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Product Details of [ 71759-89-2 ]

CAS No. :71759-89-2 MDL No. :MFCD01632213
Formula : C3H3IN2 Boiling Point : -
Linear Structure Formula :- InChI Key :BHCMXJKPZOPRNN-UHFFFAOYSA-N
M.W : 193.97 Pubchem ID :606522
Synonyms :
5-Iodo-1H-imidazole
Chemical Name :5-Iodo-1H-imidazole

Calculated chemistry of [ 71759-89-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.3
TPSA : 28.68 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) : -7.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.85
Log Po/w (XLOGP3) : 0.52
Log Po/w (WLOGP) : 1.01
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 2.24
Consensus Log Po/w : 0.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.99
Solubility : 2.0 mg/ml ; 0.0103 mol/l
Class : Very soluble
Log S (Ali) : -0.69
Solubility : 39.3 mg/ml ; 0.203 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.19
Solubility : 1.26 mg/ml ; 0.00649 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.63

Safety of [ 71759-89-2 ]

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 [ 71759-89-2 ]

* 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 [ 71759-89-2 ]
  • Downstream synthetic route of [ 71759-89-2 ]

[ 71759-89-2 ] Synthesis Path-Upstream   1~14

  • 1
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YieldReaction ConditionsOperation in experiment
55% With sodium sulfite In N,N-dimethyl-formamide at 110℃; Inert atmosphere 2,4,5-triiodo-1H-imidazole was reacted with Na2SO3 in DMF (250 mL) and stirring at 110° C. for over night under N2 atmosphere. The reactin mixture was filtered, the filtrate was concentrated and poured into water, then extracted with EtOAc, the organic was washed with water, dried over Na2SO4, concentrated and purified by silica gel column to give 4-iodo-1H-imidazole (Yield=55percent). LC-MS: m/z=195 [M+H+]
Reference: [1] Patent: US2012/245144, 2012, A1, . Location in patent: Page/Page column 118
[2] Journal of Medicinal Chemistry, 1996, vol. 39, # 15, p. 3001 - 3013
[3] Patent: WO2006/38100, 2006, A1, . Location in patent: Page/Page column 78
  • 2
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YieldReaction ConditionsOperation in experiment
48.1% With water; sodium sulfite In ethanol for 72 h; Reflux A mixture of 2 (12.0 g, 37.5 mmol)and Na2SO3 (23.6 g, 187.3 mmol) in EtOH (120 mL) and H2O (20 mL)was refluxed for 72 h. The mixture was concentrated in vacuo andthe residue was extracted with ethyl acetate. The crude productwas purified by recrystallization from dichloromethane to afford 3as a white solid (3.5 g, 48.1percent). Mp 137e139 C. 1H NMR (300 MHz,Chloroform-d) d(ppm) 7.0 (s, 1H), 7.5 (s, 1H). MS (EI) m/z 194.9[MH].
48.1% With sodium sulfite In ethanol; water for 72 h; Reflux 1 (12.0 g, 37.5 mmol) was dissolved in a reaction system of ethanol (120 mL) and water (20 mL)Na2SO3 (23.6 g, 188.0 mmol),The reaction was refluxed for 72 hours,Ethanol was removed under reduced pressure,Ethyl acetate extraction,Dried over anhydrous magnesium sulfate,Remove the solvent,Methylene chloride was recrystallized to give a white solid,Yield 48.1percent.
38 kg With sodium sulfite In water; isopropyl alcoholReflux; Large scale (2) The product of the previous step (4-iodo-1H-imidazole and a little diiodo-substituted imidazole, 78 kg)60 kg of isopropyl alcohol and 240 kg of water were added,Adding 67.5 kg of sodium sulfite,Reflux reaction to raw material disappears.Cooled and filtered (the filtrate used as solvent in the next batch, no emissions)Extraction (using ethyl acetate extraction),Concentration under reduced pressure gave the compound 4-iodo-1H-imidazole (38 kg, purity was 99.2percent by high performance liquid phase).
