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[ CAS No. 790-75-0 ] {[proInfo.proName]}

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Chemical Structure| 790-75-0
Chemical Structure| 790-75-0
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Product Details of [ 790-75-0 ]

CAS No. :790-75-0 MDL No. :MFCD00077474
Formula : C10H6ClF6NO Boiling Point : -
Linear Structure Formula :- InChI Key :LEYIUTOAQOUAFG-UHFFFAOYSA-N
M.W : 305.60 Pubchem ID :1800613
Synonyms :

Calculated chemistry of [ 790-75-0 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 5
Num. H-bond acceptors : 7.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.55
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 4.34
Log Po/w (WLOGP) : 6.02
Log Po/w (MLOGP) : 3.79
Log Po/w (SILICOS-IT) : 4.11
Consensus Log Po/w : 4.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.37
Solubility : 0.013 mg/ml ; 0.0000424 mol/l
Class : Moderately soluble
Log S (Ali) : -4.67
Solubility : 0.0066 mg/ml ; 0.0000216 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.18
Solubility : 0.00203 mg/ml ; 0.00000664 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 790-75-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P302+P352-P305+P351+P338-P280-P261 UN#:N/A
Hazard Statements:H335-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 790-75-0 ]

* 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 [ 790-75-0 ]

[ 790-75-0 ] Synthesis Path-Downstream   1~40

  • 1
  • [ 790-75-0 ]
  • [ 25947-13-1 ]
  • [ 138129-24-5 ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate 1.) DMF, RT, 30 min, 2.) DMF, RT, 30 min; Multistep reaction;
  • 2
  • [ 790-75-0 ]
  • [ 109-89-7 ]
  • N(S),N(S)-diethyl-N(O)-[3,5-di(trifluoromethyl)phenyl]thiooxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sulfur In N,N-dimethyl-formamide at 20℃; for 8h;
  • 3
  • [ 387350-79-0 ]
  • [ 790-75-0 ]
  • N-(3,5-bis-trifluoromethylphenyl)-2-{4-[cyclopropyl-(3-trifluoromethylbenzenesulfonyl)amino]-piperidin-1-yl}-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With potassium carbonate; potassium iodide In acetonitrile at 50℃; for 48h; 11 General procedure for preparing compounds 63-84: A mixture of the corresponding compound 62a-r (100 mg, 1.0 eq.), an amine (6, 19, or 19a-g, 1.1 eq.), KI (0.1 eq.), and K2CO3 (3 eq.) in 4 mL of CH3CN was shaken at 50 0C for 48 hours. After cooling to room temperature, the mixture was participated between water (4 mL) and EtOAc (20 mL). The organic layer was separated, concentrated and purified by column (silica gel, EtOAc/hexane 1/1) to give the title compounds 63-84.[0550] N-(3,5-Bis-trifluoromethylphenyl)-2- {4-[cyclopropyl-(3- trifluoromethylbenzenesulfonyl)amino]-piperidin-l-yl}-acetamide (63, white solid, 80 mg, yield 40%): 1R NMR (400 MHz, CDCl3): δ 9.25 (s, IH), 8.14 (s, IH), 8.04 - 8.09 (m, 3H), 7.86 (d, IH, 7.9 Hz), 7.69 (dd, IH, 7.6 & 7.8 Hz), 7.61 (s, IH), 3.88 - 3.92 (m, IH), 3.18 (s, 2H), 2.94 - 2.98 (m, 2H), 2.36 - 2.42 (m, 2H), 2.04 - 2.11 (m, 3H), 1.64 - 1.68 (m, 2H), 0.98 - 1.02 (m, 2H), 0.84 - 0.88 (m, 2H); LC: 100%; MS: m/z = 618 (M+l).
  • 4
  • [ 79-04-9 ]
  • [ 328-74-5 ]
  • [ 790-75-0 ]
YieldReaction ConditionsOperation in experiment
94.8% In acetic acid at 0 - 20℃;
92% With acetic acid at 0 - 20℃; for 4h;
92% In acetic acid at 0 - 20℃; for 4h;
75% Stage #1: 3,5-Bis-(trifluoromethyl)aniline With triethylamine In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: chloroacetyl chloride at 20℃; for 2h; Cooling with ice; N-(3,5-Bis(trifluoromethyl)phenyl)acrylamide (1) S1 General procedure: To a solution of 3,5-bis(trifluoromethyl)aniline (1.56 mL, 10 mmol) in DCM (30 mL) triethyl amine (1.40 mL, 10 mmol) was added, and the mixture was allowed to stir under Ar at room temperature (RT) for 10 min. The mixture was cooled with iced water and then acryloyl chloride (0.81 mL, 10 mmol) was added dropwise, and the reaction was left to stir at RT for 2 h. The reaction was concentrated under vacuum. The residue was diluted with H2O and extracted with EtOAc. The organic layer was washed with 1 M aq. HCl, dried over Na2SO4, filtered, and concentrated under vacuum. The product was washed with Et2O and then vacuum dried to afford 1 as a white powder (2.06 g, 70%).
