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Canale, Vittorio ; Czekajewska, Joanna ; Klesiewicz, Karolina ; Papiez, Monika ; Kuziak, Agata ; Witek, Karolina , et al.
Abstract: The alarming increase in the resistance of bacteria to the currently available antibiotics necessitates the development of new effective antimicrobial agents that are active against bacterial pathogens causing major public health problems. For this purpose, our inhouse libraries were screened against a wide panel of clin. relevant Gram-pos. and Gram-neg. bacteria, based on which compound I was selected for further optimization. Synthetic efforts in a group of arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines, followed with an in vitro evaluation of the activity against multidrug-resistant strains identified compound 44 (1-(3-chlorophenyl)-3-(1-{3-phenyl-3-[3-(trifluoromethyl)phenoxy] propyl}piperidin-4-yl)urea). Compound 44 showed antibacterial activity against Gram-pos. bacteria including fatal drug-resistant strains i.e., Staphylococcus aureus (methicillin-resistant, MRSA; vancomycin-intermediate, VISA) and Enterococcus faecium (vancomycin-resistant, VREfm) at low concentrations (0.78-3.125 μg/mL) comparable to last resort antibiotics (i.e., vancomycin and linezolid). It is also potent against biofilm-forming S. aureus and Staphylococcus epidermidis (including linezolid-resistant, LRSE) strains, but with no activity against Gram-neg. bacteria (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa). Compound 44 showed strong bactericidal properties against susceptible and drug-resistant Gram-pos. bacteria. Depolarization of the bacterial cytoplasmic membrane induced by compound 44 suggests a dissipation of the bacterial membrane potential as its mechanism of antibacterial action. The high antimicrobial activity of compound 44, along with its selectivity over mammalian cells (lung MCR-5 and skin BJ fibroblast cell lines) and no hemolytic properties toward horse erythrocytes, proposes arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines for development of novel antibacterial agents.
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Keywords: Arylurea derivatives ; Antibacterial properties ; Anti-MRSA activity ; Anti-VRE activity ; Anti-LRSE activity ; Depolarization of bacterial cell membrane
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Purchased from AmBeed: 122536-76-9 ; 936-59-4 ; 135632-53-0 ; 404-71-7 ; 73874-95-0 ; 372-20-3 ; 98-17-9 ; 402-45-9 ; 57260-71-6 ; 122536-77-0 ; 444-30-4 ; 165800-03-3 ; 150-19-6 ; 1195-45-5 ; 2909-38-8 ; 165800-03-3
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CAS No. : | 57260-71-6 |
Formula : | C9H18N2O2 |
M.W : | 186.25 |
SMILES Code : | O=C(N1CCNCC1)OC(C)(C)C |
MDL No. : | MFCD00075265 |
InChI Key : | CWXPZXBSDSIRCS-UHFFFAOYSA-N |
Pubchem ID : | 143452 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | at 0℃; for 1 h; | To a cold methylene chloride solution (10 ml) of piperazine (30.23 mmol, 2.60 g) was added methylene chloride solution (10 ml) of BOC anhydride (1.50 mmol) and the mixture was stirred at 0°C for 1 hour. After the reaction is complete, water is added and the aqueous K2CO3 solution is added to make the reaction mixture basic. All of the reaction mixture was extracted with methylene chloride and the product was isolated by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate In acetonitrile at 95℃; for 4 h; | Intermediate 121: tert-Butyl 4-(3-hvdroxypropyr)piperazine-l -carboxylate A mixture of tert-butyl piperazine-1 -carboxylate (2.75 g, 14.8 mmol), l-bromo-3- propanol (1.43 mL, 16.2 mmol) and potassium carbonate (2.25 mL, 27.5 mmol) in acetonitrile (75 mL) was heated at 950C for 4 hours. The solvent was removed under