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[ CAS No. 1878-68-8 ]

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Chemical Structure| 1878-68-8
Chemical Structure| 1878-68-8
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Product Details of [ 1878-68-8 ]

CAS No. :1878-68-8MDL No. :MFCD00004342
Formula : C8H7BrO2 Boiling Point : 326°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :215.04Pubchem ID :74654
Synonyms :

Computed Properties of [ 1878-68-8 ]

TPSA : 37.3 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.13 Rotatable Bond Count : 2

Safety of [ 1878-68-8 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1878-68-8 ]

  • Upstream synthesis route of [ 1878-68-8 ]
  • Downstream synthetic route of [ 1878-68-8 ]

[ 1878-68-8 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 1670-14-0 ]
  • [ 1878-68-8 ]
  • [ 23449-08-3 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 18, p. 2098 - 2102
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  • [ 5188-07-8 ]
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  • [ 16188-55-9 ]
YieldReaction ConditionsOperation in experiment
76.1% With copper(I) bromide In N,N-dimethyl-formamide at 130℃; Inert atmosphere Taking 4- bromobenzene acetic acid 10g in 100 ml in three-mouth bottle, by adding DMF20mL, adding a thiol sodium 5.0g, adding cuprous bromide 0.1g, after the replacement of nitrogen, to improving the reaction temperature under stirring 130 °C, under the protection of nitrogen stirring for 4 hours, cooling the reaction liquid, by adding 40percent NaOH5mL, stirring 10 minutes. Cooling the reaction liquid, by adding ethyl acetate 25 ml extraction two, by adding ethyl acetate in 50 ml, by adding 10percent dilute sulfuric acid adjusted to pH 2-4, collecting ethyl acetate, ethyl acetate with water 10 ml after washing, distillation of the ethyl acetate to 20 ml left and right, by adding hexane 20 ml, raise the reaction temperature to reflux, after to be solid entirely dissolved, a slow cooling to room temperature, filtered, scaled to obtain yellowish crystalline, to obtain a target product after drying 6.38g, yield 76.1percent.
Reference: [1] Patent: CN105646306, 2016, A, . Location in patent: Paragraph 0010
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  • [ 64-17-5 ]
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  • [ 14062-25-0 ]
YieldReaction ConditionsOperation in experiment
97% for 24 h; Reflux Preparation of Intermediate 1-bromo-4-(2-methoxy-2-methylDroDyl)benzene (1AG-1); 2-(4-Bromophenyl)acetic acid (75g, 340mmol) suspended in ethanol (341 mL) . Concentrated sulfuric acid (0.682mL, 12.79mmol) was added and reaction heated to reflux for 24 hours. Reaction concentrated and residue diluted with diethyl ether and saturation sodium bicarobonate. Layers carefully separated and organic was washed with brine, dried over sodium sulfate, filtered and concentrated to give ethyl 2-(4- bromophenyl)acetate (80.2g, 97percent) as off-white solid.
96% at 100℃; Step 1: To a solution of 2-(4-bromophenyl)acetic acid (3 g, 13.95 mmol) in ethanol was slowly added sulfuric acid (0.3 mL, cat.) at room temperature.
The reaction mixture was heated to 100° C. for overnight. TLC showed complete consumption of starting material.
The reaction mixture was cooled to room temperature and neutralized with NaHCO3.
The mixture was extracted with ethyl acetateand washed with water and brine.
The extract was dried over magnesium sulfate and concentrated under reduced pressure to give ethyl 2-(4-bromophenyl)acetate (3.24 g, 96percent).
96% With sulfuric acid In ethanol at 20 - 100℃; Step 1 : To a solution of 2-(4-bromophenyl)acetic acid (3 g, 13.95 mmol) in ethanol was slowly added sulfuric acid (0.3 ml_, cat.) at room temperature. The reaction mixture was heated to 100 °C for overnight. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature and neutralized with NaHC03. The mixture was extracted with ethyl acetateand washed with water and brine. The extract was dried over magnesium sulfate and concentrated under reduced pressure to give ethyl 2-(4- bromophenyl)acetate (3.24 g, 96 percent).