75% Stage #1: 3,5-Bis-(trifluoromethyl)aniline With triethylamine In dichloromethane at 20℃; Inert atmosphere; Stage #2: chloroacetyl chloride In dichloromethane at 20℃; 4.3.5. N-(3,5-Bis-trifluoromethyl-phenyl)-2-chloro-acetamide (20) The same procedure as for 12 except using chloroacetyl chloride(0.80 mL, 10 mmol). Pure 21 was obtained as a white powder (2.31 g,75%). 1H NMR (500 MHz, DMSO-d6): δ 10.90 (s, 1H), 8.24 (s, 2H), 7.80(s, 1H), 4.32 (s, 2H) ppm.
75% Stage #1: 3,5-Bis-(trifluoromethyl)aniline With triethylamine In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: chloroacetyl chloride In dichloromethane at 20℃; for 2h; Cooling with ice;
39% Stage #1: 3,5-Bis-(trifluoromethyl)aniline With triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: chloroacetyl chloride In dichloromethane at 20℃; 4.5.16. N-(3,5-Bis-trifluoromethyl-phenyl)-2-chloro-acetamide (21) Procedure as for 14 except using 3,5-bis(trifluoromethyl)aniline(2.4 mL, 15 mmol) and the mixture was allowed to stir at RT overnight. The precipitate obtained was washed with PE and vacuum dried. Pure 21 was obtained as a brick-red powder (1.77 g, 39%). δH/ppm (400 MHz, d6-DMSO): 10.93 (1H, s, NH), 8.25 (2H,s, Ar-H), 7.80 (1H, s, Ar-H), 4.34 (2H, s, CH2).
In toluene at 20 - 70℃; for 15h; 11.a a) Preparation of intermediates 62a-j and 621-r: Compound 15 (1.2 eq.) was added to a solution of the corresponding amine (61a-j or 611-r, TABLE 2, 1.0 eq.) in toluene at room temperature. The resulting mixture was shaken at 70 0C for 15 hours. After cooling to room temperature, the solid was collected, washed with hexane and purified by column (silica gel, EtOAc/hexane 3/7 to 1/1) to give the desired intermediate 62a-j and 621-r.
With triethylamine In acetone at 0 - 20℃;
With triethylamine In dichloromethane
Stage #1: 3,5-Bis-(trifluoromethyl)aniline 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 triethylamine In dichloromethane at 0 - 20℃; for 3h; 4 EXAMPLE 4 iV-(3,5-Bis-(trifluoromethyl)phenyl)-2-[l-(3-trifluoromethyl- benzenesulfonyl)piperidin-4-ylamino]acetamide (18); [0280] N-(3,5-Bis-(trifluoromethyl)phenyl)-2-[l-(3-trifluoromethyl- benzenesulfonyl)piperidin-4-ylamino]acetamide (18) was prepared as follows. Compound 16 (1.2 g, Aldrich) was added to a solution of compound 15 (2.0 g, Aldrich) and TEA (2mL) in DCM (20 mL) at 0 °C. The reaction mixture was warmed to room temperature over 3 hours and then quenched with water (6 mL), washed with brine (4 mL), concentrated, and purified by column (silica gel, EtOAc/hexanes 1/9) to give compound 17 as colorless oil. A mixture of compound 17 (150 mg), compound 4 (180 mg), K2CO3 (300 mg), and KI (20 mg) in CH3CN (4 mL) was shaken at 40 °C for 72 hours. The reaction mixture was diluted with EtOAc (4 mL), washed with water (2 mL), brine (4 mL), concentrated under vacuum and purified by column (Silica gel, EtOAc/Hexanes 7/3) to obtain the title compound 18 as white solid (100 mg, yield 37%). 1H NMR (400 MHz, CD3OD): δ 9.54 (br, IH, NH), 8.06 (s, 2H), 8.0 (s, IH), 7.94 (d, IH, 7.9 Hz), 7.87 (d, IH, 7.9 Hz), 7.70 (dd, IH, 7.9 & 7.9 Hz), 7.59 (s, IH), 3.81 - 3.84 (m, 2H), 3.42 (s, 2H), 2.45 - 2.51 (m, IH), 2.35 - 2.42 (m, 2H), 1.98 - 2.04 (m, 2H), 1.49 - 1.59 (m, 2H); LC: 100%; MS: m/z = 578 (M+ 1).

