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[ CAS No. 347-66-0 ] {[proInfo.proName]}

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Chemical Structure| 347-66-0
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Product Details of [ 347-66-0 ]

CAS No. :347-66-0 MDL No. :MFCD00730970
Formula : C8H7ClFNO Boiling Point : -
Linear Structure Formula :- InChI Key :YHJYFDQKFJQLNL-UHFFFAOYSA-N
M.W : 187.60 Pubchem ID :1522874
Synonyms :

Calculated chemistry of [ 347-66-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.51
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) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 2.23
Log Po/w (MLOGP) : 2.27
Log Po/w (SILICOS-IT) : 2.3
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.21
Solubility : 1.14 mg/ml ; 0.0061 mol/l
Class : Soluble
Log S (Ali) : -1.87
Solubility : 2.5 mg/ml ; 0.0134 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.7
Solubility : 0.0375 mg/ml ; 0.0002 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 347-66-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 347-66-0 ]

* 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 [ 347-66-0 ]

[ 347-66-0 ] Synthesis Path-Downstream   1~92

  • 1
  • [ 348-54-9 ]
  • [ 347-66-0 ]
YieldReaction ConditionsOperation in experiment
88% 28.A 2-chloro-N-(2-fluorophenyl)acetamide EXAMPLE 28A 2-chloro-N-(2-fluorophenyl)acetamide The procedure described in Example 22A was followed, substituting 2-fluoroaniline (Aldrich) for 3,4,5-trimethoxyaniline, to provide the title compound (88% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ4.35 (s, 2H), 7.23 (m, 3H), 7.87 (m, 1H), 10.17 (br s, 1H); MS (DCI/NH3) m/e 188 (M+H)+.
  • 2
  • [ 348-54-9 ]
  • [ 79-04-9 ]
  • [ 347-66-0 ]
YieldReaction ConditionsOperation in experiment
89%
88% In toluene at 100℃;
88% In toluene at 100℃; for 24h; 28A EXAMPLE 28 ; 2-[4-(3-cyano-2-pyridinyl)-1-piperazinyl]-N-(2-fluorophenyl)acetamide ; EXAMPLE 28A ; 2-chloro-N-(2-fluorophenyl)acetamide The procedure described in Example 22A was followed, substituting 2-fluoroaniline (Aldrich) for 3,4,5-trimethoxyaniline, to provide the title compound (88% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) ? 4.35 (s, 2H), 7.23 (m, 3H), 7.87 (m, 1H), 10.17 (br s, 1H); MS (DCI/NH3) m/e 188 (M+H)+.
84% With anhydrous Sodium acetate In glacial acetic acid for 0.5h; Cooling with ice; 4.1.1 General synthetic procedure for 2-chloro-N-(substituted) phenyl acetamides (12a-o) General procedure: Initially, appropriate amine (0.05mol) was dissolved in glacial acetic acid (25ml) containing saturated solution of sodium acetate (25ml). In case, if the substance did not dissolve completely then the mixture was warmed and the resultant solution was cooled in an ice-bath with stirring. To the ice cold solution chloroacetyl chloride (4.8ml, 0.06mol) was added drop wise with continuous stirring to avoid the vigorous reaction. After half an hour, a white colored product was separated out and filtered. The product was firstly washed with 50% aqueous acetic acid and finally with water. The crude product was then recrystallized from ethanol. The product so obtained was dried under vacuum to obtain the series of intermediate compounds (12a-o).
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.
75% With potassium carbonate In propan-2-one at 20℃; Preparationof intermediates 2a-m. General procedure: Tothe mixture of corresponding amine (4.2 mmol) and K2CO3(0.691 g, 5.0 mmol)in acetone chloroacetyl chloride (0.565 g, 5.0 mmol)was dropped in. The reaction mixture was stirred at room temperature for 1-1.5 h.After the reaction finished, the mixture was poured into 20 ml of icewater. The precipitate formed was filtrated and washed withwater. The product was dried under vacuum to obtain 2a-m as solid without any furtherpurification.
70% With triethylamine In propan-2-one at 0 - 20℃; 4.7 General procedure for the synthesis of compounds 10a-e General procedure: Triethylamine (3.67mL, 0.03mol) was added to a solution of substituted aniline (0.02mol) in acetone (25mL), and then 2-chloroacetyl chloride (2.14mL, 0.026mol) was added dropwise to the reaction mixture at 0-10°C. The reaction mixture was stirred at room temperature for 4-8h. The mixture was concentrated under reduced pressure. The residue was poured into ice water (20mL), stirred at room temperature for 1h and separated by filtration to obtain 10a-e.
64% Stage #1: 2-Fluoroaniline With potassium carbonate In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: chloroacetyl chloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; 4.1.1 General procedure for synthesis of 2-chloro-N-phenyl substituted acetamides (2a-2t and 5a-5b) General procedure: To a solution of substituted aniline (compounds 1a-1t) or 5-aminoindole and 6-aminoquinoline (1.0 equiv.) in dichloromethane (CH2Cl2) (15mL) at 0°C, potassium carbonate (K2CO3) (2.0 equiv.) was added. The reaction was stirred at 0°C for 15min. Into this stirring solution, chloroacetyl chloride (1.0 equiv.) was added dropwise at 0°C. The mixture was stirred for 2hat room temperature. After completion of the reaction, water (20mL) was added, and the mixture was extracted with dichloromethane. The organic solvent phase was concentrated under vacuum to afford the desired compounds 2a-2t, 5a and 5b.
In toluene for 3h; Heating;
In 1,4-dioxane at 0 - 25℃; for 1h;
In dichloromethane at 0 - 23℃;
With triethylamine In propan-2-one at 20℃;
With triethylamine In dichloromethane
With triethylamine In dichloromethane at 20℃; for 4h; General procedure: To a solution of substituted aniline (0.05 mol) andtriethylamine (0.055 mol) in dichloromethane (50 mL),chloroacetyl chloride (0.55 mol) was added dropwise to themixture under ice bath. After stirring at room temperature for4 h, the residue was separated by filtering off the solution invacuo, which further purified by recrystallisation fromethanol to yield substituted chloroacetyl aniline.
With potassium carbonate In acetonitrile at 0℃; for 2h;
With potassium carbonate In propan-2-one at 20℃; 4.2 Procedure for the synthesis of intermediates 3n-r General procedure: Compounds 3a-m were synthesized previously in our group [23], so only the spectra data of compounds 3n-r were given below. To the mixture of corresponding amine (4.2mmol) and K2CO3 (0.691g, 5.0mmol) in acetone was added chloroacetyl chloride (0.565g, 5.0mmol) dropwise. The reaction mixture was stirred at room temperature for 1-1.5h. Upon completion of the reaction, the mixture was poured into 20mL of ice water. The precipitate formed was filtrated and washed with water. The product was dried under vacuum to obtain compounds 3n-r, which were pure enough without further purification.
With anhydrous Sodium acetate; glacial acetic acid In water monomer at 20℃; for 4h;
With triethanolamine In dichloromethane
With triethylamine In dichloromethane at 20℃;
With anhydrous Sodium acetate; glacial acetic acid
With triethylamine In dichloromethane at 20℃;
With potassium carbonate In dichloromethane
With potassium carbonate In propan-2-one at 0 - 20℃; for 0.5h;
In N,N-dimethyl-formamide at 20℃; for 0.333333h; 4.1. General procedure for the synthesis of compounds 7a-7q General procedure: To a stirred solution of substituted aniline (1 mmol) and chloroacetyl chloride (1 mmol) which was stirred in 5 mL DMF for 20 min, were added benzyl amine derivatives (1.3 mmol) and CS2 (5 mmol). The reaction mixture was allowed to stir for required additional time (Table 2). Then, 5 mL of water was added and the solution was extracted with ethyl acetate and dried over sodium sulfate and purified by passing over a silica gel column chromatography using petroleum ether/ethyl acetate (8:2).
With triethylamine In dichloromethane at 20℃; for 0.5h; General synthetic procedure for the intermediate 2-chloro-N-substituted acetamides (15a-v) General procedure: To a solution of the appropriate amine (50 mmol) in triethylamine (5.1 mg, 50.5 mmol) and dichloromethane (50 mL), chloroacetyl chloride (70 mmol) was added dropwise, and the mixture was allowed to stir at room temperature for 30 min. Then, it was slowly poured into a saturated solution of NaHCO3 (100 mL). The layers were separated, and the aqueous layer was extracted with CH2-Cl2 (30 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The product was dried and recrystallized from ethyl acetate andpetroleum ether to obtain 2-chloro-N-substituted acetamides. The properties and analytical data for these compounds 15a-v were listed in the supporting information.
With triethylamine In dichloromethane at 30℃; 3.8. General Procedure for the Synthesis of Intermediates (IIa-IIe, IVa-IVj, Va-Ve, VIa-VIe) General procedure: Chloroacetyl chloride (1.23 g, 11 mmol), Et3N (1.11 g, 11 mmol) and different amines (10 mmol)were added to CH2Cl2 (20 mL) and the resulting mixture was stirred at 30 °C for 2-8 h. Then, thesolvent was evaporated in vacuo, water was added (15 mL), the mixture was filtered and the residuewas washed with water to obtain the different intermediates (Scheme 2).
With NEt3/C
With triethylamine In dichloromethane Cooling with ice; 7.3 third step:2-fluoroaniline as raw material,Dichloromethane as a solvent,Add triethylamine (1 mmol),Chloroacetyl chloride (1 mmol) diluted slowly with dichloromethane in a constant pressure dropping funnel under ice conditions, after the reaction is completed, the system is poured into water, the pH is adjusted to weakly basic with Na2CO3, and dichloromethane is extracted The organic phase was concentrated under reduced pressure, and stirred and filtered with n-hexane to obtain 2-chloro-N- (2-fluorophenyl) acetamide.
With triethylamine In dichloromethane at 20℃; for 5h; General procedure for the synthesis of compounds 6a-6k. General procedure: 2-Chloroacetamide (6a) was purchased from Sigma Aldrich; the synthesis of the titled compounds was achieved by following the reported methods,1-5 with an overall yield of 80%, and confirmed by 1H NMR. Briefly,chloroacetylchloride (5) (1.4 equiv.) was added dropwise to a solution of Et3N (2 equiv.) and the corresponding aniline (4b-4k) (1 equiv.) in dry dichloromethane (20 mL). The reaction mixturewas stirred for 5h at RT and monitored by TLC. Once completed (as judged by TLC), ethyl acetate(20 mL) were added to the reaction mixture, which yielded a precipitated in the form of whitecrystals, which were removed by filtration; the filtered solution was washed with water (3x, 20mL) and dried with MgSO4. Ethyl acetate was removed under reduced pressure, to yield a powderthat was recrystallized from a mixture of hexane and ethyl acetate (90:10).
