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Chemical Structure| 83948-53-2
Chemical Structure| 83948-53-2
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Product Details of [ 83948-53-2 ]

CAS No. :83948-53-2 MDL No. :MFCD02683429
Formula : C8H16BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IOKGWQZQCNXXLD-UHFFFAOYSA-N
M.W : 238.12 Pubchem ID :4460490
Synonyms :

Calculated chemistry of [ 83948-53-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 6
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.95
TPSA : 38.33 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) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.65
Log Po/w (XLOGP3) : 2.05
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 1.96
Log Po/w (SILICOS-IT) : 1.53
Consensus Log Po/w : 2.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.21
Solubility : 1.46 mg/ml ; 0.00614 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.782 mg/ml ; 0.00329 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.9
Solubility : 0.296 mg/ml ; 0.00124 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.49

Safety of [ 83948-53-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 83948-53-2 ]

* 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 [ 83948-53-2 ]
  • Downstream synthetic route of [ 83948-53-2 ]

[ 83948-53-2 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 83948-53-2 ]
  • [ 75178-96-0 ]
Reference: [1] Patent: EP1366018, 2016, B1,
  • 2
  • [ 24424-99-5 ]
  • [ 5003-71-4 ]
  • [ 83948-53-2 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine In dichloromethane; ethyl acetate Reference Example 4
Synthesis of Boc-aminopropyl bromide:
In 20 ml of dichloromethane, 1.222 g (5.58 mmol) of 3-bromopropylamine hydrobromide was dissolved, 0.778 ml (5.58 mmol) of triethylamine was added thereto under ice-cooling, and 50 ml dichloromethane solution of 1.214 g (5.56 mmol) of Boc2O was further added dropwise thereto in 10 minutes, followed by stirring.
After stirring at room temperature for 50 minutes, ethyl acetate was added thereto, followed by separation by washing with 5percent aqueous citric acid solution, water and saturated brine consecutively.
After dehydration with sodium sulfate, the solvent was evaporated under reduced pressure to give 1.304 of the titled compound (98percent).
The structure was identified by 1H-NMR.
1H-NMR (500 MHz,CDCl3) δ (ppm) = 1.44 (9H, s, Boc), 2.05 (2H, quant, -NHCH2CH2CH2Br), 3.28 (2H, q, -NHCH2CH2CH2Br), 3.44 (2H, t, -NHCH2CH2CH2Br), 4.64 (1H, s, NH)
98% With triethylamine In dichloromethane at 20℃; for 1 h; Cooling with ice In 20 ml of 6 dichloromethane, 1.222 g (5.58 mmol) of 3-bromopropylamine hydrobromide was dissolved, 0.778 ml (5.58 mmol) of 126 triethylamine was added thereto under ice-cooling, and 50 ml dichloromethane solution of 1.214 g (5.56 mmol) of Boc2O was further added dropwise thereto in 10 minutes, followed by stirring. After stirring at room temperature for 50 minutes, ethyl acetate was added thereto, followed by separation by washing with 5percent aqueous citric acid solution, water and saturated brine consecutively. After dehydration with sodium sulfate, the solvent was evaporated under reduced pressure to give 1.304 of the titled compound (98percent). The structure was identified by 1H-NMR. 1H-NMR (500 MHz,CDCl3) δ (ppm) = 1.44 (9H, s, Boc), 2.05 (2H, quant, - NHCH2CH2CH2Br), 3.28 (2H, q, -NHCH2CH2CH2Br), 3.44 (2H, t, -NHCH2CH2CH2Br), 4.64 (1H, s, NH)
97% With triethylamine In tetrahydrofuran at 0 - 20℃; 3-Bromopropylamine hydrobromide (100 g, [457] mmol) was suspended in 1.6 L of anhydrous THF. This mixture was cooled to [0°C] in an ice/water bath and stirred vigorously while 190 mL of triethylamine was added. To this mixture was added dropwise tert-butoxycarbonyl anhydride (112.6 g, 516 mmol) in 200 mL THF. The ice bath was allowed to warm to ambient temperature and the mixture was stirred overnight at which time TLC indicated the reaction was complete. The mixture was then filtered and the filtrate was concentrated under vacuum. The residual oil was diluted with 1500 mL hexane and stored at-20°C for 3 days. The mixture was then decanted and the residual solid was dried under vacuum to give [101] g (94percent yield) of the title intermediate as a crystalline white solid. [APOS;H NMR (DMSO-D6,] 300 MHz): [8] 1.35-1. 39 (s, 9H), 1.91-1. 95 [(M,] 2H), 2.99-3. 04 (t, 2H), 3.43-3. 52 (t, 2H), 6.95-6. 99 (t, 1H).
95% With triethylamine In dichloromethane at 20℃; for 14 h; 3-bromopropylamine hydrobromide 4 (5.00 g, 22.8 mmol) was dissolved in dry 100 ml dichloromethane and Boc 2 O (5.48 g, 25.1 mmol) and triethylamine (3.5 mL, 25.1 mmol) were added thereto. The reaction mixture was stirred at room temperature for 14 hours. Thereafter, 100 ml of dichloromethane was added, followed by washing with 1 M hydrochloric acid aqueous solution, water and brine in this order. The organic phase was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 5.17 g of Compound 5 as a colorless oil. Yield 95percent.
94% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; To a mixture of 3-bromopropan-1 -amine hydrobromide (98.5 g, 45 mmol, 1 .0 eq) and Boc20 (93.3 g, 42.8 mmol, 0.95 eq) in DCM (500 ml) was added dropwise DIPEA (64.0 g, 49.5 mmol). The resulting mixture was stirred at room temperature overnight. Then, the reaction mixture was washed with water, 1 N HCI and brine, dried over Na2S04 and filtered. The solvent was evaporated to give the expected compound (95.8 g, 94percent yield) as a white solid.To a suspension of NaH (60 percent in mineral oil) (1 1.1 g, 278 mmol, 1 .3 eq) in DMF (150 ml) was added dropwise a solution of 2-(1 H-indol-3-yl)acetamide (37.2 g, 214 mmol, 1 .0 eq) in DMF (150 ml) at 0°C under N2 and the reaction mixture was stirred for 30 min. Then a solution of the previous compound (55.9 g, 235 mmol, 1.1 eq) in DMF (100 ml) was added dropwise at 0 °C. The mixture was stirred at 0 °C for 30 min and at room temperature for 10 hrs. The reaction mixture was diluted in water (500 ml) and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2S04 and filtered. The solvent was evaporated under vacuum. The crude product was purified by column chromatography over silica gel eluted with MeOH/DCM (0/100 to 3/97) to give the intermediate 3 (52.8 g, 75percent yield) as a solid.
93% With potassium carbonate In 1,4-dioxane; water at 0 - 20℃; for 15 h; A solution of 3-bromopropylamine hydrobromide (1.0 g, 4.6 mmol) in a 2:1 dioxane/H2O (45 mL) was cooled to 0° C. and treated with K2CO3 (6.22 g, 45 mmol) and di-tert-butyl dicarbonate (1.5 g, 6.9 mmol). The reaction was stirred for 15 h while warming to room temperature. The dioxane was removed in vacuo and the remaining aqueous mixture was acidified with 5 N HCl and extracted with ethyl acetate (5*25 mL). The combined organic layers were dried with MgSO4 and yielded 3-bromo-N-(tert-butoxycarbonyl)propylamine as a colorless oil (0.93 g, 93percent). 1H-NMR (CDCl3/TMS, ppm): 1.41 (s 9H, CH3), 2.02 (quintet, J=6.4 Hz, 2H, CH2), 3.23 (m, 2H, NCH2), 3.41 (t, J=6.6 Hz, CH2Br), 4.8 (broad, 1H, NH); 13C-NMR (CDCl3, ppm): 28.3 (CH3), 30.7, 32.6, 38.9 (CH2), 79.3 (quaternary C), 155.9 (CO); MS (CI, m/z): 239, 241 (M+H+ Calc. for C8H16BrNO2 237.03644).
90% With triethylamine In dichloromethane at 0 - 20℃; -Butyl (3-bromopropyI)carbamate. To a suspension of 3-bromopropylamine hydrobromide (10 g, 45.7 mmol) in CH2CI2 (100 mL) cooled in an ice bath was added triethylamine (15.9 mL, 113 mmol). Di-t-butyl-dicarbonate (10 g, 45.7 mmol) was added slowly in portions and the resulting mixture was stirred at 0 °C for 2 hrs and allowed to warm up to room temperature and stirred over-night. The reaction mixture was filtered, condensed and purified by flash chromatography to yield t-butyl (3- bromopropyl)carbamate (9.8 g, 90percent). 3/4 NMR (500 MHz, CDCl3/MeOH-rf,): δ 4.75 ( br s, 1H), 3.44 (t, = 6.6 Hz, 2H), 3.27 (m, 2H), 2.05 (m, 2H), 1.45 (s, 9H).
87% With triethylamine In dichloromethane at 20℃; for 12 h; Di-tert-butyl dicarbonate (3.71 g, 16 9 mmol) and triethylamine (10 mL). were added to a solution of 3-bromopropylamine hydrobromide 3 (3.72 g, 16.9 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at room temperature for 12 hours. The reaction progress was monitored by TLC. After this period, the reaction was complete. The solvent was removed under reduced pressure. Saturated sodium chloride solution (100 mL) was added to this residue and the mixture was extracted with diethyl ether (2×50 mL). The organic phases were combined, washed with saturated sodium chloride solution (3×50 mL) and dried over sodium sulfate. After filtration, the solvent was removed under reduced pressure to give compound 4 in the form of a slightly brown solid. The compound was sufficiently pure to be used in the rest of the synthesis without further purification (3.50 g, 87percent). 1H NMR (200 MHz, CDCl3) δ: 4.63 (s, 1H), 3.42 (t, J=6.5 Hz, 2H), 3.26 (td, J=6.5; 6.5 Hz, 2H), 2.03 (m, J=6.5 Hz, 2H), 1.43 (s, 9H). HMRS (ESI) calculated for C8H16NO2Br [M+H+], m/z 255.0703. found: 255.0695.
87% With triethylamine In dichloromethane at 20℃; for 12 h; di-tert-Butyl dicarbonate (3.71 g, 16.9 mmol) and triethylamine (10 mL) were added to a solution of 3-bromopropylamine hydrobromide 7b (3.72 g, 16.9 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at room temperature for 12 h. The progress of the reaction was monitored by TLC. After this time, reaction was complete. The solvent was removed under reduced pressure. A saturated solution of sodium chloride (100 mL) was added to this residue and the mixture was extracted with diethyl ether (2×50 mL). The organic phases were combined, washed with a saturated solution of sodium chloride (3×50 mL) and dried over sodium sulfate. After filtration, the solvent was removed under reduced pressure to give compound 8 in the form of a slightly brown solid. The compound was sufficiently pure to be used in the rest of the synthesis without additional purification (3.50 g, 87percent). M.p.: 32-33° C. 1H NMR (200 MHz, CDCl3) δ: 4.63 (s, 1H), 3.42 (t, J=6.5 Hz, 2H), 3.26 (td, J=6.5; 6.5 Hz, 2H), 2.03 (m, J=6.5 Hz, 2H), 1.43 (s, 9H); 13C NMR (125 MHz, CDCl3) δ: 156.09, 79.54, 39.96, 32.82, 30.90, 28.48. HRMS (ESI+) calculated for C8H16NO2Br [M+H]+, m/z 255.0703. found: 255.0695. Rf=0.59 (silica; cyclohexane-ethyl acetate 50:50).
