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Chemical Structure| 38560-30-4
Chemical Structure| 38560-30-4
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Product Details of [ 38560-30-4 ]

CAS No. :38560-30-4 MDL No. :MFCD04037154
Formula : C11H12N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :VPCQXIGQMFWXII-UHFFFAOYSA-N
M.W : 220.22 Pubchem ID :22324463
Synonyms :

Calculated chemistry of [ 38560-30-4 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 64.91
TPSA : 66.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.73
Log Po/w (MLOGP) : 1.77
Log Po/w (SILICOS-IT) : 0.01
Consensus Log Po/w : 1.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.31
Solubility : 1.07 mg/ml ; 0.00484 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.654 mg/ml ; 0.00297 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.4
Solubility : 0.879 mg/ml ; 0.00399 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 38560-30-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 38560-30-4 ]

* 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.

  • Upstream synthesis route of [ 38560-30-4 ]
  • Downstream synthetic route of [ 38560-30-4 ]

[ 38560-30-4 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 1039914-85-6 ]
  • [ 38560-30-4 ]
YieldReaction ConditionsOperation in experiment
89.6% at 80℃; for 6 h; A mixture of compound 1 (72.3 g, 0.28 mol), K2CO3 and DMSO(360 mL) was stirred at 80 °C for 6 h. Upon cooling to rt, the mixture was poured into ice-water (200 mL). The resulting precipitate was filtered, washed with water and dried under reduced pressure to yield the title compound as a yellow powder (55.7 g, 89.6percent), Mp:96.4–98.3 C; MS (ESI) m/z (percent): 221.08 [M+H]+.
78.3% With sodium hydride In tetrahydrofuran at 10 - 25℃; Inert atmosphere The 1a (82.0g, 0.32mol) was dissolved in tetrahydrofuran (350ml) in an ice bath was added portionwise sodium hydride (15.3g, 0.64mol) in order to obtain a reaction mixture, reaction mixture at room temperature overnight. Tracking progress of the reaction by TLC, the reaction was complete, the ice bath was added ice-water to the reaction mixture to quench sodium hydride, tetrahydrofuran was removed by distillation under reduced pressure, and extracted twice with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and reduced after the solvent was removed by atmospheric distillation residue was purified by column chromatography to give 1b (55.0g, yellow solid), yield: 78.3percent;
75.2% With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; To the suspension of compound 25 (50.0 gm, 0.195 mol) in 300 ml THF, was added TBAB (1.0 gm) & aqueous solution of KOH (43.68 gm, 0.78 mol) at 0-10° C. and stirred for 10-12 hrs at room temperature.
After completion of reaction THF was evaporated and cold water and ethyl acetate were added.
Organic layer was separated, washed with water (200 ml) and distilled out atmospherically at 50° C. to get a residue.
Isopropyl alcohol was added and the resulting crystals was gradually cooled to 0-5° C. and filtered.
Solid dried at about 50° C. to afford the desired product as off white crystalline solid. Yield: 47.2 g, 75.2percent; Purity: 97.55percent.
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5646 - 5661
[2] Patent: CN104650072, 2016, B, . Location in patent: Paragraph 0122; 0125; 0129; 0130
[3] Patent: US2017/15663, 2017, A1, . Location in patent: Paragraph 0141
[4] Synthetic Communications, 2013, vol. 43, # 1, p. 72 - 79
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 10, p. 2800 - 2810
  • 2
  • [ 1575-61-7 ]
  • [ 100-01-6 ]
  • [ 38560-30-4 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With tetraethylammonium hydroxide In 1,2-dichloro-ethane at 0℃; for 0.166667 h;
Stage #2: at 0 - 85℃; for 5 h;
