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[ CAS No. 3609-53-8 ]

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Chemical Structure| 3609-53-8
Chemical Structure| 3609-53-8
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CAS No. :3609-53-8 MDL No. :MFCD00216474
Formula : C10H10O3 Boiling Point : 295.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :178.18 g/mol Pubchem ID :137990
Synonyms :

Safety of [ 3609-53-8 ]

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:

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  • Upstream synthesis route of [ 3609-53-8 ]
  • Downstream synthetic route of [ 3609-53-8 ]

[ 3609-53-8 ] Synthesis Path-Upstream   1~11

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  • [ 3609-53-8 ]
  • [ 69316-08-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 6, p. 2899 - 2903
[2] Journal of Organic Chemistry, 2015, vol. 80, # 14, p. 7212 - 7218
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  • [ 3609-53-8 ]
  • [ 50446-44-1 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 257,259
[2] Journal of the American Chemical Society, 1959, vol. 81, p. 257,259
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  • [ 56893-25-5 ]
YieldReaction ConditionsOperation in experiment
89% With bromine In chloroform for 3 h; 4-(2-Bromo-acetyl)-benzoic acid methyl ester (A): To a solution of methyl 4-acetylbenzoate (25 g, 0.14 mol) in 500 mL chloroform was added , drop- wise, bromine (22.42 g, 0.14 mol) in 60 mL chloroform over a period of 3 h. The mixture was stirred over night. Water (200 mL) was carefully added to the reaction mixture, mixed well and the organic layer isolated was washed with saturated sodium hydrogen carbonate in water (200 mL), followed by brine (200 mL), dried over anhydrous sodium sulfate, filtered and filtrate evaporated to get pure product as a light yellow powder (32 g, 89percent).-
82% at 20℃; for 2 h; To a solution of methyl 4-acetylbenzoate (8.91 g, 50.0 mmol) in AcOH (80 mL) was added Br2 (2.71 mL, 52.5 mmol) dropwise. The mixture was stirred at room temperature for 2 h. The mixture was cooled to 0° C. and the solid was filtered. The precipitate was washed with 1:1 MeOH in water and was desiccated to give methyl 4-(2-bromoacetyl)benzoate (10.6 g, 82percent) as a tan solid. 1H NMR (400 MHz, CDCl3) δ 8.19-8.12 (m, 2H), 8.04 (d, J=8.5 Hz, 2H), 4.47 (s, 2H), 3.96 (s, 3H).
77% With bromine In acetic acid at 20℃; Methyl 4-acetylbenzoate 105 (8.91 g, 50 mmol) was suspended in acetic acid(80 mL) and the mixture was stirred until a clear solution was reached. Then bromine(8.39 g, 52 mmol) was added dropwise to the mixture. The mixture was stirred at room temperature until the strong orange color was disappeared. The solution was cooled toO0C and the solid was collected and washed with 50percent aqueous methanol, dried to give <n="72"/>the title compound 106 (9.9 g, 77percent) : LCMS: 257 [M+l]+; 1H NMR (CDCl3): δ: 3.96 (s, 3H), 4.47 (s, 2H), 8.03 (t, IH), 8.06 (t,lH), 8.14 (t, IH), 8.16 (t, IH).
77% With bromine In acetic acid at 20℃; Methyl 4-acetylbenzoate 105 (8.91 g, 50 mmol) was suspended in acetic acid (80 mL) and the mixture was stirred until a clear solution was reached. Then bromine (8.39 g, 52 mmol) was added dropwise to the mixture. The mixture was stirred at room temperature until the strong orange color was disappeared. The solution was cooled to O0C and the solid was collected and washed with 50percent aqueous methanol, dried to give the title compound 106 (9.9 g, 77percent) : LCMS: 257 [M+l]+; 1H NMR (CDCl3): δ: 3.96 (s, 3H), 4.47 (s, 2H), 8.03 (t, IH), 8.06 (t,lH), 8.14 (t, IH), 8.16 (t, IH).
75% With bromine In chloroform at 0 - 20℃; Inert atmosphere To a solution of 4-acetyl derivative C or E (1.0 equiv.) in chloroform under nitrogen atmosphere and cooled at 0°C, a solution of bromine (1.1 equiv.) in chloroform was added dropwise. The mixture was stirred at 0°C for 30 min, then was allowed to warm to R.T. and stirred for 1H30. The reaction mixture was treated with a saturated aqueous solution of NaHCO3 and was extracted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The resulting oil was purified by flash-chromatography to afford the desired product.; Compound 56 was obtained according to general procedure IV, method B, starting from methyl 4-acetylbenzoate. Purification by flash-chromatography (EtOAc 10percent in cyclohexane) afforded the product in 75percent yield. M/Z (M[79Br]+H)+ = 257.
