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Product Details of [ 2564-02-5 ]

CAS No. :2564-02-5 MDL No. :MFCD00018903
Formula : C8H7BrClNO Boiling Point : -
Linear Structure Formula :- InChI Key :FRZKCMCCQAJIBN-UHFFFAOYSA-N
M.W : 248.50 Pubchem ID :17374
Synonyms :

Calculated chemistry of [ 2564-02-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.25
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) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 2.32
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 2.56
Log Po/w (SILICOS-IT) : 2.56
Consensus Log Po/w : 2.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.01
Solubility : 0.24 mg/ml ; 0.000968 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.669 mg/ml ; 0.00269 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.28
Solubility : 0.0132 mg/ml ; 0.000053 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 2564-02-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P272-P280-P302+P352-P305+P351+P338-P310-P321-P333+P313-P363-P501 UN#:3261
Hazard Statements:H317-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2564-02-5 ]

* 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 [ 2564-02-5 ]

[ 2564-02-5 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 79-04-9 ]
  • [ 106-40-1 ]
  • [ 2564-02-5 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine; In dichloromethane; at 0 - 20℃; for 16h; 4-Bromoaniline (4.12 g, 23.95 mmol) was dissolved in 50 mL of dichloromethane in a round bottomed flask containing a stir bar. While stirring, triethylamine (2.91 g, 28.74 mmol) was added to the reaction mixture and then cooled to 0 C. 2-Chloroacetyl chloride (2.71 g, 23.95 mmol) was added dropwise to the reaction mixture, which was then allowed to slowly warm to room temperature and stir for 16 hours. The reaction mixture was diluted with 100 mL of dichloromethane, washed twice with 1N HCl, run through a silica gel plug, and then concentrated in vacuo to give N-(4-bromophenyl)-2-chloroacetamide (5.74 g, 97 % yield).
93% With 1,3-dimethyl-2-imidazolidinone; at 0 - 23℃; for 1.5h;Green chemistry; A solution of acid chloride 3a (1.1451 g, 10.14 mmol) in DMI (5 mL) was prepared at r.t. The solution was transferred to a 30 mL round-bottomed flask and cooled to 0 C (ice-water bath). While stirring and cooling at 0 C, a solution of amine 2b (1.8394 g, 10.69 mmol) in DMI (5 mL) was added over 5 min. The mixture turned yellow and was stirred at 0 C for 10 min. The ice bath was replaced with a water bath and the mixture was stirred at 23 C for 1.5 h. The completion of the reaction was confirmed by TLC, and H2O (30 mL) was added. The mixture became pale yellow and a white precipitate was formed. The mixture was stirred overnight. The solid was filtered by suction,washed with H2O (100 mL), and dried in vacuum. Amide 4b was obtained as a white solid (2.3506 g, 93%). The product was identical with the authentic compound in terms of 1H NMR (CDCl3) and combustion analysis.
88.5% With triethylamine; In dichloromethane; at 0 - 25℃; General procedure: 2-Chloroacetyl chloride (24 mmol) was slowly added dropwise to a mixture of R-NH2 (20 mmol) and Et3N (24 mmol, 3.3 mL) in anhydrous CH2Cl2 (20 mL) at 0 C. The reaction mixture was warmed to room temperature and stirred for an additional 20 h. After the solvent was removed under reduced pressure, the residue was washed with ice water (3 × 20 mL) and the precipitate was separated by filtration. The crude product was purified by crystallization from a mixture solvent of Et2O/petroleum.
86% With triethylamine; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; General procedure: To a mixture of substituted amine (1 eq.) and TEA (1.2 eq.) in dry THF chloroacetyl chloride (1.1 eq.) was added dropwise at 0C. After completion of reaction, triethylammonium chloride was filtered off and the filtrate was concentrated under vacuum and quenched with water. The solid obtained was filtered at suction and washed to neutral filtrate, air dried and used without any further purification.
85% With triethylamine; In dichloromethane; at 0 - 20℃; for 18h;Inert atmosphere; 4-Bromoaniline (5.16 g, 30 mmol), Et3N (5.60 g, 30 mmol) and100mL driedCH2Cl2were added into three-neckedflask, after cooledto 0 C, chloroacetyl chloride (2.40 g, 32mmol) in 30 mL CH2Cl2 wasadded slowly under N2. Then the mixture was stirred 18 h at roomtemperature. H2O (50 mL) was added to quench the reaction,extracted with CH2Cl2 (50 mL) and washed with brine, dried overNa2SO4, the solvent was removed under vacuum. Column chromatography(silica,CH2Cl2) gave the product as a yellowpowder. (6.30 g,85%) 1H NMR (400 MHz, CDCl3) d: 4.21 (s, 2H), 7.49 (m, 4H).
85% With triethylamine; In dichloromethane; at 0 - 20℃; General procedure: To the mixture of substituted aromatic amine (0.020 mol)and Et3N (0.024 mol), solubilized in 20 mL of CH2Cl2at a temperature of 0 C, maintained by an ice bath,2-chloroacetyl chloride (0.024 mol) was slowly added. Theice bath was then removed, and the reaction stayed underagitation for 6 h at room temperature. The reaction mixturewas monitored by TLC (hexane/methyl acetate 1:1). At theend of reaction, the reaction mixture was concentrated atreduced pressure and cold water was added to the reactionmixture, causing the formation of a solid. The solid wasthen filtered and washed with cold water (3 × 20 mL), andthe final product was purified by recrystallization with anethanol/water (1:1) mixture. alpha-Chloro-N-phenylacetamide (2a)Yield: 93%,
85% With triethylamine; In dichloromethane; at 0 - 20℃; General procedure: Chloroacetyl chloride (0.024 mol) was slowly added to the mixture of substituted aromatic amine (0.020 mol) and Et3N(0.024 mol), solubilized in 20 mL of CH2Cl2 at a temperature of 0 C,maintained by an ice bath. The ice bath was then removed, and the reaction kept under agitation for 6 h at room temperature. The reaction mixture was monitored by TLC (hexane/methyl acetate 1:1).At the end of the reaction, the reaction mixture was concentrated at reduced pressure and cold water was added to the reaction mixture, causing the formation of a solid. The solid was then nfiltered and washed with cold water (3 20 mL), and the final product was purified by recrystallization with an ethanol/water(1:1) mixture [41].