p-nitroaniline (13.8 g, 0.1 mol), 276 mL of dichloroethane was added to a three-necked flask, cooled to 0 °C in an ice bath, tetraethylammonium hydroxide (103 g, 0.7 mol) was added, and stirred for 10 min in an ice bath. Then, 5-chloropentanoyl chloride (18.6 g, 0.12 mol) was added dropwise, and the temperature was controlled at 0 to 5 °C. After the completion of the dropwise addition, the ice bath was heated to reflux (80 to 85 °C), and the reaction was carried out for 5 hours. The reaction materials and the intermediate state were monitored. The synthesis solution was cooled to room temperature, washed with 500 mL of water, and the organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from acetonitrile to give 19.1 g of Compound 2 as a yellow solid.Its yield: 87percent.
85.4%
Stage #1: With triethylamine In tetrahydrofuran at 60℃; for 2 h;
Stage #2: With sodium t-butanolate In tetrahydrofuran at -10 - 50℃; for 6 h;
Para-nitroaniline (40 g, 0.28 mol) was added to a 1000 mL three-necked flask,Dry tetrahydrofuran (600 ml),Triethylamine (60 mL, 0.44 mol),Under mechanical agitation,5-Chlorovaleryl chloride (56 mL, 0.44 mol) was added portionwiseAfter adding 60 reaction 2h. Then cooled to -10 ° C,Sodium tert-butoxide (69.8 g, 0.92 mol) was added portionwiseJoin the process of controlling the temperature below 0 ,After the temperature was raised to 50 reaction 6h.The tetrahydrofuran was distilled off under reduced pressure,To the residue was added saturated sodium carbonate aqueous 500mL slurry,A large number of solid precipitation, suction filter products, Earthy yellow solid, 52.6 g, m.p.96-99 °C ,Yield 85.4percent.
83.2%
Stage #1: With sodium hydroxide In acetonitrile at 0℃; for 0.166667 h;
Stage #2: at 0 - 20℃; for 2 h;
5 g paranitroaniline and 150 ml acetonitrile were added into a 500 ml three-necked flask, stirred, and cooled to 0° C. in an ice bath. 8.7 g (6 eq) sodium hydroxide was added and stirred in the ice bath for 10 min. Then 9.4 ml of 5-chloro-valeryl chloride (2 eq) (diluted with 10 ml acetonitrile) was dropwise added while controlling the temperature to 0-5° C. After completing the addition, the content of the flask was stirred for 10 min while keeping the temperature. The temperature was naturally raised to 20° C. after removing the ice bath. The reaction was performed for 2 hours. After observing the absence of the reaction intermediate, the reaction solution was cooled to 0° C. in an ice bath, and adjusted to a neutral pH with 2 N of hydrochloric acid. The reaction solution was stood for layering. The resultant acetonitrile layer was concentrated to dryness, and washed with saturated sodium bicarbonate solution (30 ml*3) after adding 50 ml ethyl acetate. All the aqueous phases were combined, and then extracted with ethyl acetate. The resultant organic phases were combined, washed with saturated saline, dried, and concentrated to provide yellow solid containing parts of oil. The mixed solvent of ethyl acetate/petroleum ether (1:1, 8 ml) was added, heated to reflux, completely dissolved, stirred, naturally cooled to crystallize and filtered to obtain 6.64 g yellow solid. Yield: 83.2percent. Purity: 99.0percent (HPLC). EI-MS (m/z): 220.1. HNMR (400 MHz, DMSO, ppm) δ: 8.24 (d, J=8.8 Hz, 2H), 7.63 (d, J=8.8 Hz, 2H), 3.71 (t, J=6.0 Hz, 2H), 2.48 (t, J=6.6 Hz, 2H), 1.84-1.91 (m, 4H).
Reference: [1] Patent: CN108558741, 2018, A, . Location in patent: Paragraph 0055-0066
[2] Patent: CN107400131, 2017, A, . Location in patent: Paragraph 0026; 0031; 0033-0035
[3] Patent: US2016/280646, 2016, A1, . Location in patent: Paragraph 0020-0022
[4] Patent: WO2015/162551, 2015, A1, . Location in patent: Page/Page column 13
  • 3
  • [ 4509-90-4 ]
  • [ 100-01-6 ]
  • [ 38560-30-4 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃;
Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃;
