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[ CAS No. 73874-95-0 ] {[proInfo.proName]}

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Product Citations

Canale, Vittorio ; Czekajewska, Joanna ; Klesiewicz, Karolina , et al. DOI: PubMed ID:

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.

Keywords: Arylurea derivatives ; Antibacterial properties ; Anti-MRSA activity ; Anti-VRE activity ; Anti-LRSE activity ; Depolarization of bacterial cell membrane

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Product Details of [ 73874-95-0 ]

CAS No. :73874-95-0 MDL No. :MFCD00798171
Formula : C10H20N2O2 Boiling Point : -
Linear Structure Formula :NHC5H9NHCOOC(CH3)3 InChI Key :CKXZPVPIDOJLLM-UHFFFAOYSA-N
M.W : 200.28 Pubchem ID :723833
Synonyms :
4-(N-Boc-amino)piperidine;4-(tert-Butoxycarbonylamino)piperidine;4-(t-Butoxycarbonylamino)piperidine
Chemical Name :tert-Butyl piperidin-4-ylcarbamate

Calculated chemistry of [ 73874-95-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 59.3
TPSA : 50.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.5
Log Po/w (XLOGP3) : 1.05
Log Po/w (WLOGP) : 0.88
Log Po/w (MLOGP) : 0.86
Log Po/w (SILICOS-IT) : 0.83
Consensus Log Po/w : 1.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.48
Solubility : 6.64 mg/ml ; 0.0332 mol/l
Class : Very soluble
Log S (Ali) : -1.7
Solubility : 4.01 mg/ml ; 0.02 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.05
Solubility : 1.8 mg/ml ; 0.00899 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.1

Safety of [ 73874-95-0 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P280-P301+P312+P330-P302+P352-P305+P351+P338+P310 UN#:N/A
Hazard Statements:H302-H315-H318-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 73874-95-0 ]

* 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 [ 73874-95-0 ]
  • Downstream synthetic route of [ 73874-95-0 ]