Reference: [1]Location in patent: experimental part Xiaohe, Zhu; Yu, Qin; Hong, Yan; Xiuqing, Song; Rugang, Zhong [Chemical Biology and Drug Design, 2010, vol. 76, # 4, p. 330 - 339]
[2]Pujales-Paradela, Rosa; Savić, Tanja; Esteban-Gómez, David; Angelovski, Goran; Carniato, Fabio; Botta, Mauro; Platas-Iglesias, Carlos [Chemistry - A European Journal, 2019, vol. 25, # 18, p. 4782 - 4792]
[3]Pujales-Paradela, Rosa; Savić, Tanja; Brandariz, Isabel; Pérez-Lourido, Paulo; Angelovski, Goran; Esteban-Gómez, David; Platas-Iglesias, Carlos [Chemical Communications, 2019, vol. 55, # 28, p. 4115 - 4118]
[4]Petri, László; Egyed, Attila; Bajusz, Dávid; Imre, Tímea; Hetényi, Anasztázia; Martinek, Tamás; Ábrányi-Balogh, Péter; Keserű, György M. [European Journal of Medicinal Chemistry, 2020, vol. 207]
[5]Ábrányi-Balogh, Péter; Imre, Tímea; Keserű, György Miklós; Petri, László; Varga, Petra Regina [Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 7]
[6]Petri, László; Ábrányi-Balogh, Péter; Tímea, Imre; Pálfy, Gyula; Perczel, András; Knez, Damijan; Hrast, Martina; Gobec, Martina; Sosič, Izidor; Nyíri, Kinga; Vértessy, Beáta G.; Jänsch, Niklas; Desczyk, Charlotte; Meyer-Almes, Franz-Josef; Ogris, Iza; Golič Grdadolnik, Simona; Iacovino, Luca Giacinto; Binda, Claudia; Gobec, Stanislav; Keserű, György M. [ChemBioChem, 2021, vol. 22, # 4, p. 743 - 753]
[7]Reddy, Tummala R.K.; Li, Chan; Guo, Xiaoxia; Fischer, Peter M.; Dekker, Lodewijk V. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5378 - 5391]
[8]Current Patent Assignee: PURDUE PHARMA L.P. - WO2007/118853, 2007, A1 Location in patent: Page/Page column 179-180
[9]Location in patent: experimental part Liu, Yajing; Zhang, Shulan; Li, Ye; Wang, Jianqiang; Song, Yu; Gong, Ping [Archiv der Pharmazie, 2012, vol. 345, # 4, p. 287 - 293]
[10]Wang, Fang; Lu, Wen; Zhang, Tao; Dong, Jinyun; Gao, Hongping; Li, Pengfei; Wang, Sicen; Zhang, Jie [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 6973 - 6980]
[11]Cai, Nan; Liu, Caixiu; Feng, Zhihui; Li, Xinghai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Ahmed, Wasim; Cui, Zining [Molecules, 2018, vol. 23, # 4]
[12]Current Patent Assignee: PURDUE PHARMA L.P. - WO2008/124118, 2008, A1 Location in patent: Page/Page column 66-67
  • 5
  • [ 790-75-0 ]
  • [ 138151-14-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) potassium tert-butoxide / 1.) DMF, RT, 30 min, 2.) DMF, RT, 30 min 2: aq. KOH
  • 6
  • [ 1068436-69-0 ]
  • [ 790-75-0 ]
  • [ 1068436-78-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide In acetonitrile at 40℃; for 72h; 4 EXAMPLE 4 iV-(3,5-Bis-(trifluoromethyl)phenyl)-2-[l-(3-trifluoromethyl- benzenesulfonyl)piperidin-4-ylamino]acetamide (18); [0280] N-(3,5-Bis-(trifluoromethyl)phenyl)-2-[l-(3-trifluoromethyl- benzenesulfonyl)piperidin-4-ylamino]acetamide (18) was prepared as follows. Compound 16 (1.2 g, Aldrich) was added to a solution of compound 15 (2.0 g, Aldrich) and TEA (2mL) in DCM (20 mL) at 0 °C. The reaction mixture was warmed to room temperature over 3 hours and then quenched with water (6 mL), washed with brine (4 mL), concentrated, and purified by column (silica gel, EtOAc/hexanes 1/9) to give compound 17 as colorless oil. A mixture of compound 17 (150 mg), compound 4 (180 mg), K2CO3 (300 mg), and KI (20 mg) in CH3CN (4 mL) was shaken at 40 °C for 72 hours. The reaction mixture was diluted with EtOAc (4 mL), washed with water (2 mL), brine (4 mL), concentrated under vacuum and purified by column (Silica gel, EtOAc/Hexanes 7/3) to obtain the title compound 18 as white solid (100 mg, yield 37%). 1H NMR (400 MHz, CD3OD): δ 9.54 (br, IH, NH), 8.06 (s, 2H), 8.0 (s, IH), 7.94 (d, IH, 7.9 Hz), 7.87 (d, IH, 7.9 Hz), 7.70 (dd, IH, 7.9 & 7.9 Hz), 7.59 (s, IH), 3.81 - 3.84 (m, 2H), 3.42 (s, 2H), 2.45 - 2.51 (m, IH), 2.35 - 2.42 (m, 2H), 1.98 - 2.04 (m, 2H), 1.49 - 1.59 (m, 2H); LC: 100%; MS: m/z = 578 (M+ 1).