Part A: 4-Nitroaniline (30.0 g, 217.2 mmol) and 400 mL of dry THF were stirred together at 0° C. and N,N-diisopropylethylamine (28.3 g, 219.0 mmol) dissolved in 100 mL of THF was slowly added. Then 5-bromovaleryl chloride (43.3 g, 217.2 mmol) in 180 mL of THF was slowly added while maintaining the temperature at 0-5° C. After addition was complete, the reaction was allowed to warm to rt over 2.5 hours. [0732] The reaction was again cooled to 0° C. and potassium t-butoxide (1.0 M in THF, 434 ml, 434 mmol) was added and the reaction allowed to warm to rt overnight. The reaction was evaporated, dissolved in EtOAc and washed with NaHCO3, water, then brine. Next it was dried over sodium sulfate and evaporated to give the corresponding lactam (44.68 g, 96percent yield). LRMS (AP+) 221.1 (M+H)+.
96.82% With pyridine; dmap In tetrahydrofuran at 0 - 100℃; for 1 h; A mixture of 13.8 g (0.l mol) of p-nitroaniline Was added to 55. 2 mL of tetrahydrofuran,11.85 g (0.15 mol) of pyridine was added, And 1. 38 g (10percent w / w) DMAP, The temperature 0 ° C -10 ° C drop of 5-bromo valeryl chloride 23.94 (0.12mol), within 1 hour drop finished,TLC detection of the disappearance of p-nitroaniline, a large number of white crystals precipitated, filtered and washed with 13. 8mL tetrahydrofuran filter cake, 0 ° C -10 ° C to the filtrate slowly add potassium hydroxide 0. 93g(Content: 90percent, 0.15 mol) was added over 1 hour, and the reaction was continued until the completion of the TLC reaction.5 ml of concentrated hydrochloric acid (0.05 mol) was added dropwise to a solution of 5-6. The reaction solution was evaporated to dryness under reduced pressure, and the cake was washed with tetrahydrofuran.And dried to obtain 21.30 g (yield 96.82percent) of the target compound 7.
90%
Stage #1: at 20℃; for 1 h; Green chemistry
Stage #2: at 20℃; for 4 h; Green chemistry
Potassium carbonate 40 g, water 30 mL, p-nitroaniline 57.2 g, tetrahydrofuran 272 mL were added to the reaction flask.Tetra-n-butylammonium bromide (2.0 g) was stirred at room temperature, and 89.5 g of 5-bromovaleryl chloride was added dropwise.After stirring for 1 hour, add 26.4 g of potassium hydroxide and stir at room temperature for 4 hours.40 mL of water and 60 mL of ethyl acetate were added. After stirring, the mixture was allowed to stand for stratification. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo (45°-55° C., -0.085 MPa--0.1 MPa). Light yellow solid.Add 100 mL of ethyl acetate, stir at room temperature for 2 hours, filter, vacuum dry and dry at -0.01 MPa to -0.1 MPa, 45°C to 55°C for 8 hours to 12 hours to obtain 1-(4-nitrophenyl) )-2-Piperidinone 76 g, 90percent yield.
Reference: [1] Patent: US2003/232804, 2003, A1, . Location in patent: Page 102
[2] Patent: CN103694237, 2016, B, . Location in patent: Paragraph 0069-0071
[3] Patent: CN107955002, 2018, A, . Location in patent: Paragraph 0121
[4] Patent: US2003/232804, 2003, A1, . Location in patent: Page 96
  • 4
  • [ 1575-61-7 ]
  • [ 99-99-0 ]
  • [ 38560-30-4 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide In water at 0 - 20℃; for 2.5 h; 4-Nitroaniline(15.0 g, 108.6 mmol), THF (220 mL) and 1N aqueous sodiumhydroxide solution (217 mL) were stirred together at 0 °C, Then5-chlorovalerylchloride (20.20 g, 130.32 mmol) in 50 mL of THF was slowly addedwhile maintaining the temperature at 0-5 °C. After addition wascomplete, the reaction was allowed to warm to rt over 2.5 hours. Thereaction was again cooled to 0 °C. and Sodium hydroxide (13.03 g, 325.8 mmol)was added and the reaction allowed to warm to rt overnight. The reaction wasevaporated, dissolved in EtOAc and washed with 1 N hydrochloric acidwater, and brine. Next it was dried over sodium sulfate and evaporated to givethe corresponding lactam (21.05 g, 88percent yield). 1H NMR (300 MHz, CDCI3):δ 8.26 (d, J = 8.8 Hz, 2H), 7.51 (d, J = 8.8 Hz, 2H), 3.73 (t, J = 5.9 Hz,2H), 2.62 (t, J = 6.5 Hz, 4H),1.96-2.01 (m, 4H).