82% With triethylamine; In dichloromethane; at 0 - 20℃; for 16h; . 4-Bromoaniline (4.12 g, 23.95 mmol) is dissolved in 50 mE of dichioromethane in a round bottomed flask containing a stir bat While stirring, triethylamine (2.91 g, 28.74 mmol) is added to the reaction mixture and then cooled to 0 C. 2-Chloroacetyl chloride (2.71 g, 23.95 mmol) is added dropwise to the reaction mixture, which is then allowed to slowly warm to room temperature and stirred for 16 hours. The reaction mixture is diluted with 100 mE of dichloromethane, washed twice with iN HC1, run through a silica gel plug, and then concentrated in vacuo to give compound 2 as a white solid (2.25 g).
80% With sodium acetate; In acetic acid; for 0.5h;Cooling with ice; 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).
77% In dichloromethane; General procedure: Substituted aniline (0.01 mol) I (i-xi) and Dichloromethane (20 ml) were mixed in a conical flask and Chloroacetylchloride (1.02 ml; 0.01 M) in a separating funnel was added drop by drop to the conical flask. The reaction mixture was stirred for 4-6 h resulting in the formation of white precipitate. The product obtained was filtered, and washed with a little cold water and recrystallized from water or from methanol or ethanol either alone or dilute with water.
70% With potassium carbonate; In acetone; at 20℃; 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.
67% With potassium carbonate; In acetone;Reflux; General procedure: Chloroacetyl chloride (0.06 mol) was added dropwise to a mixture of the appropriate amine (0.05 mol) and K2CO3 (0.06 mol) in acetone (50 mL) at room temperature. The reaction mixture was refluxed for 4-8 h, then, after cooling to room temperature, it was slowly poured into 100 mL of ice water. A solid was formed thereafter. The precipitate was separated by filtration and washed successively with water. The product was dried under vacuum to obtain 2a-k. The progress of the reaction was monitored by Thin Layer Chromatography using toluene: acetone (8:2) solvent system.
42% With pyridine; In dichloromethane; at 20℃; for 1h; Synthesis of N-(4-bromophenyl)-2-chloroacetamide (7a) 4-bromoaniline (1.72 g, 10 mmol) was dissolved in 50 mL dichloromethane. Pyridine (cat.) was added and then 2-chloroacetyl chloride (800 uL, 10 mmol) was added dropwise. The reaction was stirred at room temperature for 1 hr. The reaction was quenched with water and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated to give the intermediate 7a (1.03 g, 4 mmol, 42% yield). 1H NMR (400 MHz, Chloroform-d) delta 8.24 (broad s, 1H), 7.54-7.44 (m, 4H), 4.21 (s, 2H).
24% To a solution of 4-bromoaniline (2.66 g, 15 mmol) in CH2Cl2(60 mL) was added Et3N (2.1 mL, 15.2 mmol) and the mixture was allowed to stir at RT for 10 min. To this was added chloro acetylchloride (1.19 mL, 15 mmol) and the reaction was left to stir at RTfor 4 h. The white precipitate formed was separated by filtration and washed with CH2Cl2. Pure 24 was obtained as a white powder (898 mg, 24%). m/z (ES), found 247.9191 (C8H8BrClNO [M+H]+) requires 247.9400; deltaH/ppm (400 MHz, d6-DMSO): 10.41 (1H, s,NH), 7.56 (2H, d, J = 9.0, Ar-H), 7.51 (2H, d, J = 9.0, Ar-H), 4.25(2H, s, CH2).
With potassium carbonate; In acetone;Reflux; General procedure: To 0.05 mol of each amine derivative (1a-k) and 0.06 mol of anhydrous K2CO3 in 50 mL of acetone, 0.06 mol of chloroacetyl chloride (0.06 mol) was added dropwise at room temperature and mixture was allowed to reflux for 4 to 8 h. The reaction progress was monitored by TLC using toluene : acetone (V/V, 8:2) solvent system. After the completion of the reaction, the mixture was cooled and poured into crushed ice. A solid thus obtained was filtered, washed with water and dried on vacuum oven to get 2a-k.
With potassium carbonate; In acetone;Reflux; General procedure: Chloroacetyl chloride (0.06 mol) was added dropwise to a mixture of the appropriate amine (0.05 mol) and K2CO3 (0.06 mol) in acetone (50 mL) at room temperature. The reaction mixture was refluxed for 4 to 8 h, then, after cooling to room temperature, it was slowly poured into 100 mL of ice water. The solid that formed was separated byfiltration and washed repeatedly with water. The product was dried under vacuum to obtain 2a-k.8-12 The progress of the reaction was monitored by TLC using toluene: acetone (8 : 2) solvent system.
In benzene; for 6h;Reflux; General procedure: Compound 1 (1.0 equiv.) and chloroacetyl chloride (1.0 equiv.) were taken in benzene and the reaction mixture was refluxed for 6 h after completion of the reaction monitored by TLC, the reaction mixture was diluted with EtOAc and washed with sat NaHCO3, H2O and brine. The combined organic layer was dried over anhyd. Na2SO4, evaporated to get compound corresponding 2a-o.
With potassium carbonate; In acetone; at 20℃; 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 triethylamine; In dichloromethane; at 0 - 20℃; for 20h; General procedure: In an ice bath, substituted aniline (20 mmol) wasdissolved along with triethylamine (24 mmol) in 20 mL of dichloromethane (DCM) at 0 C, and then 2-chloroacetylchloride (24 mmol) was slowly added. The ice bath wasremoved and the reaction was kept stirring for 20 h at roomtemperature. After this time, the reaction mixture wasconcentrated at reduced pressure, the residue was washedwith cold water (3 × 20 mL) and the precipitate was filtered.The product was recrystallized with ethanol/water.
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.
