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[ CAS No. 675-20-7 ] {[proInfo.proName]}

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Chemical Structure| 675-20-7
Chemical Structure| 675-20-7
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Product Citations

Product Citations

Rodriguez, Diego F. ; Duran-Osorio, Francisca ; Duarte, Yorley , et al. DOI: PubMed ID:

Abstract: Green chemistry implementation has led to promising results in waste reduction in the pharmaceutical industry. However, the early sustainable development of pharmaceutically active compounds and ingredients remains a considerable challenge. Herein, we wish to report a green synthesis of new pharmaceutically active peptide triazoles as potent factor Xa inhibitors, an important drug target associated with the treatment of diverse cardiovascular diseases. The new inhibitors were synthesized in three steps, featuring cycloaddition reactions (high atom economy), microwave-assisted organic synthesis (energy efficiency), and copper nanoparticle catalysis, thus featuring Earth-abundant metals. The molecules obtained showed FXa inhibition, with IC50-values as low as 17.2 μM and no associated cytotoxicity in HEK293 and HeLa cells. These results showcase the environmental potential and chemical implications of the applied methodologies for the development of new molecules with pharmacological potential.

Keywords: DOACs ; FXa inhibitors ; Ullmann-Goldberg reaction ; click chemistry ; drug discovery ; green chemistry ; microwave synthesis

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Product Details of [ 675-20-7 ]

CAS No. :675-20-7 MDL No. :MFCD00006037
Formula : C5H9NO Boiling Point : -
Linear Structure Formula :HNCH2CH2CH2CH2CO InChI Key :XUWHAWMETYGRKB-UHFFFAOYSA-N
M.W : 99.13 Pubchem ID :12665
Synonyms :
Chemical Name :Piperidin-2-one

Calculated chemistry of [ 675-20-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 30.95
TPSA : 29.1 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : -0.46
Log Po/w (WLOGP) : -0.09
Log Po/w (MLOGP) : 0.1
Log Po/w (SILICOS-IT) : 1.32
Consensus Log Po/w : 0.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.16
Solubility : 67.8 mg/ml ; 0.684 mol/l
Class : Very soluble
Log S (Ali) : 0.32
Solubility : 205.0 mg/ml ; 2.07 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.13
Solubility : 7.38 mg/ml ; 0.0745 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 675-20-7 ]

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

Application In Synthesis of [ 675-20-7 ]

* 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 [ 675-20-7 ]