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 21, p. 4658 - 4666
[2] Synthesis, 1994, # 7, p. 681 - 682
[3] Tetrahedron Asymmetry, 2004, vol. 15, # 13, p. 2021 - 2028
[4] Medicinal Chemistry Research, 2011, vol. 20, # 4, p. 401 - 407
[5] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 293 - 304
[6] Patent: CN107501272, 2017, A, . Location in patent: Paragraph 0085; 0086; 0089; 0090
[7] Patent: CN106674121, 2017, A, . Location in patent: Paragraph 0031; 0034
  • 3
  • [ 288-32-4 ]
  • [ 71759-89-2 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 21, p. 4658 - 4666
[2] Synthetic Communications, 2008, vol. 38, # 17, p. 2881 - 2888
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 10, p. 2944 - 2953
[4] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3741 - 3749
[5] Advanced Synthesis and Catalysis, 2013, vol. 355, # 2-3, p. 499 - 507
  • 4
  • [ 15813-09-9 ]
  • [ 71759-89-2 ]
Reference: [1] Patent: US6313312, 2001, B1,
  • 5
  • [ 1443425-57-7 ]
  • [ 71759-89-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 2-3, p. 499 - 507
  • 6
  • [ 71759-89-2 ]
  • [ 1692-25-7 ]
  • [ 51746-85-1 ]
YieldReaction ConditionsOperation in experiment
52% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 110℃; for 2 h; Microwave irradiation; Inert atmosphere General procedure: Method B: In a20 mL microwave Biotage tube, a 1M Na2CO3 aqueous solution(5 mL) purged with argon were introduced into a mixture purged with argon of 4-iodo-1H-imidazole (1a) (0.194 g, 1.0 mmol), a boronicacid 2 (1.6 mmol) and Pd(PPh3)4 (0.80 g, 0.05 mmol) in DMF (15 mL). The mixture washeated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3j and 3p-3u in yields ranging from 30 to 95percent. Time and temperaturereactions were collected in Table 1.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 46, p. 6347 - 6350
  • 7
  • [ 71759-89-2 ]
  • [ 74-88-4 ]
  • [ 71759-87-0 ]
  • [ 71759-88-1 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 28, p. 5529 - 5532
[2] Patent: WO2017/87837, 2017, A1, . Location in patent: Paragraph 00394
  • 8
  • [ 77-78-1 ]
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  • [ 71759-88-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 4, p. 735 - 739
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 4, p. 735 - 739
  • 9
  • [ 71759-89-2 ]
  • [ 74-88-4 ]
  • [ 71759-87-0 ]
  • [ 71759-88-1 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 28, p. 5529 - 5532
[2] Patent: WO2017/87837, 2017, A1, . Location in patent: Paragraph 00394
  • 10
  • [ 77-78-1 ]
  • [ 71759-89-2 ]
  • [ 71759-88-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 4, p. 735 - 739
  • 11
  • [ 333-27-7 ]
  • [ 71759-89-2 ]
  • [ 71759-88-1 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 23, p. 12220 - 12223
  • 12
  • [ 77-78-1 ]
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  • [ 71759-87-0 ]
  • [ 71759-88-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 4, p. 735 - 739
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 4, p. 735 - 739
  • 13
  • [ 71759-89-2 ]
  • [ 76-83-5 ]
  • [ 96797-15-8 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine In N,N-dimethyl-formamide at 20℃; for 24 h; To a solution of 3 (3.5 g,18.0 mmol) in DMF (70 mL) was added TEA (3.0 mL, 21.7 mmol) andtrityl chloride (5.5 g, 19.7 mmol). After stirring at 20 C for 24 h, thesolution was poured into water. The solid was filtered to yield thecrude compound that was purified by flash column chromatographyon silica gel to afford 4 as a white solid (7.4 g, 94.0percent). Mp148e150 C. 1H NMR (300 MHz, Chloroform-d) d(ppm) 6.9 (m, 1H),7.0e7.2 (m, 6H), 7.25e7.4 (m, 10H). MS (EI) m/z 437.1 [MH].
