [Structural Chemistry, 2021, vol. 32, # 1, p. 37 - 48]
[16]Joshi, Hardik; Patil, Vijay; Tilekar, Kalpana; Upadhyay, Neha; Gota, Vikram; Ramaa [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 23]
[17]Tilekar, Kalpana; Hess, Jessica D.; Upadhyay, Neha; Bianco, Alessandra Lo; Schweipert, Markus; Laghezza, Antonio; Loiodice, Fulvio; Meyer-Almes, Franz-Josef; Aguilera, Renato J.; Lavecchia, Antonio; Ramaa [Journal of Medicinal Chemistry, 2021, vol. 64, # 10, p. 6949 - 6971]
[18]Liu, Mei-Ling; Li, Wei-Yi; Fang, Hai-Lian; Ye, Ya-Xi; Li, Su-Ya; Song, Wan-Qing; Xiao, Zhu-Ping; Ouyang, Hui; Zhu, Hai-Liang [ChemMedChem, 2022, vol. 17, # 2]
[19]Hosseini, Samanesadat; Mahdavi, Mohammad; Pourmousavi, Seied Ali; Taslimi, Parham [Journal of Molecular Structure, 2022, vol. 1255]
  • 3
  • [ 56278-50-3 ]
  • [ 96980-65-3 ]
  • 5-amino-4-(2-benzothiazolyl)-2,3-dihydro-1-(2,4-difluorophenyl)-2-pyrrolone [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate In ethanol for 1h; Heating;
  • 4
  • [ 53-86-1 ]
  • [ 96980-65-3 ]
  • [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid (2,4-difluorophenylcarbamoyl)methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With dmap; triethylamine at 25℃; for 24h;
  • 5
  • [ 96980-65-3 ]
  • (1S,3S,4S)-1-Isopropyl-4-methyl-2-thia-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (2,4-difluoro-phenyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / K2CO3 / tetrahydrofuran / 6 h / 50 °C 2: dimethylformamide; benzene / 7 h / Irradiation
  • 6
  • [ 96980-65-3 ]
  • (1R,3S,4R)-4-Isopropyl-1-methyl-2-thia-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (2,4-difluoro-phenyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / K2CO3 / tetrahydrofuran / 6 h / 50 °C 2: dimethylformamide; benzene / 7 h / Irradiation
  • 7
  • [ 96980-65-3 ]
  • 4,5-Dipentyl-3,6-dihydro-2H-thiopyran-2-carboxylic acid (2,4-difluoro-phenyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / K2CO3 / tetrahydrofuran / 6 h / 50 °C 2: 51 percent / dimethylformamide; benzene / 7 h / Irradiation
  • 8
  • [ 96980-65-3 ]
  • (2S,3R,6S)-3,6-Dipentyl-3,6-dihydro-2H-thiopyran-2-carboxylic acid (2,4-difluoro-phenyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / K2CO3 / tetrahydrofuran / 6 h / 50 °C 2: 47 percent / dimethylformamide; benzene / 7 h / Irradiation
  • 9
  • [ 34803-66-2 ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-[4-(2-pyridinyl)-1-piperazinyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.8% With sodium carbonate In DMF (N,N-dimethyl-formamide); water at 20℃; for 18h; 183 EXAMPLE 183; N-(2,4-difluorophenyl)-2-[4-(2-pyridinyl)-1-piperazinyl]acetamide [1576] A mixture of 1-pyridin-2-ylpiperazine (24 mg, 0.15 mmol, Aldrich), N-(2,4-difluorophenyl)-2-chloroacetamide (41 mg, 0.20 mmol, Maybridge) and sodium carbonate (50 mg) in N,N-dimethylformamide/water (2:1, 2 mL) was shaken at room temperature for 18 hours. The resulting mixture was decanted, concentrated under reduced pressure and the residue purified by preparative HPLC to provide 37.3 mg (74.8%) of the desired product. 1H NMR (500 MHz, DMSO-d6) δ2.52 (t, J=4 Hz, 4H), 3.23 (s, 2H), 3.58 (t, J=4 Hz, 4H), 6.63 (t, J=5 Hz, 1H), 6.83 (d, J=6 Hz, 1H), 7.08 (t, J=6 Hz, 1H), 7.38 (t, J=6 Hz, 1H), 7.92 (m, 1H), 8.12 (d, J=5 Hz, 1H), 9.60 (s, 1H); MS (ESI/APCI+) m/e 333 (M+H)+.
