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Product Details of [ 17641-08-6 ]

CAS No. :17641-08-6 MDL No. :MFCD00018900
Formula : C9H10ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JJNAIBJFYFWTIA-UHFFFAOYSA-N
M.W : 199.63 Pubchem ID :28667
Synonyms :

Calculated chemistry of [ 17641-08-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.04
TPSA : 38.33 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) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.92
Log Po/w (WLOGP) : 1.68
Log Po/w (MLOGP) : 1.54
Log Po/w (SILICOS-IT) : 1.9
Consensus Log Po/w : 1.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.862 mg/ml ; 0.00432 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 0.895 mg/ml ; 0.00448 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.0561 mg/ml ; 0.000281 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 17641-08-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330-P501 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17641-08-6 ]

* 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 [ 17641-08-6 ]

[ 17641-08-6 ] Synthesis Path-Downstream   1~93

  • 2
  • [ 536-90-3 ]
  • [ 79-04-9 ]
  • [ 17641-08-6 ]
YieldReaction ConditionsOperation in experiment
91.5% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 1h;Inert atmosphere; To a solution of compound A (0.5 g, 4.05 mmoles) in ACN (10.0 mL) was added DIPEA (1.56 mL, 8.93 mmoles) , followed by dropwise addition of compound B (0.387 mL, 4.87 mmoles) under argon atmosphere. After the addition was complete the reaction was stirred at rt for 1 hour. The completion of the reaction was monitored by TLC. The reactionmixture was concentrated, purified by column chromatography (20 %EtOAc:Hexanes) to isolate the required compound as brown solid (0.74 g, 91.5%). 1H NMR (CDCl3, 400 MHz) delta 8.30 ( s, 1 H),7.28-7.23(m, 2 H), 7.03 (d, J=7.6 Hz, 1 H), 6.74-6.70(m, 1 H), 4.18 (s, 2 H), 3.81 (s, 3 H).
80.7% With pyridine; In dichloromethane; at 0 - 20℃; for 12h; Example 34 IV-1 6-(4-(4-(3-(6-fluoro-benzisoxazolyl))-1-piperidinyl)-n-butoxy)-indoline-2-one 1) 2 ml of pyridine is added to 30 ml of a solution of 3-methoxyaniline (4.92g, 40 mmol) in dichloromethane and the mixture is stirred for 5 minutes, while maintaining the temperature inside vessel at lower than 0C, and thereto 20 ml of a solution of chloroacetyl chloride (6.78g, 60 mmol) in dichloromethane is drop-added slowly. A reaction is carried out at room temperature for 12 hours after completion of drop-addition, and then terminated. The reaction solution is washed with 5% of HCl (30ml×3), 5% of NaOH (30ml×3), water (30ml×3), and saturated saline (30 ml) successively, dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated to remove the solvent to obtain 6.43g of 2-chloro-N-(3-methoxyphenyl)acetamide , with a yield of 80.7%.
80.7% With pyridine; In dichloromethane; at 0 - 20℃; for 12h; 2 ml of pyridine was added to 30 ml of a dichloromethane solution of 3-methoxyaniline (4.92 g, 40 mmol), and the mixture was stirred for 5 minutes. While maintaining the internal temperature at 0 C, a solution of chloroacetyl chloride (6.78 g, 60 mmol) in dichloromethane After completion of the dropwise addition, the reaction was stopped and the reaction solution was successively washed with 5% HCl 30 ml * 3, 5% NaOH 30 ml * 3, water 30 ml * 3, saturated Washed with 30 ml of brine, dried over anhydrous magnesium sulfate, filtered, the solvent was distilled off from the filtrate,6.43 g of 2-chloro-N-(3-methoxyphenyl)acetamide are obtained. Yield is 80.7%.
70% 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 0C, potassium carbonate (K2CO3) (2.0 equiv.) was added. The reaction was stirred at 0C for 15min. Into this stirring solution, chloroacetyl chloride (1.0 equiv.) was added dropwise at 0C. 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.
With pyridine; In water; at 0℃; for 1h; General procedure: Generalprocedure: To a solution of aniline or benzylamine (10 mmol) inwater (20 ml) and pyridine (1.6 ml) was added chloracetyl chloride(1.69 g, 15 mmol) slowly at 0 C. The reaction mixture was stirredat 0 C for 1.0 h and then diluted with water (50 ml). The precipitatewas collected by filtration, washed with water and dried undervacuum. N-substituted-2-chloroacetamides 3a-3r were obtainedas solid (yield 50-80%).
In N,N-dimethyl-formamide; at 20℃; for 0.333333h; 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 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.
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.
In N,N-dimethyl-formamide; at 20℃; for 0.5h; General procedure: Mixture of amines 6 and chloroacetyl chloride 7 in DMF werestirred at room temperature for 30 min. At the end of the reaction(checked by TLC), the reaction mixture was diluted with water, pouredinto ice, and the obtained white precipitate was filtered off. The residuewas washed with water to obtain pure N-phenyl (or benzyl)-2-chloroacetamide8.
With triethylamine; In dichloromethane; at 0 - 25℃; for 20h; General procedure: 2-Chloroacetyl chloride (24 mmol) wasslowly added dropwise to a mixture of various anilines(20 mmol) and Et3N (24 mmol) in anhydrous CH2Cl2(20 mL) at 0 C. The reaction mixture was warmed to roomtemperature and stirred for an additional 20 h. After the solventwas removed under reduced pressure, the residue waswashed with ice water, and the precipitate was separatedby filtration. The crude product was purified by crystallizationusing a mixture of ether/hexane (2a-r).