  • 7
  • pet [ No CAS ]
  • [ 328-74-5 ]
  • [ 790-75-0 ]
YieldReaction ConditionsOperation in experiment
74% With dmap; 1,2-dichloro-ethane; chloroacetic acid In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 4.A A. A. Synthesis of N-(3,5-bis(trifluoromethyl)phenyl)-2-chloroacetamide To a solution of 3,5-bis(trifluoromethyl)aniline (3.74 g, 16.3 mmol) in DCM (60 mL) was added chloroacetic acid (2.31 g, 24.4 mmol), EDC (5.0 g, 32.6 mmol) and DMAP (cat.). The reaction mixture was stirred at RT overnight. The contents were transferred to a separatory funnel and DCM layer was washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4. The crude product was purified by flash column chromatography using 3:1 Pet. Ether:DCM in. Purified product was isolated as a white solid weighing 3.67 g (yield: 74%).
  • 8
  • 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester [ No CAS ]
  • [ 790-75-0 ]
  • [ 1080474-88-9 ]
YieldReaction ConditionsOperation in experiment
90% With Ki; potassium carbonate In acetonitrile 4.B B. B. Synthesis of methyl 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate To a suspension of methyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (1.62 g, 7.2 mmol) in CH3CN (35 mL) was added K2CO3 (1.0 g, 7.24 mmol), KI (1.2 g, 7.23 mmol), and N-(3,5-bis(trifluoromethyl)phenyl)-2-chloroacetamide 1 (2.2 g, 7.19 mmol). The reaction mixture was refluxed overnight and quenched with H2O (100 mL). The resultant precipitate was filtered and dried to afford 3.33 g of methyl 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate, as a solid (yield: 90%).
  • 9
  • [ 5625-67-2 ]
  • [ 790-75-0 ]
  • [ 930909-20-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile at 20℃; 3 Example 3: Synthesis of N-(3,5-bis(trifluoromethyl)phenyl)-2-(3-oxopiperazin-l- yl)acetamide (Compound 9[00107] A mixture of N-(3,5-bis(trifluoromethyl)phenyl)-2-chloroacetamide (0.20 g, 0.65 mmol), piperazin-2-one (0.10 g, 0.98 mol), K2C03 (0.18 g, 1.31 mmol), and KI (cat.) in CH3CN (10 mL) was stirred overnight at room temperature. The reaction mixture was then diluted with EtOAc, washed with water, dried with Na2S04, filtered, and the solvent was removed in vacuo to provide a white solid. The residue was purified by adding CH2C12, centrifuging, and pipetting off the supernatant (2 times). This provided the product in moderate yield and excellent purity.
  • 10
  • [ 790-75-0 ]
  • [ 57260-71-6 ]
  • [ 1269773-69-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile at 20℃; 2.A A. Synthesis of tert-butyl-4-(2-(3,5-bis(trifluoromethyl)phenylamino)-2- oxoethyl)piperazine-l-carbox late[00104] A mixture of N-(3,5-bis(trifluoromethyl)phenyl-2-chloroacetamide (1.60 g, 5.23 mmol), tert-butyl piperazine-l-carboxylate (1.46 g, 7.85 mmol), K2C03 (2.17 g, 15.7 mmol), and KI (cat.) in CH3CN (50 mL) was stirred at room temperature overnight. The reaction was then diluted with EtOAc and washed with water. The organic layer was dried with Na2S04, filtered, and the solvent was removed in vacuo to provide a solid. The solid was purified via automated flash chromatography (EtO Ac/petroleum ether) to provide the product as a solid in excellent yield.
YieldReaction ConditionsOperation in experiment
86% Stage #1: With sodium hydrogencarbonate In dichloromethane at 20℃; for 0.166667h; Stage #2: In dichloromethane for 2h; Cooling with ice; 6 Example 6 General procedure: To a 50 mL round bottom flask was added 7a (0.456 g, 5 mmol)CH2Cl2 (10 mL),Sodium bicarbonate (1.050 g, 25 mmol)After stirring at room temperature for 10 min, chloroacetyl chloride (0.672 g, 6 mmol)In dichloromethane (15 mL), the reaction was stopped by an ice bath reaction for 2 h,40 mL of water was added and extracted with dichloromethane (15 mL x 3). The organic layers were combined,The organic layer was washed with water (30 mL x 3), the organic layer was dried over magnesium sulfate, the solvent was removed to give a white solid,Recrystallization from a mixed solvent of petroleum ether and ethyl acetate gave a white powdery solid 8. The synthesis of compound 8b-8u was the same as that of 8a, and the physical constants and spectral data of 8a-8u are shown below.