74% at 20℃; for 16 h; Methyl 4-acetylbenzoate (8.0 g, 45.0 mmol, 1.0 eq) was suspended in AcOH (80 mL) and stirred until all solid dissolved. Bromine (8.5 g, 54.0 mmol, 1.2 eq) was added dropwise to the mixture and stirred at rt until all the bromine was consumed. The solution was cooled to 0 °C upon which a precipitate formed which the solid was collected and washed with 50percent aqueous MeOH, dried to give the title compound (8.5 g, yield 74percent) as a white solid. ESI-MS (M+H)+: 258.1.1H NMR (400 MHz, CD3Cl) : 8.16 (d, J = 7.6 Hz, 2H), 7.60 (d, J = 8.4 Hz, 2H), 4.48 (s, 2H), 3.97 (s, 3H).
71% With bromine In methanol; water; acetic acid hydrobromide Referential Example 18
Methyl 4-bromoacetylbenzoate
At 15° C., methyl 4-acetylbenzoate (2.23 g) was dissolved in a hydrobromic acid acetic acid solution (30percent, 10 ml).
Bromine was gradually added dropwise to the reaction mixture to maintain its temperature at 15° C.
After stirring for 10 minutes, the reaction mixture was cooled to 4° C.
A mixed solvent of methanol (50 ml) and water (50 ml) was added to the reaction mixture for crystallization, followed by washing with hexane.
By the collection through filtration, the title compound (2.29 g, 71percent) was obtained as a colorless solid.
1H-NMR (CDCl3) δ: 3.96(3H,s), 4,47(2H,s), 8.05(2H,d,J=8.8 Hz), 8.16(2H,d,J=8.8 Hz).
MS (FAB) m/z: 257 [(M+H)+, 79Br], 259 [(M+H)+, 81Br].
71% With bromine In methanol; water; acetic acid hydrobromide [Referential Example 18] Methyl 4-bromoacetylbenzoate
At 15°C, methyl 4-acetylbenzoate (2.23 g) was dissolved in a hydrobromic acid acetic acid solution (30percent, 10 ml).
Bromine was gradually added dropwise to the reaction mixture to maintain its temperature at 15°C.
After stirring for 10 minutes, the reaction mixture was cooled to 4°C.
A mixed solvent of methanol (50 ml) and water (50 ml) was added to the reaction mixture for crystallization, followed by washing with hexane.
By the collection through filtration, the title compound (2.29 g, 71percent) was obtained as a colorless solid.
1H-NMR (CDCl3) δ: 3.96(3H,s), 4,47(2H,s), 8.05(2H,d,J=8.8Hz), 8.16(2H,d,J=8.8Hz).
MS (FAB) m/z: 257 [(M+H)+, 79Br], 259 [(M+H)+, 81Br].
Elementary analysis for C10H9BrO3
Calculated: C, 46.72; H, 3.53.
Found: C, 46.36; H, 3.63.
71% With hydrogen bromide; bromine In acetic acid at 4 - 15℃; for 0.166667 h; At 15°C, methyl 4-acetylbenzoate (2.23 g) was dissolved in a solution (30percent, 10 ml) of hydrobromic acid in acetic acid. Bromine was added dropwise to the resulting solution slowly while maintaining the temperature at 15°C. After stirring for 10 minutes, the reaction mixture was cooled to 4°C. A mixed solvent of methanol (50 ml) and water (50 ml) was added to the reaction mixture to crystallize the same. The crystals were washed with hexane and then, collected by filtration, whereby the title compound (2.29 g, 71percent) was obtained as a colorless solid.1H-NMR (CDCl3) δ: 3.96(3H,s), 4.47(2H,s), 8.05 (2H, d, J=8.8Hz), 8.16 (2H, d, J=8.8Hz). MS(FAB)m/z: 257 [(M+H)+, 79Br], 259 [(M+H)+, 81Br].