In dichloromethane at 0 - 20℃;
With potassium carbonate In dichloromethane at 0℃;
With potassium carbonate In dichloromethane for 24h;
With triethylamine In dichloromethane Cooling with ice;
With triethylamine In dichloromethane
With triethylamine In ethanol at 0 - 90℃; for 3h; Procedure for synthesis of intermediates 7a-n General procedure: To a stirred solution of substituted aniline (8.2 mmol) inethanol (10 mL), added dry triethylamine (8.2 mmol). Thereaction mixture was cooled to 0 °C, chloroacetyl chloride(8.2 mmol) was added dropwise and heated under reflux for3 h. The reaction mass was quenched with ice-cold water.The precipitate formed was filtered, dried and washed withhexane to yield intermediate 7a-n in good yield. Yield:70-90%.
In propan-2-one at 20℃; General synthetic process for substituted 2-chloro-N-phenylacetamide derivatives. General procedure: To a solution of variousaniline (1.0 equiv ) in acetone were added chloroacetylchloride (1.1 equiv ) and reaction mixture stirredat room temperature for 2-3 h, reaction was monitoredby TLC, after completion of reaction mixture poured incold water, the separated solid product collected andwashed with cold water and dry in vacuum filter toafford 2-chloro-N-phenylacetamide derivatives.
With triethylamine In dichloromethane at 0 - 25℃; for 20h; Inert atmosphere; 4.2.3. Preparation of 2-chloro- N -phenylacetamide derivatives (5f-5p) Assembly for synthesis includes oven-dried flat bottom flask fa- cilitated with a Teflon-coated magnetic stirring bar, rubber septa, nitrogen balloon and cooling bath. An appropriate primary amine (1.0 mmol) was added drop wise to a mixture of triethylamine (1.2 mmol) in dichloromethane (4.5 mL) under nitrogen atmosphere at 0 °C. Chloroacetyl chloride (1.2 mmol) was added drop wise at 0 °C, then the reaction mixture was stirred at ambient temperature for 20 h. Consumption of starting material was monitored by TLC in Ethyl acetate: Hexane (80:20), and ninhydrin spraying reagent. The reaction mixture was concentrated under reduced pressure and the residue washed with ice water (3 ×20 mL) and filtered. Precipi- tates of desired compound were dried in oven at 48 °C temp and was carried on without further purification [34] .
Stage #1: 2-Fluoroaniline With Sodium hydrogenocarbonate In chloroform at 20℃; for 0.25h; Stage #2: chloroacetyl chloride In chloroform at 20℃; for 2h;
With triethylamine In propan-2-one at 20℃; for 1.5h;
With Sodium hydrogenocarbonate In propan-2-one at 20℃; for 1h;
In propan-2-one at 20℃; for 0.5h; General procedure for the synthesis of N-aryl-2-chloroacetamides. General procedure: Chloroacetyl chloride (1.1 equiv)was added dropwise with constant stirring to a solutionof the corresponding amine (1.0 equiv) in acetone. Themixture was stirred for 30 min at room temperature(TLC) and poured onto crushed ice. The solid productwas filtered off, washed with water, and dried.
In N,N-dimethyl-formamide at 20℃; for 0.5h;
With triethylamine In dichloromethane at 0℃;
In propan-2-one for 0.333333h; 2-Azido-N-(substituted phenyl)acetamides 6a-6j(general procedure). General procedure: A vacuum-dried round-bottomflask was charged with substituted aniline 4a-4j(1.4 mmol) and chloroacetyl chloride (1.7 mmol) inacetone, and the mixture was stirred at room temperaturefor 20 min. After completion of the reaction, thesolid was filtered off and dried under reduced pressure.The product was dissolved in DMF, sodium azide(3.0 mmol) was added, and the mixture was stirred atroom temperature for 1.5 h. After completion of thereaction (TLC; ethyl acetate-n-hexane, 3:7; yellowish-reddish color appeared in iodine vapor), the mixturewas poured into a mixture of water and crushed icewater, and the solid product was filtered off underreduced pressure.

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[42]Baluja, S. H.; Bhensdadia, K. A.; Lalavani, N. H. [Russian Journal of Organic Chemistry, 2021, vol. 57, # 10, p. 1668 - 1677][Zh. Org. Khim., 2021, vol. 57, # 10, p. 1668 - 1677]
[43]Mohammadi-Khanaposhtani, Maryam; Nori, Milad; Valizadeh, Yousef; Javanshir, Shahrzad; Dastyafteh, Navid; Moaazam, Ali; Hosseini, Samanesadat; Larijani, Bagher; Adibi, Hossein; Biglar, Mahmood; Hamedifar, Haleh; Mahdavi, Mohammad; Kamci, Hamdi; Karakus, Ahmet; Taslimi, Parham [Archiv der Pharmazie, 2022, vol. 355, # 5] Yari Boroujeni, Shahriar; Haghighijoo, Zahra; Mohammadi-Khanaposhtani, Maryam; Mosadeghkhah, Ali; Moazzam, Ali; Yavari, Ali; Hajimahmoodi, Manan; Sabourian, Reyhaneh; Hosseini, Samesadat; Larijani, Bagher; Hamedifar, Halleh; Ansari, Samira; Mahdavi, Mohammad [Chemistry and biodiversity, 2022, vol. 19, # 4]
[44]Bulitta, Jürgen B.; Dharuman, Suresh; Lee, Richard E.; Reeve, Stephanie M.; Wallace, Miranda J. [Molecules, 2022, vol. 27, # 5]
[45]Butani, S. C.; Desai, N. D.; Dholaria, P. V.; Kapadiya, K. M.; Vekariya, M. K. [Russian Journal of Organic Chemistry, 2022, vol. 58, # 3, p. 405 - 411][Zh. Org. Khim.]
  • 3
  • [ 347-66-0 ]
  • [ 76809-57-9 ]
YieldReaction ConditionsOperation in experiment
96% With sodium iodide
  • 4
  • [ 347-66-0 ]
  • [ 147-93-3 ]
  • [ 97457-51-7 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate In N,N-dimethyl-formamide Heating;
  • 5
  • [ 347-66-0 ]
  • [ 84951-44-0 ]
  • 2-[4-(3-cyano-2-pyridinyl)-1-piperazinyl]-N-(2-fluorophenyl) acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With N-ethyl-N,N-diisopropylamine In toluene at 80℃;
42% With N-ethyl-N,N-diisopropylamine In toluene at 20 - 90℃; for 18h; 28B EXAMPLE 28B ;2-[4-(3-cyano-2-pyridinyl)-1-piperazinyl]-N-(2-fluorophenyl) Acetamide The procedure described in Example 8 was followed, substituting the product from Example 28A for N-chloroacetyl-3-nitroaniline, to provide the title compound (42% yield) as a white solid. mp 78-79 C.; 1H NMR (300 MHz, DMSO-d6) ? 2.71 (m, 4H), 3.27 (s, 2H), 3.67 (m, 4H), 6.94 (dd, 1H, J=7.8, 4.8 Hz), 7.18 (m, 2H), 7.26 (m, 1H), 7.98 (m, 1H), 8.08 (dd, 1H, J=7.8, 2.0 Hz), 8.42 (dd, 1H, J=5.1, 2.1 Hz), 9.65 (br s, 1H); MS (DCI/NH3) m/e 340 (M+H)+; Anal. calcd for C18H18FN5O: C, 63.70; H, 5.35; N, 20.64. Found: C, 63.48; H, 5.32; N, 20.54.
  • 6
  • [ 347-66-0 ]
  • [ 53-86-1 ]
  • [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid (2-fluorophenylcarbamoyl)methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With dmap; triethylamine at 25℃; for 24h;
  • 7
  • [ 347-66-0 ]
  • [ 76809-91-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 96 percent / NaI 2: 51 percent / NaOEt / ethanol / Ambient temperature 3: 25 percent / conc HCl / methanol / 13 h / 50 °C
  • 8
  • [ 347-66-0 ]
  • [ 76810-10-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 96 percent / NaI 2: 51 percent / NaOEt / ethanol / Ambient temperature 3: 25 percent / conc HCl / methanol / 13 h / 50 °C 4: 2) 10N NaOH / 1) MeOH, -40 to -30 deg C 2) -30 to RT
  • 9
  • [ 347-66-0 ]
  • [ 76809-70-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 96 percent / NaI 2: 51 percent / NaOEt / ethanol / Ambient temperature
  • 10
  • [ 347-66-0 ]
  • [ 74-89-5 ]
  • 2'-Fluoro-2-methylamino acetanilide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% 1 Preparation of Intermediate: 2'-Fluoro-2-methylamino acetanilide EXAMPLE 1 Preparation of Intermediate: 2'-Fluoro-2-methylamino acetanilide To an ethanolic (70 ml) solution of N-(2-fluoro)phenyl-2-chloroacetamide (21.6 g, 0.11 mol) was added 40% aqueous methylamine (70 ml) and stirred at room temperature overnight. The mixture was concentrated on a rotary evaporator. The product was extracted into ethyl ether (200 ml) and the organic layer dried with magnesium sulfate (MgSO4) and concentrated. The crude product was passed through a short column of silica gel using 1:1 methylene chloride-hexane as the eluent. The product obtained was a yellow oil weighing 18.2 g (88% yield).
  • 11
  • [ 347-66-0 ]
  • [ 74-89-5 ]
  • N-(2-fluoro)phenyl sarcosine amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% 1 N-(2-Fluoro)phenyl sarcosine amide N-(2-Fluoro)phenyl sarcosine amide To an ethanolic (70 ml) solution of N-(2-fluoro)phenyl-2-chloroacetamide (21.6 g, 0.11 mol) was added 40% aqueous methylamine (70 ml) and stirred at room temperature overnight. The mixture was concentrated on a rotary evaporator. The product was extracted into ethyl ether (200 ml) and the organic layer dried with magnesium sulfate and concentrated. The crude product was passed through a short column of silica gel using 1:1 methylene chloride-hexane as the eluent. The product obtained was a yellow oil weighing 18.2 g (88% yield).