83% With sodium hydroxide In dichloromethane; water at 20℃; for 3 - 16 h; To a solution of 3-bromopropylamine hydrobromide (100 g, 457 mmol) in water (250 mL) was added a solution of di-tert-butyl dicarbonate (49.84 g, 228 mmol) in dichloromethane (600 mL). The resulting biphasic mixture was stirred vigorously, then a solution of sodium hydroxide (36.56 g, 914 mmol) in water (250 mL) was added and the mixture was stirred at room temperature for 3 to 16 hours. The organic layer was washed sequentially with water, 0.2 N HCl until the pH reached 1, then again with water until the pH reached 6 to 7. The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 45.18 grams (83percent) of l-tert-butoxycarbonylamino-3-bromopropane as a pale orange oil. 1NMRFAB-MS, m/z 238.0 (m+1), 240.0 (m+1). Analysis for CgHigBrNC^:Calcd: C, 40.35; H, 6.77; N, 5.88; Found: C, 40.12; H, 6.62; N, 6.06.
83%
Stage #1: With trimethylamine In tetrahydrofuran for 0.5 h; Cooling with ice
Stage #2: With 2-(N-methylamino)pyridine In tetrahydrofuran
In a solution of 3-bromopropan-1 -amine hydrobromide (1.00 g, 0.46 mmol) in THE (40m1) trimethylamine (imI, 0.58 mmol) is added and the resulting reaction mixture isstirred for half an hour, then catalytic amount of 2-methylaminopyridine is added into the reaction mixture. Einally, in ice cold condition 1.23 ml of Boc anhydride is also added into it, in a dropwise manner and the reaction mixture is stirred for overnight. Now slowly, the reaction mixture is quenched with ammonium chloride and extracted with ethyl acetate. The combined organic phase is washed with brine and finally dried over anhydrousNa2504. The crude product is further purified by flash chromatography by using 60-1 20mesh silica gel and ethyl acetate/hexane as mobile phase. The product tert-butyl (3-bromopropyl)carbamate is obtained as a yellowish solid upon cooling at 4 00 (Yield: 0.9 g(83percent))
80% With sodium hydrogencarbonate; potassium bromide In chloroform; water for 5 h; Reflux Example A: 2-Amino-N-(3-(3-(2,5-dioxo-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrol-3-yl)-1H-indol-1-yl)propyl)-4-methylpentanamideTert.-butyl-3-bromopropylcarbamate A modified procedure of Wescott et al. (J. Org. Chem. 2003, 68(26): 10058-10066) was used to prepare the title compound. A solution of NaHCO3 (24.4 mmole; 2.0 g) in 80 ml water, di-tert.-butyldicarbonate (24.4 mmole; 5.33 g) and KBr (48.8 mmole; 5.8 g) were added to a stirred suspension of 3-bromopropylammoniumbromide (24.4 mmole; 5.0 g) in 100 ml chloroform. The reaction was refluxed for 5 hours. After cooling to ambient temperature, the organic layer was separated, the aqueous layer extracted with chloroform and the combined organic layers dried with MgSO4, filtered, concentrated and purified by column chromatography. The title compound was obtained as a colorless oil (19.46 mmole; 80 percent).1H NMR (300 MHz, CDCl3) 4.73 (bs, 1H; NH); 3.41 (t; 3J = 6.5 Hz; 2H; CH2Br); 3.24 (m; 2H; CH2N); 2.02 (quint; 3J = 6.5 Hz; 2H; CH2CH2CH2); 1.41 (s; 9H; C(CH3)3).
80% With sodium hydrogencarbonate; potassium bromide In chloroform; water for 5 h; Reflux Example A: 2-Amino-N-(3-(3-(2,5-dioxo-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1 H- pyrrol-3-yl)-1 H-indol-1 -yl)propyl)-4-methylpentanamide rerf.-butyl-3-bromopropylcarbamate A modified procedure of Wescott et al. (J. Org. Chem. 2003, 68(26): 10058-10066) was used to prepare the title compound. A solution of NaHC03 (24.4 mmole; 2.0 g) in 80 ml water, di-te/t-butyldicarbonate (24.4 mmole; 5.33 g) and KBr (48.8 mmole; 5.8 g) were added to a stirred suspension of 3-bromopropylammoniumbromide (24.4 mmole; 5.0 g) in 100 ml chloroform. The reaction was refluxed for 5 hours. After cooling to ambient temperature, the organic layer was separated, the aqueous layer extracted with chloroform and the combined organic layers dried with MgS04, filtered, concentrated and purified by column chromatography. The title compound was obtained as a colorless oil(19.46 mmole; 80 percent). 1 H NMR (300 MHz, CDCI3) 4.73 (bs, 1 H; NH); 3.41 (t; 3J = 6.5 Hz; 2H; CH2Br); 3.24 (m; 2H; CH2N); 2.02 (quint; 3J = 6.5 Hz; 2H; CH?CH?CH?); 1.41 (s; 9H; C(CH3)3).