reduced pressure, and the residue was taken up in dichloromethane (300 mL) and washed with water, brine, EPO <DP n="118"/>dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel with methanol in dichloromethane (0-10percent) gave a tan solid 2.88 g (80percent yield). MS (ESV 245 (MH+) for C12H24N2O3,1H-NMR TCDCl1) δ: 1.44 (m, 9H); 1.70-1.82 (m, 2H); 2.40-2.53 (m, 2H); 2.62-2.65 (m, 2H); 3.43-3.50 (m, 4H); 2.77 (m, 2H); 3.73-3.82 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With N-ethyl-N,N-diisopropylamine; at 30℃; for 72h;Inert atmosphere; | Example 24 tert-Butyl 4-(2-bromoethyl)piperazine-1-carboxylate A mixture of tert-butyl piperazine-1-carboxylate (5.0 g, 26.9 mmol), 1,2-dibromoethane (25 mL), DIPEA (3.5 g, 26.9 mmol) was stirred at 30° C. under argon for 72 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (1-2percent methanol/dichloroethane) to afford the desired product (2.8 g, 36percent yield) as a solid. ESI-MS m/z: 293.1[M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate; In dimethyl sulfoxide; at 75℃; | A solution of <strong>[19745-07-4]2,5-dichloropyrazine</strong> (1.03 g, 6.91 mmol) in DMSO (10 mL) was treated sequentially with K2C03(s) (2.867 g, 20.74 mmol) and tert-butyl piperazine-1-carboxylate (1.288 g, 6.9 14 mmol), then stirred overnight at 75 °C. After cooling to ambient temperature, the mixture was partitioned between EtOAc (10 mL) and water (20 mL). After phase separation, the organic extracts were concentrated in vacuo to provide the title compound (1.928 g, 93percent yield). MS (apci) m/z = 199.1 (M-Boc). ?HNIVIR(CDC13) 8.07 (m, 1H), 7.86 (m, 1H), 3.56 (s, 8H), 1.48 (s, 9H). |
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 1h; | To an NMP (7.5 ml) solution of 1.51 g of <strong>[19745-07-4]2,5-dichloropyrazine</strong> were added 2.00 g of 1-(t-butoxycarbonyl)piperazine and 2.00 g of potassium carbonate, followed by 1 hour of stirring under heating at 100°C. The mixture was cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate, and thereafter, the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 2.73 g of 2-chloro-5-(4-t-butoxycarbonylpiperazin-1-yl)pyrazine. Using this compound, 2-chloro-5-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}pyrazine was obtained in a similar manner to Example 14 as colorless crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ISOPROPYLAMIDE; at 80℃; for 2h; | 4- 4-CYANO-2, 3-DIFLUORO-PHENYL)-PIPERAZINE-L-CARBOXYLIC ACID TERT-BUTYL ester To a solution OF N-BOC-PIPERAZINE (0.65 g) in DMA (20 mL) was slowly added a solution of 2, 3, 4-<strong>[143879-80-5]trifluorobenzonitrile</strong> (0.49 g) in DMA (10 mL). The reaction mixture was stirred for 2 hours at 80°C. After such time the solvent was removed in vacuo and purified by column chromatography (SIO2) to yield the title compound as white solid (0.76 g). | |
In ISOPROPYLAMIDE; at 80℃; for 2h; | To a solution of N-Boc-Piperazine (0.65 g) in DMA (20 mL) was slowly added a solution of <strong>[143879-80-5]2,3,4-<strong>[143879-80-5]trifluorobenzonitrile</strong></strong> (0.49 g) in DMA (10 mL). The reaction mixture was stirred for 2 hours at 80° C. After such time the solvent was removed in vacuo and purified by column chromatography (SiO2) to yield the title compound as white solid (0.76 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; ethyl acetate; | Example 123A 4-(5-Bromo-pyridin-3-yl)-piperazine-1-carboxylic Acid Tert-Butyl Ester A solution of the 3,5-dibromo-pyridine (12.8 g, 68.8 mmol) and piperazine-1-carboxylic acid tert butyl ester (10 g, 42.4 mmol) in 200 mL of dioxane was treated with Pd2(dba)3 (5 g, 5.5 mmol), 2-(di-tbutyl-phosphino)biphenyl (4 g, 13.4 mmol), and sodium t-butoxide (7.2 g, 75 mmol). The reaction was heated to 95° C. for 