  • 12
  • [ 2637-34-5 ]
  • [ 790-75-0 ]
  • [ 270262-80-1 ]
YieldReaction ConditionsOperation in experiment
57.4% With potassium iodide; sodium hydroxide In ethanol; water at 20℃; for 1h;
  • 13
  • [ 790-75-0 ]
  • [ 134469-07-1 ]
  • [ 312499-63-1 ]
YieldReaction ConditionsOperation in experiment
89.2% With potassium iodide; sodium hydroxide In ethanol; water at 20℃; for 1h;
  • 14
  • [ 790-75-0 ]
  • [ 2349-67-9 ]
  • [ 610264-47-6 ]
YieldReaction ConditionsOperation in experiment
82.2% With potassium iodide; sodium hydroxide In ethanol; water at 20℃; for 1h;
  • 15
  • [ 1236306-14-1 ]
  • [ 790-75-0 ]
  • [ 1313222-83-1 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate In acetone Reflux;
  • 16
  • [ 1376449-84-1 ]
  • [ 790-75-0 ]
  • [ 1313223-45-8 ]
YieldReaction ConditionsOperation in experiment
41% With potassium carbonate In acetone Reflux;
  • 17
  • [ 790-75-0 ]
  • 1-(piperazin-1-yl)-4-benzylphthalazine [ No CAS ]
  • [ 1313223-13-0 ]
YieldReaction ConditionsOperation in experiment
37% With potassium carbonate In acetone Reflux;
  • 18
  • [ 1233979-42-4 ]
  • [ 790-75-0 ]
  • [ 1384282-49-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6,6'-dihydroxy-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide With potassium carbonate In ethanol at 20℃; for 0.5h; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide for 10h; Reflux;
  • 19
  • C22H28N2O6 [ No CAS ]
  • [ 790-75-0 ]
  • [ 1384282-50-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C22H28N2O6 With potassium carbonate In ethanol at 20℃; for 0.5h; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide for 10h; Reflux;
  • 20
  • [ 1285535-51-4 ]
  • [ 790-75-0 ]
  • [ 1384282-56-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C24H32N2O6 With potassium carbonate In ethanol at 20℃; for 0.5h; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide In ethanol for 10h; Reflux;
  • 21
  • [ 1384282-59-0 ]
  • [ 790-75-0 ]
  • [ 1384282-48-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6,6'-dihydroxy-5,5'-dimethoxy-N,N'-diethylbiphenyl-2,2'-dicarboxamide With potassium carbonate In ethanol at 20℃; for 0.5h; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide In ethanol for 10h; Reflux;
  • 22
  • C17H18N2O3 [ No CAS ]
  • [ 790-75-0 ]
  • (2E)-N-(2-amino-4-methylphenyl)-3-[4-(2-[3,5-bis(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-3-methoxyphenyl]acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C17H18N2O3 With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide In acetone for 10h; Reflux; Inert atmosphere; 16 (2E)-N-(2-Amino-4-methylphenyl)-3-[4-(2-[3,5-bis(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-3-methoxyphenyl]acrylamide (FA26) General procedure: 5.1.5 (2E)-N-(2-Aminophenyl)-3-(4-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylamide (FA10) To a suspension of 5a (1.43 g, 5 mmol) in dehydrated acetone (70 mL) was added anhydrous potassium carbonate (2.07 g, 15 mmol). The mixture was stirred at room temperature for 30 min and then 2-chloro-N-(3-chloro-4-fluorophenyl)acetamide (3.33 g, 15 mmol) was added. The reaction mixture was refluxed for another 10 h. Filtration and evaporation of acetone was done in vacuum. The residue was extracted with EtOAc (150 mL). The combined layers were washed with water, 2 M NaOH, 2 M HCl and brine, dried over Na2SO4 and solvent was removed. The crude product was purified by silica gel column chromatography (CH2Cl2:MeOH = 80:1 to 20:1) to yield FA10 as white solid (1.33 g, 56.45%). 5.1.5.16 (2E)-N-(2-Amino-4-methylphenyl)-3-[4-(2-[3,5-bis(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-3-methoxyphenyl]acrylamide (FA26) Mp: 204-206 °C. EI-MS (m/z): 567.1(M+). 1H NMR (400 MHz, (CD3)2SO) δ 8.35(s, 2H), 7.83(s, 1H), 7.49(d, J = 8 Hz, 1H), 7.29(s, 1H), 7.19(d, J = 2 Hz, 1H), 7.17(d, J = 6 Hz, 1H), 7.02(d, J = 4 Hz, 1H), 6.78(d, J = 8 Hz, 1H), 6.56(s, 1H), 6.39(d, J = 4 Hz, 1H), 4.83(s, 2H), 3.87(s, 3H), 2.17(s, 3H).