[ 73874-95-0 ] Synthesis Path-Upstream   1~20

  • 1
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YieldReaction ConditionsOperation in experiment
99% With hydrogen In methanol for 12 h; J-Butyl-l-benzylpiperidin-4-ylcarbamate (3.80 g, 13.1 mmol) obtained in Preparation Example 1-i was dissolved in 26 ml of methanol in a 100 ml vessel, and a catalytic quantity of 10percent active palladium/carbon was added thereto, and the resulting mixture was reacted under a hydrogen atmosphere for 12 hrs. After the completion of reaction, the reaction mixture was filtered through a cellite pad to remove the active palladium/carbon and the solvent was removed under reduced pressure therefrom. Then, the residue was subjected to a silica gel column chromatography to obtain 2.64 g of the title compound (yield 99percent).1H-NMR (200 MHz, CD3OD) δ 1.36 (s, 9H), 1.84-2.36 (m, 4H), 2.74 (m, 2H), 3.42 (m, 2H), 3.60 (br, IH). LC/MS (M+H): 201; r-Butyl-l-benzylpiperidin-4-ylcarbamate (3.80 g, 13.1 mmol) obtained in Preparation Example 2-i was dissolved in methanol (26 ml) in a 100 ml vessel, and a catalytic quantity of 10percent active palladium/carbon was added thereto. The resulting mixture was reacted under a hydrogen atmosphere for 12 hrs. After the completion of reaction, the reaction mixture was filtered through a cellite pad to remove the active palladium/carbon and the solvent was removed under reduced pressure. Then, the mixture was subjected to a silica gel column chromatography to obtain 2.64 g of the title compound (yield 99percent).1H-NMR (200 MHz, CD3OD) δ 1.36 (s, 9H), 1.84-2.36 (m, 4H), 2.74 (m, 2H), 3.42 (m, 2H), 3.60 (br, IH). LC/MS (M+H): 201; /-Butyl- l-benzylpiperidin-4-ylcarbamate (3.801 g, 13.1 mmol) obtained in Preparation Example 4-i was dissolved in 26 ml of methanol in a100 ml vessel, and a catalytic quantity of 10percent active palladium/carbon was added thereto, and the resulting mixture was reacted under a hydrogen5 atmosphere for 12 hrs. After the completion of reaction, the reaction mixture was filtered through a cellite pad to remove the active palladium/carbon catalyst and the solvent was removed under reduced pressure therefrom. Then, the residue thus obtained was subjected to a silica gel column chromatography to obtain 2.64 g of the title compound (yieldLO 99percent).1H-NMR (200 MHz, CD3OD) δ 1.36 (s, 9H), 1.84-2.36 (m, 4H), 2.74 (m, 2H), 3.42 (m, 2H), 3.60 (br, IH).LC/MS (M+H): 201.
99% With hydrogen In methanol for 12 h; f-Butyl-l-benzylpiperidin-4-ylcarbamate (3.80 g, 13.1 mmol) obtained in Preparation Example I was dissolved in 26 ml of methanol in the 100 ml reaction vessel, catalytic quantities of 10percent active palladium/carbon was added thereto, and reacted under the hydrogen for 12 hrs. After the completion of the reaction, the reduction mixture was filtered through a cellite pad to remove palladium/carbon and the solvent was removed under a reduced pressure. Then, the mixture was subjected to silica gel column chromatography to obtain 2.64 g of the title compound (yield: 99percent).1H-NMR (200 MHz5 CD3OD) δ 1.36 (s, 9H), 1.84-2.36 (m, 4H), 2.74 (m,2H), 3.42 (m, 2H)5 3.60 (br, IH). LC/MS (M+H): 201
96% With hydrogen In methanol at 20℃; To a solution of the compound obtained in the above step (1) (72.6 g) in methanol (350 mL) was added 20 percent palladium-carbon (17.5 g) and the mixture was stirred at room temperature under hydrogen-gas atmosphere overnight. The reaction mixture was filtered by a membrane filter and the filtrate was concentrated in vacuo to obtain 4-(tert-butoxycarbonyl)aminopiperidine (48.3 g, yield: 96 percent) as a pale yellow solid. MS(APCI)m/z; 201 [M+H]+
94% With hydrogenchloride; 10 wt% Pd(OH)2 on carbon; water; hydrogen In methanol Tert-butyl 1-benzylpiperidin-4-ylcarbamate (500 mg, 1.72 mmol) was dissolved in methanol (10 ml) and stirred. 36percent aqueous HCl (169 µl, 1.72 mmol) was added followed by Pd(OH)2/C (525 mg, 689 µmol). Oxygen was then removed under reduced pressure and H2 added to the system (via a balloon) and stirred overnight. The reaction mixture was then filtered through celite and fitrate reduced in vacuo. DCM was then added and washed with 2M NaOH, H2O, saturated NaCl, dried with anhydrous Na2SO4, filtered and concentrated in vacuo to yield a yellow oil (321 mg, 94percent). 1H NMR (300 MHz, MeOH) δ 3.63 - 3.46 (m, 1H, CH), 3.34, (s, NH), 3.23 (ad, J = 12.9 Hz, 2H, 2 × CHpip), 2.97 - 2.71 (m, 2H, 2 × CHpip), 2.08 - 1.09 (m, 2H, 2 × CHpip), 1.61 - 1.40 (m, 11H, 2 × CHpip, 3 × Boc CH3). Mass Spectrum (ESI): m/z 201.2 [M+H]+.
76% With hydrogen In ethanol at 20℃; for 16 h; A solution of the ester 2 from above (66 g, 227.27 mmol) in 1 1 of ethanol is hydrogenated under normal pressure with 10 g of Pd/C (10percent) for 16 hours at room temperature. The mixture is filtered over celite and evaporated under reduced pressure. Recrystallisation from ether gave 34.5 g (76percent) of white crystals. MS (ESI) : 201 [M+H] +, 401 [2M+H] +, 1H-NMR (DMSO-d6) : b (ppm) 6.7 (br d, NH), 3.22 (br m, 1H), 2.88 (dt, 2H), 2.39 (dt, 2H), 1.8 (brs, NH), 1.6 (dt, 2H), 1.35 (s, 9H), 1.18 (dt, 2H).