  • 12
  • [ 347-66-0 ]
  • [ 76578-79-5 ]
  • 2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In butanone 3 2-[4-(6-chloro-2-quinoxalinyl)oxy]phenoxy]-N-(2-fluorophenyl)acetamide Example 3 2-[4-(6-chloro-2-quinoxalinyl)oxy]phenoxy]-N-(2-fluorophenyl)acetamide In a nitrogen atmosphere 1.5 g (0.011 mol) of finely powdered potassium carbonate was added to a solution of 1.9 g (0.007 mol) 6-chloro-2-(4-hydroxyphenoxy)quinoxaline and 1.3 g (0.007 mol) 2-chloro-N-(2-fluorophenyl)acetamide in 35 cc of 2-butanone. The mixture was stirred and heated under reflux overnight. The excess potassium carbonate and potassium chloride were removed by filtration and the filtrate was concentrated to give the crude product. Crystallization from n-chlorobutane gave 1.24 g of the title compound; m.p. 158-161°C and NMR (CDCl3) δ 4.70 (s, 2H), 7.05-7.25 (m, 5H), 7.3 (d, 2H), 7.60 (dd, 1H), 7.70 (d, 1H), 8.05 (d, 1H), 8.38 (t, 1H), 8.65 (s broad, 1H), 8.70 (s, 1H).
  • 15
  • [ 347-66-0 ]
  • [ 23671-38-7 ]
  • [ 1187945-89-6 ]
YieldReaction ConditionsOperation in experiment
88% With sodium carbonate In N,N-dimethyl-formamide
  • 16
  • [ 347-66-0 ]
  • 1-(naphthalen-1-yl)-1H-imidazole-2-thiol [ No CAS ]
  • [ 1187945-85-2 ]
YieldReaction ConditionsOperation in experiment
48.5% With sodium hydroxide In ethanol at 20℃;
  • 17
  • [ 347-66-0 ]
  • [ 17452-12-9 ]
  • [ 688337-11-3 ]
YieldReaction ConditionsOperation in experiment
45.8% With sodium hydroxide In ethanol at 20℃;
  • 18
  • [ 347-66-0 ]
  • [ 17452-14-1 ]
  • [ 688335-87-7 ]
YieldReaction ConditionsOperation in experiment
28.1% With sodium carbonate In N,N-dimethyl-formamide
  • 20
  • [ 1190213-42-3 ]
  • [ 347-66-0 ]
  • [ 1190213-43-4 ]
YieldReaction ConditionsOperation in experiment
80.3% In ethanol at 20℃;
  • 21
  • [ 1207858-36-3 ]
  • [ 347-66-0 ]
  • C18H15FN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 4-methyl-2-oxo-1,2-dihydroquinoline-6-sulfinic acid With potassium carbonate In dimethyl sulfoxide at 50 - 60℃; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide In dimethyl sulfoxide at 80℃;
  • 22
  • [ 1200398-09-9 ]
  • [ 347-66-0 ]
  • [ 1200397-71-2 ]
YieldReaction ConditionsOperation in experiment
69% In ethanol at 20℃;
  • 23
  • [ 1236306-14-1 ]
  • [ 347-66-0 ]
  • [ 1242606-57-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetone Reflux;
  • 24
  • [ 1285535-51-4 ]
  • [ 347-66-0 ]
  • [ 1384282-54-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C24H32N2O6 With potassium carbonate In ethanol at 20℃; for 0.5h; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide In ethanol for 10h; Reflux;
  • 25
  • [ 1384282-59-0 ]
  • [ 347-66-0 ]
  • [ 1384282-46-5 ]
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: 2-chloro-N-(2-fluorophenyl)acetamide In ethanol for 10h; Reflux;
  • 26
  • [ 1383787-15-2 ]
  • [ 347-66-0 ]
  • [ 1383786-77-3 ]
YieldReaction ConditionsOperation in experiment
55.6% With potassium carbonate In acetone at 20℃; for 2h; 6 4.1.1.3 General procedure for the synthesis of 2-(3-mesityl-3H-imidazo [4,5-b]pyridin- 2-ylthio)-N-phenyl-acetamide (5a1-5a16) General procedure: Compound 4a (0.15 g, 0.5 mmol), K2CO3 (0.14 g, 1.0 mmol), from different 2-chloro-N-(substituted aromatic group)acetamides (0.05 mmol), was dissolved in acetone (10 mL).28 The reaction mixture was stirred at ambient temperature for 2 h and then evaporated under reduced pressure. The residue was dissovled with a small amount CH2Cl2 and chromatographed on silica gel using ethyl acetate-petroleum ether system. Pure fractions were collected and concentrated, giving the desired compounds 5a1-5a16.
  • 27
  • [ 1383787-17-4 ]
  • [ 347-66-0 ]
  • [ 1383786-97-7 ]
YieldReaction ConditionsOperation in experiment
70.3% With potassium carbonate In acetone at 20℃; for 2h; 6 4.1.1.3 General procedure for the synthesis of 2-(3-mesityl-3H-imidazo [4,5-b]pyridin- 2-ylthio)-N-phenyl-acetamide (5a1-5a16) General procedure: Compound 4a (0.15 g, 0.5 mmol), K2CO3 (0.14 g, 1.0 mmol), from different 2-chloro-N-(substituted aromatic group)acetamides (0.05 mmol), was dissolved in acetone (10 mL).28 The reaction mixture was stirred at ambient temperature for 2 h and then evaporated under reduced pressure. The residue was dissovled with a small amount CH2Cl2 and chromatographed on silica gel using ethyl acetate-petroleum ether system. Pure fractions were collected and concentrated, giving the desired compounds 5a1-5a16.
  • 28
  • [ 1352229-31-2 ]
  • [ 347-66-0 ]
  • [ 1352228-89-7 ]
YieldReaction ConditionsOperation in experiment
72.8% With sodium carbonate In ethanol at 20℃; 4 General procedure for the synthesis of 2-(3-(2-chlorophenyl)pyrazin-2-ylthio) acetamides (6a-o) General procedure: To the mixture solution of 3-(2-chlorophenyl)pyrazine-2(1H)-thione (5) (1.0 mmol, 0.22 g) and Na2CO3 (1.5 mmol) in ethanol (30 mL) were added ClCH2CONHPh (other alkyl halides) (1.0 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was evaporated, leaving a residue which was treated with methylene chloride (30 ml) and washed with water (3 × 30 ml). The organic layer was dried over anhydrous sodium sulfate, filtered off, and then the solvent was removed under vacuo. The residue was chromatographed on silica gel using ethyl acetate:petroleum ether. Pure fractions were collected and concentrated, giving the desired compounds (6a-6q) in good yield
  • 29
  • [ 75-15-0 ]
  • [ 347-66-0 ]
  • [ 2185-03-7 ]
  • [ 1446270-22-9 ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: carbon disulfide; L-homoserine lactone hydrochloride With sodium phosphate dodecahydrate In acetone at 20℃; for 0.5h; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide In acetone at 20℃; for 0.5h; Preparation of analogues 4a-m. General procedure: CS2 (0.22ml, 3.64 mmol) was added to the mixture of compound 3 (0.4 g, 2.91 mmol) and Na3PO4.12H2O (1.104 g,2.91 mmol) in acetone (10 ml). The mixture was stirred at room termperature for 0.5 h. Then 2a-m (2.91 mmol) wasadded to the mixture cautiously, the mixture was continued to stir at roomtemperature for another 0.5 h. Upon completion (monitored by TLC), the solventwas removed under reduced pressure, the residue was extracted withdichloromethane, washed with water, brine, dried with anhydrous Na2SO4and concentrated under reduced pressure. The residue was purified with columnchromatography to obtain analogue 4a-m as solid.
Stage #1: carbon disulfide; L-homoserine lactone hydrochloride With sodium phosphate dodecahydrate In acetone for 0.5h; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide In acetone at 20℃; for 0.5h; 4.3 Procedure for the synthesis of analogs 4n-r General procedure: Compounds 4a-m were synthesized previously in our group [23], so only the spectra data of compounds 4n-r were given below. To the mixture of compound 1 (0.4g, 2.91mmol) and Na3PO4·12H2O (1.104g, 2.91mmol) in acetone (10mL) was added CS2 (0.22mL, 3.64mmol). 30min later, acylated aniline (3n-r, 2.91mmol) was added to the mixture slowly, the mixture was stirred at room temperature for another 0.5h. Upon completion (monitored by TLC), the solvent was removed under reduced pressure, the residue was extracted with dichloromethane, washed with water, brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the residue, which was purified using column chromatography to obtain analogs 4n-r.
  • 30
  • [ 1258381-10-0 ]
  • [ 347-66-0 ]
  • [ 1412494-11-1 ]
YieldReaction ConditionsOperation in experiment
82.2% In isopropyl alcohol for 1 - 1.5h; Reflux;
  • 31
  • [ 1258381-13-3 ]
  • [ 347-66-0 ]
  • [ 1412494-10-0 ]
YieldReaction ConditionsOperation in experiment
92.3% In isopropyl alcohol for 1 - 1.5h; Reflux;
  • 32
  • [ 1258381-14-4 ]
  • [ 347-66-0 ]
  • [ 1412494-09-7 ]
YieldReaction ConditionsOperation in experiment
75.9% In isopropyl alcohol for 1 - 1.5h; Reflux;
  • 33
  • C17H18N2O3 [ No CAS ]
  • [ 347-66-0 ]
  • (2E)-N-(2-amino-4-methylphenyl)-3-(4-{2-[(2-fluorophenyl)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: 2-chloro-N-(2-fluorophenyl)acetamide In acetone for 10h; Reflux; Inert atmosphere; 14 (2E)-N-(2-Amino-4-methylphenyl)-3-(4-{2-[(2-fluorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylamide (FA24) 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%). 5.1.5.14 (2E)-N-(2-Amino-4-methylphenyl)-3-(4-{2-[(2-fluorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylamide (FA24) Mp: 187-189 °C. EI-MS (m/z): 449.1(M+). 1H NMR (400 MHz, (CD3)2SO) δ 7.96(s, 1H), 7.49(d, J = 8 Hz, 2H), 7.33-7.28(m, 2H), 7.20(d, J = 4 Hz, 2H), 7.18(d, J = 4 Hz, 1H), 7.03 (d, J = 4 Hz, 1H), 6.79(d, J = 8 Hz, 1H), 6.56(s, 1H), 6.39(d, J = 4 Hz, 1H), 4.83(s, 2H), 3.88(s, 3H), 2.17(s, 3H).