[ 675-20-7 ] Synthesis Path-Downstream   1~9

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  • [ 1121-89-7 ]
  • [ 25077-25-2 ]
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  • [ 20332-16-5 ]
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  • [ 15540-81-5 ]
  • [ 444002-66-8 ]
  • 4
  • [ 473927-69-4 ]
  • [ 675-20-7 ]
  • Cu(PPh3)3Br [ No CAS ]
  • [ 545445-44-1 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; caesium carbonate; In ethyl acetate; toluene; Part B. Soluble copper(I)-catalyzed Ullmann coupling reaction. A suspension of 1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one (10, 2.2 g, 5.73 mmol), piperidin-2-one (42, 851 mg, 8.59 mmol, 1.5 equiv), and Cs2CO3 (3.73 g, 11.46 mmol, 2.0 equiv) in toluene (15 mL) was treated with Cu(PPh3)3Br (1.065 g, 1.146 mmol, 20% equiv) at room temperature under N2, and the resulting reaction mixture was degassed three times under a steady stream of nitrogen. The reaction mixture was warmed up to reflux for 6 h. When HPLC showed the Ullmann coupling reaction was complete, the reaction mixture was cooled down to 5-10 C. before being quenched with 14% of ammonium hydroxide aqueous solution (20 mL) and EtOAc (30 mL) at 5-10 C. The mixture was stirred for an additional 4 h at 25 C. The two layers were then separated, and the aqueous layer, was extracted with EtOAc (3*20 mL). The combined organic extracts were washed with saturated NaCl aqueous solution (10 mL), dried over MgSO4, and concentrated in vacuo. The residue was directly purified by flash column chromatography (SiO2, 15-40% EtOAc/hexane gradient elution) to afford the desired 3-morpholin-4-yl-1-[4-(2-oxo-piperidin-1-yl)-phenyl]-5,6-dihydro-1H-pyridin-2-one (63, 1.568 g, 2.036 g theoretical, 77%) as a pale-yellow oil, which solidified upon standing at room temperature in vacuo. For 63, CIMS m/z 356 (M++H, C2OH25N3O3).
  • 5
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  • [ 192702-01-5 ]
  • [ 865300-49-8 ]
YieldReaction ConditionsOperation in experiment
99% To a 2000 L glass-lined reactor, under the protection of nitrogen, MTBE (633 kg) and valerolactam (34.9 kg, 350 mol) were charged by vacuum. After initiating stirring, a 33% aqueous solution of tetrabutylammonium hydrogen sulfate (8.35 kg) was added. The mixture was cooled to 20-30 C and then a 50% aqueous solution of sodium hydroxide (270 kg) was added to the mixture at a rate of 10-15 L/minute at this temperature. After the addition, the mixture was maintained at the same temperature for 30 minutes followed by the addition of 3- chloro-4-fluoro-benzylbromide (62.9 kg, 280 mol) at a rate of 2-3 kg/minute at 20-30 C. After 5-10 hours, water (283 kg) was added to the reaction mixture at a rate of 30-40 kg/minute at 20- 30 C to quench the reaction. The mixture was stirred for 30 minutes and then the water phase was separated out. The organic phase was washed with 25% aqueous brine solution (226 kg), and the organic phase was dried with anhydrous sodium sulfate (30 kg) under stirring. The dried mixture was filtered by nutsche filter and the filter cake was rinsed with MTBE (50 kg). The combined filtrate was concentrated in vacuo (T< 35 C, P< -0.08 MPa) until the mixture volume remained at about 350-500 L. Petroleum ether was added (138.4 kg) to the mixture and concentrated continuously. After the mixture volume remained at about 350-500 L, another 138 Kg of petroleum ether was added to the mixture and then concentrated in vacuo. The mixture was cooled to 0-5 C, stirred for 2-3 hours, and then filtered. The filter cake was dried by rotary conical dryer below 35 C to provide 67.7 kg of l-(3-chloro-4-fluorobenzyl)piperidin-2-one (99% yield).