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 388 - 399
  • 5
  • [ 4789-09-7 ]
  • [ 38560-30-4 ]
YieldReaction ConditionsOperation in experiment
94% at -5 - 40℃; for 2 h; Compound 4 (27.3 g, 0.16 mol) was added to 190 ml of concentrated sulfuric acid (98percent), Stirring, dissolved -5 ° C plus 65percent nitric acid 16g, plus finished warming to room temperature reaction 2h, The reaction solution was poured into 200 g of crushed ice, extracted three times with dichloromethane (200 ml) The organic phase was washed twice (200 ml), washed once with saturated sodium bicarbonate solution (300 ml), dried over anhydrous magnesium sulfate, filtered and the solvent evaporated to give a pale yellow solid (33 g, 0.15 mol) 94percent.
80% at 0 - 5℃; Cold nitric acid (70percent, 54 g, 0.6 mol) was added drop wise to the precooled solution of example-IA (100 gm, 0.57 mol) in 160 ml of Sulphuric acid at 0-5° C. over 1-2 hrs.
After complete addition, reaction mass was quenched over ice-water and stirred for 1 hr.
Filtered off solid, washed with cold water (65 ml*3 times), unloaded and dried at 50-60° C. in hot air oven for about 5-6 hrs.
Pale yellow solid was obtained. Yield: 100.5 gm, 80percent.
The product can be optionally purified from IPA to give off white solid.
Reference: [1] Patent: CN103626689, 2016, B, . Location in patent: Paragraph 0033; 0039-0041
[2] Patent: US2017/15663, 2017, A1, . Location in patent: Paragraph 0138; 0139
  • 6
  • [ 675-20-7 ]
  • [ 350-46-9 ]
  • [ 38560-30-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5339 - 5356
  • 7
  • [ 100-01-6 ]
  • [ 38560-30-4 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 1, p. 72 - 79
[2] Patent: WO2014/203275, 2014, A2,
[3] Patent: CN104650072, 2016, B,
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5646 - 5661
[5] Patent: US9603846, 2017, B2,
[6] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 10, p. 2800 - 2810
  • 8
  • [ 1575-61-7 ]
  • [ 38560-30-4 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 1, p. 72 - 79
[2] Patent: CN104650072, 2016, B,
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5646 - 5661
[4] Patent: CN103626689, 2016, B,
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 10, p. 2800 - 2810
[6] Patent: US2017/15663, 2017, A1,
[7] Patent: US2017/15663, 2017, A1,
  • 9
  • [ 62-53-3 ]
  • [ 38560-30-4 ]
Reference: [1] Patent: CN103626689, 2016, B,
[2] Patent: US2017/15663, 2017, A1,
[3] Patent: US2017/15663, 2017, A1,
  • 10
  • [ 4509-90-4 ]
  • [ 38560-30-4 ]
Reference: [1] Patent: WO2014/203275, 2014, A2,
[2] Patent: US9603846, 2017, B2,
  • 11
  • [ 91131-23-6 ]
  • [ 38560-30-4 ]
Reference: [1] Patent: CN103626689, 2016, B,
  • 12
  • [ 110-91-8 ]
  • [ 38560-30-4 ]
  • [ 503615-03-0 ]
YieldReaction ConditionsOperation in experiment
66%
Stage #1: Cooling with ice
Stage #2: for 2 h; Reflux
Compound 5 (33 g, 0.15 mol), Phosphorus pentachloride (109 g, 0.52 mol), The reaction solution was poured into 500 ml of ice water, the solution was separated, and the aqueous layer was extracted three times with chloroform (100 ml). The reaction mixture was extracted with ethyl acetate, The organic phase was combined, washed once with 500 ml of saturated brine, and dried over anhydrous magnesium sulfate. Filtered and the solvent evaporated to give 57 g of a yellow solid. The solid (57g) added to the reaction flask, morpholine 307ml added, slowly heated to reflux, the reaction 2h, cooling to morpholine hydrochloride solid precipitation, add water 600ml precipitated product, dried yellow solid 30g, two-step reaction total income Rate of 66percent.
53%
Stage #1: With phosphorus pentachloride In chloroform at 20℃;
Stage #2: for 2 h; Heating / reflux