  • 34
  • (2E)-N-(2-Aminophenyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide [ No CAS ]
  • [ 347-66-0 ]
  • (2E)-N-(2-aminophenyl)-3-(4-{2-[(2-fluorophenyl)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: 2-chloro-N-(2-fluorophenyl)acetamide In acetone for 10h; Reflux; Inert atmosphere; 5 2E)-N-(2-Aminophenyl)-3-(4-{2-[(2-fluorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylamide (FA15) 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%). 5.1.5.5 (2E)-N-(2-Aminophenyl)-3-(4-{2-[(2-fluorophenyl)amino]-2-oxoethoxy}-3-methoxyphenyl)acrylamide (FA15) Mp: 194-195 °C. EI-MS (m/z):435.0 (M+). 1H NMR (400 MHz, (CD3)2SO) δ 7.52(d, J = 8 Hz, 1H), 7.36-7.30(m, 3H), 7.18(d, J = 2 Hz, 4H), 7.03(d, J = 4 Hz, 1H), 6.94-6.92(m, 1H), 6.81(d, J = 8 Hz, 2H), 6.63(s, 1H), 4.76(s, 2H), 3.87(s, 3H).
  • 35
  • [ 2309-07-1 ]
  • [ 347-66-0 ]
  • C19H18FNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Methyl ferulate With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-N-(2-fluorophenyl)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.
  • 36
  • [ 1038308-06-3 ]
  • [ 347-66-0 ]
  • [ 1492902-40-5 ]
YieldReaction ConditionsOperation in experiment
47% With sodium hydroxide In ethanol for 0.5h; General Procedure for the Preparation of Compounds(7a-7i) General procedure: To a stirred solution of 6 (0.002 mol) in ethanol (20 mL),2N sodium hydroxide solution (0.002 mol) was added dropwiseto the mixture and followed by the substitutedchloroacetyl aniline (0.002 mol). After stirring for 30 min,solvent was removed in vacuo to obtain the crude product,which was further dissolved in dichloromethane (30 mL) andwashed with water (3 30 mL), and then dried overanhydrous magnesium sulfate. The residue was further purifiedby recrystallisation from ethanol to yield compounds 7a-7i.
  • 37
  • [ 1038384-04-1 ]
  • [ 347-66-0 ]
  • [ 1492902-37-0 ]
YieldReaction ConditionsOperation in experiment
37.1% With sodium hydroxide In ethanol for 0.5h; General Procedure for the Preparation of Compounds(7a-7i) General procedure: To a stirred solution of 6 (0.002 mol) in ethanol (20 mL),2N sodium hydroxide solution (0.002 mol) was added dropwiseto the mixture and followed by the substitutedchloroacetyl aniline (0.002 mol). After stirring for 30 min,solvent was removed in vacuo to obtain the crude product,which was further dissolved in dichloromethane (30 mL) andwashed with water (3 30 mL), and then dried overanhydrous magnesium sulfate. The residue was further purifiedby recrystallisation from ethanol to yield compounds 7a-7i.
  • 38
  • [ 347-66-0 ]
  • [ 578-95-0 ]
  • [ 389577-13-3 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 2h; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide With potassium iodide In N,N-dimethyl-formamide; mineral oil at 0℃; Reflux; 4.1. General synthetic procedure for 2-(9-oxoacridin-10(9H)-yl)-N-(substituted) phenyl acetamide (13a-o) General procedure: Acridone (10) (195mg, 1mmol) was added portion wise to a stirred suspension of NaH (56mg, 1.2mmol, 50% of mineral oil) in dry DMF (10ml) at 0°C. The reaction mixture was stirred for 2h. Afterward, 2-chloro-N-(substituted)phenyl acetamides 12a-o (2mmol) and KI (33.2mg, 0.2mmol) were added to the reaction mixture with stirring for different time intervals. After completion of the reaction (TLC), the reaction mixture was poured into crushed ice (50g) with constant stirring. The precipitated solid was collected and then extracted with chloroform. The combined organic extracts were washed with brine and water and finally dried with anhydrous sodium sulfate. Pure compounds were isolated after column chromatography and recrystallized from suitable solvent.
  • 39
  • [ 1607457-46-4 ]
  • [ 347-66-0 ]
  • [ 1607457-26-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C17H18N2O3 With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-N-(2-fluorophenyl)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%).
  • 40
  • [ 97966-29-5 ]
  • [ 347-66-0 ]
  • [ 1607457-41-9 ]
YieldReaction ConditionsOperation in experiment
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: 2-chloro-N-(2-fluorophenyl)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) General procedure: 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%).
  • 41
  • [ 1607457-45-3 ]
  • [ 347-66-0 ]
  • [ 1607457-11-3 ]
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: 2-chloro-N-(2-fluorophenyl)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%).
  • 42
  • [ 746667-09-4 ]
  • [ 347-66-0 ]
  • [ 1607465-37-1 ]
  • 2-(4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 68% 2: 5% With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 20℃; for 0.5h; 4.1.11 2-(4-([1,2,4]Triazolo[1,5-a]pyridin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (19a) and 2-(4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (20a) General procedure: To a stirred solution of 6-(3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine (17) (0.72mmol) in anhydrous DMF (6ml), a catalytic amount of NaI, 2-chloro-N-phenylacetamide (18a) (1.08mmol), and NaH (1.08mmol) were added. The mixture was stirred at room temperature for 30min and then evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using MeOH/CHCl3 (1:40) as eluent to give the two positional isomers 19a and 20a as white solids. Compound 19a: Yield 78%.
  • 43
  • [ 1567843-82-6 ]
  • [ 347-66-0 ]
  • [ 1621388-40-6 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In acetone Reflux; 4.8 General procedure for the synthesis of compounds 11a-m General procedure: K2CO3 (0.345g, 2.5mmol) was added to a stirred solution of compound (5a, 6a, 7a) (1mmol) and 2-chloro-N-(substituted-phenyl) acetamide (1.5mmol) in acetone (5mL). The reaction mixture was heated to reflux for 7-12h. The mixture was cooled, separated by filtration. The filter liquor was concentrated under reduced pressure, and purified by chromatography on silica gel using MeOH/CH2Cl2 to obtain 11a-m.
  • 44
  • [ 1567843-89-3 ]
  • [ 347-66-0 ]
  • [ 1621388-43-9 ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate In acetone Reflux; 4.8 General procedure for the synthesis of compounds 11a-m General procedure: K2CO3 (0.345g, 2.5mmol) was added to a stirred solution of compound (5a, 6a, 7a) (1mmol) and 2-chloro-N-(substituted-phenyl) acetamide (1.5mmol) in acetone (5mL). The reaction mixture was heated to reflux for 7-12h. The mixture was cooled, separated by filtration. The filter liquor was concentrated under reduced pressure, and purified by chromatography on silica gel using MeOH/CH2Cl2 to obtain 11a-m.
  • 45
  • [ 1621388-35-9 ]
  • [ 347-66-0 ]
  • [ 1621388-48-4 ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate In acetone Reflux; 4.8 General procedure for the synthesis of compounds 11a-m General procedure: K2CO3 (0.345g, 2.5mmol) was added to a stirred solution of compound (5a, 6a, 7a) (1mmol) and 2-chloro-N-(substituted-phenyl) acetamide (1.5mmol) in acetone (5mL). The reaction mixture was heated to reflux for 7-12h. The mixture was cooled, separated by filtration. The filter liquor was concentrated under reduced pressure, and purified by chromatography on silica gel using MeOH/CH2Cl2 to obtain 11a-m.
  • 46
  • [ 347-66-0 ]
  • [ 91-56-5 ]
  • C16H11FN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: indole-2,3-dione With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Cooling with ice; Stage #2: [(2-fluorophenyl)aminocarbonylmethyl]chloride In N,N-dimethyl-formamide at 80℃;
Stage #1: indole-2,3-dione With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: [(2-fluorophenyl)aminocarbonylmethyl]chloride In N,N-dimethyl-formamide at 60℃; for 5h;
  • 47
  • [ 347-66-0 ]
  • [ 60100-09-6 ]
  • 2-[(2-fluorophenyl)amino]-2-oxoethyl formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With phosphorus tribromide at 80 - 90℃; for 4h; Inert atmosphere;
With phosphorus tribromide at 80 - 90℃; for 4h; General Procedure for Sequential One-pot Multicomponent Synthesis of N,O-Disubstituted Glycolamides 5a-f, 7-11, 12a-e, and 13a-b. General procedure: The reliable procedure involved the treatment ofthe treatment of 4 h α-chloro N-arylacetamide1a-f or α-chloro N-(naphthalenyl)acetamide 2 (1.0 equiv) with PBr3(~3.0 equiv) in formamide solution (2 mL) at 80-90 °Cwithin 4 h.
  • 48
  • [ 347-66-0 ]
  • [ 837-52-5 ]
  • 2-(4-(7-chloroquinolin-4-yl)piperazine-1-yl)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 90℃;
  • 49
  • C11H14BrNO3 [ No CAS ]
  • [ 347-66-0 ]
  • 2-bromo-3-{2-[(2-fluorophenyl)amino]-2-oxoethoxy}-N-isopropyl-4-methoxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C11H14BrNO3 With potassium carbonate In ethanol at 20℃; for 0.5h; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide In ethanol for 10h; Reflux; General procedure: To a suspensionof 6a (1.53 g, 5.90 mmol) in dehydrated ethanol (70 mL) was added anhydrous potassium carbonate (2.45 g, 17.70 mmol). Themixture was stirred at room temperature for 30 min and then 2-chloro-N-(3,4-dichlorophenyl)acetamide (1.54 g, 6.49 mmol)was added. The reaction mixture was refluxed for 10 h. Filtration and evaporation of alcohol was done in vacuum. The residuewas extracted with EtOAc (3 20 mL). The combined organic layers were washed with H2O (3 10 mL), 2 M NaOH (3 10 mL),2 M HCl (3 10 mL), and brine (2 10 mL), dried over Na2SO4, and the solvent was removed. The crude product was purifiedby silica gel column chromatography to give T9 (2.13 g, 78%) as a white crystalline powder
  • 50
  • [ 347-66-0 ]
  • [ 86-74-8 ]
  • C20H15FN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl-formamide at 60℃;
  • 51
  • [ 6326-79-0 ]
  • [ 347-66-0 ]
  • 2-(6-bromo-2,3-dioxoindolin-1-yl)-N-(o-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-bromoisatin With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide With potassium iodide In N,N-dimethyl-formamide at 80℃; Preparation of Compounds 1-17 General procedure: Compounds 1-17 (Fig. 2) were synthesized in our laboratory as described previously [26]. 6-Bromoindoline-2,3-dione (1.0 g, 3.4 mmol), K2CO3 (0.6g, 3.4 mmol) and DMF 50 mL were placed on a round-bottomed flask. The mixture was stirred for 1h at room temperature. Then, 3.4 mmol N-substi-tuted phenylacetamide and 3 mmol KI were added to it, and the mixture was stirred to react at 80 °C from 2h to 24h. After the reaction was over, the product was poured into ice-water, adjusted the filtrates pH value to 3-4 using hydrochloric acid, the yellow solids were obtained (1-17). The crude product was recrystallized from MeOH or EtOH.
