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Product Details of [ 16502-01-5 ]

CAS No. :16502-01-5 MDL No. :
Formula : C11H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :CFTOTSJVQRFXOF-UHFFFAOYSA-N
M.W : 172.23 Pubchem ID :107838
Synonyms :
Chemical Name :2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole

Calculated chemistry of [ 16502-01-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.27
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 57.64
TPSA : 27.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 1.49
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 3.04
Consensus Log Po/w : 1.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.754 mg/ml ; 0.00438 mol/l
Class : Soluble
Log S (Ali) : -1.68
Solubility : 3.59 mg/ml ; 0.0208 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.16
Solubility : 0.0119 mg/ml ; 0.0000692 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 16502-01-5 ]

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

Application In Synthesis of [ 16502-01-5 ]

* 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 [ 16502-01-5 ]
  • Downstream synthetic route of [ 16502-01-5 ]

[ 16502-01-5 ] Synthesis Path-Upstream   1~31

  • 1
  • [ 50-00-0 ]
  • [ 61-54-1 ]
  • [ 16502-01-5 ]
YieldReaction ConditionsOperation in experiment
98% With acetic acid In methanol at 80℃; for 0.5 h; The 1.5 g of tryptamine (Tryptamine) dissolved in acetic acid/methanol (AcOH/MeOH=10:1) in, slowly adding 345 mg of paraformaldehyde (Paraformaldehyde), at a temperature of 80oC reaction under 30 min after, monitoring after the reaction is complete, the reaction system is added to the diluted ammonia (NH4OH/H2O=1:1, 80 ml) in, adjusting PH=10, methylene chloride/methanol (CH2Cl2/MeOH=10:1) extracting 3 times, the collection of organic phase, the obtained organic phase drying, turns on lathe does, over silica gel column chromatography separation to obtain 1.6 g intermediate A, column chromatography in eluting agent is CH2Cl2/MeOH=10:1, the reaction yield is 98percent; product at room temperature light yellow solid.
96.8% at 20℃; for 3 h; Take tryptamine I (5.0 g, 31.2 mmol) in acetic acid (25 ml) was added formaldehyde solution (2.5 mL, 32.7 mmol), and the reaction at room temperature for 3 hours. The product precipitated by suction filtration to give intermediate II (5.2 g, 96.8percent).
89% for 3 h; Reflux Formaldehyde solution 40percent (0.2 ml) was added to a solutionof compound 4 (0.2 g, 1.24 mmol) in 6 ml glacial aceticacid and the mixture was then refluxed for 3 h. The reactionmixture is then allowed to cool before aqueous ammoniawas added until the pH turned alkaline, upon which a precipitatewas formed. The precipitate was extracted 3 timeswith EtOAc. The solution is then washed with water (3 ×30 ml) and once with brine (1 × 30 ml), the filtrate is driedon anhydrous Na2SO4, evaporated under vacuum and purifiedby flash column chromatography on silica gel byeluting with a mixture of DCM/methanol (80:20) to yield89percent a brown solid. MP: 198–203 °C; 1H-NMR (400 MHz,DMSO-d6): δ 2.61 (t, J = 5.50 Hz, 2H) 3.00 (t, J = 5.50 Hz,2H) 3.25 (s., 2H) 6.90–6.96 (m, 1H, Ar–H) 6.97–7.03 (m,1H, Ar–H) 7.27 (d, J = 7.82 Hz, 1H, Ar–H) 7.36 (d, J =7.82 Hz, 1H, Ar–H) 10.67 (br. s, 1H, NH). 13C-NMR (400MHz, DMSO-d6): δ 22.40, 42.96, 43.72, 107.34, 111.26,117.64, 118.63, 120.72, 127.65, 134.25, 135.99. MS (EI+)m/z: 172 [M+].
1 g With trifluoroacetic acid In acetonitrile for 24 h; Reflux To a refluxing suspension of tryptamine (CAS number 61 -54-1 , available from Combi blocks) (1 .00 g, 6.240 mmol) in 5percent trifluoroacetic acid in acetonitrile (100 ml) was added solution of aqueous formaldehyde (37percent w/v, 0.50 ml, 6.240 mmol) in acetonitrile (25 ml) drop wise over a period of 30 min and the resulting reaction mixture was allowed to reflux for 24 h. The resulting reaction mixture was cooled to ambient temperature, concentrated under reduced pressure and poured into saturated solution of NaHCC>3 (50 ml) and extracted with ethyl acetate (4 x 25 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure yielding 2,3,4,9-tetrahydro-1H -3-carboline (1.00 g, 5.81 1 mmol) which was used further synthesis without further purification. LCMS: Method B: 3.681 min. MS: ES 173.5 (M+1 ).