78.3% With triethylamine In dichloromethane at 0℃; for 0.5 h; 3-Bromopropylamine hydrobromide (105.10 g, 0.480 mol) was placed in a 2 L four-necked flask, and 978.88 g of dichloromethane and 115.8 g of di-tert-butyl dicarbonate (115.13 g, 0.528 mol) And the mixture was stirred at 0 ° C. (ice bath). Then, triethylamine (92.58 g, 0.915 mol) was added to the dropping funnel and added dropwise to the slurry solution in the four-necked flask over 30 minutes. After the start of the dropwise addition, the reaction solution vigorously foamed and a white solid precipitated. After completion of the dropwise addition, the mixture was stirred for 2 hours. After completion of the reaction, 500 ml of pure water was added to the reaction solution and extracted. The obtained organic layer was washed twice with pure water and dried with anhydrous magnesium sulfate. After removing the desiccant, the solvent was distilled off to obtain a colorless transparent oil. 500 ml of hexane was added to this oily substance and crystallization was carried out at -78 ° C. to obtain a white solid. The solid was collected by suction filtration and dried under reduced pressure. It was confirmed by 1 H-NMR measurement that the obtained white solid was tert-butyl 3-bromopropyl carbamate. The yield was 89.55 g and the yield was 78.3percent.
74% With triethylamine In dichloromethane at 0 - 20℃; for 8 h; Inert atmosphere To a stirred solution of 3-bromopropan-l -amine hydrobromide (AQ; 1.0 g, 4.56 mmol) in CH2C12 (10 mL) was added Et3N (1.65 mL, 11.42 mmol) followed by Boc-anhydride (1.095 g, 5.02 mmol) at 0 °C under inert atmosphere. The resulting reaction mixture was stirred for 8 h at RT. After complete consumption of the starting material (by TLC), the reaction mixture was extracted with CH2C12 (2x30 mL). The combined organic extracts were washed with water, brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude. The crude material was purified by silica gel column chromatography eluting with 20percent EtOAc/hexane as eluent to afford AR (0.8 g, 3.35 mmol, 74percent) as a pale-brown liquid. JH NMR (400 MHz, CDC13): δ 4.63 (bs, NH), 3.44 (t, J = 6.4 Hz, 2H), 3.28 (t, J = 6.4 Hz, 2H), 2.08-2.01 (m, 2H), 1.44 (s, 9H).
62.6% With pyridine; sodium hydroxide In tetrahydrofuran; water at 20℃; for 6 h; In a 100 mL flask with 3-Bromo-1-propamine hydrobromide salt (11, 4.4 g, 0.02 mol) and pyridine (10 mL) dissolved in 100 mL tetrahydrofuran/20percentNaOH (w/w) aqueous solution (v/v = 1/1) mixed solution, then di-tert-butyl dicarbonate (Boc2O, 4.8 g, 0.022 mol) dissolved in 20 mL tetrahydrofuran was added dropwise and the mixture was kept stirring for 6 h under room temperature. After that, the reaction mixture was poured into distilled water and extracted with EtOAC, dried with MgSO4 anhydride and concentrated under reduced pressure, and the crude product was purified by flash column chromatography (eluent: EtOAC/hexane = 1/4, v/v) to obtain 3-Bromo-1-propamine-NHBOC (9) as a yellowish oil (3.1 g, 62.6percent yield) . 1H NMR (CDCl3, 300 Hz) δ 4.31(1H, -CHCON-), 3.34(2H, -CH2-), 3.11(2H, -CH2-), 1.99(2H, -CH2-), 1.27 (9H, Boc).
3.4 g
Stage #1: With dmap; triethylamine In dichloromethane at 20℃; for 0.5 h;
Stage #2: With hydrogenchloride In dichloromethane; water
A CH2Cl2 solution (5 mL) containing 4-dimethyl aminopyridine (0.34 g, 0.0028 mol) and triethylamine (1.39 g, 0.0138 mol) was slowly added to a solution of 3-bromopropylamine hydrobromide (3 g, 0.0138 mol) and di-tert-butyl pyrocarbonate (3.15 g, 0.0145 mol) in CH2Cl2 (10mL). After turning transparent, the mixture was continuously stirred at room temperature for 30 min. Water (10 mL) was added and the product was extracted with CH2Cl2, washed with 0.5 M HCl (2×5 mL), dried (Na2SO4), and then evaporated to yield tert-butyl 3-bromopropylcarbamate (as a colorless oil, 3.4 g). o-Methoxyphenyl piperazine (5.30 g, 0.0276 mol) and NaI (1.0 g) were added to a solution of tert-butyl 3-bromopropylcarbamate in CH2Cl2 (20 mL), and the mixture was continuously stirred at room temperature for 5 h. The reaction mixture was washed with water, and the combined organic layer was dried (Na2SO4) and evaporated under a reduced pressure. The crude was purified using silica gel chromatography with ethyl acetate and petroleum ether as eluents to produce intermediate 13 (4.1 g, yield 85percent). Excessive TFA was added to a solution of 13 (4.1 g) in CH2Cl2 (20 mL), and the mixture was stirred at room temperature overnight. Saturated Na2CO3 aq.was added and extracted with CH2Cl2. The combined organic layer was dried (Na2SO4) and then evaporated under a reduced pressure to obtain 14 (2.5 g, yield 86percent).