  • 23
  • (2E)-N-(2-Aminophenyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide [ No CAS ]
  • [ 790-75-0 ]
  • (2E)-N-(2-aminophenyl)-3-[4-(2-[3,5-bis(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-3-methoxyphenyl]acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (2E)-N-(2-Aminophenyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide In acetone for 10h; Reflux; Inert atmosphere; 7 (2E)-N-(2-Aminophenyl)-3-[4-(2-[3,5-bis(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-3-methoxyphenyl]acrylamide (FA17) General procedure: 5.1.5 (2E)-N-(2-Aminophenyl)-3-(4-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylamide (FA10) To a suspension of 5a (1.43 g, 5 mmol) in dehydrated acetone (70 mL) was added anhydrous potassium carbonate (2.07 g, 15 mmol). The mixture was stirred at room temperature for 30 min and then 2-chloro-N-(3-chloro-4-fluorophenyl)acetamide (3.33 g, 15 mmol) was added. The reaction mixture was refluxed for another 10 h. Filtration and evaporation of acetone was done in vacuum. The residue was extracted with EtOAc (150 mL). The combined layers were washed with water, 2 M NaOH, 2 M HCl and brine, dried over Na2SO4 and solvent was removed. The crude product was purified by silica gel column chromatography (CH2Cl2:MeOH = 80:1 to 20:1) to yield FA10 as white solid (1.33 g, 56.45%). 5.1.5.7 (2E)-N-(2-Aminophenyl)-3-[4-(2-[3,5-bis(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-3-methoxyphenyl]acrylamide (FA17) Mp: 190-192 °C. EI-MS (m/z):553.0 (M+). 1H NMR (400 MHz, (CD3)2SO) δ 8.35(s, 2H), 7.83(s, 1H), 7.51(d, J = 8 Hz, 1H), 7.35(d, J = 4 Hz, 1H), 7.30(s, 1H), 7.17(d, J = 4 Hz, 1H), 7.02(d, J = 4 Hz, 1H), 6.94-6.90(m, 1H), 6.81(d, J = 8 Hz, 1H), 6.76(d, J = 4 Hz, 1H), 6.61-6.57(m, 1H), 4.84(s, 2H), 3.88(s, 3H).
  • 24
  • [ 2309-07-1 ]
  • [ 790-75-0 ]
  • C21H17F6NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Methyl ferulate With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide In acetone for 10h; Reflux; Inert atmosphere; 1.2 General procedure: 5.1.2 Methyl (2E)-3-(4-{2-[(3-chloro-4-fluorophenyl)amino]-2-oxoethoxy}-3- methoxyphenyl)acrylate (4a) 17 To a suspension of 2 (2.08 g, 10 mmol) in dehydrated acetone (70 mL) was added anhydrous potassium carbonate (4.14 g, 30 mmol). The mixture was stirred at room temperature for 30 min and then 2-chloro-N-(3-chloro-4-fluorophenyl)acetamide (2.44 g, 11 mmol) was added. The reaction mixture was refluxed for another 10 h. Filtration and evaporation of acetone was done in vacuum. The residue was extracted with EtOAc (120 mL). The combined layers were washed with water, 2 M NaOH, 2 M HCl and brine, dried over Na2SO4 and solvent was removed. The crude product was purified by silica gel column chromatography (Petroleum:AcOEt = 5:1 to 1:1) to yield 4a as white solid (3.37 g, 85.65%). Compounds (4b-4l) were prepared by using the same procedure described above.
  • 25
  • [ 2309-07-1 ]
  • [ 790-75-0 ]
  • (2E)-3-[4-(2-[3,5-bis(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-3-methoxyphenyl]-N-hydroxyacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.5 h / 20 °C / Inert atmosphere 1.2: 10 h / Reflux; Inert atmosphere 2.1: hydroxylamine; hydroxylamine potassium salt / N,N-dimethyl-formamide; methanol / 72 h / 20 °C / Inert atmosphere
  • 26
  • [ 1607457-46-4 ]
  • [ 790-75-0 ]
  • [ 1607457-30-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C17H18N2O3 With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide In acetone for 10h; Inert atmosphere; Reflux; 5.1.6 (2E)-N-(2-Aminophenyl)-3-[3-(2-[3-bromo-5-(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-4-methoxyphenyl]acrylamide (IF18) General procedure: To a suspension of 5a (0.85g, 3mmol) in dehydrated acetone (70mL) was added anhydrous potassium carbonate (1.30g, 9mmol). The mixture was stirred at room temperature for 30min and then 2-chloro-N-(3-bromo-5(trifluoromethyl)acetamide (3.33g, 15mmol) was added. The reaction mixture was refluxed for another 10h. Filtration and evaporation of acetone was done in vacuum. The residue was extracted with EtOAc (120mL). The combined layers were washed with water, 2M NaOH, 2M HCl and brine, dried over Na2SO4 and solvent was removed. The crude product was purified by silica gel column chromatography (PE/AcOEt=3:1 to 1:3) to yield (IF18) as white solid (0.98g, 58.0%).