94% With triethylamine In N,N-dimethyl-formamide at 20℃; for 24 h; 2 (3.5 g, 18.0 mmol) was dissolved in DMF (70 mL),Triethylamine (3.0 mL, 21.6 mmol) was added dropwise,Trityl chloride (5.5 g, 19.7 mmol) was added,After 24 hours at room temperature,Poured into 200mL water,Precipitation of a large number of solids,Suction filtration,Ether filtered and washed,Drying gives a white solid,Yield 94.0percent
93% With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 48 h; To a solution of 4-iodoimidazole (50 g, 258 mmoles) in DMF (500 ml) was added triethyl amine (37.7 ml, 270.6 mmoles) and than triphenylmethyl chloride (69.7 g, 250 mmoles). After stirring at room temperature for 48 hours, the solution was poured into ice water (2.5 L). The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether (200 ml) was added to the crude compound and the solution was filtered to yield 4-IODO-1-TRITYL-LH-IMIDAZOLE (104.1, 93percent) as a white solid. ME (437)
93% With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 48 h; To a solution of 4-iodoimidazole (50 g, 258 mmoles) in DMF (500 ML) was added triethyl amine (37.7 ml, 270.6 mmoles) and than triphenylmethyl chloride (69.7 g, 250 mmoles). After stirring at room temperature for 48 hours, the solution was poured into ice water (2.5 L). The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether (200 ml) was added to the crude compound and the solution was filtered to yield 4-IODO-1-TRITYL-LH-IMIDAZOLE (104.1, 93percent) as a white solid. MH+ (437)
93% With triethylamine In dichloromethane at 25℃; for 17 h; Cooling with ice; Inert atmosphere After dissolving 4-iodo -1Himidazole(compound 1) (1.9g, 10mmol) in dichloromethane (40mL), under ice-cooling,triethylamine (2.1mL, 15mmol), trityl chloride (3.4g, 12mmol) It was added, under argon, andstirred for 17 hours at room temperature (25 ° C). After completion of the reaction, water wasadded, and the mixture was extracted twice with dichloromethane. The combineddichloromethane layers were dried anhydrous sodium sulfate and concentrated under reducedpressure, silica and the resulting crude product was gel column chromatography (eluent:chloroform / n-hexane = 1/1 → chloroform) at Purification, Compound 2 It was obtained (4.1g,9.3mmol, 93percent yield).
93% With triethylamine In dichloromethane at 25℃; for 17 h; Inert atmosphere 4-Iodo-1H-imidazole (Compound 25, manufactured by Wako Pure Chemical Industries, Ltd.) (1.9 g, 10 mmol) was dissolved in dichloromethane (40 mL)Triethylamine (2.1 mL, 15 mmol) and trityl chloride (3.4 g, 12 mmol) were added and the mixture was stirred at room temperature (25 ° C.) for 17 hours under an argon gas atmosphere. After completion of the reaction, water was added and the mixture was extracted twice with dichloromethane. The combined dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (eluent: chloroform / n-hexane = 1/1 → chloroform) to obtain compound 26 (4.1 g, 9.3 mmol, yield 93percent).
93% With triethylamine In dichloromethane at 25℃; for 17 h; Inert atmosphere 4-iodo-1H-imidazole (Compound 13, manufactured by Wako Pure Chemical Industries, Ltd.) (1.9 g, 10 mmol) was dissolved in dichloromethane (40 mL)below freezing,Triethylamine (2.1 mL, 15 mmol),Trityl chloride (3.4 g, 12 mmol) was added,Under an argon gas atmosphere,And the mixture was stirred at room temperature (25 ° C.) for 17 hours.After completion of the reaction,Add water,Extraction was carried out twice with dichloromethane.The combined dichloromethane layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure,The obtained crude product was purified by silica gel column chromatography (eluent (volume ratio): chloroform / n-hexane = 1/1 → chloroform) to obtain Compound 14 (4.1 g, 9.3 mmol, yield 93percent).
92% at 20℃; for 24 h; To a solution of 4-iodoimidazole (1 eq) in DMF at room temperature was added triphenylmethyl chloride (1.2 eq). After stirring at room temperature for 24 h, the solution was poured into ice water and left stirring for 30 min. The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether was added to the crude compound and the solution was filtered to yield 4-iodo-1- TRITYL-LH-IMIDAZOLE (92percent) as a white solid. MH+ (437).