8 h then cooled and filtered through celite. The mixture was evaporated and the residue was purified by flash column chromatography on silica gel, eluding with a solvent gradient of 1:4 ethyl acetate/hexane to 100percent ethyl acetate. Recovered 2.9 g of product (20percent). MS (ESI) m/z 344 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.6 g (26%) | With triethylamine; In N-methyl-acetamide; methanol; | a 4-(2-Amino-ethyl)-piperazine-1-carboxylic Acid Tert-butyl Ester A solution of N-tert-butoxycarbonyl-piperazin (5 g, 26.8 mmol), triethylamine (7.44 ml, 53.6 mmol), and chloroethylamine (3.11 g, 26.8 mmol) in dimethylformamide (50 ml) was stirred at room temperature for 72 hours. The reaction mixture was filtered, partitioned between H2O and ethyl acetate. The aqueous phase was lyophilized, the residue stirred with methanol and the precipitate collected by suction. The precipitate was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia=9/1/0.1) to give 1.6 g (26percent) of the desired product. MS m/z: 230 ((M+H)+, 91percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In methanol; 1,2-dibromomethane; | EXAMPLE X 2-(1-tert-Butyloxycarbonylpiperazin-4-yl)ethyl bromide A solution of 1.0 g of 1-tert-butyloxycarbonylpiperazine and 0.7 g (0.005 mol) of N-ethyldiisopropylamine in 5 ml of 1,2-dibromomethane is allowed to stand at room temperature for 3 days and then concentrated to dryness in vacuo. The residue is purified by means of chromatography on a silica gel column, methylene chloride which initially contains 1percent and then 2percent of methanol being used as eluent. Yield: 0.6 g (38percent of theory), Mass spectrum: (M+H)+ =293/295 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | In water; N,N-dimethyl-formamide; | 2. Intermediate 2: 4-(4-tert-Butyloxycarbonyl)piperazin-1-yl Butanal Dimethyl Acetal A mixture of <strong>[29882-07-3]4-chlorobutanal dimethyl acetal</strong> (J. Chem. Soc., Perkin Trans. 1, 1981, 251-255; 4.1 g, 26.9 mmol), K2 CO3 (4.08 g, 29.6 mmol) and tert-butyl-1-piperazinecarboxylate (5.00 g, 26.9 mmol), in anhydrous DMF (100 ml) was heated at 100° C. for 24 h. The mixture was cooled to room temperature, water (75 ml) added and extracted with ethyl acetate (5*100 ml). The combined extracts were washed with water (*3), dried (Na2 SO4) and evaporated. The crude product was chromatographed on silica gel eluding with ethyl acetate to give the title-product (3.41 g, 42percent). delta (250 MHz, CDCl3) 1.46 (9H, s, OC(Me)3); 1.50-1.68 (4H, m, 2 of CH2); 2.32-2.42 (6H, m, 3 of CH2); 3.30 (6H, s, (OMe)2); 3.40-3.48 (4H, m, 2 of CH2); 4.38 (1H, t, J=6 Hz, CH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.7% | To cooled (00C) slurry of an 80:20 mixture of 1O.1B (1.0 eq) and boc- piperazine (about 2 eq) in a mixture of HOAc and DCM (4.8 M boc-piperazine in 1:1.4 v/v HOAc/DCM) was added sodium triacetoxyborohydride as a solid over about 5 minutes. The reaction was allowed to warm to RT and stirred for two hours. The reaction mixture was quenched with saturated sodium bicarbonate and diluted with ethyl acetate. The layers were separated and the aqueous layer was washed three times with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by chromatography over silica gel using 50percent ethyl acetate/hexanes as the eluant provided ID (67.7percent) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triethylamine; In butan-1-ol; at 20 - 65℃; | Mechanically stir mixture of <strong>[22280-60-0]6-chloro-2-methyl-3-nitro-pyridine</strong> (Asymchem, 25.00 g, 144.9 mmol), tert-butyl 1-piperazinecarboxylate (29.68 g, 159.4 mmol), and triethylamine (23.2 niL, 167 mmol) in K-BuOH (250 mL) at 50 C under nitrogen for 4 hours, at 65 C for 2 hours, then at room temperature overnight. Add additional tert-butyl 1-piperazinecarboxylate (1.5 g), and heat the reaction at 65 C for 4 hours. Cool the resulting slurry to 30 C then add hexanes (75 mL). Cool the slurry to room temperature over 1 hour, then add water (150 mL). Allow the slurry to stand for 45 min then filter. Wash the cake with water (4 x 100 mL) then hexanes (100 mL) and air-dry overnight to yield 4-(6-methyl-5-nitro-pyridin-2-yl)- rhoiperazine-1-carboxylic acid tert-butyl ester as bright yellow crystals (46.30 g, 99% yield, MS(ES): m/z = 267 [MH-H-C4H8]). |