Reference: [1] Patent: CN106883230, 2017, A, . Location in patent: Paragraph 0012
[2] Patent: CN105669666, 2016, A, . Location in patent: Paragraph 0036; 0047
[3] Medicinal Chemistry Research, 2017, vol. 26, # 12, p. 3173 - 3187
[4] MedChemComm, 2017, vol. 8, # 9, p. 1824 - 1834
[5] Chemistry - A European Journal, 2018, vol. 24, # 9, p. 2065 - 2069
[6] Bioscience, Biotechnology and Biochemistry, 2011, vol. 75, # 2, p. 391 - 392
[7] Organic letters, 2003, vol. 5, # 1, p. 43 - 46
[8] Patent: WO2006/58088, 2006, A2, . Location in patent: Page/Page column 56; 57
[9] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 63 - 70
[10] Patent: WO2014/207240, 2014, A1, . Location in patent: Page/Page column 17
[11] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5964 - 5969
[12] Patent: WO2018/167276, 2018, A1, . Location in patent: Paragraph 00171; 00172; 00176; 00177
[13] Patent: CN108623585, 2018, A, . Location in patent: Paragraph 0114; 0115; 0116; 0117
  • 2
  • [ 61-54-1 ]
  • [ 298-12-4 ]
  • [ 16502-01-5 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With hydrogenchloride In water at 20℃; for 0.25 h;
Stage #2: With potassium hydroxide In water at 25℃; for 61.75 h; Inert atmosphere; Cooling; Reflux
Glyoxylic acid monohydrate (12.66 g, 137.6 mmol) was dissolved in 30.0 mL of deionized water. In addition, tryptamine (20.0 g, 124.5 mmol) was mixed with 380.0 mL of deionized water and treated with 3 drops of HCl to assist tryptamine to dissolve in deionized water. The aqueous solution of tryptamine is orange-yellow cloudy at this time. Before tryptamine was completely dissolved in deionized water, the two above aqueous solutions were mixed and stirred about 15 minutes at room temperature. Then, white emulsion is precipitated in the mixed aqueous solution. In addition, KOH (6.8 g) was dissolved in 34.0 mL of deionized water. The aqueous solution of KOH were slowly added in the mixed aqueous solution and then HCl was added until a PH of about 4. The mixture was stirred for one hour at room temperature, and then placed in a refrigerator for 12 hours. After taking out from the refrigerator, a solid was collected by suction filtration. Then, 320.00 mL of deionized water and 60.00 mL of HCl were added and refluxed for 30 minutes. Again, 60.00 mL of HCl was added and refluxed for 15 minutes, then cooled to room temperature. The mixed solution was placed in the refrigerator for 2 days and the precipitate was collected. The precipitate was added in deionized water and heated to 550 so that the precipitate was dissolved and a dark green mixed aqueous solution was obtained. KOH was added in the mixed aqueous solution until a pH of about 12 and then a large amount of light green solid was precipitated. The solid compound 3 ( 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole, 18.19 g, yield: 84percent) was collected by suction filtration. Spectral data as follow: 1H NMR (400 MHz, d6-DMSO): δ 10.67 (s, 1H), 7.34 (d, J=7.6 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 6.99 (m, 1H), 6.94-6.93 (m, 1H), 3.86 (s, 2H), 3.08 (br s, 2H), 2.98 (t, J=5.2 Hz, 2H), 2.59 (m, 2H); 13C NMR (100 MHz, d6-DMSO): δ 134.99, 133.68, 126.76, 119.67, 117.60, 116.64, 110.27, 106.42, 42.87, 42.14,