In acetic acid; at 0 - 20℃; General procedure: Various substituted anilines were dissolved in glacial acetic acidat 0 C, to this was added over 30 min choloroacetylchloride (2equivalents). The reaction mixture was brought to room temperatureand stirred overnight. Saturated sodium bicarbonate solutionwas added till complete neutralization. The resulting precipitatewas filtered off and washed with n-hexane and dried. The resultantproduct was used further without any purification. Either of 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde, vanillin or isovanillin(1 equivalent) was dissolved in acetone and potassiumcarbonate (2 equivalents) was added. Then correspondingsubstituted acetamide was mixed to the stirring solution. Finally,potassium iodide (1.5 equivalent) was added. The reaction mixturewas refluxed for 8-10 h. After completion of reaction, the resultantmixture was concentrated and treated with water and extractedwith ethyl acetate (3 x 20 mL). The organic layers were combinedand treated with brine and dried over sodium sulfate andconcentrated. The crude mixture was purified over silica gel(60-120) using petroleum ether: ethyl acetate (9:1).
With acetic acid; at 0 - 20℃; General procedure: Various substituted anilines were dissolved in glacial acetic acid at0 C, to this was added over 30 min choloroacetyl chloride (2 equivalents).The reaction mixture was brought to room temperature andstirred overnight. Saturated sodium bicarbonate solution was added tillcomplete neutralization. The resulting precipitate was filtered off andwashed with n-hexane and dried. The resultant product (1) was usedfurther without any purification. Either of 4-hydroxy benzaldehyde(2a), vanillin (2b) or isovanillin (2c) (1 equivalent) was dissolved inacetone and potassium carbonate (2 equivalents) was added. Thencorresponding substituted acetamide (1) was mixed to the stirring solution.Finally, potassium iodide (1.5 equivalent) was added. The reactionmixture was refluxed for 8-10 h. After completion of reaction,the resultant mixture was concentrated and treated with water andextracted with ethyl acetate (3×20 mL). The organic layers werecombined and treated with brine and dried over sodium sulfate andconcentrated. The crude mixture was purified over silica gel (60-120)using petroleum ether: ethyl acetate (9:1).
With triethylamine; at 0 - 20℃; for 4h; General procedure: In a round bottom flask, primary or secondary amines (0.1 mol) and triethyl amine weredissolved in DCM and stirred at 0 C. 2-Chloroacetyl chloride (0.1 mol) was added to reaction mixture drop wise with continuous stirring on magnetic stirrer. After the addition,the ice bath was removed and the reaction mixture was stirred at room temperature for 4 h.The progress of the reaction was monitored by TLC using ethyl acetate: hexane (1:9) as asolvent system. After completion of the reaction, the reaction mixture was poured on crushedice and neutralised by adding acetic acid to it. The obtained solid intermediates of respectiveamines were filtered, dried and crystallised in ethanol.
With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: The corresponding amine was dissolved in anhydrous dichloromethane at 0C, and then triethylamine (1.1 eq) was added under a nitrogen atmosphere. Chloroacetyl chloride (1.1 eq) diluted with anhydrous dichloromethane was slowly added to the reaction mixture in an ice bath. The reaction stirred at 0C for 30min, after which the reaction slowly warmed to room temperature overnight. TLC was used to monitor the reaction. After the reaction was complete, it was quenched with water and extracted with dichloromethane. The organic phase was retained and washed with an aqueous hydrochloric acid solution, an aqueous saturated sodium hydrogen carbonate solution, and brine three times. Anhydrous sodium sulfate was used to dry the organic phase, after which the solvent was removed under reduced pressure with a rotary evaporator to obtain crude product. The crude product was dissolved in ethyl acetate and recrystalized with petroleum ether to afford the final product. Compounds 5-14 were in 58-86% yield.
With triethylamine; In dichloromethane; at 0 - 20℃; for 12h; General procedure: A stirred solution of aniline derivatives 1a-h (0.05 mol) in dichloromethane DCM (50 mL) was cooled to 0 C, and chloroacetyl chloride (0.06 mol) and triethylamine (0.06 mol) was added dropwise to the solution. The resulting mixture was warmed to room temperature and stirred overnight. The organic phase was diluted with DCM (50 mL) and washed with 0.5 M HCl (50 mL), then saturated with NaHCO3 and brine. The organic layer was collected and dried over anhydrous Na2SO4. Then, the solvent was removed under reduced pressure. The 2-chloro-N-phenylancetamide derivatives (5 mmol) obtained by recrystallization were refluxed with potassium iodide (7.5 mmol) in acetone (10 mL) for 6 h, and the solvent was evaporated in vacuo. Water (50 mL) was added to the reaction mixture, and the organic phase extracted with ethyl acetate was washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated, then recrystallized from ethyl acetate to obtain Compounds 2a-h [1-3]. Moxifloxacin (2 mmol) and TEA (4.4 mmol) were added to a stirred solution of 2-iodo-N-phenylancetamide derivatives 2a-h (2.2 mmol) in acetonitrile (10 mL). The mixture was heated under reflux for 12 h, then the solvent was removed under vacuum. The resulting solid was recrystallized using acetonitrile to afford eight 4a-h [4].