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; for 6h; General procedure: 2- chloro-N-phenylacetamide derivatives 8a-d were synthesized by reacting 7a-d (2 mmol) with chloroacetylchloride (2 mmol), (triethyl amine 2 mmol) and dichloromethane (20 mL), the reaction mixture was kept on stirring for 6 h. The reaction mixture was being concentrated on low pressure and product was extracted in ethyl acetate.
With acetic acid; at 100℃; for 1h; General procedure: The appropriate aniline (4-chloro, 4-bromo, 4-methyl, 4-methoxyor 2,4-dichloroaniline) (24.4 mmol) was dissolved in glacial acetic acid(15 mL). Chloroacetyl chloride (25.1 mmol) was added dropwise. Thereaction mixture was stirred at 100 C for 1 h. The mixture was cooledto room temperature. Sodium acetate solution (0.4 M) was added togive a heavy precipitate. The mixture was stirred in an ice bath for5 min. The precipitate was collected after filtration.19 Melting points(m.p.) of the synthesized compounds were determined and were comparablewith the reported values.
With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 2h; General procedure: B23-B27 or B34-B361.0 mmol, 1.0 equiv) and Et3N (1.2 mmol,1.2 equiv) were dissolved in anhydrous tetrahydrofuran (THF), thena solution of chloroacetyl chloride (1.1 mmol, 1.1 equiv) in anhydrousTHF was added dropwise at 0 C. The reaction mixture wasthen stirred at room temperature for additional 2 h. Then water(30 mL) was added, extracted with ethyl acetate (3 10 mL). Theorganic phase was combined, dried over anhydrous Na2SO4,filtered, and concentrated to yield the crude azide substituents,which was purified by flash column chromatography to afford intermediatesC23eC27 and C34eC36. To a solution of the intermediatesin DMF were added sodium azide (1.2 mmol,1.2 equiv),and the mixture was stirred for 24 h at room temperature. Thenwater (30 mL) was added, extracted with ethyl acetate (3 10 mL).The organic phase was combined, dried over anhydrous Na2SO4,filtered, and concentrated to yield the target azide substituentsN23eN27 and N34eN36, which were used for the next stepwithout further purification.
With triethylamine; In dichloromethane; at 20℃; for 5h; 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 N,N-dimethyl-formamide; at 20℃; for 0.5h; General procedure: A mixture of aniline derivatives 5a - h and chloroacetyl chloride 6 in DMF was stirred at room temperature for 30 min.Then, the reaction mixture was diluted with water, poured intocrashed ice, and the obtained precipitate were filtered off.Finally, residue was washed with cold water to obtain pureN-phenyl-2-chloroacetamides 7a - h.
With potassium carbonate; at 20℃;Cooling with ice; General procedure: We have previously reported preparation, purification and characterization of 2a-2k in our research papers [36,37]. Briefly, Chloroacetyl chloride (0.1mol) was added drop wise to a mixture of appropriate amines (0.05mol) and anhydrous potassium carbonate (K2CO3) (0.075mol) in dichloromethane or chloroform in an ice-cold condition. The reaction mixture was then stirred at room temperature. After completion of reaction, solvent was evaporated under reduced pressure, ice cold water was added to the obtained dry mass and the insoluble product was filtered and dried and purified by recrystallization with appropriate solvents.
In N,N-dimethyl-formamide; at 20℃; for 0.5h; General procedure: A solution of amines 4a-n (1 mmol) and chloroacetyl chloride 5 (1.1 mmol) in DMF (15 mL) was stirred at RT for 30 min. Then, the mixture was diluted with cold water, poured into ice, and the obtained precipitates were filtered off. The residue was washed with water to obtain pure N-phenyl (or benzyl)-2-chloroacetamide 6a-n.
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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[65]European Journal of Organic Chemistry,2019,vol. 2019,p. 4260 - 4270
[66]Bioorganic Chemistry,2019,vol. 90
[67]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3383 - 3389
[68]European Journal of Medicinal Chemistry,2019,vol. 183
[69]Bioorganic Chemistry,2019,vol. 93
[70]Structural Chemistry,2020,vol. 31,p. 999 - 1012
[71]Bioorganic Chemistry,2019
[72]Bioorganic Chemistry,2020,vol. 95
[73]Bioorganic Chemistry,2020,vol. 95
[74]Tetrahedron Letters,2020
[75]Bioorganic Chemistry,2020,vol. 100
  • 2
  • 4-(pyridin-2-yl)piperidine hydrochloride [ No CAS ]
  • [ 2564-02-5 ]
  • N-(4-bromophenyl)-2-[4-(2-pyridinyl)-1-piperidinyl]acetamide trifluoroacetic salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.9% With sodium carbonate; In DMF (N,N-dimethyl-formamide); water; at 20℃; for 18h; The product from Example 36C (hydrochloride, 20 mg, 0.10 mmol), <strong>[2564-02-5]N-(4-bromophenyl)-2-chloroacetamide</strong> (27 mg, 0.11 mmol), and sodium carbonate (50 mg) in DMF:water (2:1, 2 mL) was shaken at ambient temperature for 18 hours. The resulting mixture was decanted and concentrated under reduced pressure. The residue was purified by preparative HPLC to provide the title compound as a trifluoroacetic acid salt (34 mg, 70.9% yield). 1H NMR (500 MHz, DMSO-d6) d2.10 (m, 4H), 3.02 (m, 1H), 3.26 (m, 2H), 3.62 (m, 2H), 4.21 (s, 2H), 7.28 (m, 2H), 7.56 (m, 4H), 7.82 (t, 1H, J=6 Hz), 8.26 (d, 1H, J=6 Hz), 9.90 (br s, 1H), 10.20 (br s, 1H); MS (ESI APCI+) m/e 373 (M-H)+.
  • 3
  • [ 123-75-1 ]
  • [ 2564-02-5 ]
  • [ 89473-71-2 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate; In acetonitrile; at 20 - 80℃; for 4h; Preparation 132; N-(4-Bromo-phenyl)-2-pyrrolidin-l-yl-acetamide; Add potassium carbonate (2.1 g, 15.5 mmol) and pyrrolidine (9.65 mL, 116 mmol) to a solution of <strong>[2564-02-5]N-(4-bromophenyl)-2-chloroacetamide</strong> (2.0 g, 7.7 mmol) in acetonitrile (78 mL) at RT. Heat the mixture at 80 0C for 4 h. Cool the mixture to RT, dilute with CH2Cl2, and wash with brine and water. Dry the organic layer over Na2SO4, filter, and concentrate to give 2.17 g (99%) of the title compound. LC-ES/MS m/z (79Br) 283.0 [M+H]+.