80%
Stage #1: With hydrogenchloride In water at 20℃; for 0.25 h;
Stage #2: With hydrogenchloride; potassium hydroxide In water at 20℃; for 1 h;
Firstly, glyoxylic acid monohydrate (12.66 g, 137.6 mmol) was mixed with and dissolved in deionized water (30.00 mL). Tryptamine (20.0 g, 124.5 mmol) was also mixed and stirred with deionized water (380.00 mL), followed by adding several drops of hydrochloric acid. The two water solutions prepared as above were mixed and stirred for 15 minutes at room temperature, and a large amount of white precipitation was formed. In addition, a potassium hydroxide solution was prepared by dissolving potassium hydroxide (KOH, 6.8 g) in deionized water (34.00 mL). The potassium hydroxide solution was slowly added by drops into the mixed solution containing glyoxylic acid monohydrate and tryptamine, followed by adjusting the pH value of the solution to around 4 by hydrochloric acid. The mixture was stirred for one hour at room temperature and was allowed to stand in a freezer for 12 hours. After taken out from the freezer, the mixture was filtered by suction to collect solid, followed by added with deionized water (320.00 mL) and hydrochloric acid (60.00 mL). After refluxed for 30 minutes, the mixture was added with hydrochloric acid (60.00 mL) and refluxed again for 15 minutes, followed by cooling to room temperature. The mixture was allowed to stand in the freezer for two days for precipitation. The solid was collected and then added with deionized water. The mixture was heated to 165° C. to dissolve the solid and a dark green solution was formed. The pH value of the solution was adjusted to 12 by adding potassium hydroxide and a large amount of ligh green precipitation was formed. The solid was filtered by suction and the compound 3 (18.19 g) was obtained. The yield is 80percent. Spectral data as follow: 1H NMR (400 MHz, d6-DMSO) : δ 6 10.67 (s, 1H), 7.34 (d, J=7.6 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 6.99 (m, 1H), 6.94-6.93 (m, 1H), 3.86 (s, 2H), 3.08 (br s, 2H), 2.98 (t, J=5.2 Hz, 2H), 2.59 (m, 2H) ; 13C NMR (100 MHz, d6-DMSO) : δ 134.99, 133.68, 126.76, 119.67, 117.60, 116.64, 110.27, 106.42, 42.87, 42.14, 21.67. The reaction was shown as the following Equation (5).
78%
Stage #1: With hydrogenchloride In water
Stage #2: With potassium hydroxide In water at 20℃; for 1 h;
Example 1; 2-(9-fluorenylmethoxycarbonyl)-2,3,4,9-tetrahydro-1 H-pyrido[3,4- b]indolo-1 -carboxylic acid; Tryptamine (8 g; 50 mmol) was dissolved in H2O (155 ml) by addition of 6M HCI solution. A solution (11 .20 ml) of glyoxalic acid (5.06 g; 68 mmol) in H2O was then added to the reaction mixture.The pH of the reaction mixture was then brought to about 3.5-4 with aqueous 3.5M KOH solution.After stirring for 1 hour at room temperature, the formation of a white precipitate was noted.The reaction mixture was filtered and the precipitate was then washed several times with H2O and acetone. 1 ,2,3,4-Tetrahydro-beta- carboline (8.5 g; yield: about 78percent) was thus obtained.HPLC-MS (MH+ 217); LC-UV purity: 99.3percent (λ = 220 nm) 98percent (λ = 254 nm).