Valerolactam (60 g) was dissolved in MTBE (1.5L) at room temperature. To this solution was added BU4NSO4 (4.9 g) as a phase transfer catalyst. The cloudy solution was stirred at room temperature for 5 minutes. Then, NaOH (50 wt%;300 mL) was slowly added as to keep the internal temperature below 3O0C. 3-Chloro-4-fluorobenzyl bromide (108.3 g) was then added slowly to this biphasic mixture, again as to keep the internal temperature under control. The reaction was then aged for 4 hours at room temperature. At this time LC showed the reaction to be complete. Water (500 mL) was then added. After phase cut, the organic layer was washed with brine (300 mL), dried under MgSO4 followed by solvent switch to heptane (400 mL). The slurry obtained was stirred at room temperature. for 1 hour and then filtered to afford the title product.
To a cold (O C) solution of valerolactam (153.30 g, 1.54 mol) in mixture of anhydrous l-methyl-2-pyrrolidinone (3.5 L) and THF (350 mL), sodium hydride (67.7 g, 1.69 mol, 60% dispersion in oil) was added over a period of 5 minutes. The reaction mixture was stirred for 30 minutes, and a solution of 3-chloro-4-fluorobenzylbromide (345.5 g, 1.54 mol) in l-methyl-2-pyrrolidinone (200 mL) was added over 30 minutes at 0 C. The reaction mixture was stirred at 0 0C for 1 hour, and was allowed to warm up and stirred at room temperature overnight. The reaction mixture was quenched with distilled water (5 L), and extracted with dichloromethane (three times; 2 L, 1 L, 1 L). The organic extracts were combined, washed with <n="20"/>water (3X; 4 L each time). The residual oil was dissolved in ethyl acetate (4 L), and extracted with water (3X; 2 L each time). The organic layer was separated, concentrated under vacuum to give the title product that solidified upon standing. lH NMR (400 MHz, CDCI3) delta 7.24 (m, 2H), 7.0 (m, 2H), 7.1 (m, IH), 4.56 (s, 2H), 3.19 (t, J=4.9 Hz, 2H), 2.46 (t, J= 6.4 Hz, 2H), 1.8-1.75 (m, 4H).
Step 1: 1-(3-Chloro-4-fluorobenzyl)piperidin-2-one To a cold (0 C.) solution of valerolactam (153.30 g, 1.54 mol) in mixture of anhydrous 1-methyl-2-pyrrolidinone (3.5 L) and THF (350 mL), sodium hydride (67.7 g, 1.69 mol, 60% dispersion in oil) was added over a period of 5 minutes. The reaction mixture was stirred for 30 minutes, and a solution of 3-chloro-4-fluorobenzylbromide (345.5 g, 1.54 mol) in 1-methyl-2-pyrrolidinone (200 mL) was added over 30 minutes at 0 C. The reaction mixture was stirred at 0 C. for 1 hour, and was allowed to warm up and stirred at room temperature overnight. The reaction mixture was quenched with distilled water (5 L), and extracted with dichloromethane (three times; 2 L, 1 L, 1 L). The organic extracts were combined, washed with water (3*; 4 L each time). The residual oil was dissolved in ethyl acetate (4 L), and extracted with water (3*; 2 L each time). The organic layer was separated, concentrated under vacuum to give the title product that solidified upon standing. 1H NMR (400 MHz, CDCl3) delta 7.24 (m, 2H), 7.0 (m, 2H), 7.1 (m, 1H), 4.56 (s, 2H), 3.19 (t, J=4.9 Hz, 2H), 2.46 (t, J=6.4 Hz, 2H), 1.8-1.75 (m, 4H).