37.3 mg (74.8%) With sodium carbonate In water; N,N-dimethyl-formamide 183 N-(2,4-difluorophenyl)-2-[4-(2-pyridinyl)-1-piperazinyl]acetamide EXAMPLE 183 N-(2,4-difluorophenyl)-2-[4-(2-pyridinyl)-1-piperazinyl]acetamide A mixture of 1-pyridin-2-ylpiperazine (24 mg, 0.15 mmol, Aldrich), N-(2,4-difluorophenyl)-2-chloroacetamide (41 mg, 0.20 mmol, Maybridge) and sodium carbonate (50 mg) in N,N-dimethylformamide/water (2:1, 2 mL) was shaken at room temperature for 18 hours. The resulting mixture was decanted, concentrated under reduced pressure and the residue purified by preparative HPLC to provide 37.3 mg (74.8%) of the desired product. 1H NMR (500 MHz, DMSO-d6) δ2.52 (t, J=4 Hz, 4H), 3.23 (s, 2H), 3.58 (t, J=4 Hz, 4H), 6.63 (t, J=5 Hz, 1H), 6.83 (d, J=6 Hz, 1H), 7.08 (t, J=6 Hz, 1H), 7.38 (t, J=6 Hz, 1H), 7.53 (t, J=6 Hz, 1H), 7.92 (m, 1H), 8.12 (d, J=5 Hz, 1H), 9.60 (s, 1H); MS (ESI/APCI+) m/e 333 (M+H)+.
  • 10
  • [ 854268-72-7 ]
  • [ 96980-65-3 ]
  • [ 249933-10-6 ]
YieldReaction ConditionsOperation in experiment
In water; dimethyl sulfoxide 66 N-(2,4-Difluorophenyl)-2-[5-methoxy-1-(toluene-4-sulphonyl)-1H-indazol-3-yloxy]acetamide STR22 EXAMPLE 66 N-(2,4-Difluorophenyl)-2-[5-methoxy-1-(toluene-4-sulphonyl)-1H-indazol-3-yloxy]acetamide STR22 3.66 g (11.5 mmol) of 5-methoxy-1H-indazol-3-yl toluene-4-sulphonate are dissolved in 50 ml of DMSO and treated in portions with 0.41 g (17.2 mmol) of sodium hydride (95 per cent). After stirring for 15 minutes, a solution of 2.36 g (11.5 mmol) of α-chloro-2,4-difluoroacetanilide in 20 ml of DMSO is added dropwise and the mixture is stirred at 60° C. for 3 hours. After cooling, it is stirred into 200 ml of water, stirred for 6 hours, and the precipitate is filtered off with suction and recrystallized from methanol. The recrystallized precipitate is filtered off with suction (by-product), the filtrate is concentrated to 30 ml and, after crystallization is complete, the product is filtered off with suction. Yield: 1.0 g (17.8% of theory); m.p. 155-159° C.; 13 C-NMR (DMSO-d6; 300 MHz): δ=20.8 CH3; 55.7 CH3 O; 67.2 CH2 O; 165.4 C=O. IR (KBr): 1706 C=O.
  • 11
  • [ 451459-51-1 ]
  • [ 96980-65-3 ]
  • [ 1080474-72-1 ]
YieldReaction ConditionsOperation in experiment
35% With Ki; potassium carbonate In acetonitrile 6.C C. C. Synthesis of N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno [2,3-d]pyrimidin-3(4H)-yl)acetamide To a suspension of 6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one, (0.06 g, 0.16 mmol) in CH3CN (0.5 mL) was added K2CO3 (22 mg, 0.16 mmol), KI (29 mg, 0.17 mmol), and 2-chloro-N-(2,4-difluorophenyl)acetamide, (36 mg, 0.16 mmol). The reaction mixture was heated at 130° C. for 25 min in a microwave reactor. The reaction was quenched with H2O (25 mL) and the aqueous layer was extracted with EtOAc (25 mL). The organic layer was washed with brine (25 mL), dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography (Et2O:DCM, 1:1) providing 30 mg of pure N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide, (yield: 35%).