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[5]Patent: JP5714152,2015,B2 .Location in patent: Page/Page column 29
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  • 3
  • [ 17641-08-6 ]
  • [ 109-89-7 ]
  • [ 40517-65-5 ]
  • 4
  • [ 17641-08-6 ]
  • [ 31523-22-5 ]
  • N-(3-Methoxy-phenyl)-2-[N'-(5H-[1,2,4]triazino[5,6-b]indol-3-yl)-hydrazino]-acetamide [ No CAS ]
  • 5
  • [ 17641-08-6 ]
  • [ 64-17-5 ]
  • [ 77775-78-1 ]
  • [ 77775-79-2 ]
  • [ 588-16-9 ]
  • 6
  • [ 17641-08-6 ]
  • [ 17641-09-7 ]
YieldReaction ConditionsOperation in experiment
With potassium iodide; In acetone; for 6h;Reflux; General procedure: A stirred solution of aniline derivatives 1a-h (0.05 mol) in dichloromethane DCM (50 mL) was cooled to 0 C, and chloroacetyl chloride (0.06 mol) and triethylamine (0.06 mol) was added dropwise to the solution. The resulting mixture was warmed to room temperature and stirred overnight. The organic phase was diluted with DCM (50 mL) and washed with 0.5 M HCl (50 mL), then saturated with NaHCO3 and brine. The organic layer was collected and dried over anhydrous Na2SO4. Then, the solvent was removed under reduced pressure. The 2-chloro-N-phenylancetamide derivatives (5 mmol) obtained by recrystallization were refluxed with potassium iodide (7.5 mmol) in acetone (10 mL) for 6 h, and the solvent was evaporated in vacuo. Water (50 mL) was added to the reaction mixture, and the organic phase extracted with ethyl acetate was washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated, then recrystallized from ethyl acetate to obtain Compounds 2a-h [1-3]. Moxifloxacin (2 mmol) and TEA (4.4 mmol) were added to a stirred solution of 2-iodo-N-phenylancetamide derivatives 2a-h (2.2 mmol) in acetonitrile (10 mL). The mixture was heated under reflux for 12 h, then the solvent was removed under vacuum. The resulting solid was recrystallized using acetonitrile to afford eight 4a-h [4].
  • 7
  • [ 17641-08-6 ]
  • [ 77775-78-1 ]
  • [ 77775-79-2 ]
  • [ 588-16-9 ]
  • 9
  • [ 17641-08-6 ]
  • [ 147-93-3 ]
  • [ 97457-48-2 ]
  • 11
  • [ 17641-08-6 ]
  • [ 37893-08-6 ]
  • [ 132659-09-7 ]
  • 12
  • [ 17641-08-6 ]
  • [ 1904-60-5 ]
  • N-(3-Methoxy-phenyl)-2-(4-oxo-2-phenyl-4H-quinazolin-3-ylamino)-acetamide [ No CAS ]
  • 13
  • [ 17641-08-6 ]
  • [ 23269-70-7 ]
  • 2-[5-(4-Acetylamino-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-N-(3-methoxy-phenyl)-acetamide [ No CAS ]
  • 14
  • [ 17641-08-6 ]
  • [ 141-43-5 ]
  • 2-(2-Hydroxy-ethylamino)-N-(3-methoxy-phenyl)-acetamide [ No CAS ]
  • 15
  • [ 17641-08-6 ]
  • [ 873-55-2 ]
  • 2-benzenesulfonyl-<i>N</i>-(3-methoxy-phenyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.8% With pyridine; In water; at 0℃; for 1h;Cooling with ice; General procedure: The 1.27g (10mmol, 1 . 0eq) 4-aminochlorobenzene into 1.6 ml pyridine with 20 ml of water in the mixed solution, under the condition in the ice bath, dripping therein 1.69g (15mmol, 1 . 5eq) chloro acetyl chloride. In 0 C reaction 1.0h, in to the system by adding 50 ml of water, filtering, filtering the solid obtained after drying 0.77g white powdery solid, can be without purification directly used for the next reaction, the yield is 37.7%
  • 17
  • [ 17641-08-6 ]
  • [ 74331-44-5 ]
  • <i>N</i>-(3-methoxy-phenyl)-2-(2-oxo-1,3-diphenyl-2,3-dihydro-1<i>H</i>-imidazol-4-ylsulfanyl)-acetamide [ No CAS ]
  • 18
  • [ 17641-08-6 ]
  • [ 74331-44-5 ]
  • 6-(3-methoxy-phenylamino)-1,3-diphenyl-1,3-dihydro-thieno[2,3-<i>d</i>]imidazol-2-one [ No CAS ]
  • 19
  • [ 17641-08-6 ]
  • 5-chloro benzoxazole 2-thiol potassium salt [ No CAS ]
  • 2-(5-chloro-benzooxazol-2-ylsulfanyl)-<i>N</i>-(3-methoxy-phenyl)-acetamide [ No CAS ]
  • 20
  • [ 17641-08-6 ]
  • [ 56278-50-3 ]
  • 5-amino-4-(2-benzothiazolyl)-2,3-dihydro-1-(3-methoxyphenyl)-2-pyrrolone [ No CAS ]
  • 21
  • [ 17641-08-6 ]
  • [ 610278-84-7 ]
  • 4-(5-amino-4-benzothiazol-2-yl-3-oxo-2,3-dihydro-pyrrol-1-yl)-benzoic acid (3-methoxy-phenylcarbamoyl)-methyl ester [ No CAS ]
  • 22
  • [ 17641-08-6 ]
  • [ 749216-03-3 ]
