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Product Details of [ 13120-77-9 ]

CAS No. :13120-77-9 MDL No. :MFCD00043912
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WVQGZNRUEVFXKR-UHFFFAOYSA-N
M.W : 167.16 Pubchem ID :83159
Synonyms :

Calculated chemistry of [ 13120-77-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.72
TPSA : 55.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 2.62
Log Po/w (WLOGP) : 1.91
Log Po/w (MLOGP) : 0.94
Log Po/w (SILICOS-IT) : 0.12
Consensus Log Po/w : 1.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.287 mg/ml ; 0.00172 mol/l
Class : Soluble
Log S (Ali) : -3.43
Solubility : 0.0627 mg/ml ; 0.000375 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.865 mg/ml ; 0.00518 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 13120-77-9 ]

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

Application In Synthesis of [ 13120-77-9 ]

* 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 [ 13120-77-9 ]
  • Downstream synthetic route of [ 13120-77-9 ]

[ 13120-77-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 13120-77-9 ]
  • [ 16452-01-0 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen In ethanol; water for 3 h; A 500 mL Parr bottle was charged with 2.0 g of 10percent palladium on carbon (50percent water) and covered with 50 mL ethanol. 2-methyl-5-nitroanisole (10.0 g, 59.8 mmol) was dissolved in 100 mL ethanol and added to the catalyst suspension. The reaction was hydrogenated at 50 psi for 3 h. The catalyst was filtered through a celite plug. The filter cake was washed with 150 mL ethanol and the filtrated concentrated under reduced pressure to yield 8.05g (98percent) of 5-amino-2-methylanisole as a clear oil. 'H NMR (400 MHz, CDC13) 8 6. 90 (d, 1 H), 6.23 (m, 2H), 3.78 (s, 3H), 2.11 (s, 3H). 5-amino-2-methylanisole (8.05 g, 58.7 mmol) was dissolved in 244 mL water and 8.1 mL concentrated H2SO4 and cooled to 0°C. NAN02 (4.86 g, 70.4 mmol) in 61 mL water was added dropwise with stirring. Reaction was stirred 30 minutes at 0°C. Urea (0.70 g, 11.7 mmol) was added and stirring continued for an additional 30 minutes. The pale yellow solution was transferred to a dropping funnel and added slowly to a stirred solution of potassium iodide (19.48 g, 117.4 mmol) in 122 mL water. The solution was stirred at ambient temperature for 1 h after completion of the addition. The reaction was extracted with diethyl ether (3 x 300 mL). The organic extracts were combined and washed with 1 M Na2S203 (2 x 200 mL), dried over NA2SO4, filtered and concentrated under reduced pressure to yield 9.60 g (66percent) of 5- iodo-2-methyl anisole as a brown oil. 1H NMR (400 MHz, CDC13) 8 7.19 (dd, 1H), 7.10 (d, 1H), 6.86 (t, 1H), 3.81 (s, 3H), 2.15 (s, 3H). 5-iodo-2-methyl anisole (9.60 g, 38.70 mmol) and diethyl- (3-pyridyl) borane (5.70 g, 38.70 mmol) were dissolved in 60 mL tetrahydrofuran in a 250 mL round bottom flask equipped with a magnetic stirrer. Sodium carbonate (8.20 g, 77.40 mmol) and 30 mL water were added followed by tetrakis (triphenylphosphine) palladium (0) (0.90g, 0.77 mmol) and 15 mL ethanol. The mixture was heated at reflux for 24 h under nitrogen then cooled to ambient temperature. The mixture was diluted with 200 mL water and extracted with diethyl ether (2 x 200 mL). The organic phases were combined and extracted with'N HCI (3 x 150 mL). The acidic extractions were combined and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with diethyl ether (3 x 150 mL) and the extracts were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 7. 