  • 12
  • N'-((5-methoxy-1H-indol-3-yl)methylene)-4-methylbenzenesulfonohydrazide [ No CAS ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-(5-methoxy-3-((2-tosylhydrazono)methyl)-1H-indol-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
14.62% Stage #1: N'-((5-methoxy-1H-indol-3-yl)methylene)-4-methylbenzenesulfonohydrazide With sodium hydride In N,N-dimethyl-formamide at 5℃; Inert atmosphere; Stage #2: 2-chloro-N-(2,4-difluorophenyl)acetamide In N,N-dimethyl-formamide at 5 - 20℃; for 6h; Inert atmosphere; 4.1.42 N-(4-Methoxyphenyl)-2-(3-(2-(4-methylphenylsulfonamido)ethyl)-1H-indol-1-yl)acetamide (IIa) General procedure: To a stirring solution of N-(2-(1H-indol-3-yl)ethyl)-4-methylbenzenesulfonamide (8c, 0.63 g, 0.002 mol) and appropriate NaH in DMF (10mL) was added 2-chloro-N-(4-methoxyphenyl)acetamide (10a, 0.80 g, 0.004 mol) at 5°C under N2 flow. After being stirred at 5°C for 2 h and at rt for another 4 h, the mixture was poured into water and extracted with CHCl3 (20mL × 3). The organic layer was concentrated and purified by CC (CH2Cl2/AcEt= 2:1) to obtain the compound IIa as white solid (0.42 g, 43.75 %).
  • 13
  • [ 92487-21-3 ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-(3-((2-tosylhydrazono)methyl)-1H-indol-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
14.53% Stage #1: N'-((1H-indol-3-yl)methylene)-4-methylbenzenesulfonohydrazide With sodium hydride In N,N-dimethyl-formamide at 5℃; Inert atmosphere; Stage #2: 2-chloro-N-(2,4-difluorophenyl)acetamide In N,N-dimethyl-formamide at 5 - 20℃; for 6h; Inert atmosphere; 4.1.42 N-(4-Methoxyphenyl)-2-(3-(2-(4-methylphenylsulfonamido)ethyl)-1H-indol-1-yl)acetamide (IIa) General procedure: To a stirring solution of N-(2-(1H-indol-3-yl)ethyl)-4-methylbenzenesulfonamide (8c, 0.63 g, 0.002 mol) and appropriate NaH in DMF (10mL) was added 2-chloro-N-(4-methoxyphenyl)acetamide (10a, 0.80 g, 0.004 mol) at 5°C under N2 flow. After being stirred at 5°C for 2 h and at rt for another 4 h, the mixture was poured into water and extracted with CHCl3 (20mL × 3). The organic layer was concentrated and purified by CC (CH2Cl2/AcEt= 2:1) to obtain the compound IIa as white solid (0.42 g, 43.75 %).
  • 14
  • C15H13N2O4S2(1-)*K(1+) [ No CAS ]
  • [ 96980-65-3 ]
  • 3,4-diamino-N-(2,4-difluorophenyl)-5-(3,4,5-trimethoxybenzoyl)thieno[2,3-b]thiophene-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol; water / 0.17 h 2: potassium hydroxide / ethanol; water / Reflux
  • 15
  • [ 28668-95-3 ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In dimethyl sulfoxide at 20℃; for 16h; Synthetic procedure for the preparation N-(subphenyl)-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamides (IV) General procedure: To a solution of 2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione (5 mmol) in dry DMSO (25 mL) containing anhydrous milled potassium carbonate (10 mmol), appropriate 2-chloro-N-substituted acetamide (5 mmol) was added. The reaction mixture was kept for stirring 16 h at room temperature. Then it was poured into the water with stirring. The formed product was filtered, washed with water, dried, and recrystallized from DMF-water mixture to get pure product.