In tetrahydrofuran; Part B. N-(4-Bromophenyl)-alpha-(1-Pyrrolidinyl)acetamide STR396 A solution of 5.0 g (0.02 mol) of N-(4-bromophenyl)-alpha-chloroacetamide (Part A) and 5.05 mL (0.06 mol) of pyrrolidine in 100 mL of THF was stirred overnight at ambient temperature. The mixture was concentrated in vacuo and the residue was partitioned between H2 O and EtOAc. The organic layer was separated, washed with H2 O, dried over Na2 SO4, filtered, and evaporated in vacuo to afford 5.74 g of analytically pure title compound as crystals. mp 60-63 C.; Anal. Calcd for C12 H15 BrN2 O: C, 50.90; H, 5.34; N, 9.89. Found: C, 50.62; H, 5.39; N, 9.74.
  • 4
  • [ 38941-98-9 ]
  • [ 2564-02-5 ]
  • [ 1134193-60-4 ]
  • 5
  • [ 75-15-0 ]
  • [ 2185-03-7 ]
  • [ 2564-02-5 ]
  • [ 1446270-26-3 ]
YieldReaction ConditionsOperation in experiment
70% 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.
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.
  • 6
  • 2-mercapto-3-phenethylquinazolin-4(3H)-one [ No CAS ]
  • [ 2564-02-5 ]
  • [ 1443441-33-5 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate; In acetone; at 20℃; General procedure: A mixture of 2-mercapto-3-phenethylquinazolin-4(3H)-one (1) (2 mmol, 564 mg) and the appropriate 2-chloro-N-phenylacetamide and/ or phenyl 2-chloroacetate (2.1 mmol) in 15 ml acetone containing anhydrous potassium carbonate (3 mmol, 415 mg was stirred at room temperature for 10-12 h. The reaction mixture was filtered, and the solvent was removed under reduced pressure and the solid obtained was dried anr recrystallized from ethanol.
  • 7
  • [ 2564-02-5 ]
  • [ 119-36-8 ]
  • [ 949969-59-9 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; Potassium carbonate (3.75 g, 27.1 mmol) was added to a mixture of N-(4- bromophenyl)-2-chloroacetamide (2.25 g, 9.05 mmol) and methyl 2-hydroxybenzoate (1.38 g, 9.05 mmol) in DMF (30 mL). The reaction mixture was stirred for 16 hours. 1 N HCl was added slowly to the reaction mixture. The combined solution was extracted three times with ethyl acetate. The resulting organic layer was washed twice with water, once with brine, run through a silica plug, and then concentrated in vacuo to give methyl 2-(2-((4-bromophenyl)amino)-2-oxoethoxy)benzoate (3.1 1 g, 94 % yield)
2.12 g With potassium carbonate; In N,N-dimethyl-formamide; for 16h; Potassium carbonate (3.75 g, 27.1 mmol) is added to a mixture of N-(4-bromophenyl)-2- chioroacetamide (2.25 g, 9.05 mmol) and methyl 2-hydroxy- benzoate (1.38 g, 9.05 mmol) in DMF (30 mE). The reaction mixture is stirred for 16 hours. 1 N HC1 is added slowly to the reaction mixture. The combined solution is extracted three times with ethyl acetate. The resulting organic layer is washed twice with water, once with brine, run through a silica plug, and then concentrated in vacuo to give a yellow solid. The solid is washed with ethyl acetate and filtered to obtain compound 3 as a white solid (2.12 g).
  • 8
  • [ 2309-07-1 ]
  • [ 2564-02-5 ]
  • C19H18BrNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Methyl ferulate With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: N-(4-bromophenyl)-2-chloroacetamide 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.
  • 9
  • [ 2564-02-5 ]
  • [ 578-95-0 ]
  • [ 948741-75-1 ]
YieldReaction ConditionsOperation in experiment
65% 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 0C. 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.
  • 10
  • [ 5011-34-7 ]
  • [ 2564-02-5 ]
  • [ 1642863-37-3 ]
YieldReaction ConditionsOperation in experiment
67% With potassium carbonate In acetone Reflux; Synthesis of 6a-k and 7a-k; general procedure To a solution of 5 (0.01 mol) in acetone (30 mL), the appropriate quantities of 2a-k and 4a-k (0.01 mol) was added and the reaction mixture was refluxed for 15-25 h. Potassium carbonate (0.01 mol) was used for neutralisation of the reaction mixture. Progress of the reaction was monitored by TLC using toluene: acetone (8 : 2) as eluent. The mixture was then treated with crushed ice. The precipitate thusobtained was filtered off, dried and recrystallised from acetone toafford 6a-k and 7a-k.6
  • 11
  • [ 717-21-5 ]
  • [ 7357-70-2 ]
  • [ 2564-02-5 ]
  • N-(4-bromophenyl)-2-[6-phenyl-4-(furan-2-yl)-3-cyanopyridine-2-yl]sulfanyl}acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% General procedure: A mixture of 10 mmol of chalcone 1a-1e, 10 mmol of CH-acid 2a and 2b, and 1.1 mL (10 mmol) of N-methylmorpholine in 10 mL of ethanol at 20 C was stirred for 1 h, then 10 mmol of alkyl halide 3a-3l and 9, was added, the reaction mixture was stirred for 2 h and left standing for 24 h. Then the mixture was diluted with an equal volume of water, the separated precipitate was filtered off, washed with water, ethanol, and hexane. N-(4-Bromophenyl)-2-[6-phenyl-4-(furan-2-yl)-3-cyanopyridine-2-yl]sulfanyl}acetamide (6d). Yield 3.7 g (75%), mp 273-275 C (AcOH). IR spectrum, nu, cm-1: 3315 (N-H), 2224 (C?N), 1678 (CONH). 1H NMR spectrum, delta, ppm: 4.31 s (2H, CH2), 6.83 d.d(1H, H4furan, J 4.4 Hz), 7.28-7.51 m (7H, Harom), 7.65 d (2H, Harom, J 7.4 Hz), 8.04 s (1H, H5pyridine), 8.17 d (2H, Harom, J 7.4 Hz), 10.36 br.s (1H, NH). Mass spectrum, m/z (Irel, %): 491 (100) [M + 1]+. Found, %: C 58.67; H 3.14; N 8.42. C24H16BrN3O2S. Calculated, %: C 58.78; H 3.29; N 8.57. M 490.383.