  • 52
  • [ 110-91-8 ]
  • [ 347-66-0 ]
  • C12H13FN2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: morpholine With sulfur; triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 4.2.2. General procedure for the preparation of compounds 6a-e General procedure: To a suspension of elementary sulfur (512 mg, 16.0 mmol) indry DMF (20 mL) was sequentially added (in dropwise fashion)triethylamine (2.25 mL, 16.0 mmol) and morpholine (1.06 mmol)and the resulting mixture was stirred for 30 min. Then it was treatedwith a solution of respective 2-chloroacetamides 8 (0.5 mmol).The mixture was stirred overnight, poured into water (50 mL) andthe resulting precipitate was separated by filtration and air-dried.It was then suspended in acetone (50 mL) and the insoluble residueof excess of unreacted sulfur was filtered off and discarded.The filtrate was evaporated to dryness and the dry residue wasdissolved in dry DMF (15 mL), treated with hydrazine hydrate(2.5 mL) and stirred for 12 h. The reaction mixture was poured intowater, the pH of the aqueous medium was adjusted to 5.0 with 2 M aqueous HCl. The resulting precipitate of 10 was filtered off andused in the next step without further purification (purity of at least90% was estimated based on 1H NMR analysis). Thiohydrazide 10 was obtained was placed in a thick-walled crew-capped glass tubealong with succinic anhydride (1.2 mmol) and glacial acetic acid(3.0 mL). The reaction mixture was heated at reflux temperatureon vigorous stirring over 2 h, cooled down and poured into water(25 mL). The precipitate formed was filtered off and air dried todeliver analytically pure compounds 6a-e in yields indicated.
Stage #1: morpholine With sulfur; triethylamine In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
With sulfur In N,N-dimethyl-formamide at 20℃; Representative compound: 2-Hydrazinyl-N-(4-methoxyphenyl)-2-thioxoacetamide (2c). General procedure: To a solution of sulfur (2.0 g, 62.5 mmol) in morpholine (7 mL) and DMF (7 mL), chloroacetanilide (2.0g, 10.0 mmol) was added with stirring. The reaction mixture was kept overnight at room temperature(TLC monitoring). The mixture was poured into water (70 mL). The precipitate that formed was filteredoff, dried, and dissolved in acetone to remove the sulfur excess. The organic fraction was separated, andthe solvent was evaporated in vacuo. The solid residue was recrystallized from ethanol to give monothiooxamide as a white solid in 95% yield (2.7 g, 9.5 mmol).
With sulfur; triethylamine In N,N-dimethyl-formamide at 20℃; General procedure: N-aryl-2-thioxoacetamides (9a-j) All the 2-hydrazinyl-N-aryl-2-thioxoacetamides (9a-j) were synthesized following the reported procedure [12]. To asuspension of elementary sulfur (1024 mg, 32.0 mmol) in dry dimethylformamide (DMF) (40 mL) was sequentially added (in a dropwise fashion) triethylamine (4.45 mL, 32.0mmol) and morpholine (2.12 mmol) and the resulting mixture was stirred for 30 min. Then, it was treated with asolution of respective 2-chloroacetamides (1.0 mmol), all of which are known compounds. The mixture was stirred overnight, poured into water (100 mL) and the resulting precipitate was separated by filtration and air-dried. It was then suspended in acetone (100 mL) and the insoluble residue of excess of unreacted sulfur was filtered off and discarded. The filtrate was evaporated to dryness and the dry residue was dissolved in dry DMF (30 mL), treated with hydrazine hydrate (5.0 mL) and stirred for 12 h. The reaction mixture was poured into water, and the pH of the aqueous medium was adjusted to 5.0 with 2M aqueous HCl. The resulting precipitate was filtered off, washed with water, airdried and crystallized from ethanol to deliver analytically pure thiohydrazides (9). The yields and 1H NMR data of compounds (9a-j) are identical to those described earlier [12]. Compounds (9a-j) was used in the next step without further purification.

  • 53
  • [ 31821-78-0 ]
  • [ 347-66-0 ]
  • C19H20FN5O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With potassium carbonate In ethanol Reflux; 5.1.3 General procedure for the target compounds 8k-x. General procedure: A mixture of the key intermediate 13 (1.0 mmol), diverse 2-chloro-N-sbustituted acetamidederivatives 15 (1.0 mmol) and potassium carbonate (K2CO3) (0.15 g, 1.1 mmol) in 5.0 mL ofanhydrous ethanol was stirred and refluxed for 2.0-2.5 h. After the reaction was complete accordingto the TLC detection, the precipitate was filtered off and solvent was removed under reducedpressure and the residue was purified by column chromatography to give the target compounds inyields of 57-78%.
  • 54
  • C18H16N4S [ No CAS ]
  • [ 347-66-0 ]
  • 2-(5-((1H-indol-3-yl)methyl)-4-benzyl-4H-1,2,4-triazole-3-ylthio)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With potassium hydroxide In ethanol at 20℃;
  • 55
  • [ 347-66-0 ]
  • [ 2349-67-9 ]
  • 2-amino-5-[(2-fluorophenylcarbamoyl)methylthio]-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydroxide In ethanol; water at 20℃; 4.2. General Procedure for the Preparation of Compounds 3a-q General procedure: A solution of sodium hydroxide (6 mmol) in water (20 mL) was added to a mixture of 2-amino-5-mercapto-1,3,4-thiadiazole (6 mmol), appropriate 2-chloro-N-(substituted phenyl)-acetamide (2a-q, 5 mmol) and ethanol (10 mL). The mixture was stirred for 4-5 h at room temperature (the end of reaction was monitored by TLC), after completion, the mixture was poured into water. The resulting precipitate was collected by filtration, washed well with water and further puried by recrystallization from ethanol to afford target compounds.
  • 56
  • 3-amino-6,7-dimethoxy-2-phenylquinazolin-4(3H)-one [ No CAS ]
  • [ 347-66-0 ]
  • 2-((6,7-dimethoxy-4-oxo-2-phenylquinazolin-3(4H)-yl)-amino)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% In N,N-dimethyl-formamide Reflux;
  • 57
  • [ 347-66-0 ]
  • 2-hydrazinyl-N-(2-(fluoromethyl)phenyl)-2-thioxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sulfur; triethylamine / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: hydrazine hydrate / N,N-dimethyl-formamide / 12 h / Inert atmosphere
Multi-step reaction with 2 steps 1: sulfur / N,N-dimethyl-formamide / 20 °C 2: hydrazine hydrate / N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 2 steps 1: sulfur; triethylamine / N,N-dimethyl-formamide / 20 °C 2: hydrazine hydrate / N,N-dimethyl-formamide / 12 h / 20 °C
  • 58
  • [ 75-15-0 ]
  • [ 347-66-0 ]
  • [ 100-46-9 ]
  • (2-fluorophenylcarbamoyl)methyl benzylcarbamodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 20℃; for 2.33333h; 4.1. General procedure for the synthesis of compounds 7a-7q General procedure: To a stirred solution of substituted aniline (1 mmol) and chloroacetyl chloride (1 mmol) which was stirred in 5 mL DMF for 20 min, were added benzyl amine derivatives (1.3 mmol) and CS2 (5 mmol). The reaction mixture was allowed to stir for required additional time (Table 2). Then, 5 mL of water was added and the solution was extracted with ethyl acetate and dried over sodium sulfate and purified by passing over a silica gel column chromatography using petroleum ether/ethyl acetate (8:2).
  • 59
  • [ 75-15-0 ]
  • [ 347-66-0 ]
  • [ 104-84-7 ]
  • C17H17FN2OS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 20℃; for 1.66667h; 4.1. General procedure for the synthesis of compounds 7a-7q General procedure: To a stirred solution of substituted aniline (1 mmol) and chloroacetyl chloride (1 mmol) which was stirred in 5 mL DMF for 20 min, were added benzyl amine derivatives (1.3 mmol) and CS2 (5 mmol). The reaction mixture was allowed to stir for required additional time (Table 2). Then, 5 mL of water was added and the solution was extracted with ethyl acetate and dried over sodium sulfate and purified by passing over a silica gel column chromatography using petroleum ether/ethyl acetate (8:2).
  • 60
  • [ 75-15-0 ]
  • [ 347-66-0 ]
  • [ 104-86-9 ]
  • (2-fluorophenylcarbamoyl)methyl 4-chlorobenzylcarbamodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 20℃; for 2.66667h; 4.1. General procedure for the synthesis of compounds 7a-7q General procedure: To a stirred solution of substituted aniline (1 mmol) and chloroacetyl chloride (1 mmol) which was stirred in 5 mL DMF for 20 min, were added benzyl amine derivatives (1.3 mmol) and CS2 (5 mmol). The reaction mixture was allowed to stir for required additional time (Table 2). Then, 5 mL of water was added and the solution was extracted with ethyl acetate and dried over sodium sulfate and purified by passing over a silica gel column chromatography using petroleum ether/ethyl acetate (8:2).
  • 61
  • 4-(2-mercapto-4-oxobenzo[g]-quinazolin-3(4H)-yl)benzenesulfonamide [ No CAS ]
  • [ 347-66-0 ]
  • N-(2-fluorophenyl)-2-(4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydrobenzo[g]quinazolin-2-ylthio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With potassium carbonate In acetone at 20℃; for 10h;
  • 62
  • [ 34157-83-0 ]
  • [ 347-66-0 ]
  • C37H44FNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;
  • 63
  • 2-(3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-yl)isoindoline-1,3-dione [ No CAS ]
  • [ 347-66-0 ]
  • C27H22FN5O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate In acetone at 20℃; General procedure for the target compounds 6a-v General procedure: A mixture of the isoindoline-1,3-dione derivative 12 (1.0 mmol), 2-chloro-N-substituted acetamide derivatives 15 (1.0 mmol) and potassium carbonate (K2CO3) (0.15 g, 1.1 mmol) in 5.0 mL of anhydrous acetone was stirred at room temperature for 0.5-1.0 h. After the reaction was complete according to the TLC detection, the precipitate was filtered off and solvent was removed under reduced pressure and the residue was purified by column chromatography to give the target compounds in yields of 52-81%. The properties and analytical data for compound 2 are listed in Table 1, and the spectral data are shown in Table 2.