  • 16
  • [ 552-45-4 ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-((2-methylbenzyl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 1-chloromethyl-2-methylbenzene With thiourea In isopropyl alcohol at 100℃; for 2h; Sealed tube; Stage #2: 2-chloro-N-(2,4-difluorophenyl)acetamide With potassium hydroxide In methanol; isopropyl alcohol at 60℃; for 2h; Sonication;
  • 17
  • [ 345-35-7 ]
  • [ 96980-65-3 ]
  • (428)T7118 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 2-fluorobenzyl chloride With thiourea In isopropyl alcohol at 100℃; for 2h; Sealed tube; Stage #2: 2-chloro-N-(2,4-difluorophenyl)acetamide With potassium hydroxide In methanol; isopropyl alcohol at 60℃; for 2h; Sonication;
  • 18
  • [ 456-42-8 ]
  • [ 96980-65-3 ]
  • (570)T7185 [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: m-fluorobenzyl chloride With thiourea In isopropyl alcohol at 100℃; for 2h; Sealed tube; Stage #2: 2-chloro-N-(2,4-difluorophenyl)acetamide With potassium hydroxide In methanol; isopropyl alcohol at 60℃; for 2h; Sonication;
  • 19
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-((2-methylbenzyl)sulfinyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thiourea / isopropyl alcohol / 2 h / 100 °C / Sealed tube 1.2: 2 h / 60 °C / Sonication 2.1: acetic acid; dihydrogen peroxide / methanol; water / 4 h / 40 °C / Sonication
  • 20
  • [ 96980-65-3 ]
  • (383)T7136 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thiourea / isopropyl alcohol / 2 h / 100 °C / Sealed tube 1.2: 2 h / 60 °C / Sonication 2.1: acetic acid; dihydrogen peroxide / methanol; water / 4 h / 40 °C / Sonication
  • 21
  • [ 96980-65-3 ]
  • (383)T7134 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thiourea / isopropyl alcohol / 2 h / 100 °C / Sealed tube 1.2: 2 h / 60 °C / Sonication 2.1: acetic acid; dihydrogen peroxide / methanol; water / 4 h / 40 °C / Sonication
  • 22
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-((2-methylbenzyl)sulfonyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thiourea / isopropyl alcohol / 2 h / 100 °C / Sealed tube 1.2: 2 h / 60 °C / Sonication 2.1: acetic acid; dihydrogen peroxide; ammonium molybdate / methanol; water / 5 h / 70 °C / Sonication
  • 23
  • [ 96980-65-3 ]
  • (944)T6351 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thiourea / isopropyl alcohol / 2 h / 100 °C / Sealed tube 1.2: 2 h / 60 °C / Sonication 2.1: acetic acid; dihydrogen peroxide; ammonium molybdate / methanol; water / 5 h / 70 °C / Sonication
  • 24
  • [ 96980-65-3 ]
  • (351)T6453 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thiourea / isopropyl alcohol / 2 h / 100 °C / Sealed tube 1.2: 2 h / 60 °C / Sonication 2.1: acetic acid; dihydrogen peroxide; ammonium molybdate / methanol; water / 5 h / 70 °C / Sonication
  • 25
  • [ 24544-04-5 ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-((2,6-isopropenylphenyl)amino)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate; potassium iodide; potassium bromide In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere; 7 Under an argon atmosphere, into a reaction vessel of 2-chloro-N- (2,4-difluorophenyl) acetamide 4.55 g (22.1 mmol), potassium iodide 3.34 g (20.1 mmol), potassium bromide 1.20 g ( 10.1 mmol), potassium carbonate 3.81g (27.6mmol), N, N- dimethylformamide 20mL and 2,6-diisopropyl aniline 14.1g of (79.5mmol) was added.The reaction vessel was heated to 80 , and the mixture was stirred for 12 hours.The reaction vessel was cooled to room temperature, ethyl acetate 200mL was added, the organic layer was washed with water 100 mL, saturated brine 100 mL, dried over sodium sulfate.Distilling off the sodium sulfate and the solvent, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 0-9: 1) to give, N-(2,4-difluorophenyl) -2 - (( to give the 2,6-isopropenyl phenyl) amino) acetamide 5.45 g (white solid, 15.7mmol, 71% yield).