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  • [ 101166-65-8 ]
  • [ 388630-64-6 ]
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  • [ 545445-44-1 ]
YieldReaction ConditionsOperation in experiment
84% With bromotris(triphenylphosphine)copper(I); In 5,5-dimethyl-1,3-cyclohexadiene;Dean-Stark; Reflux; Example-5 Preparation of 3-morpholin-4-yl-1-[4-(2-oxo-piperidin-1-yl)-phenyl]-5,6-dihydro-1H-pyridin-2-one A suspension of 1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one (75 g, 0.194 moles), 2-piperidone (48 g, 0.485 moles) and tripotassium phosphate (103 g, 0.485 moles) in xylene (750 ml) was treated with Cu(PPh3)3Br (54.5 g, 0.058 moles) at room temperature and heated to reflux by using a dean stark water separator for 8-10 hrs. After completion, the reaction mass was cooled to 0-5 C. Aqueous ammonia (750 ml) and ethyl acetate (1125 ml) were added to the reaction mixture and stirred for 2-3 hrs. The resultant solid was filtered and washed with ethyl acetate (20 ml) to get a solid, which was dissolved in methylene dichloride (375 ml) at 35-40 C. and treated with activated carbon. The resultant solution was filtered through a hyflow bed and distilled under vacuum to get an residue; followed by addition of methanol (90 ml) and the reaction mass was cooled to 0-5 C., stirred for 1 hr at the same temperature and filtered to get a solid material. The obtained solid was washed with methanol to get 59 g (84%) of the title compound with >99% purity.
84% With potassium phosphate; bromotris(triphenylphosphine)copper(I); In 5,5-dimethyl-1,3-cyclohexadiene;Reflux; Dean-Stark; A suspension of l-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-lH-pyridin-2-one (75 g, 0.194 moles), 2-piperidone (48 g, 0.485 moles) and tripotassium phosphate (103 g, 0.485 moles) in xylene (750 ml) was treated with Cu(PPh3)3Br (54.5 g , 0.058 moles) at room temperature and heated to reflux by using a dean stark water separator for 8-10 hrs. After completion, the reaction mass was cooled to 0-5C. Aqueous ammonia (750 ml) and ethyl acetate (1125 ml) were added to the reaction mixture and stirred for 2-3 hrs. The resultant solid was filtered and washed with ethyl acetate (20 ml) to get a solid, which was dissolved in methylene dichloride (375 ml) at 35-40C and treated with activated carbon. The resultant solution was filtered through a hyflow bed and distilled under vacuum to get an residue; followed by addition of methanol (90 ml) and the reaction mass was cooled to 0-5C, stirred for 1 hr at the same temperature and filtered to get a solid material. The obtained solid was washed with methanol to get 59 g (84%) of the title compound with > 99% purity.
35 g Example-8 Preparation of 3-morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydro pyridin-2(1H)-one (Formula-8) A mixture of 1-(4-iodophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one compound of formula-7 (50 g), piperidin-2-one (32.25 g) and o-xylene (75 ml) was stirred for 10 minutes at 25-30 C. Potassium carbonate (27.0 g), followed by copper iodide (7.43 g) were added to the reaction mixture. The reaction mixture was heated to 140-145 C. under azeotropic distillation condition and stirred for 6 hours at the same temperature. Cooled the reaction mixture to 35-40 C., water (175 ml) was slowly added to the reaction mixture at 35-40 C. Cooled the reaction mixture to 10-15 C. and ammonia (125 ml) was added to the reaction mixture at 10-15 C. The temperature of the reaction mixture was raised to 25-30 C. and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with water and then dried to get title compound. Yield: 35 gm; MR: 195-200 C.; HPLC purity: 95%.
  • 8
  • [ 675-20-7 ]
  • [ 1259396-11-6 ]
  • methyl 2-methyl-5-(2-oxopiperidin-1-yl)thiophene-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In toluene; for 12h;Reflux; General procedure: A mixture of 11 (500mg, 2.13mmol), 2-pyrrolidone (210mg, 2.47mmol), CuI (20.0mg, 0.105mmol), N,N?-dimethylethylenediamine (18.5mg, 0.210mmol), and K2CO3 (580mg, 4.20mmol) in toluene (2.50mL) was refluxed for 12h. After cooling to room temperature, the reaction mixture was diluted with AcOEt and filtered through celite. The filtrate was washed with saturated aqueous NaHCO3 and brine and dried over Na2SO4. After filtration, the solvent was concentrated under reduced pressure and the residue was triturated with 50% (v/v) solution of AcOEt/n-hexane to give 166mg (33%) of 27a as a white solid:
  • 9
  • [ 675-20-7 ]
  • 1-(4-chlorophenyl)-3-morpholine-5,6-dihydropyridine-2(1H)-one [ No CAS ]
  • [ 545445-44-1 ]
YieldReaction ConditionsOperation in experiment
93.1% With bis-triphenylphosphine-palladium(II) chloride; sodium hydride; In dimethyl sulfoxide; at 20℃; for 2h; Compound VI (58.6 g, 0.2 mol), 2-piperidone (29.7 g, 0.3 mol), bistriphenylphosphine palladium dichloride (7.0 g, 0.01 mol), sodium hydride (97.7 g, 0.3 mol) 2000 mL of dimethyl sulfoxide was added to the reaction flask, and the reaction was carried out at room temperature. After TLC monitoring, the reaction was stopped after 2 hours, and 2000 mL of ice water and 1000 mL of ethyl acetate were added to the reaction solution, and the mixture was washed twice with ice water. dried over anhydrous sodium sulfate, vacuum filtration, recrystallized from ethyl acetate to give a white solid 66.1 g, yield 93.1%, HPLC purity of 99.6%.
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