Reference: [1] Patent: WO2008/54154, 2008, A1, . Location in patent: Page/Page column 33; 34; 76; 77; 162-164
[2] Patent: WO2007/52938, 2007, A1, . Location in patent: Page/Page column 18
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 14, p. 2706 - 2715
[4] Patent: WO2007/46550, 2007, A1, . Location in patent: Page/Page column 117
[5] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 24, p. 5345 - 5352
[6] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7106 - 7109
[7] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 6, p. 788 - 790
[8] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 3, p. 802 - 814
[9] Patent: WO2005/77932, 2005, A2, . Location in patent: Page/Page column 26; 30
[10] Patent: WO2004/78749, 2004, A1, . Location in patent: Page 14
[11] Patent: US6858629, 2005, B1, . Location in patent: Page/Page column 7; 9
[12] Patent: US6399616, 2002, B1,
[13] Patent: US6602872, 2003, B1,
[14] Patent: US5922717, 1999, A,
[15] Patent: US5700801, 1997, A,
[16] Patent: US6200989, 2001, B1,
[17] Patent: US6878712, 2005, B1, . Location in patent: Page/Page column 29
[18] Patent: JP2005/82508, 2005, A, . Location in patent: Page/Page column 23
[19] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3157 - 3162
[20] Medical Science Monitor, 2017, vol. 23, p. 3311 - 3317
[21] Patent: US6140333, 2000, A,
[22] Patent: WO2004/24710, 2004, A1, . Location in patent: Page 16
  • 2
  • [ 50541-93-0 ]
  • [ 24424-99-5 ]
  • [ 73874-95-0 ]
Reference: [1] Patent: US2003/162772, 2003, A1,
[2] Patent: WO2016/191412, 2016, A1, . Location in patent: Page/Page column 33
[3] Medical Science Monitor, 2017, vol. 23, p. 3311 - 3317
[4] Patent: US6140333, 2000, A,
  • 3
  • [ 159874-20-1 ]
  • [ 73874-95-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 18, p. 2475 - 2479
[2] Patent: US5798337, 1998, A,
  • 4
  • [ 50541-93-0 ]
  • [ 73874-95-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 6, p. 788 - 790
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 14, p. 2706 - 2715
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3157 - 3162
[4] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 3, p. 802 - 814
  • 5
  • [ 60211-57-6 ]
  • [ 73874-95-0 ]
Reference: [1] Patent: US2014/171403, 2014, A1, . Location in patent: Page/Page column
  • 6
  • [ 24424-99-5 ]
  • [ 73874-95-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 6, p. 788 - 790
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3157 - 3162
[3] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 3, p. 802 - 814
  • 7
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  • [ 24424-99-5 ]
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Reference: [1] Patent: US2001/51727, 2001, A1,
  • 8
  • [ 220394-91-2 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 18, p. 2475 - 2479
  • 9
  • [ 100-52-7 ]
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  • [ 73889-19-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 2680 - 2693
[2] Patent: WO2017/49295, 2017, A1, . Location in patent: Paragraph 00399
  • 10
  • [ 100-44-7 ]
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  • [ 73889-19-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 834 - 864
[2] Letters in Drug Design and Discovery, 2014, vol. 11, # 9, p. 1070 - 1078
  • 11
  • [ 100-39-0 ]
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Reference: [1] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 6, p. 1681 - 1686
[2] ACS Chemical Neuroscience, 2017, vol. 8, # 11, p. 2496 - 2511
  • 12
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  • [ 160357-94-8 ]
Reference: [1] Patent: WO2018/167276, 2018, A1,
  • 13
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  • [ 127285-08-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4511 - 4525
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 16, p. 4191 - 4195
[3] Patent: EP1433788, 2004, A1, . Location in patent: Page 41
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  • [ 402927-97-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6549 - 6560