  • 26
  • 3-amino-6,7-dimethoxy-2-phenylquinazolin-4(3H)-one [ No CAS ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-((6,7-dimethoxy-4-oxo-2-phenylquinazolin-3(4H)-yl)amino)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% In N,N-dimethyl-formamide Reflux;
  • 27
  • [ 110-91-8 ]
  • [ 96980-65-3 ]
  • C12H12F2N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: morpholine With sulfur; triethylamine In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: 2-chloro-N-(2,4-difluorophenyl)acetamide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
  • 28
  • C10H14N2O4 [ No CAS ]
  • [ 96980-65-3 ]
  • C18H19F2N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C10H14N2O4 With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-chloro-N-(2,4-difluorophenyl)acetamide In N,N-dimethyl-formamide at 20 - 100℃; for 7h;
  • 29
  • N-(2-trifluoromethyl-4-chlorophenyl)-2-aminocyclohexylsulfonamide [ No CAS ]
  • [ 96980-65-3 ]
  • (1R,2S)-2-(2-(N-(4-chloro-2-trifluoromethylphenyl)sulfamoyl)cyclohexylamino)-N-(2,4-difluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30.3% Stage #1: N-(2-trifluoromethyl-4-chlorophenyl)-2-aminocyclohexylsulfonamide With cesium hydroxide In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Molecular sieve; Stage #2: 2-chloro-N-(2,4-difluorophenyl)acetamide In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Molecular sieve; 3.2.3. Synthesis of 2-Glycinamide Cyclohexyl Sulfonamide Derivatives II-1 to II-28 General procedure: Under nitrogen atmosphere, DMF (10 mL), 4 Å molecular sieves (0.5 g), and CsOH (2 mmol) wereplaced in a three-necked round bottom flask and stirred for 10 min, then compound L-2 (1.5 mmol)was added to the flask and reacted for 0.5 h. Hereafter, intermediate I (1.8 mmol) was slowly addedat room temperature, and reaction was terminated according to TLC monitoring results [25,36].The solution was filtered in vacuum and 100 mL distilled water added. Organic compounds wereextracted with ether (3 120 mL), organic solvent was dried over anhydrous Na2SO4 and filtered.Solvent was evaporated in vacuum, and the residue was purified by silica gel column chromatography(petroleum ether/ethyl acetate as eluents). Finally, the samples were recrystallized to give targetcompounds with higher purity.
  • 30
  • 5-((2-hydroxynaphthalen-1-yl)methylene)thiazolidine-2,4-dione [ No CAS ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-((1-((2,4-dioxothiazolidin-5-ylidene)methyl)naphthalen-2-yl)oxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
24.69% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; 3.1.3. General procedure for synthesis of 3a-3k by condensation of 1a with 2a-2k. General procedure: The final compounds 3a-3k were synthesized by stirring compound 0.1mol of (1a) with 0.1mol of (2a-2k) for 24h, in presence of K2CO3 in dimethyl formamide (DMF). The reaction was monitored by TLC. On completion of the reaction, the reaction mixture was poured on crushed ice. The precipitated crude product was filtered, washed with water and purified by column chromatography using ethyl acetate and hexane in appropriate ratio.