Part B: The lactam (44.68 g, 203.1 mmol) was dissolved in 550 mL of CHCl3 and stirred at rt for 5 minutes then PCl5 (143.6 g, 690.5 mmol) was added portionwise followed by an additional 100 mL of CHCl3. The nitrogen outlet was replaced with a scrubber system consisting of 1N NaOH and the reaction was refluxed for 2 hours. The reaction was then cooled and slowly poured into a 4-liter beaker containing 860 mL of water and 250 mL of CHCl3 already cooled to 0° C. The mixture was stirred about 1/2 hour then transferred to a separatory funnel and separated. The organic layer was dried over sodium sulfate and evaporated to give the chlorinated intermediate (51.9 g, 90percent yield). The intermediate was added to morpholine (172.6 g, 1.98 mol) neat and heated to reflux for 2 hours then cooled. Next 500 mL of CHCl3 and a mixture of 500 mL saturated NaH2PO4 monohydrate and 50 mL of conc. HCl was added. The reaction was transferred to a separatory funnel and washed with saturated NaH2PO4 monohydrate then water and dried over sodium sulfate and evaporated The residue was recrystallized in EtOAc to yield the enamine (28.46 g, 53percent yield) LRMS (ES+) 304.8 (M+H)+.
16 g
Stage #1: With phosphorus pentachloride In dichloromethane at 0 - 30℃; for 2.5 h;
Stage #2: at 125 - 130℃; for 1 h;
In 3 L 4-neck round bottom flask equipped with mechanical stirrer, thermometer and addition funnel, methylene dichloride (120 mL) and PC15 (8515 gm) were added at 25°C. The reaction mixture was stirred for 15 min and cooled to 0°C to 5°C. A solution of l-(4-nitrophenyl)piperidin-2-one (3 gm) in methylene dichloride (120 ml) was added and stirred for 30 min. The reaction mixture was raised to 25°C to 30°C, stirred for 2 hours and cooled to 0°C to 5°C. Water (600 mL) was added and stirred to separate the layer. The separated methylene dichloride was dried over anhydrous sodium sulphate and distilled under vacuum at 45°C to 50°C. Morpholine (156 mL) was added and stirred for 30 min followed by heating at 125-130°C for 30 min. The reaction mixture was cooled to 70°C to 75°C and distilled to remove excess morpholine under vacuum at 70°C to 75°C and cooled to 55°C to 60°C. Methanol (120 mL) and water (60 mL) was added at 55°C to 60°C and cooled to 25°C to 30°C. The reaction mixture was stirred for 30 mins and filtered. The solid was washed with water and dried at 50°C to 55°C under vacuum to obtain 16 gm of 3 -morpholino- 1- (4-nitrophenyl)-5,6-dihydropyridin-2(IH)-one (VI)
16 g
Stage #1: With phosphorus pentachloride In dichloromethane at 0 - 30℃; for 2.5 h;
Stage #2: at 125 - 130℃; for 1 h;
In 3 L 4-neck round bottom flask equipped with mechanical stirrer, thermometer and addition funnel, methylenedichloride (120 mE) and PC15(85 .15 gm) were added at 25° C. The reaction mixture was stirred for 15 mm and cooled to 0° C. to 5° C. A solution of 1 -(4-nitrophenyl)piperidin- 2-one (30 gm) in methylene dichioride (120 ml) was added and stirred for 30 mm. The reaction mixture was raised to25° C. to 30° C., stirred for 2 hours and cooled to 0° C. to5° C. Water (600 mE) was added and stirred to separate the layer. The separated methylene dichloride was dried over anhydrous sodium sulphate and distilled under vacuum at 45°C. to 50°C. Morpholine (156 mE) was added and stirred for 30 mm followed by heating at 125-130° C. for 30 mm. The reaction mixture was cooled to 70° C. to 75° C. and distilled to remove excess morpholine under vacuum at 70° C. to 75° C. and cooled to 55° C. to 60° C. Methanol (120 mE) and water (60 mE) was added at 55° C. to 60° C. and cooled to 25° C. to 30° C. The reaction mixture was stirred for 30 mins and filtered. The solid was washed with water and dried at 50° C. to 55° C. under vacuum to obtain 16 gm of 3-morpholino-1 -(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one (VII).