71G (99percent) of 2-methyl-5- (3-pyridyl)- anisole as a brown oil. MS (LC-MS) 200.1 (M + H) +. 'H NMR (400 MHz, CDGI3) 8 8.87 (s, 1 H), 8.60 (d, 1 H), 8.03 (dd, 1 H), 7.50 (m, 1 H), 7.25 (d, 1H), 7.08 (d, 1 H), 7.00 (s, 1 H), 3.92 (s, 3H), 2.27 (s, 3H). A 500 mL L hydrogenation vessel was charged with 0.77 g platinum (II) oxide and purged with nitrogen. 2-methyl-5- (3-pyridyl)-anisole (7.71 g, 38.7 mmol) was added as a solution in 150 mL acetic acid. The suspension was hydrogenated at 45 psi for 18 h. The catalyst was filtered through celite and the filter plug was washed with 200 mL acetic acid. The filtrate was concentrated under reduced pressure. The resultant oil was taken up in 300 mL water and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with ethyl acetate (2 x 300 mL) and the extracts were combined and dried over anhydrous sodium sulfate,,. filtered and concentrated under reduced pressure. The resultant oil was taken up in 300 mL hot ethanol. L- (+)-tartaric acid (5.81 g, 38.7 mmol) in 50 mL hot ethanol was added into the ethanol solution and was allowed to stir at ambient temperature for 24 h, forming a white precipitate that was collected by filtration. The white solid was recrystallized from hot 5percent H2O/ETHANOL (200 mL) to yield 4.88 g (35percent) of 5- (3-PIPERIDINYL)-2- methylanisole-L-tartaric acid salt as a white solid. The mother liquors were combined and concentrated under reduced pressure. The resultant oil was taken up in 500 mL diethyl ether and washed with 300 mL saturated aqueous NAHCO3. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was taken up in 200 mL hot ethanol. D- (-)-tartaric acid (3.75 g, 25.0 mmol) in 50 mL hot ethanol was added and was allowed to stir at ambient temperature for 48 h, forming a white precipitate that was collected by filtration. The white solid was recrystallized from hot 5percent H20/ETHANOL (300 mL) to yield 5.36 g (39percent) of 5- (3-PIPERIDINYL)-2-METHYLANISOLE-D-TARTARIC acid salt as a white solid. 'H NMR (400 MHz, DMSOd6) 8 7.06 (d, 1 H), 6.82 (d, 1 H), 6.71 (dd, 1 H), 3.87 (s, 2H), 3.77 (s, 3H), 3.27 (m, 2H), 2.97 (t, 1H), 2.86 (q, 2H), 2.09 (s, 3H), 1.85 (d, 2H), 1.69 (m, 2H). 3- (3-methoxy-4-methylphenyl)-1 H-piperidine-L-tartaric acid salt (4.88 g, 13.73 mmol) was slowly dissolved in hydrobromic acid (50 mL) and the resulting mixture heated at 140 °C for 2 h. After cooling to ambient temperature, the hydrobromic acid and water were distilled off and the resulting brown oil was azeotroped with toluene (3 x 100 mL) and dried under hi vacuum for 18 h. The resultant tan solid (3- (3-hydroxy- 4-METHYLPHENYL)-1 H-PIPERIDINE hydrobromide salt (3.74 g, 13.73 MMOL)) was dissolved in 25 mL water and 50 mL tetrahydrofuran. Sodium bicarbonate (2.31 g, 27.46 mmol) was added followed by dibenzyl-dicarbonate (3.93 g, 13.73 MMOL). The reaction was stirred for 1 h at ambient temperature then diluted with 300 mL diethyl ether and washed with 200 mL 0.5 N HCI. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 33percent ETHYL ACETATE/HEXANES to yield 3.41 g (76percent) of the desired 3- (3-hydroxy-4-methyl-phenyl)-piperidine-1-carboxylic acid benzyl ester as a clear oil. MS (LC-MS) 324.2 (M-H)-. 'H NMR (400 MHz, CDCI3) 8 7.36 (m, 5H), 7.05 (d, 1 H), 6.70 (dd, 1 H), 6.63 (s, 1H), 5.14 (m, 2H), 4.22 (t, 2H), 2.79 (t, 2H), 2.61 (m, 1H), 2.21 (s, 3H), 1.97 (d, 1 H), 1.76 (m, 1 H), 1.57 (m, 2H). HPLC analysis : Chiralcel OJ, 1 mL/min, 40percent ethanol/heptane 0.2percent diethylamine, rt = 10.22 min. ee = 90.4percent. To a solution of 3- (3-hydroxy-4-methyl-phenyl)-piperidine-1-carboxylic acid benzyl ester (2.02g, 6.21 mmol) in 15 mL DIMETHYLFORMAMIDE was added cesium carbonate (4.05g, 12.42 mmol) and ethyl-2-bromoisobutyrate (3.64 mL, 24.83 MMOL). The mixture was heated to 60°C under N2 with stirring for 18 h and cooled to ambient temperature. The resultant brown suspension was diluted with 300 mL water and extracted with diethyl ether (2 x 200 mL). The organic phases were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 20percent ethyl acetate/hexanes to yield 1.36 g (50percent) of the desired 3- [3- (1-ETHOXYCARBONYL-1- methyl-ethoxy)-4-methyl-phenyl]-piperidine-1-carboxylic acid benzyl ester as a clear oil. MS (LC-MS) 462.1 (M + Na) +. 'H NMR (400 MHz, CDCI3) 8 7.34 (m, 5H), 7.06 (d, 1H), 6.73 (d, 1H), 6.52 (s, 1H), 5.13 (m, 2H), 4.22 (m, 4H), 2.74 (q, 1H), 2.70 (t, 1H), 2.57 (m, 1H), 2.19 (s, 3H), 1.96 (d, 1 H), 1.76 (m, 1 H), 1.57 (d, 6H), 1.53 (s, 2H), 1.22 (t, 3H). A 250 mL Parr bottle was charged with 0. 27G of 10percent palladium on carbon (50percent water) and covered with 20 mL ethanol. 3- [3- (1-ETHOXYCARBONYL-1-METHYL- ETHOXY)-4-METHYL-PHENYL]-PIPERIDINE-1-CARBOXYLIC acid benzyl ester (1.36 g, 3.09 mmol) was dissolved in 50 mL ethanol and added to the catalyst suspension. The reaction was hydrogenated at 50 psi for 2 h. The catalyst was filtered through a celite plug. The filter cake was washed with 150 mL ethanol and the filtrated concentrated under reduced pressure. The resultant oil was taken up in 20 mL hot ethanol to which was added L-tartaric acid (464 mg, 3.09 mmol) in 10 mL hot ethanol. The solution was allowed to stir 24 h at ambient temperature. The white crystalline precipitate was collected by filtration to yield 805 mg (57percent) of 2-methyl-2- (2-methyl-5- piperidin-3-yl-phenoxy)-propionic acid ethyl ester L-tartaric acid salt as a white crystalline solid. MS (LC-MS) 306.3 (M + H) +. 'H NMR (400 MHz, DMSOd6) 8 7. 11 (d, 1 H), 6.78 (d, 1 H), 6.44 (s, 1H), 4. 16 (q, 2H), 3.81 (s, 2H), 3. 21 (t, 2H), 2.78 (m, 2H), 2.10 (s, 3H), 1.81 (m, 2H), 1.69 (m, 1H), 1.56 (m, 1H), 1.51 (s, 6H), 1.14 (t, 3H). HPLC analysis: Chiralpak AD, 1 mL/min, 5percentisopropanol/heptane 0.2percent diethylamine, rt = 9.75 min. EE = 100percent. 2-METHYL-2- (2-METHYL-5-PIPERIDIN-3-YL-PHENOXY)-PROPIONIC acid ethyl ester L- tartaric acid salt (155 mg, 0.34 mmol) was dissolved in 50 mL ethyl acetate and washed with 50 mL saturated aqueous NAHCO3. The organic phase was dried over NA2SO4 and concentrated under reduced pressure. The resultant oil was taken up in 2 mL CH2CI2 and 1- (3-DIMETHYLAMINOPROPYL)-3-ETHYL carbodiimide (130 mg, 0.68 mmol) and 4-METHYL-2- [4- (TRIFLUOROMETHYL) PHENYL]-1, 3-THIAZOLE-5-CARBOXYLIC acid (98 mg, 0.34 mmol) were added. The reaction was stirred at ambient temperature under nitrogen for 72 h. The reaction was diluted with 100 mL diethyl ether and washed with water (100 mL), 0.5 N HCI (2 x 100 mL), saturated aqueous NAHCO3 (2 x 100 mL), dried over NA2SO4 and concentrated under reduced pressure to yield 2-methyl-