  • 31
  • potassium-2,4-dioxo-5-(pyridin-2-ylmethylene)thiazolidin-3-ide [ No CAS ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-(2,4-dioxo-5-(pyridin-2-ylmethylene)thiazolidin-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% In methanol Reflux; 3.2.3. Synthesis of N-(substitutedaryl/heteroaryl)-2-(2,4-dioxo-5-(pyridin-2-ylmethylene)thiazolidin-3-yl)acetamide (P1-P25) General procedure: Intermediate 6 (1g, 0.004mol) and variously substituted amides (2a-2y) (0.004mol) were dispensed together in a round-bottom flask along with 10ml methanol. This mixture was refluxed and the reaction was monitored for completion by TLC using appropriate mobile phase of Hexane: Ethyl acetate (1:1). After 5-6h the reaction was stopped and the mixture was cooled. The precipitated solid was collected by filtering under vacuum and purified by recrystallization (chloroform: methanol, 2:1) or column chromatography (hexane: ethyl acetate, 1.5: 0.5) with an appropriate solvent to give the corresponding final products (P1-P25).
  • 32
  • [ 96980-65-3 ]
  • [ 1093981-68-0 ]
YieldReaction ConditionsOperation in experiment
With sodium azide; triethylamine In water; <i>tert</i>-butyl alcohol at 20℃; for 1h;
With sodium azide In dimethyl sulfoxide at 20℃; for 1h; 4.1.3. Synthesis of 2-(4-(((1,4-dioxo-1,4-dihydronaphthalen-2- yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenylacetamide derivatives (7a-m) General procedure: A mixture of 2-chloro-N-phenylacetamide derivatives (1 mmol) and NaN3 (1.2 mmol) in DMSO (5 ml) were stirred at room temperature for 1 h, then 2-(prop-2-yn-1-yloxy)naphthalene-1,4-dione (1 mmol), Et3N (1 mmol), Cu2SO4 (20 mol%) and Sodium ascorbate (20 mol%) were added and the obtained mixture was stirred for 18-24 h. The progress of the reaction was monitored by TLC. After completion of the reaction, H2O was added and precipitate was collected by filtration. For removing the copper, the powder was dissolved in ethyl acetate and copper was filtrated, ethyl acetate was evaporated with rotary to give the desired compound in high yield. However, for characterization purposes, it was further purified by column chromatography.
  • 33
  • potassium-5-(furan-2-ylmethylene)-2,4-dioxothiazolidin-3-ide [ No CAS ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-(5-(furan-2-ylmethylene)-2,4-dioxothiazolidin-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.4% In acetone Reflux; 4.1.4. Condensation of 6 with 2a-2y to produce F1eF25 (Fig. 2) General procedure: Differently substituted chloroacetylated amides (2a-2y) wereprepared according to our previous work [40,46,71]. Acetone (10 ml) was transferred in RBF, into which variously substitutedchloroacetylated amides (2a-2y) and 6 (in equimolar ratio) wereadded and refluxed for 3-6 h and monitored by TLC for completion.After completion, the reaction was stopped and cooled. Acetonelayer was evaporated to obtain a crude product, which was purifiedby either recrystallization from an appropriate solvent or by columnchromatography (Ethyl acetate: Hexane, 1:4) to produce F1-F25.
  • 34
  • [ 71995-35-2 ]
  • [ 96980-65-3 ]
  • 2-[5-(4-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl]-N-(2,4-difluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% In acetone Reflux; 4.1.4. Synthesis of final products (G1-G17) General procedure: The final products were obtained by refluxing amides 2a-2d (0.044 mol) and potassium salts 6a-6g (0.044 mol) in an equimolar ration, for 6-10 hours, with acetone as the solvent (Scheme 1). The reaction was monitored by TLC using hexane and ethyl acetate as themobile phase. On completion of the reaction, the reaction mixture waspoured over crushed ice. The precipitated crude product was filteredand purified by column or flash chromatography with ethyl acetate:hexane as a solvent in the ration of 10:90 to 40:60.
  • 35
  • potassium 5-(2,4-difluorobenzylidene)-2,4-dioxothiazolidin-3-ide [ No CAS ]
  • [ 96980-65-3 ]
  • 2-[5-(2,4-difluorobenzylidene)-2,4-dioxothiazolidin-3-yl]-N-(2,4-difluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% In acetone Reflux; 4.1.4. Synthesis of final products (G1-G17) General procedure: The final products were obtained by refluxing amides 2a-2d (0.044 mol) and potassium salts 6a-6g (0.044 mol) in an equimolar ration, for 6-10 hours, with acetone as the solvent (Scheme 1). The reaction was monitored by TLC using hexane and ethyl acetate as themobile phase. On completion of the reaction, the reaction mixture waspoured over crushed ice. The precipitated crude product was filteredand purified by column or flash chromatography with ethyl acetate:hexane as a solvent in the ration of 10:90 to 40:60.