Reference: [1] Patent: EP1710257, 2006, A1,
[2] Chemical Communications, 2013, vol. 49, # 51, p. 5784 - 5786
[3] Patent: EP3363463, 2018, A2, . Location in patent: Paragraph 0170
[4] Patent: WO2003/99858, 2003, A1, . Location in patent: Page 37
[5] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10058 - 10066
[6] Journal of Medicinal Chemistry, 2000, vol. 43, # 14, p. 2703 - 2718
[7] Tetrahedron Letters, 2001, vol. 42, # 21, p. 3599 - 3601
[8] Organic Preparations and Procedures International, 2009, vol. 41, # 4, p. 301 - 307
[9] Chemical Communications, 2012, vol. 48, # 65, p. 8090 - 8092
[10] Patent: JP6081152, 2017, B2, . Location in patent: Paragraph 0030; 0033
[11] Patent: WO2013/4709, 2013, A1, . Location in patent: Page/Page column 51-52
[12] Patent: JP2004/504268, 2004, A, . Location in patent: Page/Page column 29
[13] Patent: US6703384, 2004, B2, . Location in patent: Page column 25-26
[14] European Journal of Medicinal Chemistry, 2010, vol. 45, # 6, p. 2480 - 2488
[15] Organic and Biomolecular Chemistry, 2006, vol. 4, # 17, p. 3228 - 3234
[16] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 15, p. 4025 - 4037
[17] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 1, p. 267 - 273
[18] Journal of Medicinal Chemistry, 2015, vol. 58, # 13, p. 5287 - 5307
[19] Tetrahedron, 1999, vol. 55, # 39, p. 11619 - 11639
[20] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 19, p. 7008 - 7014
[21] Journal of Medicinal Chemistry, 2010, vol. 53, # 18, p. 6608 - 6617
[22] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 12021 - 12030
[23] Patent: WO2012/138894, 2012, A1, . Location in patent: Page/Page column 203
[24] Molecules, 2015, vol. 20, # 10, p. 18856 - 18869
[25] Journal of Organic Chemistry, 1996, vol. 61, # 1, p. 408 - 412
[26] Organic Letters, 2005, vol. 7, # 19, p. 4091 - 4094
[27] Organic and Biomolecular Chemistry, 2014, vol. 12, # 27, p. 4848 - 4861
[28] Patent: US2014/336373, 2014, A1, . Location in patent: Paragraph 0194
[29] Patent: US2015/361116, 2015, A1, . Location in patent: Paragraph 0142
[30] Journal of the American Chemical Society, 2018, vol. 140, # 23, p. 7313 - 7323
[31] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 16, p. 5457 - 5479
[32] MedChemComm, 2014, vol. 5, # 7, p. 891 - 898
[33] Journal of Medicinal Chemistry, 2015, vol. 58, # 2, p. 718 - 738
[34] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 9, p. 1577 - 1595
[35] Journal of Carbohydrate Chemistry, 2006, vol. 25, # 4, p. 345 - 360
[36] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4924 - 4939
[37] Journal of Medicinal Chemistry, 2004, vol. 47, # 14, p. 3518 - 3536
[38] Patent: WO2006/57868, 2006, A1, . Location in patent: Page/Page column 33
[39] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 2324 - 2328
[40] Patent: WO2017/168451, 2017, A1, . Location in patent: Page/Page column 22
[41] European Journal of Medicinal Chemistry, 2002, vol. 37, # 7, p. 573 - 584
[42] Patent: EP2474541, 2012, A1, . Location in patent: Page/Page column 12
[43] Patent: WO2012/84683, 2012, A1, . Location in patent: Page/Page column 18-19
[44] Journal of the American Chemical Society, 2015, vol. 137, # 6, p. 2366 - 2374
[45] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 4, p. 285 - 288
[46] Patent: JP5846230, 2016, B2, . Location in patent: Paragraph 0202; 0203
[47] Journal of Medicinal Chemistry, 1996, vol. 39, # 7, p. 1372 - 1382
[48] Patent: WO2014/117090, 2014, A1, . Location in patent: Page/Page column 112-113
[49] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6366 - 6377
[50] European Journal of Medicinal Chemistry, 2008, vol. 43, # 2, p. 315 - 326
[51] Chemistry - A European Journal, 2006, vol. 12, # 15, p. 3975 - 3983
[52] Russian Journal of Bioorganic Chemistry, 2005, vol. 31, # 2, p. 189 - 195
[53] Organic Letters, 2000, vol. 2, # 1, p. 6 - 10
[54] Patent: WO2005/123748, 2005, A1, . Location in patent: Page/Page column 88
[55] Patent: US2003/69261, 2003, A1,
[56] Patent: US2003/82623, 2003, A1,
[57] Patent: US2001/56123, 2001, A1,
[58] Patent: US5977115, 1999, A,
[59] Patent: WO2006/135316, 2006, A1, . Location in patent: Page/Page column 65-66
[60] Patent: EP1623710, 2006, A1, . Location in patent: Page/Page column 54
[61] Patent: WO2004/4714, 2004, A1, . Location in patent: Page/Page column 111
[62] Patent: WO2004/5257, 2004, A1, . Location in patent: Page 93
[63] Journal of Organic Chemistry, 2009, vol. 74, # 1, p. 339 - 350
[64] Patent: US6727264, 2004, B1, . Location in patent: Page column 147
[65] Patent: US6727264, 2004, B1, . Location in patent: Page column 57
[66] Patent: US6727264, 2004, B1, . Location in patent: Page column 774
[67] Patent: WO2006/137770, 2006, A1, . Location in patent: Page/Page column 38-39
[68] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 18, p. 4036 - 4046
[69] Macromolecules, 2012, vol. 45, # 10, p. 4175 - 4183
[70] ChemMedChem, 2013, vol. 8, # 1, p. 118 - 124
[71] Patent: EP2599771, 2013, A1, . Location in patent: Paragraph 0419
[72] Chemical Biology and Drug Design, 2013, vol. 81, # 5, p. 577 - 582
[73] Patent: US2014/274877, 2014, A1, . Location in patent: Page/Page column
[74] Patent: US2014/275554, 2014, A1, . Location in patent: Page/Page column
[75] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 83 - 91
[76] Patent: WO2016/183050, 2016, A1, . Location in patent: Paragraph 0053
[77] Patent: WO2017/40024, 2017, A1, . Location in patent: Paragraph 0068
[78] Patent: US2018/2348, 2018, A1,
[79] Patent: US6339090, 2002, B1, . Location in patent: Example 1
  • 3
  • [ 58885-58-8 ]
  • [ 83948-53-2 ]
YieldReaction ConditionsOperation in experiment
66.46% With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 18 h; To a solution of tert-butyl 3-hydroxypropylcarbamate (5 g, 28.57 mmol) indichloromethane (200 mL) was added triphenylphosphine (1 1.52 g, 42.85 mmol) followed by carbon tetrabromide (14.22 g, 42.85 mmol) at 0 °C. The reaction mixture was stirred at rt for 18 h while monitoring by TLC. The solvent was removed under reduced pressure and the residue was purified by column chromatography (60- 120 mesh silica gel) using 5-10percent ethyl acetate in pet-ether to give tert-butyl 3 -bromopropylcarbamate (4.5 g, 66.46percent) as a light-brown liquid. 1H NMR (400 MHz, CDC13) δ ppm 4.63 (1H, s), 3.45- 3.42 (2H, t, J=6.4 Hz), 3.29-3.24 (2H, q, J=6.4 Hz), 2.08-2.01 (2H, m), 1.44 (9H, s).