  • 3-{5-amino-4-[4-(4-chloro-phenyl)-thiazol-2-yl]-3-oxo-2,3-dihydro-pyrrol-1-yl}-benzoic acid (3-methoxy-phenylcarbamoyl)-methyl ester [ No CAS ]
  • 23
  • [ 17641-08-6 ]
  • [ 84951-44-0 ]
  • 2-[4-(3-cyano-pyridin-2-yl)-piperazin-1-yl]-<i>N</i>-(3-methoxy-phenyl)-acetamide [ No CAS ]
  • 24
  • [ 17641-08-6 ]
  • [ 17969-48-1 ]
  • 5-amino-4-[4-(4-chloro-phenyl)-thiazol-2-yl]-1-(3-methoxy-phenyl)-1,3-dihydro-pyrrol-2-one [ No CAS ]
  • 25
  • [ 870537-61-4 ]
  • [ 17641-08-6 ]
  • N-(3-Methoxy-phenyl)-2-(5-{4-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-phenyl}-[1,3,4]oxadiazol-2-ylsulfanyl)-acetamide [ No CAS ]
  • 27
  • [ 17641-08-6 ]
  • [ 53-86-1 ]
  • [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid (3-methoxyphenylcarbamoyl)methyl ester [ No CAS ]
  • 28
  • [ 17641-08-6 ]
  • (Z)-3-[7-(1-phenylethoxy)benzofuran-2-yl]-2-butenoic acid (3-methoxyphenyl)amide [ No CAS ]
  • 29
  • [ 17641-08-6 ]
  • (E)-3-[7-(1-phenylethoxy)benzofuran-2-yl]-2-butenoic acid (3-methoxyphenyl)amide [ No CAS ]
  • 30
  • [ 17641-08-6 ]
  • (E)-3-[4-bromo-7-(2-dimethylaminoethoxy)benzofuran-2-yl]-N-(3-methoxyphenyl)-2-butenamide [ No CAS ]
  • 31
  • [ 17641-08-6 ]
  • (E)-4-{2-[2-(4-methoxyphenylcarbamoyl)-1-methylvinyl]benzofuran-7-yloxy}butyric acid [ No CAS ]
  • 32
  • [ 17641-08-6 ]
  • [ 859708-47-7 ]
  • 33
  • [ 17641-08-6 ]
  • (E)-3-(7-benzhydryloxybenzofuran-2-yl)-N-(3-methoxyphenyl)-2-butenamide [ No CAS ]
  • 34
  • [ 17641-08-6 ]
  • (Z)-3-{7-(3-chloropropoxy)-4-[2-(3,4-dimethoxyphenyl)ethylsulfamoyl]benzofuran-2-yl}-N-(3-methoxyphenyl)-2-butenamide [ No CAS ]
  • 35
  • [ 17641-08-6 ]
  • (E)-3-{7-(3-chloropropoxy)-4-[2-(3,4-dimethoxyphenyl)ethylsulfamoyl]benzofuran-2-yl}-N-(3-methoxyphenyl)-2-butenamide [ No CAS ]
  • 36
  • [ 17641-08-6 ]
  • 1-(3-Methoxy-phenyl)-piperazin-2-one; hydrochloride [ No CAS ]
  • 37
  • [ 17641-08-6 ]
  • [ 76810-00-9 ]
  • 38
  • [ 17641-08-6 ]
  • [ 76810-20-3 ]
  • 39
  • [ 17641-08-6 ]
  • [ 76809-80-8 ]
  • 41
  • [ 17641-08-6 ]
  • 1-(3,4-dichlorobenzyl)piperidin-4-ylamine dihydrochloride [ No CAS ]
  • 2-[1-(3,4-dichlorobenzyl)-4-piperidinyl]amino}-N-(3-methoxyphenyl)acetamide, dihydrochloride salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
2-Chloro-N-(3-methoxyphenyl)-acetamide (0.241 g) was added to a stirred solution of the product of Example 1 step (ii) (dihydrochloride salt) (0.4 g), triethylamine (0.608 g) in 1-methyl-2-pyrrolidinone (5 ml). The reaction mixture was heated at 80 C. for 6 h then partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried and evaporated under reduced pressure. Purification was by chromatography eluding with chloroform/isohexane/triethylamine/methanol 30:15:3:0.5. The resulting product was converted to the hydrochloride salt using ethereal hydrogenchloride.
  • 42
  • [ 17641-08-6 ]
  • [ 2131-61-5 ]
  • 3-(3-methoxyphenyl)-2-[(4-nitrophenyl)imino]-1,3-thiazolan-4-one [ No CAS ]
  • 43
  • [ 17641-08-6 ]
  • [ 38941-98-9 ]
  • [ 1134193-57-9 ]
  • 44
  • [ 17641-08-6 ]
  • [ 50290-45-4 ]
  • [ 1031620-28-6 ]
  • 45
  • [ 505-66-8 ]
  • [ 17641-08-6 ]
  • [ 1016760-74-9 ]
  • 46
  • [ 17641-08-6 ]
  • [ 28668-95-3 ]
  • [ 482330-23-4 ]
  • 47
  • [ 17641-08-6 ]
  • [ 51449-86-6 ]
  • [ 847940-91-4 ]
  • 48
  • [ 17641-08-6 ]
  • [ 24994-04-5 ]
  • [ 954760-00-0 ]
  • 49
  • [ 17641-08-6 ]
  • [ 6855-48-7 ]
YieldReaction ConditionsOperation in experiment
62% 2) <strong>[17641-08-6]2-chloro-N-(3-methoxyphenyl)acetamide</strong> (3.1g, 16 mmol) and anhydrous AlCl3 powder (4.4g,32 mmol) is heated and stirred at 120C for 10 minutes and exhibit a melting state. The temperature is elevated gradually to 240C in 40 minutes and then stirred 5 minutes. The reaction is allowed to cool to obtain a brown powder. The solid powder is poured into a mixture of 100g of crushed ice and 50ml of concentrated hydrochloric acid. The mixture is stirred for 10 minutes and then reflux for 10 minutes, and allowed to cool to precipitate a light yellow powder, which is filtered out and recrystallized in water to obtain 1.5g of 6-hydroxy-indoline-2-one, with a yield of 62%.