  • 36
  • potassium 5-(4-fluorobenzylidene)-2,4-dioxothiazolidin-3-ide [ No CAS ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-[5-(4-fluoro-benzylidene)-2,4-dioxothiazolidin-3-yl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% In acetone Reflux; 4.1.4. Synthesis of final products (G1-G17) General procedure: The final products were obtained by refluxing amides 2a-2d (0.044 mol) and potassium salts 6a-6g (0.044 mol) in an equimolar ration, for 6-10 hours, with acetone as the solvent (Scheme 1). The reaction was monitored by TLC using hexane and ethyl acetate as themobile phase. On completion of the reaction, the reaction mixture waspoured over crushed ice. The precipitated crude product was filteredand purified by column or flash chromatography with ethyl acetate:hexane as a solvent in the ration of 10:90 to 40:60.
  • 37
  • potassium 5-(4-methylbenzylidene)-2,4-dioxothiazolidin-3-ide [ No CAS ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-[5-(4-methylbenzylidene)-2,4-dioxothiazolidin-3-yl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% In acetone Reflux; 4.1.4. Synthesis of final products (G1-G17) General procedure: The final products were obtained by refluxing amides 2a-2d (0.044 mol) and potassium salts 6a-6g (0.044 mol) in an equimolar ration, for 6-10 hours, with acetone as the solvent (Scheme 1). The reaction was monitored by TLC using hexane and ethyl acetate as themobile phase. On completion of the reaction, the reaction mixture waspoured over crushed ice. The precipitated crude product was filteredand purified by column or flash chromatography with ethyl acetate:hexane as a solvent in the ration of 10:90 to 40:60.
  • 38
  • [ 71995-34-1 ]
  • [ 96980-65-3 ]
  • 2-[5-benzylidene-2,4-dioxothiazolidin-3-yl]-N-(2,4-difluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In acetone Reflux; 4.1.4. Synthesis of final products (G1-G17) General procedure: The final products were obtained by refluxing amides 2a-2d (0.044 mol) and potassium salts 6a-6g (0.044 mol) in an equimolar ration, for 6-10 hours, with acetone as the solvent (Scheme 1). The reaction was monitored by TLC using hexane and ethyl acetate as themobile phase. On completion of the reaction, the reaction mixture waspoured over crushed ice. The precipitated crude product was filteredand purified by column or flash chromatography with ethyl acetate:hexane as a solvent in the ration of 10:90 to 40:60.
  • 39
  • potassium 5-(4-bromobenzylidene)-2,4-dioxothiazolidin-3-ide [ No CAS ]
  • [ 96980-65-3 ]
  • 2-[5-(4-bromobenzylidene)-2,4-dioxo-thiazolidin-3-yl]-N-(2,4-difluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% In acetone Reflux; 4.1.4. Synthesis of final products (G1-G17) General procedure: The final products were obtained by refluxing amides 2a-2d (0.044 mol) and potassium salts 6a-6g (0.044 mol) in an equimolar ration, for 6-10 hours, with acetone as the solvent (Scheme 1). The reaction was monitored by TLC using hexane and ethyl acetate as themobile phase. On completion of the reaction, the reaction mixture waspoured over crushed ice. The precipitated crude product was filteredand purified by column or flash chromatography with ethyl acetate:hexane as a solvent in the ration of 10:90 to 40:60.