60% With bromine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere Triphenylphosphine (1.553 g, 5.9 mmol) was dissolved in 30 mL of dichloromethane and cooled to 0° C. Triethylamine (0.830 mL, 5.9 mmol) was added via syringe.
Bromine (0.305 mL, 5.9 mmol) diluted in 20 mL of DCM was added via syringe and the reaction vessel stirred at 0° C. for 1 hr.
Upon warming to room temperature, 8b (0.852 g, 5.4 mmol) suspended in 10 mL of DCM was added via syringe.
The reaction mixture was stirred at room temperature overnight.
Upon concentration under reduced pressure, the crude reaction was purified by flash column chromatography over silica gel with 1:5 ethyl acetate/hexanes (EtOAc:Hex) to give a yellow oil (0.713 g, 3.2 mmol, 60percent).
1H NMR (500 MHz, CDCl3): δ 4.69 (bs, 1H), 3.45 (t, 2H), 3.27 (quar, 2H), 2.06 (quin, 2H), 1.44 (s, 9H) 13C NMR (126 MHz, CDCl3): δ155.97, 79.47, 38.96, 32.65, 30.89, 28.40.)
Reference: [1] Chemistry - A European Journal, 2008, vol. 14, # 5, p. 1392 - 1401
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 1, p. 81 - 85
[3] Journal of Organic Chemistry, 1983, vol. 48, p. 24
[4] Nature Chemistry, 2011, vol. 3, # 2, p. 140 - 145
[5] Patent: WO2012/9309, 2012, A1, . Location in patent: Page/Page column 45
[6] Patent: US2017/74859, 2017, A1, . Location in patent: Paragraph 0069; 0071
[7] Tetrahedron Letters, 1997, vol. 38, # 17, p. 3085 - 3088
  • 4
  • [ 18370-81-5 ]
  • [ 24424-99-5 ]
  • [ 83948-53-2 ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine In dichloromethane at 20℃; To a mixture of 3-bromopropan-l -amine (10.95 g, 50 mmol) and TEA (15.4 mL, 110 mmol) in DCM (100 ml) at 0 °C was added (Boc)20 (11.4 g, 52.5 mmol). The reaction mixture was stirred at room temperature overnight and then washed with water (3x100 mL) and the solution of citric acid (100 mL). The organic layer was dried over anhydrous Na2S04 and concentrated to give the product as yellow oil (9.0 g, yield 76percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 7, p. 2390 - 2394
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 35, p. 6794 - 6799
[3] Angewandte Chemie, International Edition, 2015, vol. 54, # 10, p. 2960 - 2965[4] Angewandte Chemie, 2015, vol. 127, # 10, p. 3003 - 3008,6
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 19, p. 4031 - 4041
[6] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 2, p. 297 - 305
[7] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2183 - 2195
[8] Journal of the American Chemical Society, 2000, vol. 122, # 37, p. 8898 - 8909
[9] ChemMedChem, 2018, vol. 13, # 15, p. 1597 - 1607
[10] Patent: WO2012/33858, 2012, A2, . Location in patent: Page/Page column 88
[11] Journal of the American Chemical Society, 2011, vol. 133, # 50, p. 20288 - 20300
[12] Inorganic Chemistry, 2011, vol. 50, # 14, p. 6472 - 6481
[13] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 9, p. 2263 - 2275
[14] Organic Letters, 2004, vol. 6, # 2, p. 261 - 264
[15] Chemical Communications, 2007, # 4, p. 398 - 400
[16] European Journal of Organic Chemistry, 2001, # 10, p. 1903 - 1915
[17] Patent: US6362338, 2002, B1, . Location in patent: Example 5
[18] Patent: WO2015/193255, 2015, A1, . Location in patent: Page/Page column 28
  • 5
  • [ 24424-99-5 ]
  • [ 83948-53-2 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide In tetrahydrofuran at 20℃; for 3 h; The NaOH solution (1 N, 132 ml) is slowly added to the 3 - bromo - propylamine hydrobromide 9 (13.40 g, 60 mmol) of di-T-butyl ester and ((Boc)2 O, 13.1 g, 60 mmol) in THF (200 ml) stirring in the mixture, the reaction mixture stirring at room temperature 3 h. After removing the THF, the residue redissolved in diethyl ether (60 ml) in, for HCl (1 N), saturated NaHCO3 And NaCl washing, by Na2 SO4 Drying. The mixture is filtered and concentrated, to obtain compound 10 of light yellow oily matter (13.42 g, 94percent).