  • 12
  • [ 4354-73-8 ]
  • [ 2564-02-5 ]
  • N-(4-bromophenyl)-3,3-dicyano-3-(cyclohex-1-en-1-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium hydroxide; In water; N,N-dimethyl-formamide; at 20℃; for 2h; General procedure: To a solution of 10 mmol of CH acid 1-3, 8, 10a, 10b, or 13-15 in 20 ml of DMF we added under stirring at 20C 5.6 mL (10 mmol) of 10% aqueous potassium hydroxide and then 10 mmol of alkylating agent 4a-4c or 5. The mixture was stirred for 2 h and diluted with an equal volume of water, and the precipitate was filtered off and washed with water, ethanol, and hexane. In the synthesis of 6a, 6b, 11, 16a, and 16b, 11.2 mL (20 mmol) of 10% aqueous potassium hydroxide and 20 mmol of phenacyl bromide 4a or 4b were used.
  • 13
  • 5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazole-2-thiole [ No CAS ]
  • [ 2564-02-5 ]
  • N-(4-bromophenyl)-2-{5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazol-2-ylthio}acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate; In acetone; at 20 - 60℃; for 3h; General procedure: An appropriate solution of N-aryl chloroacetamide (2.5mmol) and anhydrous K2CO3 (0.28 g, ?2mmol) were added to a stirred solution of compound 4 (0.5 g, 2mmol) in 30mL of acetone at room temperature. After the addition, the reaction was stirred for further 3 hours at 60 C. The precipitated solid was filtered, dried, and recrystallized from suitable solvents to afford pure acetamides 5a-b.
  • 14
  • [ 5626-75-5 ]
  • [ 2564-02-5 ]
  • 6-amino-N-(4-bromophenyl)-7-cyano-2,3-dihydro-1H-pyrrolizine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate; In acetone; for 24h;Reflux; A mixture of<strong>[2564-02-5]N-(4-bromophenyl)-2-chloroacetamide</strong> (11, 1.86 g, 7.5 mmol), 2-(pyrrolidin-2-ylidine)malononitrile(9, 1 g, 7.5 mmol), and anhydrous potassium carbonate (1.04 g, 7.5 mmol) in dry acetone (50 mL)was stirred for 24 h under reflux. The reaction mixture was filtered while hot, concentrated and leftaside. The crystals that separated were collected, dried and recrystallized from an ethanol-acetonemixture to give pale yellow crystals of the title compound, m.p. 228-230 C, yield 68%, IR numax/cm-1 3343, 3275 (NHs), 3068 (C-H aromatic), 2970 (C-H aliphatic), 2218 (CN), 1703, 1652 (C=O). 1H-NMR(CDCl3, 500 MHz, delta ppm): 2.55 (m, 2H, CH2-2), 3.00 (t, 2H, J = 7.5 Hz, CH2-1), 3.57 (s, 2H, NH2), 4.41 (t, 2H, J = 7.5 Hz, CH2-3), 7.46 (d, 2H, J = 10 Hz, aromatic CH-31, CH-51), 7.55 (d, 2H, J = 8.7 Hz,aromatic CH-21, CH-61), 9.64 (s, H, NH). 13C-NMR (CDCl3, 125 MHz, ppm): 24.80, 25.44, 49.71, 83.48,114.13, 114.66, 116.37, 121.24, 132.00, 137.24, 137.46, 145.24, 158.43. MS (EI): m/z (%) 346 (M+ + 2, 1),344 (M+, 1); 298 (85), 262 (3), 235 (46), 219 (100), 207 (13), 191 (32), 174 (27), 165 (25), 146 (7), 109 (11),95 (15), 77 (35). Anal. Calcd. for C15H13BrN4O (345.19): C, 52.19; H, 3.80; N, 16.23. Found: C, 51.81;H, 4.23; N, 16.35.
  • 15
  • N-{4-[(4-benzyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-3-yl)methoxy]phenyl}acetamide [ No CAS ]
  • [ 2564-02-5 ]
  • C26H24BrN5O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Compound 15, 16 or 17 (0.001 mol) was dissolved in DMF (10 ml) and anhydrous potassium carbonate (0.002 mol) was added. The solution was stirred to 1 h at room temperature. Compounds 1-5 dissolved in DMF were added to this solution (3 ml).Then the reaction medium was heated by refluxing in oil bath for6 h in the range of 50-60 C. At the end of this time, the solution was poured onto ice, the resulting precipitate filtered and washed with water. Then compounds 18-32 were recrystallized. 4.1.3.8 2-[(3-[4-(Acetylamino)phenoxy]methyl}-4-benzyl-4,5-dihydro-1H-1,2,4-triazol-5-yl)sulfanyl]-N-(4-bromophenyl)acetamide [25] It was obtained as a white solid and was recrystallized from methanol. HPLC tR (min): 9.45, Mp: 223-224 C, yield 82%. UV (CH3OH) nm: 252 (epsilon: 49,467), 206 (epsilon: 72,689); IR cm-1: 3254, 3187 (N-H), 1657 (C=O), 1597 (C=N), 1171 (C-Br), 1072 (C-O-C), 710 (C-S); 1H NMR (400 MHz, DMSO-d6): delta 1.91 (s, 3H, -NH-CO-CH3), 4.07 (s, 2H, -S-CH2-CO-), 5.11 (s, 2H, -N-CH2-C6H5), 5.21 (s, 2H, -O-CH2-), 6.73-7.45 (m, 13H, Ar-H), 9.71 (s, 1H, -CH2-CO-NH-Ar, exchangeable with D2O), 10.37 (s, 1H, CH3-CO-NH-Ar, exchangeable with D2O) ppm; 13C NMR (300 MHz, DMSO-d6): delta 23.77, 37.33, 47.09, 59.97, 114.78, 115.10, 120.31, 121.01, 126.98, 127.90, 128.65, 131.61, 133.33, 135.09, 138.08, 152.97, 151.13 (triazole-C5), 151.97 (triazole-C3), 165.66 (SCH2CONH), 167.78 (CH3CONH) ppm. HRMS (ESI+) (m/z): calculated for C26H25BrN5O3S (M+H)+ 566.0856, found 566.0856. Anal. Calcd. for C26H24BrN5O3S: C, 55.13; H, 4.27 N, 12.36; S, 5.66. Found: C, 54.82; H, 4.24; N, 12.22; S, 5.42.