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 50℃; for 4h; | Step 1HLJNIG base (62.82 mL, 0.435 mol) is added to the solution of 6-chloro-3-nitro-2- methylpyridine SM-3 (50 g, 290 mmol) and N-Boc-piperazine SM-5b (53.95 g, 290 mmol) in dry AcCN (200 mL) and stirred for 4 h at 50 C. After the reaction is finished the reaction mixture is diluted with AcCN and water and stirred for 30 min. The precipitated product is collected by filtration, washed with water and the solid is dried in vacuo. | |
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 50℃; for 4h; | HUeNIG base (62.82 mL, 0.435 mol) is added to the solution of <strong>[22280-60-0]6-chloro-3-nitro-2-methylpyridine</strong> SM-3 (50 g, 290 mmol) and N-Boc-piperazine SM-5b (53.95 g, 290 mmol) in dry AcCN (200 mL) and stirred for 4 h at 50 C. After the reaction is finished the reaction mixture is diluted with AcCN and water and stirred for 30 min. The precipitated product is collected by filtration, washed with water and the solid is dried in vacuo. |
With N-ethyl-N,N-diisopropylamine; for 4h; | DIPEA (62.82 mL, 0.435 mol) is added to the solution of 6-chloro-3-nitro-2- methylpyridine (1) (50 g, 290 mmol) and N-Boc-piperazine (2) (53.95 g, 290 mmol) in dry MeCN (200 mL) and stirred for 4 h at 50 C. After the reaction is finished the reaction mixture is diluted with MeCN and water and stirred for 30 min. The precipitated product is collected by filtration, washed with water and the solid is dried in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 6-chloro-1H-pyrazolo[4,3-c]pyridine; In 1-methyl-pyrrolidin-2-one; at 140℃; for 2h; | (3) To a solution of the compound obtained in the above step (2) (0.72 g) in N-methylpyrrolidone (5.0 mL) was added N-tert-butoxycarbonylpiperazine (1.7 g) and the mixture was stirred at 140 °C for 2 hours. After cooling, to the reaction mixture was added water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a flash column chromatography on NH-silica gel (Solvent; n-hexane/ethyl acetate = 1: 1) to give 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-1H-pyrazolo[4,3-c]pyridine (0.64 g) as colorless crystals. MS(APCI)m/z; 304 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 70℃; for 1.5h; | In a sealed tube, <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (517 mg, 2.68 mmol) Pd2(dba)2 (2percent), BINAP (4percent), and sodium f-butoxide (386.4 mg, 4.02 mmol) were added to /V-Boc-piperazine (500 mg, 2.68 mmol) and the solids were dissolved in dry toluene (5 ml_). The mixture was stirred at 700C for 90 min., filtered over Celite.(R)., washing with etylacetate and the organic layer was evaporated under reduced pressure. The crude was purified by flash chromatography (40percent etylacetate in hexane) to give 7 as pail yellow solid (95percent yield): 1H NMR, 300MHz, (CDCI3) delta 1.38 (s, 9H), 2.91 (m, 4H),3.48 (m, 4H), 6.55 (m, 1 H), 6.66 (m, 1 H), 6.83 (m, 1 H). ESI-MS m/z 321 [M+Na+], 221 , 199. Anal (Ci5H20F2N2O2) C, H, N. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h; | General procedure D. 4-(6-Fluoro~pyridine-2-carbonyI)-piperazine-l- carboxylic acid tert-butyl esterTo a stirred solution of 6-fluoro-2-pyridine carboxylic acid (leqv, 2.00 g, 14.2 mmol), N-boc-piperazine (1.15eqv, 3.04 g, 16.3 mmol) and DIPEA (2.5 eqv, 6.12 ml, 35.4 mmol) in DCM (100 ml) at room temperature was added portionwise EDC (1.2eqv, 3.09 g, 17.0 mmol) and HOBt (0.2eqv, 0.383 g, 2.83 mmol). The reaction mixture was stirred at room temperature for 16 hrs then concentrated at reduced pressure. The crude material was purified by chromatography [SiO2, EtOAc / heptane, 1 :1] to give pure product (4.40 g, 84percent, 11.93 mmol) as colourless oil. LC/MS: 95percent MH+, m/z 310, Rt = 0.97 mins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 1 Step 2. To solution of 1.0 eq IB in dry Et2O (0.06 M) at 00C was added dropwise a solution of diisobutyllithiumaluminum hydride (1.1 eq, 1.0 M in hexanes) by syringe. The resulting solution was kept at 00C overnight. The reaction mixture was added to a mixture of ice and glacial acetic acid. The reaction mixture was then diluted with ethyl acetate, and the aqueous layer was extracted with ethyl acetate two additional times. The combined organic layers were washed twice with saturated sodium bicarbonate, and once with brine. The organic layers were then dried over sodium sulfate, filtered and concentrated in vacuo. Purification over silica gel using 10percent EtOAc/hexanes as the eluant afforded a yellow solid (100percent) as an 80:20 mixture of 1C:1B. Example 1 Step 3. To cooled (00C) slurry of an 80:20 mixture of 1C:1B (1.0 eq) and boc-piperazine(about 2 eq) in a mixture of HOAc and DCM (4.8 M boc-piperazine in 1:1.4 v/v HOAc/DCM) was added sodium triacetoxyborohydride as a solid over about 5 minutes. The reaction was allowed to warm to RT and stirred for two hours. The reaction mixture was quenched with saturated sodium bicarbonate and diluted with ethyl acetate. The layers were separated and the aqueous layer was washed three times with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by chromatography over silica gel using 50percent ethyl acetate/hexanes as the eluant provided ID (67.7percent) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 48h;Inert atmosphere; | To a mixture of tert-butyl piperazine-1-carboxylate (1.00 g, 5.37 mmol) and potassium carbonate (1.34 g, 9.76 mmol) in anhydrous dimethylformamide (50 mL) was added 1, 3-dichloro-5-(chloromethyl) benzene (0.95 g, 4.88 mmol) under nitrogen. The resulting mixture was stirred at ambient temperature for 2 days. The reaction mixture was diluted with ethyl acetate (200 mL) , washed with water (100 mL) , saturated ammonium chloride (2 x 50 mL) , brine (2 x 40 mL) , dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (3:1 hexanes: ethyl acetate) to provide the title compound as a colorless oil (1.22 g, 73) :1H NMR (300 MHz, CDCl3) delta 7.25-7.17 (m, 3H) , 3.45-3.35 (m, 6H) , 2.39-2.30 (m, 4H) , 1.42 (s, 9H) MS (ES+) m/z 345.1, 347.1 (M + 1) . |
With potassium carbonate; In acetonitrile; at 80℃; for 16h; | A mixed solution of compound 1-1 (1.96 g, 10.0 mmol), N-Boc-piperazine (1.95 g, 10.5 mmol), potassiumcarbonate (2.76 g, 20.0 mmol) in acetonitrile (20 ml) was stirred at 80°C for 16h. The reaction mixture was cooled toroom temperature, the solvent was removed under reduced pressure, water was added, and the mixture was extracted with ethyl acetate (2*50 ml). The organic phase was washed with saturated brine (30 ml), dried and separated, and thefiltrate was concentrated under reduced pressure to give compound 1-2 (3.5 g) as a yellow oil, purity 90.26percent, yield100percent. MS m/z(ESI): 345.0[M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; | Sodium triacetoxyborohydride (0.85 g, 4.01 mmol) was added to a solution of <strong>[131747-63-2]4-bromopicolinaldehyde</strong> (0.25 g, 1.34 mmol), tert-butyl piperazine-1-carboxylate (0.28 g,1.48 mmol) and