  • 27
  • [ 97966-29-5 ]
  • [ 790-75-0 ]
  • [ 1607457-43-1 ]
YieldReaction ConditionsOperation in experiment
71.7% Stage #1: methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide In acetone for 10h; Inert atmosphere; Reflux; 5.1.3 Methyl (2E)-3-(3-{2-[3,5-bis(trifluoromethyl)phenyl]amino]-2-oxoethoxy}-4-methoxyphenyl)acrylate (4h) To a suspension of (3) (1.67g, 8mmol) in dehydrated acetone (100mL) was added anhydrous potassium carbonate (3.31g, 24mmol). The mixture was stirred at room temperature for 30min and then 2-chloro-N-[3,5-bis(trifluoromethyl)]acetamide (2.69g, 8.8mmol) was added. The reaction mixture was refluxed for another 10h. Filtration and evaporation of acetone was done in vacuum. The residue was extracted with EtOAc (120mL). The combined layers were washed with water, 2M NaOH, 2M HCl and brine, dried over Na2SO4 and solvent was removed. The crude product was purified by silica gel column chromatography (petroleum/AcOEt=5:1 to 1:1) to yield (4h) as white solid (1.98g, 71.7%). Mp: 180-182°C. EI-MS (m/z): 476.9 (M+). 1H NMR (400MHz, CDCl3) δ 8.15 (s, 2H), 7.67 (s, 1H), 7.63 (d, J=8Hz, 1H), 7.29 (d, J=6Hz, 1H), 7.20 (s, 1H), 7.00 (d, J=4Hz, 1H), 6.35 (d, J=8Hz, 1H), 4.73 (s, 2H), 4.02 (s, 3H), 3.83 (s, 3H).
  • 28
  • [ 1607457-45-3 ]
  • [ 790-75-0 ]
  • [ 1607457-15-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (2E)-N-(2-aminophenyl)-3-(3-hydroxy-4-methoxyphenyl)acrylamide With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-acetamide In acetone for 10h; Inert atmosphere; Reflux; 5.1.6 (2E)-N-(2-Aminophenyl)-3-[3-(2-[3-bromo-5-(trifluoromethyl)phenyl]amino}-2-oxoethoxy)-4-methoxyphenyl]acrylamide (IF18) General procedure: To a suspension of 5a (0.85g, 3mmol) in dehydrated acetone (70mL) was added anhydrous potassium carbonate (1.30g, 9mmol). The mixture was stirred at room temperature for 30min and then 2-chloro-N-(3-bromo-5(trifluoromethyl)acetamide (3.33g, 15mmol) was added. The reaction mixture was refluxed for another 10h. Filtration and evaporation of acetone was done in vacuum. The residue was extracted with EtOAc (120mL). The combined layers were washed with water, 2M NaOH, 2M HCl and brine, dried over Na2SO4 and solvent was removed. The crude product was purified by silica gel column chromatography (PE/AcOEt=3:1 to 1:3) to yield (IF18) as white solid (0.98g, 58.0%).
  • 29
  • 5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4-(4-methoxyphenyl)-4H-[1,2,4]triazole-3-thiol [ No CAS ]
  • [ 790-75-0 ]
  • N-(3,5-bistrifluoromethylphenyl)-2-[5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4-(4-methoxyphenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In N,N-dimethyl-formamide for 36h; Heating; 4.5.59. N-(3,5-Bis-trifluoromethyl-phenyl)-2-[5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4-(4-methoxy-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-acetamide (54) Procedure as for 1a except using 21 (306 mg, 1 mmol) and the reaction was carried out for 36 h. The precipitate formed was collected,washed with H2O and lyophilized. Without any further purification, 54 was obtained as a pale yellow powder (526 mg,83%). m/z (ES), found 627.1069 (C26H21F6N6O2S2 [MH]) requires627.1150; dH/ppm (400 MHz, d6-DMSO): 10.97 (1H, s, NH), 8.21(2H, s, Ar-H), 7.78 (1H, s, Ar-H), 7.36 (2H, d, J = 8.9, Ar-H), 6.99(2H, d, J = 8.9, Ar-H), 6.90 (1H, s, Ar-H), 4.46 (2H, s, CH2), 4.14(2H, s, CH2), 3.78 (3H, s, OCH3), 2.26 (6H, s, 2CH3).
  • 30
  • 4-(4-chlorophenyl)-5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4H-[1,2,4]triazole-3-thiol [ No CAS ]
  • [ 790-75-0 ]
  • 2-[4-(4-chlorophenyl)-5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(4-trifluoromethylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate In N,N-dimethyl-formamide for 24h; Heating; 4.5.58. 2-[4-(4-Chloro-phenyl)-5-(4,6-dimethyl-pyrimidin-2-ylsulfanylmethyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-(4-trifluoromethyl-phenyl)-acetamide (53) Procedure as for 1a except using 20 (238 mg, 1 mmol) and the reaction was carried out for 24 h. The precipitate formed was collected,washed with H2O and lyophilized. The dried precipitate was washed with EtOH-MeOH (1:1) to afford 53 as an off-white powder(460 mg, 81%). m/z (ES), found 565.0165 (C24H20ClF3N6OS2[M+H]+) requires 565.0781; dH/ppm (400 MHz, d6-DMSO): 10.65(1H, s, NH), 7.75 (2H, d, J = 8.4, Ar-H), 7.68 (2H, d, J = 8.1, Ar-H),7.56-7.45 (4H, m, Ar-H), 6.92 (1H, s, Ar-H), 4.51 (2H, s, CH2),4.15 (2H, s, CH2), 2.26 (6H, s, 2CH3).