62% With aluminum (III) chloride; at 120℃; for 0.166667h; <strong>[17641-08-6]2-chloro-N-(3-methoxyphenyl)acetamide</strong> (3.1 g, 16 mmol) and anhydrous AlCl 3 powder (4.4 g, 32 mmol) were heated and stirred at 120 C. for 10 minutes,The melted state was allowed to appear, the temperature was gradually increased to 240 C. over 40 minutes, stirred for 5 minutes and allowed to cool to obtain a brown powder, the solid powder was poured into a mixture of 100 g of crushed ice and 50 ml of concentrated hydrochloric acid , Stirred for 10 minutes, then refluxed for 10 minutes, cooled, precipitated a light yellow powder, filtered and recrystallized from water,1.5 g of 6-hydroxy-indolin-2-one are obtained. Yield is 62%.
  • 50
  • [ 17641-08-6 ]
  • [ 1206898-99-8 ]
  • 51
  • [ 17641-08-6 ]
  • [ 95-56-7 ]
  • [ 1134193-44-4 ]
  • 52
  • [ 17641-08-6 ]
  • C21H20F5N5O3 [ No CAS ]
  • 53
  • [ 17641-08-6 ]
  • [ 74-89-5 ]
  • [ 901273-54-9 ]
  • 54
  • [ 17641-08-6 ]
  • [ 847240-15-7 ]
  • 55
  • [ 17641-08-6 ]
  • [ 693-98-1 ]
  • [ 1378478-71-7 ]
  • 56
  • [ 17641-08-6 ]
  • [ 402-45-9 ]
  • [ 1210031-82-5 ]
  • 57
  • [ 17641-08-6 ]
  • [ 1447585-56-9 ]
  • [ 1447585-67-2 ]
  • 58
  • [ 593-71-5 ]
  • [ 18908-07-1 ]
  • [ 17641-08-6 ]
YieldReaction ConditionsOperation in experiment
94% With methyllithium; lithium bromide; In diethyl ether; at -78℃; for 0.5h; General procedure: To a cooled (-78C) solution of isocyanate (1.0 equiv) in dry Et2O (1 M concentration) was added the dihalomethane derivative (1.5 equiv). After 2 min, an ethereal solution of 1.5 M MeLi-LiBr (1.25equiv) was added dropwise over 5 min. The resulting solution was stirred for the appropriate time (see Table 1 and Scheme 2) at that temperature. Sat. aq NH4Cl was added (2 mL/mmol substrate) and the cooling bath was removed, the mixture was stirred till it reached r.t., and then it was extracted with additional Et2O (2 × 5 mL) and washed with water (5 mL) and brine (10 mL). The organic phase was dried (anhyd Na2SO4), filtered, and the solvent removed under reduced pressure to give pure samples of haloacetamides.
  • 59
  • [ 17641-08-6 ]
  • [ 173210-06-5 ]
  • N-(3-methoxyphenyl)-2-(4-(2-oxo-2H-chromen-4-yl)-piperazin-1-yl)acetamide [ No CAS ]
  • 60
  • [ 17641-08-6 ]
  • [ 1580541-09-8 ]
  • [ 1580541-13-4 ]
YieldReaction ConditionsOperation in experiment
78% General procedure: The oxime 6 or 8 (0.7 mmol) and K2CO3(0.116 g, 0.84 mmol) were taken in dry DMF (5 mL), cooled to 0 Cand stirred for 30 min, then N-substituted acetamide (0.77 mmol)was added. The total reaction mixture was stirred at room temperature for 12-20 h. The reaction was monitored by TLC and after completion of the reaction, treated with ice cold water. Aqueous solution was extracted thrice with ethylacetate, combined extracts were washed with water till washings are neutral to pH, dried over anhydrous sodium sulfate and concentrated. The residue was purifiedby passing through a column packed with silica gel using petroleum ether/EtOAc (8:2) as eluent.
  • 61
  • [ 17641-08-6 ]
  • [ 1580541-10-1 ]
  • [ 1580541-21-4 ]
YieldReaction ConditionsOperation in experiment
76% General procedure: The oxime 6 or 8 (0.7 mmol) and K2CO3(0.116 g, 0.84 mmol) were taken in dry DMF (5 mL), cooled to 0 Cand stirred for 30 min, then N-substituted acetamide (0.77 mmol)was added. The total reaction mixture was stirred at room temperature for 12-20 h. The reaction was monitored by TLC and after completion of the reaction, treated with ice cold water. Aqueous solution was extracted thrice with ethylacetate, combined extracts were washed with water till washings are neutral to pH, dried over anhydrous sodium sulfate and concentrated. The residue was purifiedby passing through a column packed with silica gel using petroleum ether/EtOAc (8:2) as eluent.