[2] Patent: WO2014/184327, 2014, A1,
[3] Bioorganic Chemistry, 2015, vol. 61, p. 21 - 27
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  • [ 287953-38-2 ]
YieldReaction ConditionsOperation in experiment
91% at 20℃; for 16 h; Cooling with ice 5.00 g (25.0 mmol) of BOC-4-aminopiperidine are dissolved in pyridine (19.8 mL) and cooled in an ice bath. 2.13 mL (27.5 mmol) of methanesulfonyl chloride are added slowly. The reaction is stirred at RT for 16 h. After diluting with water, the reaction is extracted with DCM. Organic layers are washed with water, dried with MgS04 and filtered. The solvent is removed under reduced pressure to afford 6.30 g of (1 -Methanesulfonyl-piperidin-4-yl)-carbamic acid tert-butyl ester. Yield: 91 percent; ESI-MS: 279 [M+H]+
89% With triethylamine In dichloromethane at 20℃; for 1 h; EXAMPLE 4; Preparation of 4-(2-chloro-6-fluoro-benzoylamino)- 1 H-pyrazole-3 -carboxylic acid ( 1 -methanesulphonyl-piperidin-4-yl)-amide4A. 4-Amino-1H-pyrazole-3-carboxylic acid (l-methanesulphonyl-piperidin-4-yl) amideTo a stirred solution of 4-(N-BOC amino)piperidine (2.5 g, 12.5 mmoles) in dichloromethane (30 ml) was added triethylamine (2.1 ml, 15.0 mmoles), and then EPO <DP n="165"/>dropwise methanesulphonyl chloride (1.06 ml, 13.8 mmoles). The solution formed was stirred at room temperature for one hour. The reaction mixture was partitioned between EtOAc and water. The organic portion was washed with water, 2N HCl, brine, dried (MgSO4) filtered and evaporated in vacuo to give 4-(N-BOC-amino)-l- methanesulphonylpiperidine as a white solid (3.1g, 89percent).
55% With triethylamine In dichloromethane at 20℃; for 4 h; General procedure: To a stirred solution of 2 (0.20 g, 1.00 mmol) in anhydrous DCM(5 mL) was added Et3N (0.42 mL, 3.00 mmol) at room temperature.Then 3a–i (3.96 mmol) was added in small portions at room temperature.The reaction was stirred for 4 h at this temperature and then quenched the reaction with saturated aqueous solution ofNaHCO3. The aqueous layer was extracted with ethyl acetate(3 10 mL). The combined organic layers were dried over anhydrousNa2SO4, filtered, and concentrated. Silica gel flash columnchromatography (EtOAc/hexanes = 1:2) of the residue gave 4a–ias the product. Dissolved 4a–i (0.34 g, 0.97 mmol) in 25 mL TFAat room temperature, the reaction was stirred at room temperature for 10 h. Distilled the TFA under vacuum and then diluted with saturated aqueous solution of NaHCO3. The aqueous layer wasextracted with ethyl acetate (3 10 mL). The combined organiclayers were dried over anhydrous Na2SO4, filtered, and concentrated.Silica gel flash column chromatography (EtOAc/hexanes =1:1) of the residue gave 5a–i as the product.
Reference: [1] Patent: WO2014/184327, 2014, A1, . Location in patent: Page/Page column 27
[2] Patent: WO2006/77414, 2006, A1, . Location in patent: Page/Page column 163-164
[3] Bioorganic Chemistry, 2015, vol. 61, p. 21 - 27
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6549 - 6560
[5] Patent: US2006/14708, 2006, A1, . Location in patent: Page/Page column 13
[6] Patent: EP2261213, 2010, A1, . Location in patent: Page/Page column 44-45
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Reference: [1] Patent: US2004/259843, 2004, A1,
[2] Patent: US2005/215784, 2005, A1,
  • 17
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Reference: [1] Patent: WO2016/34673, 2016, A1,
  • 18
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  • [ 848500-12-9 ]
YieldReaction ConditionsOperation in experiment
32% at 130 - 160℃; for 9.5 h; A mixture of 2,6-dibromo-pyridine (3.5 g, 14.77 mmol) and piperidin-4-yl-carbamic acid te/f-butyl ester (1.478 g, 7.38 mmol) is heated to 130 0C in a sealed vessel for 6.5 h and 160 0C for 3 h. The residue is cooled and dissolved in CH2CI2 , washed with saturated NaHCO3 (X2), brine, dried (Na2SO4), filtered and concentrated. The residue is then separated via flash chromatography (SiO2, 10-30percent EtOAc/hexanes gradient) to give an intermediate, (6'-bromo-3,4,5,6-tetrahydro-2H-[1 ,2']bipyridinyl-4-yl)-carbamic acid te/f-butyl ester (0.83 g, 32percent). MS (ESI) m/z 356.0, 358.0 (M+1 ), which is taken on to next step.