  • 16
  • 4-benzyl-5-[[5-methyl-2-(propan-2-yl)phenoxy]methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione [ No CAS ]
  • [ 2564-02-5 ]
  • C28H29BrN4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Compound 15, 16 or 17 (0.001 mol) was dissolved in DMF (10 ml) and anhydrous potassium carbonate (0.002 mol) was added. The solution was stirred to 1 h at room temperature. Compounds 1-5 dissolved in DMF were added to this solution (3 ml).Then the reaction medium was heated by refluxing in oil bath for6 h in the range of 50-60 C. At the end of this time, the solution was poured onto ice, the resulting precipitate filtered and washed with water. Then compounds 18-32 were recrystallized. 4.1.3.3 2-[3-[[5-Methyl-2-(propan-2-yl)phenoxy]methyl]-4-benzyl-4,5-dihydro-1H-1,2,4-triazol-5-yl]sulfanyl}-N-(4-bromophenyl)acetamide [20] It was obtained as a white solid and was recrystallized from methanol. HPLC tR (min): 15.76, Mp: 180 C, yield 78%. UV (CH3OH) nm: 254 (epsilon: 21,564), 205 (epsilon: 55,092); IR cm-1: 3302, 3258 (N-H), 1674 (C=O), 1601 (C=N), 1157 (C-Br), 1094 (C-O-C), 719 (C-S); 1H NMR (400 MHz, DMSO-d6): delta 0.81 (d, 6H, -CH(CH3)2), 2.14 (s, 3H, Ar-CH3), 2.69-2.71 (m, 1H, -CH(CH3)2), 4.05 (s, 2H, -S-CH2-), 5.12 (s, 2H, -N-CH2-C6H5), 5.22 (s, 2H, -O-CH2-), 6.62-7.43 (12H, Ar-H), 10.35 (s, 1H, -CO-NH-) ppm. HRMS (ESI+) (m/z): calculated for C28H30BrN4O2S (M+H)+ 565.1267, found 565.1267. Anal. Calcd. for C28H29BrN4O2S: C, 59.47; H, 5.17; N, 9.91; S, 5.67. Found: C, 59.30; H, 5.10; N, 9.84; S, 5.49.
  • 17
  • (Z)-4-amino-5-(heptadec-8-en-1-yl)-4H-1,2,4-triazole-3-thiol [ No CAS ]
  • [ 2564-02-5 ]
  • 2-[[4-amino-5-(heptadec-8-en-1-yl)-4H-1,2,4-triazol-3-yl]thio]-N-(4-bromophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate; In acetone; at 4℃;Reflux; General procedure: A solution of the appropriate 2-chloro-N-arylacetamide (10 mmol) in 20 cm3 acetone was added to a solution of 3.52 g triazole 2 (10 mmol) in 20 cm3 acetone containing 1.38 g K2CO3 (10 mmol). The reaction mixture was refluxed for 4 h, and then it was cooled and filtered off. The filtrate was concentrated to afford an oily residue, which was purified by column chromatography using an appropriate solvent system to give compounds 10a-10g.
  • 18
  • [ 100114-19-0 ]
  • [ 2564-02-5 ]
  • N-(4-bromophenyl)-2-[3,4-dimethyl-6-oxopyridazin-1(6H)-yl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate In acetonitrile Reflux;
  • 19
  • 4-(2-mercapto-4-oxobenzo[g]-quinazolin-3(4H)-yl)benzenesulfonamide [ No CAS ]
  • [ 2564-02-5 ]
  • N-(4-bromophenyl)-2-(4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydrobenzo[g]quinazolin-2-ylthio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; In acetone; at 20℃; for 10h; A mixture of 4 (3.83g, 0.01 mol) and 2-chloro-N-substitutedacetamide derivatives (0.01 mol) in dry acetone (50 mL) andanhydrous K2CO3 (0.5g) was stirred at room temperature for 10 h.The reaction mixturewas filtered and the solid product formed wascrystallized from ethanol to give 5e19.
  • 20
  • 2-(3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-yl)isoindoline-1,3-dione [ No CAS ]
  • [ 2564-02-5 ]
  • C27H22BrN5O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% 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.
  • 21
  • [ 2564-02-5 ]
  • 2-azido-N-(4-bromophenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium azide; In N,N-dimethyl-formamide; at 20℃; for 24h; General procedure: B23-B27 or B34-B36 (1.0 mmol, 1.0 equiv) and Et3N (1.2 mmol,1.2 equiv) were dissolved in anhydrous tetrahydrofuran (THF), thena solution of chloroacetyl chloride (1.1 mmol, 1.1 equiv) in anhydrousTHF was added dropwise at 0 C. The reaction mixture wasthen stirred at room temperature for additional 2 h. Then water(30 mL) was added, extracted with ethyl acetate (3 10 mL). Theorganic phase was combined, dried over anhydrous Na2SO4,filtered, and concentrated to yield the crude azide substituents,which was purified by flash column chromatography to afford intermediatesC23eC27 and C34eC36. To a solution of the intermediatesin DMF were added sodium azide (1.2 mmol,1.2 equiv),and the mixture was stirred for 24 h at room temperature. Thenwater (30 mL) was added, extracted with ethyl acetate (3 10 mL).The organic phase was combined, dried over anhydrous Na2SO4,filtered, and concentrated to yield the target azide substituentsN23eN27 and N34eN36, which were used for the next stepwithout further purification.