  • 62
  • [ 17641-08-6 ]
  • 2-(3-(2-carbamimidoylhydrazono)-2-oxoindolin-1-yl)-N-(3-methoxyphenyl)acetamide [ No CAS ]
  • 63
  • [ 17641-08-6 ]
  • [ 91-56-5 ]
  • C17H14N2O4 [ No CAS ]
  • 64
  • [ 870537-61-4 ]
  • [ 17641-08-6 ]
  • N-(3-Methoxy-phenyl)-2-(5-{4-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-phenyl}-[1,3,4]oxadiazol-2-ylsulfanyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.2% With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 12h;Reflux; To a solution ofcompound C ( 0.5 g, 2.50 mmoles) and compound D (0.3 mL, 2.75 mmoles) in Acetonitrile (8.0 mL) was added di-isopropylethyl amine (0.96 mL, 5.50 mmoles) drop-wise. After the addition was complete the reaction was refluxed for 12 hours. The completion of the reaction was monitored by TLC. The reaction mixture was concentrated, purified by column chromatography ( 20 %EtOAc:Hexanes) to isolate the required compound as an brown solid (0.34 g, 50.2%). 1H NMR (CDCl3, 400 MHz) delta 8.43 (s, 1 H), 7.35-7.31(m, 3 H), 7.23 (t, J= 8.0 Hz, 1 H),7.04-7.97 (m, 1 H), 6.92 (t, J=7.6Hz, 1 H), 6.86 (d, J= 8.4 Hz, 2 H),6.70 (dd, J=2.4, 8.0 Hz, 1 H), 3.97(s, 2 H), 3.82 (s, 3 H), 3.10 ( s, 3 H).
  • 65
  • [ 17641-08-6 ]
  • [ 35416-72-9 ]
  • 66
  • [ 17641-08-6 ]
  • 4-(4-hydroxybenzylidene)-1-(3-methoxyphenyl)-2-phenyl-1H-imidazol-5(4H)-one [ No CAS ]
  • N-(3-methoxyphenyl)-2-(4-((1-(3-methoxyphenyl)-5-oxo-2-phenyl-1,5-dihydro-4H-imidazol-4-ylidene)methyl)phenoxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% General procedure: Potassium carbonate (10 mmol, 1.38 g) was added to a solution of compound 3 or 4 (10 mmol, 3.70 g) in dry DMF (15 mL) and stirred at room temperature for 0.5 h. Then, the appropriate 2-chloro-N-un/substituted phenylacetamide 5a-j (10 mmol) was added and heated at 100 C for 8 h. The reaction mixture was poured onto ice/water and the precipitated solid was filtered off, washed with water, dried and crystallized from ethanol.
  • 67
  • [ 17641-08-6 ]
  • 4-(4-hydroxybenzylidene)-1-(4-methoxyphenyl)-2-phenyl-1H-imidazol-5(4H)-one [ No CAS ]
  • N-(3-methoxyphenyl)-2-(4-((1-(4-methoxyphenyl)-5-oxo-2-phenyl-1,5-dihydro-4H-imidazol-4-ylidene)methyl)phenoxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% General procedure: Potassium carbonate (10 mmol, 1.38 g) was added to a solution of compound 3 or 4 (10 mmol, 3.70 g) in dry DMF (15 mL) and stirred at room temperature for 0.5 h. Then, the appropriate 2-chloro-N-un/substituted phenylacetamide 5a-j (10 mmol) was added and heated at 100 C for 8 h. The reaction mixture was poured onto ice/water and the precipitated solid was filtered off, washed with water, dried and crystallized from ethanol.
  • 68
  • [ 17641-08-6 ]
  • 4-hydroxy-N-(2-phenylethyl)benzene-1-sulfonamide [ No CAS ]
  • N-(3-methoxyphenyl)-2-(4-(N-phenethyl-sulfamoyl)phenoxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate; potassium iodide; In [(2)H6]acetone; at 60℃; for 7h; General procedure: A mixture of 2-chloro-N-(4-chlorobenzyl)acetamide 3a (0.22 g, 1.0 mmol), 4-hydroxy-N-phenethyl-benzenesulfonamide 7a (0.42 g, 1.5 mmol), K2CO3 (0.21 g, 1.5 mmol) and KI (33 mg, 0.2 mmol) in acetone (20 ml) was stirred at 60 C for 7.0 h. After the organic solvent was evaporated, the residual was diluted with water (20 ml), extracted with dichloromethane, washed with brine and then dried over Na2SO4. After filtration and condensation, the crude product was obtained and recrystallized in ethyl acetate/hexane (1:1, v: v) to afford 1a as white solid (0.19 g, yield 42%). SAPA 1v was prepared by the reaction of <strong>[17641-08-6]2-chloro-N-(3-methoxyphenyl)acetamide</strong> 3q with 7a according to the procedure described for SAPA 1a. Yield 46%; mp 107.0-108.0 C. ESI-MS m/z 441.3 (M+H)+. HRMS (ESI) of C23H24N2O5S (M+H)+ calcd, 441.1479; found, 441.1479. 1H NMR (400 MHz, DMSO-d6) delta 10.13 (s, 1H), 7.71 (d, J = 8.7 Hz, 2H), 7.57 (s, 1H), 7.30 (s, 1H), 7.28-7.10 (m, 9H), 6.65 (d, J = 7.9 Hz, 1H), 4.79 (s, 2H), 3.70 (s, 3H), 2.91 (s, 2H), 2.65 (t, J = 7.5 Hz, 2H). 13C NMR (151 MHz, DMSO-d6) delta 166.4, 161.1, 160.0, 140.0, 139.2, 133.2, 130.1, 129.1, 128.8, 126.7, 115.5, 112.4, 109.7, 105.9, 67.5, 55.5, 44.6, 35.7. HPLC purity: tR = 8.100, 98.9%.