Reference: [1] Patent: CN107501297, 2017, A, . Location in patent: Paragraph 0114; 0115; 0116
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2787 - 2798
  • 6
  • [ 24424-99-5 ]
  • [ 83948-53-2 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12 h; Inert atmosphere
Stage #2: With 1H-imidazole In ethanol at 20℃; for 0.5 h;
3-bromopropylamine hydrobromide 1(4.000 g, 18.3 mmol) and di-tert-butyl dicarbonate (7.987 g, 36.6 mmol) were dissolved in anhydrous DCM (100 mL) under nitrogen gas flow. To the stirred solution was added DiPEA (3.50 mL, 20.2 mmol). After 12 hours the solvent was removed and the residue dissolved in ethanol (10 mL) to which imidazole(18.7 mmol) was added and stirred for 30 minutes. The mixture was diluted with chloroform (100 mL) and washed with 1percent HCI solution (3 x 50 mL). The organic phase was dried with sodium sulphate and evaporated to yield 2 (4.389 g, 95percent). 1H NMR (500 MHz, CDCI3): O 3.44 (t, J = 6.5 Hz, 2H), 3.27 (t, J = 6.5 Hz, 2H), 2.05 (p, J = 6.5 Hz, 2H), 1.44 (5, 9H).
Reference: [1] Patent: WO2015/176135, 2015, A1, . Location in patent: Page/Page column 14; 33
  • 7
  • [ 24424-99-5 ]
  • [ 5003-71-4 ]
  • [ 83948-53-2 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In 1,4-dioxane; water 3-(2,5,7,8-Tetramethyl-(2R-(4R,8,12-trimethyltridecyl)chroman-6-yloxy)propyl-1-ammonium Chloride (19)
A solution of 3-bromopropylamine hydrobromide (1.0 g, 4.6 mmol) in a 2:1 dioxane/H2O (45 mL) was cooled to 0° C. and treated with K2CO3 (6.22 g, 45 mmol) and di-tert-butyl dicarbonate (1.5 g, 6.9 mmol).
The reaction was stirred for 15 h while warming to room temperature.
The dioxane was removed in vacuo and the remaining aqueous mixture was acidified with 5 N HCl and extracted with ethyl acetate (5*25 mL).
The combined organic layers were dried with MgSO4 and yielded 3-bromo-N-(tert-butoxycarbonyl)propylamine as a colorless oil (0.93 g, 93percent).
1H-NMR (CDCl3/TMS, ppm): 1.41 (s 9H, CH3), 2.02 (quintet, J=6.4 Hz, 2H, CH2), 3.23 (m, 2H, NCH2), 3.41 (t, J=6.6 Hz, CH2Br), 4.8 (broad, 1H, NH); 13C-NMR (CDCl3, ppm): 28.3 (CH3), 30.7, 32.6, 38.9 (CH2), 79.3 (quaternary C), 155.9 (CO); MS (CI, m/z): 239, 241 (M+H+Calc. for C8H16BrNO2 237.03644).
93% With K2CO3 In 1,4-dioxane; water 3-(2,5,7,8-Tetramethyl-(2R-(4R,8,12-trimethyltridecyl)chroman-6-yloxy)propyl-1-ammonium Chloride (19)
A solution of 3-bromopropylamine hydrobromide (1.0 g, 4.6 mmol) in a 2:1 dioxane/H2O (45 mL) was cooled to 0° C. and treated with K2CO3 (6.22 g, 45 mmol) and di-tert-butyl dicarbonate (1.5 g, 6.9 mmol).
The reaction was stirred for 15 h while warming to room temperature.
The dioxane was removed in vacuo and the remaining aqueous mixture was acidified with 5 N HCl and extracted with ethyl acetate (5*25 mL).
The combined organic layers were dried with MgSO4 and yielded 3-bromo-N-(tert-butoxycarbonyl)propylamine as a colorless oil (0.93 g, 93 percent).
1H-NMR (CDCl3/TMS, ppm): 1.41 (s 9H, CH3), 2.02 (quintet, J=6.4 Hz, 2H, CH2), 3.23 (m, 2H, NCH2), 3.41 (t, J=6.6 Hz, CH2Br), 4.8 (broad, 1H, NH); 13C-NMR (CDCl3, ppm): 28.3 (CH3), 30.7, 32.6, 38.9 (CH2), 79.3 (quaternary C), 155.9 (CO); MS (CI, m/z): 239, 241 (M+H+ Calc. for C8H16BrNO2 237.03644).
Reference: [1] Patent: US6417223, 2002, B1,
[2] Patent: US6770672, 2004, B1,
  • 8
  • [ 24424-99-5 ]
  • [ 5003-71-4 ]
  • [ 83948-53-2 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In 1,4-dioxane; water 3-(2,5,7,8-tetramethyl-(2R-(4R,8, 12-trimethyltridecyl) chroman-6-yl oxy)propyl-1-ammonium chloride (1 9)
A solution of 3-bromopropylamine hydrobromide (1.0 g, 4.6 mmol) in a 2:1 dioxane/H2O (45 mL) was cooled to 0° C. and treated with K2CO3 (6.22 g, 45 mmol) and di-tert-butyl dicarbonate (1.5 g, 6.9 mmol).
The reaction was stirred for 15 h while warming to room temperature.
The dioxane was removed in vacuo and the remaining aqueous mixture was acidified with 5 N HCl and extracted with ethyl acetate (5*25 mL).