  • 64
  • [ 347-66-0 ]
  • 6-(3-(pyrimidin-4-yl)-1H-pyrazol-4-yl)quinoxaline [ No CAS ]
  • N-(2-fluorophenyl)-2-(3-(pyrimidin-4-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)acetamide [ No CAS ]
  • C23H16FN7O [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 58% 2: 7% With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 20℃; for 2h; 3.1.4. General Procedure for the Preparation of 2-(3-(6-(Dimethylamino)pyridin-2-yl)-,2-(3-(4-Methylthiazol-2-yl)- or 2-(3-(Pyrimidin-4-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)acetamide(14a-d, 16a-d, 25a, 25b, 25d) and 2-(5-(6-(Dimethylamino)pyridin-2-yl)-, 2-(5-(4-Methylthiazol-2-yl)-or 2-(5-(Pyrimidin-4-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (15a-d, 17a-d, 26a,26b, 26d) General procedure: To a solution of pyrazole 12a, 12b, or 23 (0.63 mmol) in anhydrous DMF (8.3 mL), a catalytic amount of sodium iodide, NaH (0.75 mmol), and 2-chloro-N-phenylacetamide 13a, 13b, 13c, 13d,24a, 24b, or 24d (0.79 mmol) were added. The mixture was stirred at room temperature for 2 h and then evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol, 50:1) to give the two positional isomers 14a-d, 16a-d,25a, 25b, 25d and 15a-d, 17a-d, 26a, 26b, 26d as white solids.
  • 65
  • [ 347-66-0 ]
  • N,N-dimethyl-6-(4-(quinoxalin-6-yl)-1H-pyrazol-3-yl)pyridin-2-amine [ No CAS ]
  • 2-(5-(6-(dimethylamino)pyridin-2-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)-N-(2-fluorophenyl)acetamide [ No CAS ]
  • 2-(3-(6-(dimethylamino)pyridin-2-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 40% 2: 13% With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 20℃; for 2h; 3.1.4. General Procedure for the Preparation of 2-(3-(6-(Dimethylamino)pyridin-2-yl)-,2-(3-(4-Methylthiazol-2-yl)- or 2-(3-(Pyrimidin-4-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)acetamide(14a-d, 16a-d, 25a, 25b, 25d) and 2-(5-(6-(Dimethylamino)pyridin-2-yl)-, 2-(5-(4-Methylthiazol-2-yl)-or 2-(5-(Pyrimidin-4-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (15a-d, 17a-d, 26a,26b, 26d) General procedure: To a solution of pyrazole 12a, 12b, or 23 (0.63 mmol) in anhydrous DMF (8.3 mL), a catalytic amount of sodium iodide, NaH (0.75 mmol), and 2-chloro-N-phenylacetamide 13a, 13b, 13c, 13d,24a, 24b, or 24d (0.79 mmol) were added. The mixture was stirred at room temperature for 2 h and then evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol, 50:1) to give the two positional isomers 14a-d, 16a-d,25a, 25b, 25d and 15a-d, 17a-d, 26a, 26b, 26d as white solids.
  • 66
  • [ 347-66-0 ]
  • 4-methyl-2-(4-(quinoxalin-6-yl)-1H-pyrazol-3-yl)thiazole [ No CAS ]
  • N-(2-fluorophenyl)-2-(3-(4-methylthiazol-2-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)acetamide [ No CAS ]
  • N-(2-fluorophenyl)-2-(5-(4-methylthiazol-2-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 70% 2: 7% With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 20℃; for 2h; 3.1.4. General Procedure for the Preparation of 2-(3-(6-(Dimethylamino)pyridin-2-yl)-,2-(3-(4-Methylthiazol-2-yl)- or 2-(3-(Pyrimidin-4-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)acetamide(14a-d, 16a-d, 25a, 25b, 25d) and 2-(5-(6-(Dimethylamino)pyridin-2-yl)-, 2-(5-(4-Methylthiazol-2-yl)-or 2-(5-(Pyrimidin-4-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (15a-d, 17a-d, 26a,26b, 26d) General procedure: To a solution of pyrazole 12a, 12b, or 23 (0.63 mmol) in anhydrous DMF (8.3 mL), a catalytic amount of sodium iodide, NaH (0.75 mmol), and 2-chloro-N-phenylacetamide 13a, 13b, 13c, 13d,24a, 24b, or 24d (0.79 mmol) were added. The mixture was stirred at room temperature for 2 h and then evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol, 50:1) to give the two positional isomers 14a-d, 16a-d,25a, 25b, 25d and 15a-d, 17a-d, 26a, 26b, 26d as white solids.
  • 67
  • [ 27975-19-5 ]
  • [ 347-66-0 ]
  • 2-((2-fluorophenyl)amino)-2-oxoethyl (4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate; In acetonitrile; at 80℃; for 2h; General procedure: A mixture of <strong>[27975-19-5]isosteviol</strong> (63.6 mg, 0.20 mmol), K2CO3 (41.5 mg, 0.30 mmol) and differentchloroacetanilides (0.21 mmol) in CH3CN (10 mL) was stirred at 80 C for 2 h. After confirmingthe reaction progress by thin-layer chromatography, the solvent was evaporated in vacuo, the mixturewas dissolved with 15 mL ethyl acetate and then washed with saline (5 mL x 3). The mixture was then puried using silica gel column chromatography and eluted with a gradient of petroleum ether:ethylacetate (4:1-5:1) to obtain the target compound4a-4j.
  • 68
  • [ 347-66-0 ]
  • [ 100-39-0 ]
  • [ 13145-41-0 ]
  • C17H14FN3OS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-chloro-N-(2-fluorophenyl)acetamide; potassium cyanocarbonimidodithioate With sodium hydroxide In water; acetone at 20 - 80℃; for 2.5h; Stage #2: benzyl bromide In water; acetone at 20℃;
  • 69
  • [ 347-66-0 ]
  • [ 37536-29-1 ]
  • N-(2-fluorophenyl)-5-(5-phenyl-4H-1,2,4-triazolyl)thioacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.2% In ethanol; water for 6h; Reflux; Alkaline conditions; Halogen-substituted triazolethioacetamides (1-13): General procedure: A solution of 2-(5-mercapto-4H-1,2,4-triazol-3-yl)phenol (s4) (3 mmol) and NaOH (3.6 mmol)dissolved in H2O (15 mL) was added in a 50 mL three-neck round bottomed flask, kept stirring for 30 min.After N-substituted-2-chloroacetamides (N1-13) (3 mmol) dissolved in hot ethanol (5 mL) was added dropwise, the reaction mixture was heated to reflux for 6 h. Reaction mixture was cooled to RT and neutralizedwith 5 M HCl to a pH approximately 7.0. The resulting white solid was collected by filtration, washed withH2O repeatedly (3×80 mL) and dried in vacuo to obtain 1-13.
  • 70
  • [ 347-66-0 ]
  • 2-(3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl)thieno[3,2-c]pyridine [ No CAS ]
  • N-(2-fluorophenyl)-2-(3-(6-methylpyridin-2-yl)-4-(thieno[3,2-c]pyridin-2-yl)-1H-pyrazol-1-yl)acetamide [ No CAS ]
  • C24H18FN5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 49% 2: 13% With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 20℃; for 2h; 6 4.1.7. General procedure of 2-(4-substituted-3-(6-methylpyridin-2-yl)-1H-pyrazol-1- yl)-N-phenylacetamide (18a-d and 20a-d) and 2-(4-substituted-5-(6- methylpyridin-2-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (19a-d and 21a-d) General procedure: To a solution of pyrazole 16a or 16b (0.35 mmol) in anhydrousDMF (5 mL), a catalytic amount of sodium iodide, NaH (0.42 mmol),and 2-chloro-N-phenylacetamides 17aed (0.42 mmol) were added.The mixture was stirred at room temperature for 2 h and thenevaporated to dryness under reduced pressure. The residue waspurified by the silica gel column using CH2Cl2/MeOH as eluent togive the two positional isomers 18aed, 20aed and 19aed, 21aedas light yellow solids.
  • 71
  • 5-(3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl)benzo[c][1,2,5]thiadiazole [ No CAS ]
  • [ 347-66-0 ]
  • 2-(4-(benzo[c][1,2,5]thiadiazol-5-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)-N-(2-fluorophenyl)acetamide [ No CAS ]
  • 2-(4-(benzo[c][1,2,5]thiadiazol-5-yl)-5-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 64% 2: 14% With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 20℃; for 2h; 2 4.1.7. General procedure of 2-(4-substituted-3-(6-methylpyridin-2-yl)-1H-pyrazol-1- yl)-N-phenylacetamide (18a-d and 20a-d) and 2-(4-substituted-5-(6- methylpyridin-2-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (19a-d and 21a-d) General procedure: To a solution of pyrazole 16a or 16b (0.35 mmol) in anhydrousDMF (5 mL), a catalytic amount of sodium iodide, NaH (0.42 mmol),and 2-chloro-N-phenylacetamides 17aed (0.42 mmol) were added.The mixture was stirred at room temperature for 2 h and thenevaporated to dryness under reduced pressure. The residue waspurified by the silica gel column using CH2Cl2/MeOH as eluent togive the two positional isomers 18aed, 20aed and 19aed, 21aedas light yellow solids.
  • 72
  • [ 104960-50-1 ]
  • [ 347-66-0 ]
  • 3-amino-N-(2-fluorophenyl)-6-(thiophen-2-yl)-4-(trifluoromethyl)thieno[2,3-b]pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In ethanol at 90℃; for 2h; Microwave irradiation; 4.2. General procedure for synthesis of compounds 7a-7k General procedure: The corresponding chloroacetamide 6a-6 k (1 equiv.), compound 3(suppl. info.; 1 equiv.) was mixed with K2CO3 (1 equiv.), and ethanol(5 mL) in a microwave reaction vessel. This mixture was stirred at 90 °Cfor 2 h using a “high energy absorption” setting. The crude product wasfiltered-off, washed with water and fixed onto silica gel powder beforerunning a solvent gradient (flash column chromatography). Combinedorganic fractions were dried under vacuum and the corresponding finalproduct was recrystallized from ethanol (when needed).