  • 31
  • 5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4-furan-2-ylmethyl-4H-[1,2,4]triazole-3-thiol [ No CAS ]
  • [ 790-75-0 ]
  • N-(3,5-bis-trifluoromethylphenyl)-2-[5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4-furan-2-ylmethyl-4H-[1,2,4]triazol-3-ylsulfanyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With potassium carbonate In N,N-dimethyl-formamide for 48h; Heating; 4.5.43. N-(3,5-Bis-trifluoromethyl-phenyl)-2-[5-(4,6-dimethylpyrimidin-2-ylsulfanylmethyl)-4-furan-2-ylmethyl-4H-[1,2,4]triazol-3-ylsulfanyl]-acetamide (38) Procedure as for 1a except using 21 (306 mg, 1 mmol) and there action was carried out for 48 h. The precipitate was collected by filtration, washed with H2O and lyophilized, followed by recrystallization from EtOH. Pure 38 was obtained as a white powder (264 mg, 44%). m/z (ES), found 603.9979 (C24H21F6N6O2S2[M+H]+) requires 603.0993; δH/ppm (400 MHz, d6-DMSO): 10.95(1H, s, NH), 8.20 (2H, s, Ar-H), 7.78 (1H, s, Ar-H), 7.63 (1H, dd, J = 0.8 + 1.8, Ar-H), 6.96 (1H, s, Ar-H), 6.48-6.42 (2H, m, Ar-H), 5.39(2H, s, CH2), 4.63 (2H, s, CH2), 4.16 (2H, s, CH2), 2.33 (6H, s, 2CH3).
  • 32
  • N-(2-trifluoromethyl-4-chlorophenyl)-2-aminocyclohexylsulfonamide [ No CAS ]
  • [ 790-75-0 ]
  • (1R,2S)-2-(2-(N-(4-chloro-2-trifluoromethylphenyl)sulfamoyl)cyclohexylamino)-N-(3,5-ditrifluoromethylphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% 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: N-(3,5-bis-trifluoromethyl-phenyl)-2-chloro-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.
  • 33
  • [ 790-75-0 ]
  • [ 122555-91-3 ]
  • 1,4,7-tris(tert-butoxycarboxymethyl)-10-[3,5-(trifluoromethyl)-phenyl]acetamide}-1,4,7,10-tetraazacyclododecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate In acetonitrile at 45℃; for 216h;
  • 34
  • [ 790-75-0 ]
  • C24H28F6N5O7(3-)*Gd(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 216 h / 45 °C 2: formic acid / 48 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / butan-1-ol / 6 h / 112 °C / Sonication
  • 35
  • [ 790-75-0 ]
  • C24H28F6N5O7(3-)*Tb(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 216 h / 45 °C 2: formic acid / 48 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / butan-1-ol / 6 h / 112 °C / Sonication
  • 36
  • [ 790-75-0 ]
  • 1,4,7-tris(carboxymethyl)-10-[3,5-bis(trifluoromethyl)phenylcarbamoylmethyl]-1,4,7,10-tetraazacyclododecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 216 h / 45 °C 2: formic acid / 48 h / 80 °C
  • 37
  • [ 790-75-0 ]
  • C24H28F6N5O7(3-)*Eu(3+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 216 h / 45 °C 2: formic acid / 48 h / 80 °C 3: N-ethyl-N,N-diisopropylamine / butan-1-ol / 6 h / 112 °C / Sonication
  • 38
  • [ 942300-94-9 ]
  • [ 790-75-0 ]
  • 1-carboxymethyl-8-(3,5-(trifluoromethylphenyl)acetamide)-1,4,8,11-tetraazabicyclo[6.6.2]hexadecane acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 432 h / 20 °C / Alkaline conditions 2: formic acid / 48 h / Reflux
  • 39
  • [ 942300-94-9 ]
  • [ 790-75-0 ]
  • 1-tert-(butoxycarboxymethyl)-8-(3,5-(trifluoromethylphenyl)acetamide)-1,4,8,11-tetraazabicyclo[6.6.2]hexadecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 20℃; for 432h; Alkaline conditions;
  • 40
  • meso-3,5-diazadibenzo[h,k]tricyclo[5.2.2.2.2,6]undeca-8,10-diene [ No CAS ]
  • [ 790-75-0 ]
  • C37H24F12N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With N-ethyl-N,N-diisopropylamine In ethanol at 80℃; for 24h; Inert atmosphere; Compound 3a General procedure: A flask was charged with 2 (373 mg, 1.50 mmol), 2-chloro-N-phenylacetamide (1.02 g, 6.00 mmol), and a magnetic stir bar at 25 °C. The flask was evacuated and backfilled with argon (repeated this sequence three times). EtOH (15.0 mL) and N,N-diisopropylethylamine (1.28 mL, 7.50 mmol) were then added to the resulting flask at 25 °C, and the reaction mixture was stirred at reflux for 24 h. The reaction solution was cooled to 25 °C, Et2O (15.0 mL) was added and the precipitate was filtered. The white solid was washed three times with 50% Et2O/EtOH three times and dried under reduced pressure to afford the title compound. Yield: 707 mg, 92%;
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