92%
Stage #1: With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.166667 h;
Stage #2: at 20℃; for 16 h;
At 0° C., to a solution of 4-iodo-1H-imidazole (5 g, 25.8 mmol) in DMF (100 mL) was added triethylamine (3.13 g, 30.9 mmol) slowly. After stirring for additional 10 min at 0° C., the reaction mixture was added by TrtCl (7.17 g, 25.7 mmol). The resulting solution was then stirred at room temperature for 16 h. The reaction mixture was poured into 1 L water. A white solid precipitated out and were collected by filtration. The solid was rinsed with MeOH (50 mL×2) and Et2O (50 mL×3), and then dried in vacuo to yield 4-iodo-1-(triphenylmethyl)-1H-imidazole as white solid (10.4 g, 92percent).
90% at 0 - 20℃; 4-lodo-1tf-imidazole (2.8g, 14.6mmol) and trityl chloride (5.Og, 20.5mmol) were dissolved in λ/,λ/-dimethylacetamide (45mL). The solution was cooled to 0"C and triethylamine (4mL, 29.2mmol) added slowly. The reaction mixture was slowly warmed to room temperature. After 48 hours the solution was poured to water(15OmL). The solid was filtered, washed with water, hexane and dried to give a white solid (5.7g) with a yield of 90percent. The product was pure enough for the next step reaction without further purification.
88.9% With triethylamine In N,N-dimethyl-formamide at 20℃; for 48 h; 4-iodo-1H-imidazole (20 g, 103 mmoles) was dissolved in DMF (100 mL) then triethylamine (15.1 mL, 108 mmoles) and triphenylmethyl chloride (27.8 g, 100 mmoles). The reaction mixture was stirred at room temperature for 48 h, then poured into ice water (500 mL), and then evaporated to dryness, and filtered, and dried to give white crystals of 4-iodo-1-triphenylmethyl-1H-imidazole (40 g, 91.7 mmol, 88.9percent).
81% With triethylamine In tetrahydrofuran at 70℃; for 3 h; Inert atmosphere Triethylamine (36.0 mL, 258 mmol) was added to a mixture of 4-iodoimidazole (24.8 g, 128 mmol) and trityl chloride (39.2 g, 141 mmol) in THF (275 mL), the resulting mixture was heated at 70 °C for 3 hours under nitrogen. The reaction was cooled to 45 °C and filtered to remove thesuspended white solid (Et3N.HCI). The filtrate was concentrated in vacuo, dissolved in DCM (500 mL) and washed with 5 wtpercent aq. sodium thiosulfate solution (300 mL). The aqueous layer was extracted with DCM (150 mL). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to afford an off white solid. Hot filtration was carried out with methanol (500 ml) at 90°C to afford a white solid characterised as 4-iodo-1-trityl-imidazole (45.2 g, 104 mmol, 81percentyield). 1H NMR (CDCI3, 400 MHz) O: 7.36-7.44 (m, 9H), 7.28-7.32 (m, 1H), 7.10-7.15 (m, 6H), 6.94 (5, 1 H). LCMS purity >95percent, [M+H] = 437.0, 4.47 mm (analytical long).
71% With triethylamine In tetrahydrofuran at 80℃; 4-Iodoimidazole (0101-1) (10.0 g, 51.6 mmol, 1.0 eq.)Dissolved in 150 ml of tetrahydrofuran,Triphenylmethyl chloride (17.2 g, 61.7 mmol, 1.2 equivalents) andTriethylamine (14.5 ml, 10.4 mmol, 2.0 eq),Heat to 80°C and react overnight.Cooled to room temperature, concentrated under reduced pressure, added ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Methanol and a small amount of dichloromethane were added and stirred for half an hour. The solid was collected by suction, washed twice with methanol, and vacuum dried. ,4-Iodo-1-trityl-1H-imidazole (16 g, yield: 71percent) was obtained as a white solid.
66% With triethylamine In N,N-dimethyl-formamide at 20℃; for 14 h; After dissolving 4-iodo-1H-imidazole (3.0 g, 0.015 mol) and triphenylmethyl chloride (6.0 g, 0.021 mol) in anhydrous N, N-dimethylformamide (50 mL) Deg.] C, triethylamine (7.2 mL, 0.052 mol) was added slowly, and the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated, and then distilled water (100 mL) was added thereto. After stirring at room temperature for 20 minutes, the solid was filtered The filtrate was washed with distilled water and diethyl ether to give the title compound 60-a (4.4 g, 66percent) as a white solid.