  • 73
  • [ 347-66-0 ]
  • [ 552-89-6 ]
  • trans-N-(2-fluorophenyl)-3-(2-nitrophenyl)oxirane-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium methylate In methanol at 20℃; Synthesis trans-(2-nitrophenyl)oxirane-2-carboxamides 3a-h (Darzens condensation) General procedure: A solution of MeONa obtained when dissolving Na (0.73 g, 0.032 g-atom) in MeOH (20 mL) was added to the stirred solution of 2-nitrobenzaldegyde (4.08 g, 0.027 mol) with the 2-chloro-N-arylacetamides (0.027 mol) in MeOH (70 mL). After stirring for 7 h at room temperature the mixture was allowed to react at this temperature overnight. The resulting precipitate was filtered off, washed with water (2 x 70 mL) and dried in air to yield the pure samples of trans-isomer 3. Spectra and melting point of 3a and 3h were in accordance with our previous syntheses,24c the characteristic data for 3b-g are given below.
  • 74
  • [ 35195-77-8 ]
  • [ 347-66-0 ]
  • 3-(4-((2-fluorophenyl)amino)thiazol-2-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% In N,N-dimethyl-formamide at 80℃; Inert atmosphere; 1.d . SYNTHESIS OF 3-(4-((2-FLUOROPHENYL)AMINO)THIAZOL-2- (0722) YL)BENZOIC ACID (44) [00466] A solution of 2-chloro-N-(2-fluorophenyl)acetamide (104 mg, 0.552 mmol) and 3-carbamothioylbenzoic acid (100 mg, 0.552 mmol) in DMF (2 ml) was heated at 80 °C for overnight. Solvent was removed and purified on Teledyne Isco Combiflash Rf purification machine to afford 3-(4-((2-fluorophenyl)amino)thiazol-2-yl)benzoic acid in 8% yield.
8% In N,N-dimethyl-formamide at 80℃; 4.6.60. 3-(4-((2-Fluorophenyl)amino)thiazol-2-yl)benzoic acid (60) A solution of 2-chloro-N-(2-fluorophenyl)acetamide (104 mg,0.552 mmol) and 3-carbamothioylbenzoic acid (100 mg,0.552 mmol) in DMF (2 ml) was heated at 80 C for overnight.Solvent was removed and the crude residue was purified on TeledyneIsco Combiflash Rf purification machine to afford 3-(4-((2-fluorophenyl)amino)thiazol-2-yl)benzoic acid, 60 as a pale yellowsolid in 8% yield (HPLC purity: 100%). TLC Rf 0.25 (30% EtOAc inHexanes). M. P. 191e193 C. ESI-MS m/z: 315.0. 1H NMR(400 MHz, DMSO-d6): d 13.25 (s, 1H), 8.67 (d, J 2.0 Hz, 1H), 8.43 (t,J 1.8 Hz, 1H), 8.13 (dt, J 7.8, 1.5 Hz, 1H), 8.00 (dt, J 7.8, 1.4 Hz,1H), 7.78e7.57 (m, 2H), 7.24e7.04 (m, 2H), 6.90e6.83 (m, 1H), 6.73(s, 1H). HRMS calcd for [C16H11FN2O2S H]: 315.0598, Found:315.06004.
  • 75
  • [ 347-66-0 ]
  • N-cyclohexyl-2-(4-hydroxy-3-methoxyphenyl)-2-oxoacetamide [ No CAS ]
  • N-cyclohexyl-2-(4-(2-((2-fluorophenyl)amino)-2-oxoethoxy)-3-methoxyphenyl)-2-oxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.44% With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 0.8h; 7.4 Example 7: Preparation of N-cyclohexyl-2- (4- (2-((2-fluorophenyl) amino) -2-oxoethoxy) -3-methoxyphenyl) -2-oxo acetamide. Step 4: Add DMF (N, N-dimethylformamide) to intermediate 2 (1mmol) to dissolve, add potassium carbonate K2CO3 (1.2mmol) and potassium iodide KI (0.5mmol) and stir for about 1h, then add 2- Chloro-N- (2-fluorophenyl) acetamide (1.1 mmol) was stirred at room temperature for about 7 hours to stop the reaction. The system was poured into water and stirred. A large amount of solids were precipitated, filtered with suction, and the solid was stirred and filtered with n-hexane. Dry to obtain compound I-7.
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 7h;
  • 76
  • [ 347-66-0 ]
  • 4-(3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl)-2-phenylpyridine [ No CAS ]
  • N-(2-fluorophenyl)-2-(3-(6-methylpyridin-2-yl)-4-(2-phenylpyridin-4-yl)-1H-pyrazol-1-yl)acetamide [ No CAS ]
  • N-(2-fluorophenyl)-2-(5-(6-methylpyridin-2-yl)-4-(2-phenylpyridin-4-yl)-1H-pyrazol-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With sodium iodide In N,N-dimethyl-formamide at 20℃; for 2h; 1.3General procedure for the preparation of 2-(3-(6-methylpyridin-2-yl)-4-(quinolin-4-yl) or 2-(3-(6-methylpyridin-2-yl)-4-(2- phenylpyridin-4-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (11a-d and 18a-d)and 2-(5-(6-methylpyridin-2-yl)-4-(quinolin-4-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (12a-d and 19a-d) General procedure: To a solution ofpyrazole 9 (0.73 mmol) in anhydrous DMF (5 mL), a catalytic amount of sodiumiodide, NaH (0.88 mmol), and substituted phenylacetamides 10a-d (0.88 mmol) were added. The mixture was stirred atroomtemperature for 2 h and then evaporatedto dryness under reduced pressure. The residue was purified by MPLC on silica gel using MeOH/CH2Cl2 as eluent to give the four positional isomers 11a-d and 12a-d, 18a-d and 19a-d as white solids.
  • 77
  • [ 347-66-0 ]
  • 4-(3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl)quinoline [ No CAS ]
  • N-(2-fluorophenyl)-2-(5-(6-methylpyridin-2-yl)-4-(quinolin-4-yl)-1H-pyrazol-1-yl)acetamide [ No CAS ]
  • N-(2-fluorophenyl)-2-(3-(6-methylpyridin-2-yl)-4-(quinolin-4-yl)-1H-pyrazol-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 32% 2: 15% With sodium iodide In N,N-dimethyl-formamide at 20℃; for 2h; 1.3General procedure for the preparation of 2-(3-(6-methylpyridin-2-yl)-4-(quinolin-4-yl) or 2-(3-(6-methylpyridin-2-yl)-4-(2- phenylpyridin-4-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (11a-d and 18a-d)and 2-(5-(6-methylpyridin-2-yl)-4-(quinolin-4-yl)-1H-pyrazol-1-yl)-N-phenylacetamide (12a-d and 19a-d) General procedure: To a solution ofpyrazole 9 (0.73 mmol) in anhydrous DMF (5 mL), a catalytic amount of sodiumiodide, NaH (0.88 mmol), and substituted phenylacetamides 10a-d (0.88 mmol) were added. The mixture was stirred atroomtemperature for 2 h and then evaporatedto dryness under reduced pressure. The residue was purified by MPLC on silica gel using MeOH/CH2Cl2 as eluent to give the four positional isomers 11a-d and 12a-d, 18a-d and 19a-d as white solids.
  • 78
  • [ 347-66-0 ]
  • N-(2-fluoro-phenyl)-2-(4-piperidin-1-yl-quinazoline-2-sulfonyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / Reflux 2: trichlorophosphate / 4 h / Reflux 3: triethylamine / tetrahydrofuran / 6 h / Reflux 4: dihydrogen peroxide; acetic acid / 1 h / 20 °C
  • 79
  • [ 347-66-0 ]
  • N-(2-fluoro-phenyl)-2-(4-morpholin-4-ylquinazoline-2-sulfonyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / Reflux 2: trichlorophosphate / 4 h / Reflux 3: triethylamine / tetrahydrofuran / 6 h / Reflux 4: dihydrogen peroxide; acetic acid / 1 h / 20 °C
  • 80
  • [ 347-66-0 ]
  • N-(2-fluoro-phenyl)-2-(4-pyrrolidin-1-yl-quinazoline-2-sulfonyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / Reflux 2: trichlorophosphate / 4 h / Reflux 3: triethylamine / tetrahydrofuran / 6 h / Reflux 4: dihydrogen peroxide; acetic acid / 1 h / 20 °C
  • 81
  • [ 347-66-0 ]
  • 2-amino-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With ammonium hydroxide at 60℃; for 6h; Inert atmosphere; 4.1.2 General procedure for synthesis of compounds 2-amino-N-phenyl substituted acetamide (3a-3t, 6a and 6b) General procedure: To a solution of substituted phenyl acetamide, 2a-2t or 5a or 5b (0.25g, 1.0 equiv) excess of liquid ammonia (NH3) (10mL) was added, and the reaction was heated at 60°C for 6h. The reaction mixture was allowed to cool to room temperature, after which 30mL of ethyl acetate was added and the organic layer was separated and dried over anhydrous Na2SO4, and concentrated in vacuo, which provided the free amine of compounds 3a-3t, 6a, and 6b as a solid/oily product with 50-60% yield. Purification of the crude products was done by column chromatography using DCM:MeOH (9.5:0.5) as eluents to afford the aforementioned compounds.
  • 82
  • [ 347-66-0 ]
  • (E)-N-(2-((2-fluorophenyl)amino)-2-oxoethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: ammonium hydroxide / 6 h / 60 °C / Inert atmosphere 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere 2.2: 70 °C / Inert atmosphere
  • 83
  • [ 347-66-0 ]
  • potassium-2,4-dioxo-5-(pyridin-2-ylmethylene)thiazolidin-3-ide [ No CAS ]
  • 2-(2,4-dioxo-5-(pyridin-2-ylmethylene)thiazolidin-3-yl)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% 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).
  • 84
  • [ 347-66-0 ]
  • potassium-5-(furan-2-ylmethylene)-2,4-dioxothiazolidin-3-ide [ No CAS ]
  • N-(2-fluorophenyl)-2-(5-(furan-2-ylmethylene)-2,4-dioxothiazolidin-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.5% 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.
  • 85
  • [ 31821-78-0 ]
  • [ 347-66-0 ]
  • N-(2-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With trichlorophosphate Reflux; 4.1.1. General protocol for preparation of compounds Ia-as General procedure: 4-amino-3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione 8 was synthesized according to the literature [50] and intermediates 10 and 12 were prepared according to our previously reported approach [33,51]. Method A. To a solution of 8 (282mg, 1.0mmol) in 5mL anhydrou sphosphorus oxychloride was added the appropriate N-substituted 2-chloroacetamides 10 (1.05mmol). After stirring for 2-4h under reflux, excess phosphorus oxychloride was removed at reduced pressure to afford an oily residue, which was purified through column chromatography with petroleum ether/acetone 5:1 (v/v) as eluent to give target compounds Ia-w. Method B. To a solution of 8 (282mg, 1.0mmol) and the appropriately α-bromoketones 12 (1.05mmol) in 5mL anhydrous ethanol was added K2CO3 (152mg, 1.1mmol). The reactions were stirred under reflux for 0.5-4h. After reaction completed, the solution was cooled and poured slowly in 20mL water. Precipitate was filtered, washed with water and recrystallized from EtOH to provide target compounds Ix-as.