  • 69
  • [ 17641-08-6 ]
  • [ 30437-09-3 ]
  • N-(3-methoxyphenyl)-2-[4-(4-phenylphthalazin-1-yl)piperazin-1-yl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With potassium carbonate; In acetone; for 5h;Reflux; General procedure: To a stirred mixture of 1-phenyl-4-(1-piperazinyl)phthalazine 14 (0.58 g, 2.0 mmol) and anhydrous potassium carbonate (0.55 g, 4.0 mmol) in dry acetone, a solution of the appropriate 2-chloro-N-(substituted phenyl) acetamide derivative 15a-k (2.0 mmol) in dry acetone was added. The mixture was heated under reflux for 5 h, filtered while hot and the residue was washed with hot acetone. The combined filtrate and wash were evaporated under vacuum.The residue was collected, washed with water, dried and crystallizedfrom an appropriate solvent. 5.1.5.9 N-(3-methoxyphenyl)-2-[4-(4-phenylphthalazin-1-yl)piperazin-1-yl]acetamide (16i) Crystallized from ethanol/water mixture (yield 59%); m.p. 187-188 C; IR (KBr, nu cm-1): 3313 (NH), 3062 (aromatic CH), 1681 (C=O); 1H NMR (CDCl3, 300 MHz) delta ppm: 2.92 (s, br, 4H, 2CH2 piperazine), 3.26 (s, 2H, COCH2), 3.64 (s, br, 4H, 2CH2 piperazine), 3.79 (s, 3H, OCH3), 6.63 (d, 1H, H-4 of 3-OCH3-C6H4, J = 7.8 Hz), 7.02 (d, 1H, H-6 of 3-OCH3-C6H4, J = 7.8 Hz), 7.21 (t, 1H, H-5 of 3-OCH3-C6H4, J = 7.8 Hz), 7.33 (s, 1H, H-2 of 3-OCH3-C6H4), 7.50-7.56 (m, 3H, H-3, H-4 and H-5 of C6H5), 7.67 (d, 2H, H-2 and H-6 of C6H5, J = 7.2 Hz), 7.72-7.86 (m, 2H, H-6 and H-7 phthalazine), 7.99 (d, 1H, H-5 phthalazine, J = 8.1 Hz), 8.10 (d, 1H, H-8 phthalazine, J = 7.2 Hz), 9.17 (s, 1H, NH); 13C NMR (DMSO-d6, 100 MHz) delta: 51.17 (2CH2 piperazine), 53.10 (2CH2 piperazine), 55.49 (OCH3), 62.26 (COCH2), 105.68, 109.38, 112.18, 121.23, 125.06, 126.67, 126.97, 128.94, 129.31, 129.93, 130.15, 132.28, 132.64, 136.85, 140.30, 156.16, 159.39, 159.98, 168.77 (C=O); MS, m/z (%): M+ 453 (3.6); Anal. Calcd. for C27H27N5O2: C, 71.50; H, 6.00; N, 15.44; Found C, 71.52; H, 6.03; N, 15.51.
  • 70
  • [ 17641-08-6 ]
  • [ 57644-24-3 ]
  • C23H18ClN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% General procedure: To the appropriate Schiff bases of isatin (10 mmol) in8-10 cm3 of anhydrous DMF, K2CO3 (15 mmol) was addedand stirred at room temperature for 1 h. After completion of1 h, the solution turned red brown in color. Appropriatechloroanilides (10 mmol) and KI (2 mmol) were then addedto this solution drop wise and heated at 60 C for 5.5-9 h.After conforming the end of reaction by TLC (ethyl acetate:n-hexane 30:70), the mixture was poured into ice cold water.Precipitated crude product was filtered and washed thoroughlywith cold water (3 9 200 cm3). Compounds wererecrystallized from ethanol/water mixture (1:1). Reactiontimes, melting points, and yields are depicted in Table 1.
  • 72
  • [ 17641-08-6 ]
  • C22H23N3O5S [ No CAS ]
  • 73
  • [ 17641-08-6 ]
  • 3-[4-({5-[(3-methoxyphenyl)carbamoyl]-1,3,4-thiadiazol-2-yl}methoxy)phenyl]propanoic acid [ No CAS ]
  • 74
  • [ 110-91-8 ]
  • [ 17641-08-6 ]
  • <i>N</i>-(3-methoxy-phenyl)-2-morpholin-4-yl-2-thioxo-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
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.
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.
  • 75
  • [ 17641-08-6 ]
  • 12-phenethyl-6-thioxo-6,7,11b,12-tetrahydro-13H-quinazolino[3,4-a]quinazolin-13-one [ No CAS ]
  • 2-((13-oxo-12-phenethyl-11b,12-dihydro-13H-quinazolino[3,4-a]quinazolin-6-yl)thio)-N-(3-methoxyphenyl)acetamide [ No CAS ]
  • 76
  • [ 17641-08-6 ]
  • [ 31821-78-0 ]
  • C20H23N5O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With potassium carbonate; In ethanol;Reflux; 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%.