acetic acid (0.02 mL, 0.4 mmol) in dichloromethane (5 mL) and the resulting mixture was stirred overnight at room temperature. The solvent was then evaporated and the residue was triturated with diethyl ether, filtered and the solvent evaporated in vacuo. The residue was purified by flash chromatography to yield the titlecompound (363 mg, 68percent) as a solid. LRMS (m/z): 356/358 (M+1).1H-NMR (300 MHz, CDCI3): 1.46 (s, 9H), 2.46 (t, 4H), 3.46 (t, 4H), 3.64 (s, 2H), 7.62 (d, 1H), 8.37 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.81% | With potassium carbonate; In dimethyl sulfoxide; at 100 - 110℃;Microwave irradiation; | A microwave vial was charged with <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (1 g, 6.31 mmol), 1 -boc-piperazine (1 .29g, 6.94mmol) and potassium carbonate (3.3ml_, 18.92mmol), which was suspended in DMSO (15ml_). The resulting mixture was irradiated for 1 hour at 100°C. After this time, the mixture had solidified. LC-MS showed the reaction had not gone to completion. The solid mixture was then transferred to a flask along with DMSO (5ml_) and heated to 1 10°C, at which point the solid mixture had melted. This was left heating overnight, after which LC-MS showed product formation and no starting material. Reaction was allowed to cool. The reaction mixture was then added to water and extracted with EtOAc (x3). The organics were then combined, washed with brine, dried over sodium sulfate, filtered and concentrated to dryness, affording an orange solid. Purification by flash column chromatography was then performed, (40g S1O2, eluting with 0-50percent EtOAc in heptane). The fractions containing product were combined and concentrated to dryness, affording tert-butyl 4-(6- nitro-3-pyridyl)piperazine-1 -carboxylate (1 .24g, 4.02mmol, 63.81 percent yield) as a bright orange/yellow solid. MS Method 2: RT: 1 .61 min, ES+ m/z 309.1 [M+H]+ H NMR (400MHz, CDC ) delta/ppm: 8.10-8.13 (d, J=9.1 Hz, 1 H), 8.06-8.07 (d, J=3.0Hz, 1 H), 7.12-7.16 (dd, J=9.2, 3.0Hz, 1 H), 3.55-3.59 (m, 4H), 3.36-3.41 (m, 4H), 1 .42 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | [00204] A flask was charged with <strong>[109179-31-9]2-bromo-3-methylbenzaldehyde</strong> (3.00 g, 15.1 mmol, 1.00 equiv), tert-butyl piperazine-1-carboxylate (3.40 g, 18.2 mmol, 1.20 equiv), and 1,2- dichloroethane (50 mL). The mixture was stirred for 30 min at rt. NaBH(OAc)3 (9.60 g, 45.3 mmol, 3.00 equiv) was added. The resulting solution was stirred overnight at rt and then diluted with H2O (20 mL). The resulting mixture was extracted with DCM (3 x 20 mL) and the organic layers were combined, washed with brine (1 x 100 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was chromatographed on a silica gel column (20:80 EtOAc/petroleum ether) to provide tert-butyl 4-[(2-bromo-3-methylphenyl)methyl]piperazine-1- carboxylate (4.80 g, 86percent yield) as colorless oil. LCMS (ESI, m/z): 369 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16 mg | To a mixture of tert-butyl piperazine-1-carboxylate (31.7 g), 1,3-thiazole-4-carboxylic acid (20 g) and 1-hydroxybenzotriazole hydrate (28.5 g) in anhydrous DMF (500 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (35.6 g) at room temperature. The mixture was stirred at room temperature for 22 hr. The mixture was poured into water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The solid was washed with diisopropyl ether. The solid was suspended with ethyl acetate (100 mL) and added hydrogen chloride (4 M in ethyl acetate, 171 mL). The mixture was stirred at 50° C. for 2 hr. The solid was collected by filtration. The residue was purified by column chromatography (NH silica gel, methanol/ethyl acetate) to give the title compound (16.00 g). MS: [M+H]+ 198.