Reference: [1] Patent: US2018/40836, 2018, A1, . Location in patent: Paragraph 0075
[2] Patent: US2017/162794, 2017, A1, . Location in patent: Paragraph 0066
[3] Patent: WO2008/148617, 2008, A1, . Location in patent: Page/Page column 12
[4] Organic Letters, 2014, vol. 16, # 16, p. 4194 - 4197
  • 3
  • [ 343-94-2 ]
  • [ 298-12-4 ]
  • [ 16502-01-5 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With potassium hydroxide In water at 20℃; for 1 h; Inert atmosphere
Stage #2: With hydrogenchloride In water for 1 h; Reflux; Inert atmosphere
General procedure: Commercial tryptamine hydrochloride (4.9 g, 24.9 mmol, 1 eq) and glyoxylic acid (2.6 g, 27.4 mmol, 1.1 eq) were dissolved in 78 mL H2O,and then the solution of KOH (1.38 g, 24.9 mmol, 1 eq) in 6 mL H2O was added dropwise. The mixture was stirredfor 1h and the white precipitate was collected by filtration. The precipitate was dissolved in 78 mL H2O and thesolution was added conc. HCl (6.6 mL) at room temperature. After stirring for one hour under reflux, the solutionwas added 6.6 mL conc. HCl again and stirred for another 0.5 h under reflux. After cooling to r.t., the light-greencrystal was obtained and collected by filtration and then dissolved in 78 mL H2O. The solution was basified by 20percentKOH until pH > 13, and the white precipitate was filtered off and washed with water three times to the titlecompound S16a (3.1 g, 73percent). 1H NMR (400 MHz, DMSO) δ 10.67 (s, 1H), 7.35 (d, J = 7.7 Hz, 1H), 7.27 (d, J =7.9 Hz, 1H), 7.05 – 6.96 (m, 1H), 6.96 – 6.86 (m, 1H), 3.87 (s, 2H), 2.99 (t, J = 5.6 Hz, 2H), 2.60 (t, J = 5.6 Hz,2H). 13C NMR (101 MHz, DMSO) δ 135.9, 134.5, 127.7, 120.6, 118.6, 117.6, 111.2, 107.3, 43.8, 43.1, 22.6.ESI-MS m/z 173 [M + H]+.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 30 - 38
  • 4
  • [ 50-00-0 ]
  • [ 343-94-2 ]
  • [ 16502-01-5 ]
YieldReaction ConditionsOperation in experiment
58.4% With sodium acetate; sodium hydroxide In water takeTryptamine hydrochloride1 (983 mg, 5.0 mmol)withParaformaldehyde(150 mg, 5.0 mmol) stirred in water,Add 3M aqueous sodium acetate solution (2.5 ml),Reflow reaction for more than 4 hours,Add alkaline sodium hydroxide solution to make it alkaline.extraction,Evaporated dry to a yellow solid 2 (502 mg, 58.4percent).
Reference: [1] Patent: CN108084178, 2018, A, . Location in patent: Paragraph 0019
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 5, p. 323 - 330
  • 5
  • [ 606926-46-9 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 29, p. 5507 - 5514
  • 6
  • [ 89424-03-3 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 22, p. 3767 - 3776
  • 7
  • [ 102991-38-8 ]
  • [ 16502-01-5 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1988, vol. 42, # 7, p. 433 - 441
[2] Molecules, 2017, vol. 22, # 12,
[3] ChemMedChem, 2018, vol. 13, # 13, p. 1343 - 1352
[4] Journal of Materials Chemistry C, 2018, vol. 6, # 42, p. 11248 - 11254
  • 8
  • [ 27970-32-7 ]
  • [ 61-54-1 ]
  • [ 16502-01-5 ]
Reference: [1] Heterocycles, 1985, vol. 23, # 1, p. 107 - 110
[2] Journal of Chemical Research, Miniprint, 1988, # 10, p. 2623 - 2640
  • 9
  • [ 20503-92-8 ]
  • [ 61-54-1 ]
  • [ 16502-01-5 ]
Reference: [1] Heterocycles, 1985, vol. 23, # 1, p. 107 - 110
[2] Journal of Chemical Research, Miniprint, 1988, # 10, p. 2623 - 2640
  • 10
  • [ 61-54-1 ]
  • [ 16502-01-5 ]
Reference: [1] Chemische Berichte, 1930, vol. 63, p. 2102,2106
[2] Molecules, 2017, vol. 22, # 12,
[3] Journal of Materials Chemistry C, 2018, vol. 6, # 42, p. 11248 - 11254
  • 11
  • [ 14558-49-7 ]
  • [ 61-54-1 ]
  • [ 16502-01-5 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 10, p. 802 - 805
  • 12
  • [ 3612-20-2 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 29, p. 5507 - 5514
  • 13
  • [ 126781-38-2 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 29, p. 5507 - 5514
  • 14
  • [ 143427-63-8 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 29, p. 5507 - 5514
  • 15
  • [ 606926-43-6 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 29, p. 5507 - 5514
  • 16
  • [ 47064-53-9 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 13, p. 2150 - 2153
  • 17
  • [ 61-54-1 ]
  • [ 73955-61-0 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 23, p. 3981 - 3986