59% With triethylamine In water; N,N-dimethyl-formamide Preparation 72
4-Iodo-1-triphenylmethyl-1H-imidazole
To 4-iodo-1H-imidazole (Preparation 71, 3.0 g, 15.3 mmol) in N,N-dimethylformamide (25 ml) was added triphenylmethyl chloride (4.72 g, 16.9 mmol) and then triethylamine (2.5 ml, 18.4 mmol).
After stirring at room temperature for 2.5 h, water (200 ml) was added and the reaction mixture was filtered and washed with water.
The crude solid was chromatographed on silica gel eluding with hexane:ethyl acetate (5:1 and then 2:1).
The material was then recrystallized from hexane and dichloromethane to give the title compound as a white solid (4.0 g, 59percent).
NMR (CDCl3, selected data for the free base: 6.9 (m, 1H), 7.0-7.2 (m, 6H), 7.25-7.4 (m, 10H).
MS (TSP): M/Z (MH+): 436.3; C22H17129IN2+H requires 437.1.
55.57% With triethylamine In tetrahydrofuran at 70℃; for 3 h; 4-iodoimidazole (5.38g, 27.72mmol) was dissolved in THF (86ml_). Trityl chloride, (8.5g, 30.49mmol) and triethylamine (7.73ml_, 55.44mmol) were added and the reaction was heated at 70 °C. After 3 h, TLC showed that the reaction had gone to completion. Therefore, the reaction mixture was allowed to cool to 45 C and filtered to remove the suspended white solid. The filtrate was concentrated, redissolved in DCM (300 mL) and washed with 5 wtpercent aq. sodium thiosulfate solution (300 mL), which was back-extracted with DCM (150 mL). The organics were combined, dried over sodium sulfate, filtered and concentrated to yield the crude product. The white solid was taken up in EtOAc (300ml) and heated to reflux for 30 minutes. The mixture was cooled and the solid was obtained by vacuum filtration. The white solid was dried in the vacuum oven for 3 hours affording 4- iodo-1 -trityl-imidazole (6.721 g, 15.40mmol, 55.57percent yield). MS Method 2: RT 2.08 min, ES+ m/z 459 [M+Na]+ H NMR (400MHz, DMSO) δ/ppm: 7.35-7.40 (m, 10H), 7.06-7.1 1 (m, 7H).

Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 57 - 59
[2] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 293 - 304
[3] Patent: CN107501272, 2017, A, . Location in patent: Paragraph 0085; 0086; 0091; 0092
[4] Patent: WO2004/96822, 2004, A2, . Location in patent: Page 262
[5] Patent: WO2004/96823, 2004, A2, . Location in patent: Page 44; 45
[6] Patent: JP2015/93833, 2015, A, . Location in patent: Paragraph 0057; 0058
[7] Patent: JP2015/93831, 2015, A, . Location in patent: Paragraph 0016; 0100; 0101
[8] Patent: JP2015/110563, 2015, A, . Location in patent: Paragraph 0016; 0078; 0079
[9] Patent: WO2004/96822, 2004, A2, . Location in patent: Page 239; 240
[10] Patent: US2016/75711, 2016, A1, . Location in patent: Paragraph 0216-0217
[11] Patent: WO2009/93981, 2009, A1, . Location in patent: Page/Page column 96
[12] Patent: CN108203438, 2018, A, . Location in patent: Paragraph 0142; 0143; 0144; 0145
[13] Patent: WO2016/59412, 2016, A1, . Location in patent: Paragraph 00200; 00201
[14] Synthesis, 1994, # 7, p. 681 - 682
[15] Patent: CN107383024, 2017, A, . Location in patent: Paragraph 0112
[16] Patent: KR101798840, 2017, B1, . Location in patent: Paragraph 1139-1142
[17] Journal of Medicinal Chemistry, 2008, vol. 51, # 10, p. 2944 - 2953
[18] Patent: US6313312, 2001, B1,
[19] Patent: WO2016/55786, 2016, A1, . Location in patent: Paragraph 00231
[20] Journal of Medicinal Chemistry, 1996, vol. 39, # 15, p. 3001 - 3013
[21] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3741 - 3749
[22] Patent: US5932606, 1999, A,
[23] Patent: US2002/19527, 2002, A1,
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Reference: [1] Patent: US2003/125266, 2003, A1,
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