  • 77
  • [ 17641-08-6 ]
  • [ 3790-45-2 ]
  • 2-(3,4-dihydro-1-phenyl-1H-pyrido[3,4-b]indol-2(9H)-yl)-N-(3-methoxyphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% General procedure: To a stirred solution of 3 (0.47g, 2mmol) in dry DMF (3mL), K2CO3 (0.83g, 6mmol) was added and stirred the reaction mixture at room temperature for 30min. Thereafter, 2-Chloro-N-phenylacetamide 6a (0.34g, 2mmol) was added and the reaction mixture was stirred for additional 3h at room temperature. On completion of the reaction as monitored by TLC, the contents were poured into ice water (50mL) whilst stirring with a glass rod. Thereafter, the aqueous layer was extracted with EtOAc (3×20mL). The organic layers were combined and washed with brine (40mL), dried with anhydrous Na2SO4 and concentrated to yield the product (0.59g from 0.47g, 78%). For analytical grade, the compound was passed through short silica gel (100-200 mesh) column chromatography (ethylacetate: hexane=6:4, Rf 0.40) to get 7a as a white solid.
  • 78
  • [ 17641-08-6 ]
  • 2-{2-[(3-methoxyphenylcarbamoyl)methylthio]-1,3,4-thiadiazol-5-yl}-1,2-benzisoselenazol-3(2H)-one [ No CAS ]
  • 79
  • [ 17641-08-6 ]
  • [ 2349-67-9 ]
  • 2-amino-5-[(3-methoxyphenylcarbamoyl)methylthio]-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium hydroxide; In ethanol; water; at 20℃; 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.
  • 80
  • [ 17641-08-6 ]
  • 3-amino-6,7-dimethoxy-2-phenylquinazolin-4(3H)-one [ No CAS ]
  • 2-((6,7-dimethoxy-4-oxo-2-phenylquinazolin-3(4H)-yl)-amino)-N-(3-methoxyphenyl)acetamide [ No CAS ]
  • 81
  • [ 17641-08-6 ]
  • 3-(5-[(3-methoxyphenyl)amino]carbonyl}-1,3,4-thiadiazol-2-yl)propanoic acid [ No CAS ]
  • 82
  • [ 75-15-0 ]
  • [ 17641-08-6 ]
  • [ 100-46-9 ]
  • (3-methoxyphenylcarbamoyl)methyl benzylcarbamodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 20℃; for 1.5h; 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).
  • 83
  • [ 75-15-0 ]
  • [ 17641-08-6 ]
  • [ 104-84-7 ]
  • (3-methoxyphenylcarbamoyl)methyl 4-methylbenzylcarbamodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 20℃; for 1h; 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).
  • 84
  • [ 75-15-0 ]
  • [ 17641-08-6 ]
  • [ 104-86-9 ]
  • (3-methoxyphenylcarbamoyl)methyl 4-chlorobenzylcarbamodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 20℃; for 1.75h; 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).
  • 85
  • [ 17641-08-6 ]
  • [ 1486520-92-6 ]
  • 2-((13-oxo-12-benzyl-11b,12-dihydro-13H-quinazolino[3,4-a]quinazolin-6-yl)thio)-N-(3-methoxyphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium iodide; In acetone; at 20℃; General procedure: A mixture of 12-benzyl-6-thioxo-6,7,11b,12-tetrahydro-13H-quinazolino[3,4-a]quinazolin-13-one 8 (1 mmol), 2-chloro-N-substituted acetamide 9 (1 mmol), and potassium iodide (1 mmol) in acetone (8 mL) was heated at room temperature for 5-48 h. After completion of the reaction, water (8 mL) was added to the reaction mixture, and the precipitates were filtered off and recrystallized from EtOH/H2O (90/10) to give the corresponding product 10.
  • 86
  • [ 17641-08-6 ]
  • [ 126921-96-8 ]
  • 2-[(4-cyano-1-phenyl-6,7-dihydro-5H-cyclopenta[c]pyridin-3-yl)oxy]-N-(3-methoxyphenyl)acetamide [ No CAS ]
  • 87
  • [ 17641-08-6 ]
  • [ 126921-96-8 ]
  • 1-amino-N-(3-methoxyphenyl)-5-phenyl-7,8-dihydro-6Hcyclopenta[d]furo[2,3-b]pyridine-2-carboxamide [ No CAS ]
  • 88
  • [ 17641-08-6 ]
  • C13H10N2O2 [ No CAS ]
  • 2-[4-cyano-1-(2-furyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-3-yl]oxy}-N-(3-methoxyphenyl)acetamide [ No CAS ]
  • 89
  • [ 17641-08-6 ]
  • C13H10N2O2 [ No CAS ]
  • 1-amino-5-(2-furyl)-N-(3-methoxyphenyl)-7,8-dihydro-6Hcyclopenta[d]furo[2,3-b]pyridine-2-carboxamide [ No CAS ]
  • 90
  • [ 17641-08-6 ]
  • [ 94482-51-6 ]
  • C39H55NO5 [ No CAS ]
  • 91
  • [ 17641-08-6 ]
  • C11H16N2O4 [ No CAS ]
  • C20H25N3O6 [ No CAS ]
  • 92
  • [ 17641-08-6 ]
  • 2-(3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-yl)isoindoline-1,3-dione [ No CAS ]
  • C28H25N5O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With potassium carbonate; In acetone; at 20℃; 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.
  • 93
  • [ 17641-08-6 ]
  • N-(2-trifluoromethyl-4-chlorophenyl)-2-aminocyclohexylsulfonamide [ No CAS ]
  • (1R,2S)-2-(2-(N-(4-chloro-2-trifluoromethylphenyl)sulfamoyl)cyclohexylamino)-N-(3-methoxyphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.4% General procedure: Under nitrogen atmosphere, DMF (10 mL), 4 A 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.
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