  • 18
  • [ 526-55-6 ]
  • [ 16502-01-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 39, p. 9423 - 9430
  • 19
  • [ 101079-48-5 ]
  • [ 16502-01-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 39, p. 9423 - 9430
  • 20
  • [ 140920-82-7 ]
  • [ 16502-01-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 39, p. 9423 - 9430
  • 21
  • [ 411208-90-7 ]
  • [ 16502-01-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 39, p. 9423 - 9430
  • 22
  • [ 2727-71-1 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 22, p. 3767 - 3776
  • 23
  • [ 89424-04-4 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 22, p. 3767 - 3776
  • 24
  • [ 89424-05-5 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 22, p. 3767 - 3776
  • 25
  • [ 29976-53-2 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 22, p. 3767 - 3776
  • 26
  • [ 615-36-1 ]
  • [ 16502-01-5 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 22, p. 3767 - 3776
  • 27
  • [ 120-72-9 ]
  • [ 16502-01-5 ]
Reference: [1] Medicinal Chemistry Research, 2017, vol. 26, # 12, p. 3173 - 3187
[2] Patent: CN108623585, 2018, A,
  • 28
  • [ 487-89-8 ]
  • [ 16502-01-5 ]
Reference: [1] Medicinal Chemistry Research, 2017, vol. 26, # 12, p. 3173 - 3187
[2] Patent: CN108623585, 2018, A,
  • 29
  • [ 3156-51-2 ]
  • [ 16502-01-5 ]
Reference: [1] Medicinal Chemistry Research, 2017, vol. 26, # 12, p. 3173 - 3187
[2] Patent: CN108623585, 2018, A,
  • 30
  • [ 343-94-2 ]
  • [ 16502-01-5 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1988, vol. 42, # 7, p. 433 - 441
  • 31
  • [ 16502-01-5 ]
  • [ 24424-99-5 ]
  • [ 168824-94-0 ]
YieldReaction ConditionsOperation in experiment
81% for 9 h; 516 mg of intermediate A was dissolved in CH2C12, di-tert-butyl dicarbonate ((Boc) 20) was added,After the reaction was stirred at room temperature for 9 h. After the reaction was monitored, the reaction system was diluted with CH2C12 (20 mL) and extracted with pure waterThree times, and finally washed with saturated brine once, the extracted organic phase collected dry, spin dry, under the silica gel column chromatography665 mg of intermediate B3 was isolated and the eluent in column chromatography was PE / EtOAc = 4: 1 with a reaction yield of 81percent; product
2.5 g With triethylamine In dichloromethane at 0 - 20℃; for 2 h; Inert atmosphere To a stirred solution of 2,3 ,4,9-tetrahydro-1 Η-β-carboline (2.3 g, 13.364 mmol) and triethylamine (2.80 ml, 20.046 mmol) in dichloromethane (45 ml) was added boc anhydride (3.50 g, 16.037 mmol) at 0°C under N2 atmosphere and the resulting reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with dichloromethane (50 ml) and washed with water (2 x 20 ml). The combined organic phase was dried over Na2SC>4, filtered and concentrated under reduced pressure yielding crude fe/f-butyl 1 ,3,4,9-tetrahydro- 2H-β-3-carboline-2-carboxylate (2.50 g, 9.186 mmol), which was used further synthesis without further purification. LCMS: Method B: 2.422 min. MS: ES 217.3 (M-56).
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 11, p. 2197 - 2206
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 639 - 651
[3] Patent: CN106883230, 2017, A, . Location in patent: Paragraph 0037
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 47, p. 14968 - 14972[5] Angew. Chem., 2017, vol. 129, # 47, p. 15164 - 15168,5
[6] Angewandte Chemie - International Edition, 2017, vol. 56, # 21, p. 5760 - 5764[7] Angew. Chem., 2017, vol. 129, p. 5854 - 5858,5
[8] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4780 - 4785
[9] Patent: US5563147, 1996, A,
[10] Patent: WO2006/55752, 2006, A2, . Location in patent: Page/Page column 24
[11] Patent: WO2009/3003, 2008, A2, . Location in patent: Page/Page column 56
[12] Patent: US2005/288317, 2005, A1, . Location in patent: Page/Page column 23
[13] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5964 - 5969
[14] Chemistry - A European Journal, 2018, vol. 24, # 9, p. 2065 - 2069
[15] Patent: WO2018/167276, 2018, A1, . Location in patent: Paragraph 00176; 00178
[16] Patent: CN108623585, 2018, A, . Location in patent: Paragraph 0114; 0115; 0116; 0117
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