With sodium azide; triethylamine; In water; tert-butyl alcohol; at 20℃; for 1h; General procedure: In order to do a click reaction, azide derivatives 7a-n were prepared in situ of reaction between N-phenyl (or benzyl)-2-chloroacetamide 6a-n (1.1 mmol), sodium azide (0.9 mmol), and Et3N (1.3 mmol) in the mixture of H2O and t-BuOH(10 mL, 1:1) at RT for 1 h.
  • 22
  • [ 2564-02-5 ]
  • 1-(4-bromophenyl)-5-(chloromethyl)-1H-tetrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% General procedure: Finely ground PCl5 (35.0 g, 0.17 mol) was added to a suspension of chloroacetic acid arylamide (0.15 mol) in PhH (150 ml). The reaction mixture was stirred protected from atmospheric moisture until evolution of HCl ceased, gradually increasing the temperature to 50-60C. The mixture was then cooled to 5-10C, and a solution of HN3 (0.25-0.30 mol) in PhH (150 ml) was added in small portions with stirring.15 The reaction mixture was slowly heated to boiling with stirring,maintaining a moderate evolution of HCl, then heated under reflux for 1 h, cooled, and poured into a mixture of water and ice (250-300 ml). After the ice melted, the formed two-phase mixture was heated under reflux for 30 min with vigorous stirring to decompose POCl3. After the reaction mixture was cooled to room temperature, the organic layer was separated and washed with H2O (2×100 ml). The solvent was evaporated under reduced pressure, and the residue was crystallized from CCl4. Compound 5b was obtained as an oil, which was used in the next step without additional purification.
  • 23
  • [ 13679-70-4 ]
  • [ 92-15-9 ]
  • [ 7357-70-2 ]
  • [ 2564-02-5 ]
  • 3-amino-N2-(4-bromophenyl)-N5-(2-methoxyphenyl)-6-methyl-4-(5-methylthiophen-2-yl)-thieno[2,3-b]pyridine-2,5-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% General procedure: Three drops of triethylamine were added at 20C to a mixture of 10 mmol of the corresponding aldehyde 1 and cyanothioacetamide 2 in 40 mL of ethanol. The mixture was stirred for 30 min, 10 mmol of acetoacetanilide 3a-3d and 1.4 mL (10 mmol) of triethylamine were added, and the mixture was stirred for 30 min and left to stand for 24 h. Alkylating agent 4i, 16a, or 19a-19i, was then added, the mixture was stirred for 4 h and diluted with 20 mL of DMF, 5.6 mL (10 mmol) of 10% aqueous potassium hydroxide was added, and the mixture was stirred for 2 h, left to stand for 24 h, and diluted with an equal volume of water.
  • 24
  • [ 498-60-2 ]
  • [ 92-15-9 ]
  • [ 7357-70-2 ]
  • [ 2564-02-5 ]
  • 3-amino-N2-(4-bromophenyl)-4-(furan-3-yl)-N5-(2-methoxyphenyl)-6-methylthieno[2,3-b]pyridine-2,5-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Three drops of triethylamine were added at 20C to a mixture of 10 mmol of the corresponding aldehyde 1 and cyanothioacetamide 2 in 40 mL of ethanol. The mixture was stirred for 30 min, 10 mmol of acetoacetanilide 3a-3d and 1.4 mL (10 mmol) of triethylamine were added, and the mixture was stirred for 30 min and left to stand for 24 h. Alkylating agent 4i, 16a, or 19a-19i, was then added, the mixture was stirred for 4 h and diluted with 20 mL of DMF, 5.6 mL (10 mmol) of 10% aqueous potassium hydroxide was added, and the mixture was stirred for 2 h, left to stand for 24 h, and diluted with an equal volume of water. The precipitate was filtered off and washed with water, ethanol, and hexane. 3-Amino-N2-(4-bromophenyl)-4-(furan-3-yl)-N5-(2-methoxyphenyl)-6-methylthieno[2,3-b]pyridine-2,5-dicarboxamide (20a). Yield 4.4 g (77%), yellow powder, mp 255-257C (from BuOH). IR spectrum, nu, cm-1: 3285-3412 (N-H), 1666 (C=O), 1645 (delta N-H). 1H NMR spectrum (CDCl3), delta, ppm: 2.54 s (3H, Me), 3.77 s (3H, MeO), 6.31 br.s (2H, NH2), 6.90 t (1H, Harom, J = 7.4 Hz), 7.02 d (1H, Harom, J = 7.6 Hz), 7.12 t (1H, Harom, J = 7.4 Hz), 7.48 d (2H, Harom, J =8.8 Hz), 7.52 d (1H, 4-HFu, J = 3.6 Hz), 7.66 d (2H, Harom, J = 8.8 Hz), 7.86 br.s (2H, 5-HFu, Harom), 7.94 s (1H, 2-HFu), 9.66 br.s (1H, CONH), 9.77 br.s (1H, CONH). 13C NMR spectrum (CDCl3), deltaC, ppm: 22.5, 55.7, 111.7, 112.2, 115.3, 117.6, 120.2, 120.4, 123.1, 123.8 (2C), 125.9, 126.2, 131.3 (2C), 131.6, 135.0, 138.3, 141.9, 144.1, 147.6, 151.4, 155.4, 158.5, 163.1, 163.9, 165.4. HRMS (ESI): m/z 579.0518 [M + 2]+. C27H21BrN4O4S. Calculated: M + 2 579.0467.