Reference: [1] Patent: CN103626689, 2016, B, . Location in patent: Paragraph 0033; 0044-0046
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5339 - 5356
[3] Patent: US2003/232804, 2003, A1, . Location in patent: Page 102
[4] Patent: US2003/232804, 2003, A1, . Location in patent: Page 96
[5] Patent: WO2014/203275, 2014, A2, . Location in patent: Page/Page column 35
[6] Patent: US9603846, 2017, B2, . Location in patent: Page/Page column 20; 21
  • 13
  • [ 38560-30-4 ]
  • [ 503615-03-0 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 1, p. 72 - 79
[2] Patent: CN104650072, 2016, B,
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5646 - 5661
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 10, p. 2800 - 2810
[5] Patent: US2017/15663, 2017, A1,
[6] Patent: CN107400131, 2017, A,
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Similarity: 0.81

Chemical Structure| 5367-58-8

[ 5367-58-8 ]

5-Nitro-2-(piperidin-1-yl)aniline

Similarity: 0.76

Chemical Structure| 188604-99-1

[ 188604-99-1 ]

2-(4-Methylpiperidin-1-yl)-5-nitroaniline

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Chemical Structure| 446292-04-2

[ 446292-04-2 ]

4-(4-Nitrophenyl)morpholin-3-one

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Chemical Structure| 170353-34-1

[ 170353-34-1 ]

1-Phenylpiperidine-4-carboxamide

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Piperidines

Chemical Structure| 6574-15-8

[ 6574-15-8 ]

1-(4-Nitrophenyl)piperidine

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Chemical Structure| 5367-58-8

[ 5367-58-8 ]

5-Nitro-2-(piperidin-1-yl)aniline

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Chemical Structure| 188604-99-1

[ 188604-99-1 ]

2-(4-Methylpiperidin-1-yl)-5-nitroaniline

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Chemical Structure| 166438-83-1

[ 166438-83-1 ]

(1-(4-Nitrophenyl)piperidin-3-yl)methanol

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Chemical Structure| 170353-34-1

[ 170353-34-1 ]

1-Phenylpiperidine-4-carboxamide

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