The combined organic layers were dried with MgSO4 and yielded 3-bromo-N-(tert-butoxycarbonyl)propylamine as a colorless oil (0.93 g, 93percent).
1H-NMR (CDCl3/TMS, ppm): 1.41 (s 9H, CH3), 2.02 (quintet, J=6.4 Hz, 2H, CH2), 3.23 (m, 2H, NCH2), 3.41 (t, J=6.6 Hz, CH2Br), 4.8 (broad, 1H, NH); 13C-NMR (CDCl3, ppm): 28.3 (CH3), 30.7, 32.6, 38.9 (CH2), 79.3 (quaternary C), 155.9 (CO); MS (CI, m/z): 239, 241 (M+H+Calc. for C8H16BrNO2 237.03644).
Reference: [1] Patent: US2002/107207, 2002, A1,
  • 9
  • [ 24424-99-5 ]
  • [ 5003-71-4 ]
  • [ 144-55-8 ]
  • [ 83948-53-2 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine In 1,4-dioxane Step 1:
N-tert-butoxycarbonyl-3-bromopropylamine.
To a 0° C. solution of 3-bromopropylamine hydrobromide (10.0 g, 45.7 mmol) in 1:1 aqueous dioxane was added triethylamine (12.8 mL, 91.8 mmol), di-tert-butyldicarbonate (20.2 g, 92.6 mmol), and saturated aqueous NaHCO3 (3 mL).
The cold bath was removed and the reaction mixture was stirred for 3.5 hours.
The reaction mixture was extracted three times with ethyl acetate.
The combined organic extracts were washed with 10percent aqueous citric acid and brine, dried over Na2 SO4, filtered, and concentrated in vacuo.
Chromatography on silica gel (10:1, then 6:1, then 3:1 hexane, ethyl acetate) gave N-tert-butoxycarbonyl-3-bromopropylamine (21.1 g, 79percent) as a clear yellow oil.
Reference: [1] Patent: US5486525, 1996, A,
  • 10
  • [ 18370-81-5 ]
  • [ 34619-03-9 ]
  • [ 83948-53-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 964 - 978
  • 11
  • [ 24424-99-5 ]
  • [ 5003-71-4 ]
  • [ 497-19-8 ]
  • [ 83948-53-2 ]
Reference: [1] Patent: US5654431, 1997, A,
  • 12
  • [ 558-13-4 ]
  • [ 58885-58-8 ]
  • [ 83948-53-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 32, p. 6720 - 6724
  • 13
  • [ 541-16-2 ]
  • [ 5003-71-4 ]
  • [ 83948-53-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 33, p. 9715 - 9718[2] Angew. Chem., 2015, vol. 127, p. 9851 - 9855,5
  • 14
  • [ 24424-99-5 ]
  • [ 83948-53-2 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 17, p. 3085 - 3088
[2] Journal of Organic Chemistry, 1983, vol. 48, p. 24
[3] Patent: WO2012/9309, 2012, A1,
[4] Patent: US2017/74859, 2017, A1,
  • 15
  • [ 1069-31-4 ]
  • [ 107-13-1 ]
  • [ 83948-53-2 ]
Reference: [1] Patent: US6281371, 2001, B1,
  • 16
  • [ 112663-43-1 ]
  • [ 83948-53-2 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 17, p. 3085 - 3088
  • 17
  • [ 216959-34-1 ]
  • [ 83948-53-2 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 45, p. 8275 - 8276
  • 18
  • [ 216959-40-9 ]
  • [ 553-91-3 ]
  • [ 83948-53-2 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 45, p. 8275 - 8276
  • 19
  • [ 83948-53-2 ]
  • [ 128550-06-1 ]
Reference: [1] Journal of the American Chemical Society, 1990, vol. 112, # 18, p. 6696 - 6704
  • 20
  • [ 83948-53-2 ]
  • [ 74-89-5 ]
  • [ 442514-22-9 ]
YieldReaction ConditionsOperation in experiment
86% at 20℃; for 4 h; (3-Bromo-propyl)-carbamic acid tert-butyl ester (11.2 g, 47.0 mmol) was combined with 2.0 M Methylamine in THF (100 mL, 200 mmol) and was stirred at room temperature for 4 h. After this period, a precipitate formed in the solution. The solution was filtered and concentrated under reduced pressure to yield 7.58 g (86percent) of (3-methylamino-propyl)-carbamic acid tert-butyl ester as a clear oil. [M+H]+ 188.94.
86% at 20℃; for 4 h; Step 1
Preparation of Example 5a: (3-Methylamino-propyl)-carbamic Acid tert-butyl Ester
Methylamine (100 mL of a 2.00 M solution in THF, 200 mmol) was added to (3-bromo-propyl)-carbamic acid tert-butyl ester (11.2 g, 47.0 mmol) at room temperature under nitrogen and the solution was stirred for 4 h.
The resulting suspension was filtered and concentrated under reduced pressure to give 7.58 g (86percent) of (3-methylamino-propyl)-carbamic acid tert-butyl ester (5a) as a clear oil. [M+H]+188.94.
Reference: [1] Patent: US2006/116515, 2006, A1, . Location in patent: Page/Page column 34
[2] Patent: US2007/123572, 2007, A1, . Location in patent: Page/Page column 16
[3] Organic Preparations and Procedures International, 2009, vol. 41, # 4, p. 301 - 307
  • 21
  • [ 83948-53-2 ]
  • [ 167479-01-8 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 48, p. 17293 - 17296
[2] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10058 - 10066
[3] Russian Journal of Bioorganic Chemistry, 2005, vol. 31, # 2, p. 189 - 195
[4] Journal of the American Chemical Society, 2017, vol. 139, # 16, p. 5680 - 5683
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