  • 25
  • [ 104960-50-1 ]
  • [ 2564-02-5 ]
  • 3-amino-N-(4-bromophenyl)-6-(thiophen-2-yl)-4-(trifluoromethyl)thieno[2,3-b]pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; In ethanol; at 90℃; for 2h;Microwave irradiation; 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). 4.2.1. 3-Amino-N-(4-bromophenyl)-6-(thiophen-2-yl)-4-(trifluoromethyl)thieno[2,3-b]pyridine-2-carboxamide (7d) 6d (65 mg, 0.22 mmol), 3 (63 mg, 0.22 mmol) and K2CO3 (30 mg,0.22 mmol) in 5 mL of ethanol, yellow (flocculent) crystals, 90% yield(100 mg, 0.2 mmol), mp: 225-227 C; 1H NMR (600 MHz, DMSO-d6) delta9.78 (s, 1H), 8.33 (s, 1H), 8.25 (dd, J=3.8, 1.1 Hz, 1H), 7.89 (dd,J=5.0, 1.1 Hz, 1H), 7.75-7.68 (m, 2H), 7.56-7.51 (m, 2H), 7.32 (dd,J=5.0, 3.7 Hz, 1H), 6.91 (s, 2H). 13C NMR (151 MHz, DMSO-d6) delta131.55, 131.38, 129.49, 129.23, 124.26, 40.52, 40.24. 13C NMR (151 MHz, DMSO) delta 164.49, 160.99, 152.15, 142.72, 132.16, 131.91,131.55, 131.38, 129.49, 129.23, 125.93, 124.26, 124.12, 122.30,120.49, 118.74, 112.86, 112.82. Anal. Calc. for (%) C19H11BrF3N3OS2,C 45.79; H 2.23, N 8.43; S 12.87; found C 45.72, H 2.44, N 8.10, S12.51.
  • 26
  • [ 2564-02-5 ]
  • [ 552-89-6 ]
  • trans-N-(4-bromophenyl)-3-(2-nitrophenyl)oxirane-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sodium methylate; In methanol; at 20℃; 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.
  • 27
  • 4-(2-(4-oxo-2-thioxo-1,4-dihydroquinazolin-3(2H)-yl)ethyl)benzenesulfonamide [ No CAS ]
  • [ 2564-02-5 ]
  • N-(4-bromophenyl)-2-((4-oxo-3-(4-sulfamoylphenethyl)-3,4-dihydroquinazolin-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate; In acetone; at 20℃; General procedure: To a mixture of 4-(2-(4-Oxo-2-thioxo-1,4-dihydroquinazolin-3(2H)-yl)ethyl)benzenesulfonamide (1) (1 mmol, 361 mg) and potassium carbonate (2 mmol, 277 mg) in acetone (10 mL), was added appropriate 2-chloro-N-(substituted)anilide (1 mmol) and the resulting mixture was stirred at room temperature for 10-12 h. The reaction mixture was filtered, the solvent removed, and the obtained solid was washed with water and dried.
  • 28
  • [ 245449-99-4 ]
  • [ 2564-02-5 ]
  • N-(4-bromophenyl)-2-[4-(5,6,7,8-tetrahydro[1]benzothieno [2,3-d]pyrimidin-4-yl)piperazin-1-yl] acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydrogencarbonate; sodium iodide; In N,N-dimethyl-formamide; at 20℃; for 36h; General procedure: The target compounds 9a-f and 14a-f were prepared by nucleophilic substitution of chloro of 2-chloro-N-substitutedphenyl acetamide derivatives 1a-h with 4-(1-piperazinyl) thieno[2,3-d]pyrimidine derivatives 8a,b. Briefly, sodium bicarbonate (2.36mmol, 0.2g) and sodium iodide (2.36mmol, 0.51g) were added to a solution of intermediates 8a,b (2.36mmol) and intermediates 1a-h (2.36mmol) in DMF (30mL). The reaction mixture was stirred for 36h at room temperature, then added to water (50mL) affording a precipitate which was filtered under vacuum and left to dry. The resulting solid was recrystallized from absolute ethanol to give the titled compounds.
  • 29
  • [ 26131-62-4 ]
  • [ 2564-02-5 ]
  • N-(4-bromophenyl)-2-(4-butyl-5-phenyl-4H-1,2,4-triazol-3-ylthio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 4-butyl-5-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: N-(4-bromophenyl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 30
  • [ 536-17-4 ]
  • [ 2564-02-5 ]
  • Z-N-(4-bromophenyl)-2-(5-(4-(dimethylamino)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With sodium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 36h; 4.1.14 2-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-N-(substituted phenyl) acetamide series (A-G) General procedure: Sodium bicarbonate (2.36mmol) and sodium iodide (2.36mmol) were added to a solution of compounds 3(A-D) (2.36mmol) and compounds 5(A-G), (2.36mmol) in DMF (30mL). The reaction mixture was stirred at RT for 36 hrs. The mixture was then poured into water (50mL) to afford the desired product. The precipitate was filtered and recrystallized from absolute ethanol [15].
  • 31
  • [ 2564-02-5 ]
  • [ 60719-84-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In acetonitrile for 3h; Reflux; 2-(5-Amino-6-oxo-[3,4'-bipyridin]-1(6H)-yl)-N-(4-bromophenyl)acetamide (139). To a suspension of commercially available 5-amino-[3,4'-bipyridin]-6(1H)-one (178) (0.53 mmol) in 10 mL of acetonitrile, 0.53 mmol of N-(4-bromophenyl)-2-chloroacetamide and 1.06 mmol of K2CO3 were added, and the mixture was kept stirring at reflux for 3h. After cooling, the solventwas evaporated and diluted with cold water. The precipitate was recovered by vacuum filtration, and the final compound 2 was purified by crystallization with ethanol. Yield = 88%; mp = 292-294°C. 1H-NMR (400 MHz, DMSO-d6) δ 4.79 (s, 2H, CH2), 5.28 (exch br s, 2H, NH2), 6.90 (s, 1H, Ar), 7.46 (m, 4H, Ar), 7.54 (m, 2H, Ar), 7.61 (s, 1H, Ar), 8.52 (m, 2H, Ar), 10.48 (exch br s, 1H, NH). 13C-NMR (100 MHz, DMSO-d6) δ 53.9 (CH2), 109.4 (CH), 121.7 (CH), 122.3 (C), 123.3 (C), 131.8 (CH), 134.8 (CH), 137.5 (C), 143.3 (CH), 144.8 (C), 149.3 (C), 158.6 (C), 168.5 (C). ESI-MS calcd. for C32H27BrN4O4, 399.25, found m/z 399,04 [M+H]+. Anal. C32H27BrN4O4 (C, H, N).
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