  • 40
  • potassium 5-(3,4-dimethylbenzylidene)-2,4-dioxothiazolidin-3-ide [ No CAS ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-[5-(3,4-dimethylbenzylidene)-2,4-dioxothiazolidin-3-yl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% In acetone Reflux; 4.1.4. Synthesis of final products (G1-G17) General procedure: The final products were obtained by refluxing amides 2a-2d (0.044 mol) and potassium salts 6a-6g (0.044 mol) in an equimolar ration, for 6-10 hours, with acetone as the solvent (Scheme 1). The reaction was monitored by TLC using hexane and ethyl acetate as themobile phase. On completion of the reaction, the reaction mixture waspoured over crushed ice. The precipitated crude product was filteredand purified by column or flash chromatography with ethyl acetate:hexane as a solvent in the ration of 10:90 to 40:60.
  • 41
  • N-cyclohexyl-2-(4-hydroxy-3-methoxyphenyl)-2-oxoacetamide [ No CAS ]
  • [ 96980-65-3 ]
  • N-cyclohexyl-2-(4-(2-((2,4-difluorophenyl)amino)-2-oxoethoxy)-3-methoxyphenyl)-2-oxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 7h;
  • 43
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl)phenoxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / Reflux 2: toluene-4-sulfonic acid / methanol; water / Reflux
  • 44
  • [ 123-08-0 ]
  • [ 96980-65-3 ]
  • C15H11F2NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide Reflux; General procedure for synthesis of 2-(4-formylphenoxy)-N-phenylacetamide derivatives 5a-g General procedure: A mixture of 2-chloro-N-phenylacetamide derivatives 3a-g (1 mmol), 4-hydroxybenzaldehyde 1 mmol 4, and K2CO3 in DMF was heated at reflux for 3 h. After completion of reaction (checked by TLC), the reaction mixture was poured into crushed ice and filtered and washed with cold water to give pure 2-(4-formylphenoxy)-N-phenylacetamide derivatives 5a-g.
  • 45
  • [ 103788-60-9 ]
  • [ 96980-65-3 ]
  • C18H12F2N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; 1.1.3 General procedure for synthesis of 3k-3y General procedure: Final products 3k-3y were synthesized by condensing 2k-2y with compound 1 in equimolar ratio in the presence of base such as potassium carbonate in Dimethylformamide. The reaction was allowed to stir at room temperature for 24 hrs, the water was added to generate the crude products, which was filtered and further purified by recrystallization or TLC column chromatography.
  • 46
  • 5-((6-hydroxynaphthalen-2-yl)methylene)thiazolidine-2,4-dione [ No CAS ]
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-((6-((2,4-dioxothiazolidin-5-ylidene)methyl)naphthalen-2-yl)oxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.3% With potassium carbonate In N,N-dimethyl-formamide at 20℃;
  • 48
  • (S)-5-(1-(6-methoxynaphthalen-2-yl)ethyl)-1,3,4-oxadiazole-2-thiol [ No CAS ]
  • [ 96980-65-3 ]
  • C23H19F2N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (S)-5-(1-(6-methoxynaphthalen-2-yl)ethyl)-1,3,4-oxadiazole-2-thiol With potassium carbonate In acetone at 50 - 60℃; for 1h; Stage #2: 2-chloro-N-(2,4-difluorophenyl)acetamide In acetone at 50 - 60℃;
  • 49
  • [ 96980-65-3 ]
  • N-(2,4-difluorophenyl)-2-(4-(((1,4-dioxo-1,4-dihydronaphthalen-2-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / dimethyl sulfoxide / 1 h / 20 °C 2: copper(ll) sulfate pentahydrate; sodium L-ascorbate; triethylamine / dimethyl sulfoxide / 20 °C
  • 50
  • [ 64-17-5 ]
  • [ 1147550-11-5 ]
  • [ 96980-65-3 ]
  • 2-((2,4-difluorophenyl)imino)thiazolidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% for 8h; Reflux; 3.1.2. Synthesis of 2-(Substituted Phenyl Imino)Thiazolidin-4-One (3a-c) General procedure: A mixture of 2-chloro-N-(substituted phenyl) acetamide (2a-c) (0.10mol) and ammonium thiocyanate (0.20 mol) was subjected to heating under reflux in ethanol for 5 hours. The mixture was allowed to stand overnight leading to the separation of solid precipitates. The solid precipitates were then filtered, washed with cold water and recrystallized from 1,4-dioxane [11].
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