67% With bromine In chloroform at 20℃; for 2 h; Intermediate 7: {2-Methylamino-1-[4-(pyridin-4-ylcarbamoyl)-phenyl]-ethyl}-carbamic acid terf-butyl ester.; To a solution of 4-acetyl-benzoιc acid methyl ester (345 7 g, 1 94 mmol, 1 eq ) in chloroform (1700 ml) was added dropwise bromine (100 ml, 31O g, 1 94 mmol, 1 eq ) in chloroform (3100 ml) with stirring at RT During addition of bromine the reaction displayed an exotherm of 1O0C After 2 h at RT, the mixture was diluted with ice water (1000 ml) and aqueous Na2S2O3 (700 ml) and extracted with DCM (3 x 1200 ml) The organic layer was washed with water (4500 ml), dried over MgSO4 and concentrated in vacuo to give the 4-(2-Bromo-acety.)-benzoιc acid methyl ester (527 2 g) The crude residue was recrystallized from methanol (2500 ml) to give 334 g (67percent yield)To a stirred solution of bromoketone (590 5 g) in MeOH (5900 ml) at O0C was added NaBH4 (91 2 g) portionwise The reaction was allowed to warm to RT and stirred for 1 h after which time TLC analysis indicated the formation of the bromo alcohol K2CO3 (318 g) was added to the same flask EPO <DP n="45"/>and the reaction mixture stirred over the weekend TLC analysis indicated the reaction was complete Water (3000 ml) was added and the mixture extracted with Et2O (3 x 5000 ml) The organic extracts were washed with brine (2 x 5000 ml), dried over MgSO4 and concentrated in vacuo to give the 4-oxιranyl-benzoιc acid methyl ester as an orange solid, 405 8 g (99percent yield) The 4-oxιranyl-benzoιc acid methyl ester (405 g) was dissolved in methylamine 33 wtpercent in EtOH and stirred overnight TLC analysis indicated the reaction was complete Water was added and the mixture extracted with EtOAc (4 x 500 ml) The organic extracts were washed with water (3 x 500 ml), dried over MgSO4 and concentrated in vacuo to give 495 g of 4-(1-hydroxy-2-methylamιno- ethyl)-benzoιc acid methyl ester The amino alcohol (412 3 g) was dissolved in THF (6000 ml) and NaHCO3 (336 g, 2 eq ) was added with stirring The solution was cooled to 0-50C and benzyl chloroformate (416 ml, 1 5 equiv ) in THF (6000 ml) was added dropwise The mixture was stirred at 0-50C for 1 h and allowed to warm to RT overnight TLC analysis indicated the reaction was complete Water (9000 ml) was added and the aqueous layer extracted with EtOAc (2 x 5000 ml) The organic layer was back extracted with saturated aqueous NaHCO3 solution (2 x 2500 ml) The combined organic layers were dried over MgSO4 and concentrated in vacuo to give a crude product, 760 7 g The crude product was purified by column chromatography to give 4-[2-(Benzyloxycarbonyl-methyl-amιno)-1- hydroxy-ethyl]-benzoιc acid methyl ester (137 g, 20 percent yield from the bromoketone)To a solution of the previous alcohol (137 g, 0 4 mol) in DCM (1400 ml) was added triethylamine (123 ml, 0 88 mol, 2 2 eq ) and the reaction cooled to <5°C Mesylate chloride (48 ml, 0 6 mol, 1 5 eq ) was added dropwise and after complete addition, the reaction mixture was allowed to warm toRT After 1 h LC analysis indicated the reaction was complete The DCM layer was washed withH2O (1400 ml), 1 M HCI (1400 ml) and H2O (1400 ml) The DCM layer was dried over MgSO4 and concentrated in vacuo to give the 4-[2-(benzyloxycarbonyl-methyl-amιno)-1-methanesulfonyloxy- ethyl]-benzoιc acid methyl ester (166 7 g, 99percent yield)To a 2000 ml flask was added the previous mesylated product (166 7 g, 0 4 mol) and DMF (1700 ml) NaN3 (25 7 g, 0 4 mol, 1 eq ) was added portionwise The reaction mixture was heated to 5O0C and stirred for 14 h LC analysis indicated the reaction was complete The reaction was cooled to RT and Ph3P (105 g, 0 4 mol, 1 eq ) and H2O (105 ml) were added The reaction was stirred for 2 h and LC analysis indicated the reaction was complete The reaction mixture was concentrated in vacuo to give the 4-[1-amιno-2-(benzyloxycarbonyl-methyl-amιno)-ethyl]-benzoιc acid methyl ester as a sticky solid (351 8 g), which was used without further purificationThe amine (351 8 g, active charge 135 g. 0 39 mol) was dissolved in a mixture