2- (2-METHYL-5- {1- [4-METHYL-2- (4-TRIFLUOROMETHYL-PHENYL)-THIAZOLE-5-CARBONYL]-PIPERIDIN- 3-YL}-PHENOXY)-PROPIONIC acid ethyl ester (179 mg, 91percent) as a clear oil. MS (LC-MS) 575.0 (M-H)-. 'H NMR (400 MHz, CD3) 6 8.04 (d, 2H), 7.70 (d, 2H), 7.07 (d, 1 H), 6.73 (m, 1H), 6.52 (m, 1H), 4.21 (m, 2H), 2.64 (m, 1H), 2.53 (s, 3H), 2.18 (s, 3H), 2.05 (m, 1 H), 1.81 (m, 2H), 1.62 (m, 2H), 1.57 (m, 6H), 1.21 (m, 3H). A mixture of 2-METHYL-2- (2-METHYL-5- {1- [4-METHYL-2- (4-TRIFLUOROMETHYL-PHENYL)- THIAZOLE-5-CARBONYL]-PIPERIDIN-3-YL}-PHENOXY)-PROPIONIC acid ethyl ester (179 mg, 0.31 MMOL), potassium carbonate (86 mg, 0. 62MMOL), METHANOL (10 mL) and water (2 mL) was heated at reflux for 3 h, cooled to room temperature and concentrated under reduced pressure. The resulting residue was taken up in water (50 mL), acidified with 1 N aqueous hydrochloric acid and extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to yield 151 mg (89percent) OF 2-METHYL-2- (2-METHYL-5- {L- [4-METHYL-2- (4-TRIFLUOROMETHYL- PHENYL)-THIAZOLE-5-CARBONYL]-PIPERIDIN-3-YL}-PHENOXY)-PROPIONIC acid as a white solid. MS (LC-MS) 547.0 (M + H) +. 1 H NMR (400 MHz, CD30D) 88. 13 (d, 2H), 7.78 (d, 2H), 7.08 (d, 1 H), 6.79 (m, 1H), 6.68 (m, 1H), 2.74 (m, 1H), 2.47 (s, 3H), 2.15 (s, 3H), 2.03 (d, 1H), 1.91 (brm, 2H), 1.79 (m, 2H), 1.54 (brs, 6H).
97% With hydrogen In ethanol at 18 - 22℃; for 6.5 h; To a suspension of 2-METHYI-5-NITROANISOLE F1 (1.54 g; 9.21 MMOL) in absolute ethanol (15 mL) was added 10percent Pd/C catalyst (249 mg). The suspension was hydrogenated under a hydrogen filled balloon at atmospheric pressure and room temperature for 6.5 h. The reaction mixture was filtered through a Millex 0.45 micron filter and evaporated to dryness to provide 4-methyl-m-anisidine F2 (1.22 g; 8. 89 mmol ; 97 percent YIELD)
95% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 5.5 h; General procedure: Compound 13a (221 mg, 1.05 mmol) was dissolved in MeOH (8.0 mL) and hydrogenated (1 bar H2) over 10percent palladium on charcoal for 5.5 h at r.t. The mixture was filtered through a pad of Celite and the filtrate was concentrated. The residue was recrystallized from DCM and n-hexane to afford the title compound (193 mg, 1.05 mmol, quant.) as a white solid.
1.86 g With hydrogen In methanol at 20℃; Reference Intermediate R1 4-methyl-3-(methyloxy)aniline [1373] 1-methyl-2-(methyloxy)-4-nitrobenzene (2.5 g, 14.96 mmol) in methanol (50 mL) Ni-Raney (2 g) was added and the reaction mixture was stirred overnight at room temperature under H2 atmosphere (1 atm). The catalyst was filtered off and the residue was purified by SCX cartridge (50 g) to afford the title compound (1.86 g) as a colourless oil. [1375] 1H-NMR (400 MHz, DMSO-d6) δ ppm: 6.73 (1H, d), 6.19 (1H, d), 6.05 (1H, dd), 4.85 (2H, s), 3.68 (3H, s), 1.97 (3H, s); UPLC_B: 0.62 min, 138 [M+H]+.

Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 42, p. 14098 - 14111
[2] European Journal of Organic Chemistry, 2013, # 1, p. 59 - 64
[3] Patent: WO2004/48334, 2004, A1, . Location in patent: Page 159-163
[4] Patent: WO2004/103996, 2004, A1, . Location in patent: Page 48
[5] European Journal of Organic Chemistry, 2009, # 27, p. 4614 - 4621
[6] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 10, p. 979 - 988
[7] Proceedings - Indian Academy of Sciences, Section A, 1951, # 33, p. 35,40
[8] Recueil des Travaux Chimiques des Pays-Bas, 1910, vol. 29, p. 411
[9] Chemische Berichte, 1905, vol. 38, p. 3792
[10] Patent: WO2010/151737, 2010, A2, . Location in patent: Page/Page column 41; 107
[11] Patent: WO2011/69951, 2011, A1, . Location in patent: Page/Page column 45
[12] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4399 - 4426
[13] Patent: WO2012/76877, 2012, A1, . Location in patent: Page/Page column 221-222
[14] Patent: US2013/267510, 2013, A1, . Location in patent: Paragraph 1373-1375
  • 2
  • [ 13120-77-9 ]
  • [ 16452-01-0 ]
Reference: [1] Patent: US2003/144329, 2003, A1,
  • 3
  • [ 13120-77-9 ]
  • [ 1196-65-2 ]
  • [ 16452-01-0 ]
Reference: [1] Chemische Berichte, 1951, vol. 84, p. 557,561
[2] Recueil des Travaux Chimiques des Pays-Bas, 1910, vol. 29, p. 411
  • 4
  • [ 5428-54-6 ]
  • [ 74-88-4 ]
  • [ 13120-77-9 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In N,N-dimethyl-formamide at 40℃; Inert atmosphere General procedure: To a solution of 2-methyl-5-nitrophenol (613 mg, 4.0 mmol) in dehydrated DMF (7 mL) were added potassium carbonate (608 mg, 4.4 mmol) and iodoalkane (12.0 mmol) under an argon atmosphere. The mixture was heated at 40 °C for 2-3 h, then poured into water and extracted with EtOAc. The organic layer was washed with H2O and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the target compound.
74% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 9 h; To a solution of 2-methyl-5-nitrophenol (309 mg, 2.02 mmol) and K2CO3 (400 mg, 2.90 mmol) in DMF (4.0 mL) was added MeI (855 mg, 6.02 mmol). The reaction mixture was stirred for 9 h at r.t. and then diluted with AcOEt. The organic layer was washed with water and brine, dried over MgSO4 and concentrated to give compound 13c as a dark yellow solid (251 mg, 1.50 mmol, 74percent), which was used for the next step without further purification. 1H-NMR (500 MHz, CDCl3) δ: 7.74 (1H, dd, J=2.0, 8.0 Hz), 7.64 (1H, d, J=2.0 Hz), 7.23 (1H, d, J=8.0 Hz), 3.90 (3H, s), 2.28 (3H, s).
72% With potassium carbonate In acetone for 5 h; Heating / reflux [0133] 2-Methoxy-4 nitrobenzyl N,N-bis(2-chloroethyl)phos-phordiamidate (15i). 2-methy-5-nitrophenol (1.53 g, 10 mmol), anhydrous potassium carbonate (1.03 g, 7.5 mmol), and iodomethane (1.56 g, 11 mmol) were suspended in 20 mL of dry acetone and heated to reflux for 5 hours. Water (10 mL) was added and acetone was evaporated. The residue was extracted with CH2Cl2 (220 mL). The CH2Cl2 phase was washed with saturated NaCl solution (220 mL) and dried over Na2SO4. After evaporation, the residue was purified by flash silica gel column chromatography (hexanes/EtOAc, 10:1) to afford 1-methyl-2-methoxy-4-nitrobenzene as a light yellow solid (1.2 g, 72percent). m.p. 72-73° C.; 1H NMR (CDCl3, 200 MHz) δ 2.32 (s, 3H), 3.94 (s, 2H), 7.29 (d, 1H, J=8.2 Hz), 7.68 (d, 1H, J=2.2 Hz), 7.79 (dd, 1H, J=2.2, 8.0 Hz).
Reference: [1] European Journal of Organic Chemistry, 2009, # 27, p. 4614 - 4621
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 10, p. 3156 - 3172
[3] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 10, p. 979 - 988
[4] Patent: US2004/214798, 2004, A1, . Location in patent: Page 18
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  • [ 55730-09-1 ]
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Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 1315
  • 6
  • [ 31910-25-5 ]
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Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 1315
  • 7
  • [ 518990-51-7 ]
  • [ 13120-77-9 ]
Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 1315
  • 8
  • [ 5428-54-6 ]
  • [ 80-48-8 ]
  • [ 13120-77-9 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2801
  • 9
  • [ 67-56-1 ]
  • [ 1427-07-2 ]
  • [ 124-41-4 ]
  • [ 13120-77-9 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 4284,4286
  • 10
  • [ 13120-77-9 ]
  • [ 198821-79-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2879 - 2882
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 9, p. 1323 - 1326
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