  • 86
  • [ 347-66-0 ]
  • 5‑(5‑methyl‑1‑(2,4,5‑trichlorophenyl)‑1H‑1,2,3‑triazol‑4‑yl)‑4‑phenyl‑2,4‑dihydro‑3H‑1,2,4‑triazole‑3‑thione [ No CAS ]
  • N‑(2‑fluorophenyl)‑2‑((5‑(5‑methyl‑1‑(2,4,5‑trichlorophenyl)‑1H‑1,2,3‑triazol‑4‑yl)‑4‑phenyl‑4H‑1,2,4‑triazol‑3‑yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate In acetone at 20℃; Procedure for synthesis of target compound 8a-n General procedure: To a mixture of triazole (0.3 g, 0.7 mmol) and substitutedamides (0.7 mmol) in acetone, added K2CO3(0.7 mmol) andstirred at room temperature for 5 h. The completion of thereaction was monitored by thin-layer chromatography. Thereaction mass was filtered, and the filtrate was evaporatedunder a high vacuum to yield the desired product which wasrecrystallized using ethanol.
  • 87
  • [ 347-66-0 ]
  • [ 1211438-90-2 ]
YieldReaction ConditionsOperation in experiment
With Caswell No. 744A In N,N-dimethyl-formamide at 20℃; General synthetic process for substituted 2-azido-N-phenylacetamide derivatives. General procedure: To a solution of 2-chloro-N-phenylacetamide derivatives (1.0 equiv) in DMF were added sodium azide (3.0 equiv) andreaction mixture stirred at room temperature for 10-12 h, reaction was monitored by TLC, after complicationof reaction mixture poured in cold water, the separatedsolid collected and washed with cold water anddry in vacuum filter to afford 2-azido-N-phenylacetamide derivatives.
With Caswell No. 744A In N,N-dimethyl-formamide at 20℃; General procedure for the synthesis of N-aryl-2-azidophenylacetamides. General procedure: Sodium azide (3.0 equiv), was added to a solution of N-aryl-2-chloroacetamide(1.0 equiv) in DMF, and the resulting solution wasstirred at room temperature for 10-12 h. Aftercompletion of the reaction, the mixture was poured intocold water, and the solid product was filtered off,washed with cold water, and dried under reducedpressure.
With Caswell No. 744A at 0 - 20℃; for 1.5h; 2-Azido-N-(substituted phenyl)acetamides 6a-6j(general procedure). General procedure: A vacuum-dried round-bottomflask was charged with substituted aniline 4a-4j(1.4 mmol) and chloroacetyl chloride (1.7 mmol) inacetone, and the mixture was stirred at room temperaturefor 20 min. After completion of the reaction, thesolid was filtered off and dried under reduced pressure.The product was dissolved in DMF, sodium azide(3.0 mmol) was added, and the mixture was stirred atroom temperature for 1.5 h. After completion of thereaction (TLC; ethyl acetate-n-hexane, 3:7; yellowish-reddish color appeared in iodine vapor), the mixturewas poured into a mixture of water and crushed icewater, and the solid product was filtered off underreduced pressure.
  • 88
  • [ 347-66-0 ]
  • 4-(6-iodo-2-mercapto-4-oxoquinazolin-3(4H)-yl)benzenesulfonamide [ No CAS ]
  • N-(2-fluorophenyl)-2-(6-iodo-4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydroquinazolin-2-ylthio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In acetone at 20℃; for 8h; 4.1.1. N-(Substituted)-2-(6-iodo-4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydroquinazolin-2-ylthio) acetamide (4-17) General procedure: A mixture of 3 (4.59 g, 0.01 mol) and 2-chloro-N-substituted acetamide derivatives (0.01 mol) in dry acetone (20 mL) containing anhydrous K2CO3 (1.38 g, 0.01 mol) was stirred at room temp. for 8 h, filtered and the precipitate was crystallized from ethanol to give 4-17. 4.1.1.1. N-(2-Fluorophenyl)-2-(6-iodo-4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydroquinazolin-2-ylthio) acetamide (4). 4: Yield, 84%; m.p. 242.1 C.IR (KBr, cm 1): 3431, 3363, 3230 (NH, NH2), 3100 (arom.), 2982, 2856(aliph.), 1697, 1669 (2CO), 1621 (CN), 1377, 1151 (SO2). 1H NMR (500MHz, DMSO d6): δ 4.17 (s, 2H), 7.15-7.16 (m, 1H), 7.27-7.29 (m, 2H),7.39 (d, 1H, J = 7 Hz), 7.84 (d, 2H, J = 7.5 Hz, AB), 8.02 (dd, 1H, J = 6.5& 2.5 Hz), 8.03 (s, 2H), 8.16-8.17 (m, 3H), 8.34 (d, 1H, J = 3 Hz), 10.08(s, 1H). 13C NMR (126 MHz, DMSO d6): δ 31.25, 91.11, 115.94,116.05, 121.89 (2), 124.43, 124.87, 127.45, 128.60, 130.61 (2), 135.14(2), 138.59, 143.83, 146.86 (2), 157.68, 159.82 (2), 166.59. Anal.Calcd. for C22H16FIN4O4S2: C, 43.29; H, 2.64; N, 9.18. Found: C, 43.52;H, 2.98; N, 9.49.
  • 89
  • [ 347-66-0 ]
  • [ 93300-54-0 ]
  • 2-((5-(4-chlorophenyl)-4-phenyl-4 H-1,2,4-triazol-3-yl)thio)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 3-mercapto-5-(4-chlorophenyl)-4-phenyl-1,2,4-triazole With triethylamine In tetrahydrofuran Inert atmosphere; Stage #2: 2-chloro-N-(2-fluorophenyl)acetamide 4.2.5. Preparation of 2-((5-(4-chlorophenyl)-4-phenyl-4 H -1,2,4- triazol-3-yl)thio)- N -phenylacetamide derivatives (6f-6p) General procedure: Synthetic procedure was performed in oven-dried flat bot- tom flask enabled with a Teflon-coated magnetic stirring bar, rubber septa and nitrogen balloon. It was charged with 5- (4-chlorophenyl)-4-phenyl-4 H -1,2,4-triazole-3-thiol (1.0 mmol) in 20 mL tetrahydrofuran followed by dropwise addition of tri- ethyl amine (1.0 mmol) in stirring condition. After few minutes sui table 2 -chloro- N -phenylacetamide derivative (1.0 mmol) was added and reflux for 5-8 hours. Reaction completion was con- cluded by TLC in Ethyl acetate: Hexane (40:60). Reaction mixture was quenched by pouring it into cold water. Crude product was filtered and washed with ice water (3 ×20 mL). Precipitates were dried in oven at 48 °C temp to remove bound water molecules. Pu- rification was achieved by crystallization in hot methanol, results in characteristic shaped pure crystalline product.
  • 90
  • [ 347-66-0 ]
  • 4-(6,8-diiodo-2-mercapto-4-oxoquinazolin-3-(4H)-yl)benzenesulfonamide [ No CAS ]
  • 2-((6,8-diiodo-4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydroquinazolin-2-yl)thio)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate In acetone at 20℃; for 18h; General procedure for the synthesis of 3,4-dihydroquinazolin-sulfonamide derivatives (5-18) General procedure: A mixture of 4 (5.85 g, 0.01 mol) and 2-chloro-N-substituted acetamide derivatives (0.01 mol) in dry acetone (30 mL) and anhydrous K2CO3 (1.38 g) was stirred at room temperature for 18 h., filtered and the product formed was crystallized from dioxane to give 5-18. 5: Yield, 69%; m.p. 300 oC. IR (KBr, cm-1): 3403, 3371, 3255 (NH, NH2), 3063 (arom.), 2976, 2832 (aliph.), 1691, 1675 (2CO), 1608 (CN), 1377, 1155 (SO2). 1H NMR (500 MHz, DMSOd6): δ 4.32 (s, 2H), 6.98-7.01 (m, 1H), 7.20-7.25 (m, 2H), 7.85 (d, 2H, J= 8 Hz, AB), 7.94 (dd, 1H, J= 6.5 & 2 Hz), 8.09 (s, 2H), 8.10 (d, 2H, J= 8 Hz, AB), 8.27, 8.55 (2d, 2H, J= 2 Hz), 10.32 (s, 1H). 13C NMR (126 MHz, DMSOd6): δ 30.06, 83.64, 95.21, 115.94, 122.35, 122.91 (2), 124.16, 124.35, 127.36, 130.61 (2), 131.07, 135.60, 136.98, 137.86, 147.31, 152.74, 158.97 (2), 163.02, 164.13. Anal. Calcd. for C22H15I2N4O4S2 (736.32): C, 35.89; H, 2.05; N, 7.61. Found: C, 35.58; H, 1.78; N, 7.34.
  • 91
  • [ 347-66-0 ]
  • [ 332026-86-5 ]
  • 2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1H-benzo[d]imidazol-1-yl)-N-(2-fluorophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 7h;
  • 92
  • [ 347-66-0 ]
  • [ 74-89-5 ]
  • [ 74-88-4 ]
  • N-(2-fluorophenyl)-N-methyl-2-(methylamino)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.38 g Stage #1: 2-chloro-N-(2-fluorophenyl)acetamide With potassium carbonate Stage #2: methyl iodide In tetrahydrofuran; N,N-dimethyl-formamide at 45℃; Stage #3: methylamine In tetrahydrofuran at 20℃; for 16h; General procedure: The corresponding amine solution 2M in THF (methylamine and ethylamine, 10- 20 eq.) or cyclopropylamine (10 eq.) dissolved in THF or propylamine (10 eq.) dissolved in THF was added over the mixture of 2-chloro-N-(2-chlorophenyl)-N-methylacetamide and 2-iodo-N-(2-chlorophenyl)-N-methylacetamide (1.0 eq.). The resulting mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated to dryness and the crude was treated with ethyl acetate (50 mL). The organic layer was washed twice with water (25 mL), dried over anhydrous sodium sulphate, filtered and concentrated to dryness. The resultant crude was purified by flash column chromatography (EtO Ac/Hexanes, 20%- 50%) or (DCM/DCMMeOH (90:10) (sometimes with NH32%), 0%-50%) to obtain the corresponding acetamides.
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