of 1 1 acetone/1 M Na2CO3 solution (5000 ml) Boc anhydride (197 ml, 0 86 mol, 2 2 eq ) was added and the reaction mixture stirred overnight at RT LC analysis indicated the reaction was complete The acetone was removed in vacuo and the aqueous layer was extracted with EtOAc (3 x 2000 ml) The combined organic extracts were washed with brine (3000 ml), dried over MgSO4 and concentrated in vacuo The 4-[2-(benzyloxycarbonyl-methyl-amιno)-1 -tert-butoxycarbonylamino-ethylj-benzoic acid methyl EPO <DP n="46"/>ester was purified by flash chromatography on silica gel (21 percent yield from the CBz protected amino alcohol)To a solution of the previous ester (35 9 g) in MeOH (1500 ml) was added 1 M NaOH solution (700 ml) slowly The reaction mixture was stirred for 4 h after which time the reaction was complete The methanol was removed in vacuo, the aqueous layer acidified to pH 5-6 using 0 5M HCI (1400 ml) and the product extracted with EtOAc (3 x 1500 ml) The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give the corresponding benzoic acid (100 percent yield)To a solution of the acid (34 76 g, 0 081 mol) in DMF (1000 ml) were added DIEA (42 ml, 0 243 mol, 3 equiv ), HBTU (40 g, 0 1053 mol, 1 3 equiv ), HOBt (3 2 g, 0 0243 mol, 0 3 equiv ) and 4- aminopyπdine (9 15 g, 0 0972 mol 1 2 equiv ) The reaction mixture was stirred overnight at RT TLC analysis indicated the reaction was complete DMF was evaporated and the residue taken up in EtOAc (2500 ml) and 1 M Na2CO3 (2500 ml) The layers were separated and the aqueous layer was extracted with EtOAc (2500 ml) The organic layer was washed with brine (5000 ml), dried over MgSO4 and concentrated in vacuo The {2-(benzyloxycarbonyl-methyl-amιno)-1-[4-(pyπdιn-4- ylcarbamoyl)-phenyl]-ethyl}-carbamιc acid tert-butyl ester was purified by flash chromatography on silica gel (85 percent yield)The previous compound (34 7 g) was dissolved in MeOH (250 ml) and transferred to a 300 ml Parr hydrogenator vessel The vessel was purged with N2 and 10percent Pd/C (wet catalyst) (20 g) were added The reaction was purged with hydrogen and stirred for 5 h at 5 bar pressure of hydrogen TLC analysis indicated the reaction was complete The reaction mixture was filtered through Celite (100 g) and the filter cake washed with MeOH (750 ml) The reaction mixture was concentrated in vacuo The crude residue was purified by flash chromatography on silica gel to give the title compound (67 percent yield)
55% With bromine In acetic acid at 20℃; for 2 h; i. AcOH, bromine, RT, 2 h, 55percent yield. Step a) 4-(2-Bromo-acetyl)-benzoic acid methyl ester
To a solution of 4-acetyl-benzoic acid methyl ester (8.4 mmol) in acetic acid (20 mL) was added bromine (8.4 mmol).
The reaction was stirred at RT for 2 h over which time the red colour disappeared and an off white precipitate formed.
The product was collected by filtration and washed with cold methanol/water (200 mL 1:1) to yield a white powder (55percent).
1H NMR (400 MHz, CDCl3) 3.98 (3H, s), 4.20 (2H, s), 8.02 (2H, d, J=8 Hz), 8.18 (2H, d, J=8 Hz).
55% With bromine In acetic acid at 20℃; for 2 h; To a solution of 4-acetyl-benzoic acid methyl ester (8.4 mmol) in acetic acid (20 mL) was added bromine (8.4 mmol). The reaction was stirred at RT for 2 h over which time the red colour disappeared and an off white precipitate formed. The product was collected by filtration and washed with cold methanol/water (200 mL 1 :1 ) to yield a white powder (55 percent). 1H NMR (400MHz, CDCI3) 3.98 (3H, s), 4.20 (2H, s), 8.02 (2H, d, J = 8Hz), 8.18 (2H, d, J = 8Hz).
55% With bromine In acetic acid at 20℃; for 2 h; To a solution of 4-acetyl-benzoic acid methyl ester (8.4 mmol) in acetic acid (20 ml.) was added bromine (8.4 mmol). The reaction was stirred at RT for 2 h over which time the red colour disappeared and an off white precipitate formed. The product was collected by filtration and washed with cold methanol/water (200 ml. 1 :1 ) to yield a white powder (55 percent). 1H NMR (400MHz, CDCI3) 3.98 (3H, s), 4.20 (2H, s), 8.02 (2H, d, J = 8Hz), 8.18 (2H, d, J = 8Hz).

Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 39, p. 9361 - 9366
[2] Patent: WO2006/78698, 2006, A1, . Location in patent: Page/Page column 64
[3] Patent: US2012/196869, 2012, A1, . Location in patent: Paragraph 0467; 0468; 0469
[4] Inorganic Chemistry, 2018, vol. 57, # 1, p. 120 - 128
[5] Patent: WO2008/33745, 2008, A2, . Location in patent: Page/Page column 70-71
[6] Patent: WO2008/33747, 2008, A2, . Location in patent: Page/Page column 255
[7] Patent: EP2210891, 2010, A1, . Location in patent: Page/Page column 19
[8] Journal of Medicinal Chemistry, 2012, vol. 55, # 6, p. 2899 - 2903
[9] Patent: WO2015/89327, 2015, A1, . Location in patent: Paragraph 0414
[10] Patent: US6525042, 2003, B1,
[11] Patent: EP1104754, 2001, A1,
[12] Patent: EP1577302, 2005, A1, . Location in patent: Page/Page column 109
[13] Patent: WO2007/6547, 2007, A1, . Location in patent: Page/Page column 43-45
[14] Patent: US2009/23748, 2009, A1, . Location in patent: Page/Page column 24-25
[15] Patent: WO2010/34788, 2010, A1, . Location in patent: Page/Page column 38
[16] Patent: WO2010/34789, 2010, A1, . Location in patent: Page/Page column 33
[17] Journal of Medicinal Chemistry, 1987, vol. 30, # 8, p. 1497 - 1502
[18] Patent: WO2006/17124, 2006, A2, . Location in patent: Page/Page column 66
[19] Patent: EP1975149, 2008, A1, . Location in patent: Page/Page column 64
[20] Patent: US2004/248949, 2004, A1, . Location in patent: Page 35-36
[21] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 6, p. 2317 - 2326
[22] Patent: EP2172462, 2010, A1, . Location in patent: Page/Page column 87
[23] Patent: WO2006/28970, 2006, A1, . Location in patent: Page/Page column 68-69
[24] Patent: US2011/189794, 2011, A1,
[25] Patent: EP2353613, 2011, A1,
[26] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6058 - 6080
[27] Organic Letters, 2017, vol. 19, # 8, p. 1994 - 1997
[28] Organic Letters, 2018, vol. 20, # 8, p. 2257 - 2260
[29] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 86, p. 12182 - 12185
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  • [ 550366-66-0 ]
  • [ 56893-25-5 ]
YieldReaction ConditionsOperation in experiment
91.8% With bromine In acetic acid at 20℃; for 1.7 h; To a solution of methyl 4-acetyl benzoate (121) (5.0 g, 28 mmol) in glacial ACOH (25 mL), bromine (1.5 ml, 4.67 g, 29 mmol) was added over 12 min at <20°C. Towards the end of the addition, solids started to appear. After stirring for additional 1. 5H, the solids were filtered, washed first with 50 percent aq. EtOH (60 mL) to remove excess bromine (clear filtrate), then with water (20 mL). Upon drying the material, cream-colored solids were obtained (6.62 g, 91.8 percent). 1H NMR indicated traces of dibromo-derivative were present. Without further purification the material was used in the next step.
Reference: [1] Patent: WO2004/91610, 2004, A1, . Location in patent: Page/Page column 67
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  • [ 7364-20-7 ]
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  • [ 56893-25-5 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 9, p. 2414 - 2417
[2] Organic Letters, 2016, vol. 18, # 4, p. 784 - 787
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  • [ 153559-49-0 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782
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  • [ 153559-48-9 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782
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  • [ 3609-53-8 ]
  • [ 593-51-1 ]
  • [ 74-89-5 ]
  • [ 80051-07-6 ]
YieldReaction ConditionsOperation in experiment
75% With methanol; sodium cyanoborohydride In tetrahydrofuran at 65℃; for 16 h; Methyl 4-acetylbenzoate (1.07 g, 6 mmol), methylamine (33 percent in EtOH, 4.5 mL), methylamine hydrochloride (1.62 g, 24.0 mmol) and sodium cyanoborohydride (0.56 g, 9.0 mmol) were dissolved in a mixture of THF (12 mL) and Methanol (7 mL) and the reaction stirred at 65 0C for 16 h. The reaction was concentrated in vacuo and the residue redissolved in DCM (20 mL) and washed with water (20 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo to afford the title compound, which was used without further purification. Yield: 0.86 g, 75 percent LCMS method B: rt 0.98 min, 89 percent; m/z 194.05 (MH+, 100 percent).
Reference: [1] Patent: WO2010/20556, 2010, A1, . Location in patent: Page/Page column 169-170
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  • [ 80051-07-6 ]
Reference: [1] Patent: WO2017/156179, 2017, A1,
  • 10
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  • [ 1056634-68-4 ]
Reference: [1] Journal of Chemical Research, 2016, vol. 40, # 8, p. 511 - 513
[2] Patent: , 2016, ,
[3] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2902 - 2905
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  • [ 1433497-19-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3274 - 3277
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