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; In methanol; at 20.0℃; for 2.0h; | To a solution of <strong>[1074-40-4]4,6-dichloro-2-methoxy-pyrimidine</strong> (1.50 g, 8.38 mmol) and TEA (2.50 g, 25.1 mmol) in methanol (100 mL) was added a solution of piperazine-1-carboxylic acid tert30 butyl ester (1.55 g, 8.38 mmol), and the mixture was stirred at room temperature for 2 hrs.The reaction mixture was concentrated and the residue was washed with 5 mL of cold MeOH (5 mL) to get the title compound (2.4 g, yield 87percent) as a white solid.1H NMR (400 MHz, CDCI3): 66.19 (s, IH), 3.94 (s, 3H), 3.63-3.50 (m, 8H), 1.48 (s, 9H).LC-MS: [mobile phase: from 80percent water (0.02percent NH4OAc) and 20percent CH3CN to 5percent water(0.02percent NH4OAc) and 95percent CH3CN in 4 mm], Rt 2.418 mm, MS Calcd.:328, MS Found: 329[M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 7h;Inert atmosphere; | General procedure: Solid K2CO3 (2 equiv) was added to a solution of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong> (1 equiv) and amine (1 equiv) in DMF(20 mL), and the resulting solution was stirred at 110 C for 7 h.The reaction mixture was concentrated under reduced pressure and dissolved in EtOAc, washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purifiedby silica gel column chromatography (ethyl acetate: hexane= 4:1) to yield pure product |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 16h; | A mixture of <strong>[1120-95-2]3-<strong>[1120-95-2]chloropyridazine</strong></strong> (1 g, 8.73 mmol), tert-butyl piperazine-1-carboxylate(1.626 g, 8.73 mmol), and K2C03 (2.413 g, 17.46 mmol) in NMP (10 mL) was stirred at 120 °C for 16 h. The mixture was purified by chromatography (silica, EtOAc/PE =1/20) to afford tertbutyl 4-(pyridazin-3-yl)piperazine-1-carboxylate (709 mg, 2.68 mmol, 31percent) as a yellow oil. ESIMS (EI+, m/z): 265.4 [M+H]t |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
285 mg | With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 15h; | A mixture of compound 1.4 (soo mg, 1.89 mmol, 1 eq), tert-butyl piperazine-1- carboxylate (1.06 g, 5.67 mmol, 3 eq) and potassium carbonate (552 mg, 3.78 mmol, 2 eq) was stirred in DMF (18 mL) at 140°C for 15 hours. Upon completion (as monitored by LC-MS), the mixture was extracted with DCM (2 x 15 mL) and washed with water (10 mL) with the aqueous layer neutralized using a 1M solution of citric acid. Thecombined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The crude compound was recrystallized from DMF ( mL) to give pure compound 1.5 (285 mg, 35.0 percent yield) as a pale orange solid. JR (umax/cm1) 1729, 1687, 1627, 1502, 1462, 1417, 1383, 1340, 1286, 1246, 1217, 1168,1124, 1083, 1045, 1034, 940, 891, 86, 828, 8o, 782, 770, 746, 703, 667, 625; LC-MSRetention time 3.95 minutes, found 432.0 [M+H] calculated for C22H26FN305 432.46 [M+H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.09% | With methanol; sodium cyanoborohydride; at 0 - 20℃; for 16h; | To a stirred mixture of <strong>[54221-96-4]6-methoxypyridine-2-carbaldehyde</strong>( 5 g, 36.46 mmol, 1 equiv.) and tert- butyl piperazine-1-carboxylate(8.1 g, 43.49 mmol, 1.19 equiv.) in MeOH(25 mL) was added NaBH3CN(4.6 g, 73.20 mmol, 2.01 equiv.) in portions at 0 degrees C. The resulting mixture was stirred for 16 h at room temperature. The reaction was monitored by LCMS. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (40/1 to 1/1) to afford tert-butyl 1-[(6-methoxypyridin- 2-yl)methyl]piperidine-4-carboxylate(8.5 g, 76.09%) as a light yellow oil. |
Tags: 57260-71-6 synthesis path| 57260-71-6 SDS| 57260-71-6 COA| 57260-71-6 purity| 57260-71-6 application| 57260-71-6 NMR| 57260-71-6 COA| 57260-71-6 structure
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