Reference: [1] Patent: WO2009/150230, 2009, A1, . Location in patent: Page/Page column 179
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YieldReaction ConditionsOperation in experiment
93% With triethylamine In dichloromethane at 0℃; for 2 h; To a solution of ie -butyl piperidin-4-yl carbamate (5.0 g, 25 mmol) in DCM (80 mL) at 0 °C were added EtiN (3.8 g, 38 mmol) and AC2O (2.6 g, 25 mmol). The resulting mixture was stirred at 0 °C for 2 hours. The reaction was quenched with water (30 mL), separated and the organic layer was washed with saturated NaHCC>3 (30 mL), dried over a2S04 and concentrated to give the desired compound (5.6 g, 93percent yield) as a pale yellow solid. LCMS- C: T 1 .88 min; m/z 265.1 [M+Na]+
89% at 0℃; for 2 h; Acetic anhydride (4.71 mL, 49.9 mmol) was added to a solution of terf-butyl piperidin-4- ylcarbamate (10.0 g, 49.9 mmol) and triethylamine (10.4 mL, 74.9 mmol) in anhydrous DCM (100 mL) at 0 °C. The reaction mixture was stirred at 0 C for 2 hours before water (-100 mL) and DCM (-50 mL) were added. The organic phase was separated, washed with a saturated aqueous NaHCC solution (-100 mL) and dried (MgS04). The solvent was removed in vacuo to give the title compound as a white solid (10.72 g, 89percent). 1H NM (400 MHz, CDCIa) δ 4.54 - 4.42 (m, 2H), 3.80 - 3.70 (m, 1 H), 3.70 - 3.58 (m, 1 H), 3.12 (ddd, J = 14.2, 1 1.8, 2.9 Hz, 1 H), 2.78 - 2.65 (m, 1 H), 2.07 (s, 3H), 2.05 - 1.97 (m, 1 H), 1.96 - 1 .87 (m, 1 H), 1.43 (s. 9H), 1.36 - 1.20 (m, 2H).
80% With triethylamine In dichloromethane at 0℃; for 2 h; To a solution of tert-butyl piperidin-4-ylcarbamate (5.0 g, 25.0 mmol) in DCM (80 mL) at 0 00 was added Et3N (3.8 g, 37.5 mmol) and Ac20 (2.6 g, 25.0 mmol). The mixture was stirred at 0 00 for 2 hours. The reaction was quenched by the addition of water (30 mL) and theorganic layer separated and washed with a saturated aqueous solution of NaHCO3 (30 mL),dried (Na2SO4), filtered and concentrated to give the title compound as a white solid (4.8 g,80percent). LCMS: RT 1 .88 mm; m/z 265.1 [M+Na].
Reference: [1] Patent: WO2016/34673, 2016, A1, . Location in patent: Page/Page column 91
[2] Patent: WO2016/34675, 2016, A1, . Location in patent: Page/Page column 68
[3] Patent: WO2017/153520, 2017, A1, . Location in patent: Page/Page column 64
[4] Patent: US2008/227780, 2008, A1, . Location in patent: Page/Page column 53-54
[5] Patent: WO2015/198229, 2015, A1, . Location in patent: Page/Page column 21
[6] Patent: WO2017/153513, 2017, A1, . Location in patent: Page/Page column 88; 107
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YieldReaction ConditionsOperation in experiment
6.61 g With triethylamine In dichloromethane at 0 - 20℃; for 1 h; To a stirred suspension of 4-boc aminopiperidine (CAS Number 73874-95-0, available from Combi Blocks) (5.00 g, 24.960 mmol) in dichloromethane (30 ml) was added triethylamine (10.40 ml, 74.88 mmol) and acetyl chloride (2.1 1 ml, 29.950 mmol) at 0°C and the resulting reaction mixture was stirred at room temperature for 1 h. The resulting reaction mixture was poured into water (100 ml) and extracted with dichloromethane (2 x 100 ml). The combined organic layer was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by column chromatography (30percent ethyl acetate in hexane) yielding ie f-butyl (1 -acetylpiperidin-4-yl) carbamate (6.61 g, 27.310 mmol). MS: ES+ 243.6 (M+1 ).
Reference: [1] Patent: WO2018/167276, 2018, A1, . Location in patent: Paragraph 00146; 00147
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Related Parent Nucleus of
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Aliphatic Heterocycles

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Piperidines

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