95% at 80℃; for 12 h; 2-(4-bromophenyl)acetic acid (15 g, 69.8 mmol) was added to ethanol (125 mL). Then, sulfuric acid (0.186 mL, 3.49 mmol) was added to the reaction and the reaction was heated to 80° C for 12 h. The reaction was confirmed complete based on TLC. Solid NaHCO3 was added to the reaction and then the ethanol was evaporated.The product was extracted with ether and washed 2 with water and 1 with brine. The organic layer was collected, dried with MgSO4, and condensed to generate compound 2 as a clear oil (16.113 g, 95percent). 1H NMR (400 MHz, CDCl3) δ 7.45 (d, J = 8.4 Hz, 2H), 7.16 (d, J = 8.4 Hz, 2H), 4.15 (q, J = 7.1 Hz, 2H), 3.56 (s, 2H), 1.25 (t, J = 7.1 Hz, 3H). ESIMS m/z [M+H]+ 243.
91% Reflux Step 0 (Intermediate A): see example 85.[0556]Step 1: To a stirred solution of 2-(4-bromophenyl)acetic acid (2 g, 9.3 mmol) in ethanol (10 mL) were added sulfuric acid (0.3 mL). The reaction mixture was refluxed for overnight and cooled to room temperature. The solvent was evaporated. The residue was dissolved with ethylacetate and neutralized with NaHCO3. The organic layer was washed with water two times, then dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. ethyl 2-(4-bromophenyl)acetate (2.1 g) was obtained as 91percent yield.[0557]Step 2: To a stirred solution of ethyl 2-(4-bromophenyl)acetate (2.1 g, 8.445 mmol) in anhydrous dimethylformamide were added zinc cyanide (1.5 g, 12.668 mmol) and tetrakis(triphenylphosphine) palladium (1.0 g, 0.845 mmol). The reaction mixture was refluxed for overnight then cooled to room temperature. The mixture was filtered using celite pad and the filtrate was evaporated. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure to get the crude. The crude was purified by column chromatography. Ethyl 2-(4-cyanophenyl)acetate (0.8 g) was obtained as 49percent yield.[0558]Step 3: To a stirred solution of ethyl 2-(4-cyanophenyl)acetate (0.8 g, 4.101 mmol) in anhydrous dimethylformamide were added 60percent sodium hydride (180 mg, 4.511 mol) and Iodo methane were added after 10 min with an ice bath. The reaction mixture was stirred for 1 h hours, quenched with water and extracted with ethylacetate which is washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure. The residue was purified by column chromatography. Ethyl 2-(4-cyanophenyl)propanoate (453 mg) was obtained as 48percent[0559]Step 4: To a stirred solution of ethyl 2-(4-cyanophenyl)propanoate (453 mg, 1.968 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added sodium hydroxide (197 mg, 4.919 mmol). The reaction mixture was stirred for overnight at room temperature, then acidified to pH 3-4 with acetic acid. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude 2-(4-cyanophenyl)propanoic acid (422 mg) was obtained as 99percent yield.[0560]Step 5: To a stirred solution of 2-(4-cyanophenyl)propanoic acid (148 mg, 0.85 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (243 mg, 1.27 mmol), 1-hydroxybenzotriazole (171 mg, 1.27 mmol), (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (247 mg, 0.93 mmol) and triethylamine (0.29 mL, 2.11 mmol). The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-Cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (311 mg) was obtained as 87percent yield.[0561]Step 6: To a stirred solution of 2-(4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (305 mg, 0.72 mmol) in ethanol was cooled to 0° C. and added NiCl2.6H2O (17 mg, 0.072 mmol) and stirred more then 15 min. Sodium borohydride (191 mg, 5.04 mmol) was then added in small portions. The reaction was exothermic and effervescent. The resulting reaction mixture was allowed to warm to room temperature and left to stir for 2 hour. The mixture was filtered using celite pad. The filtrate was concentrated was evaporated. The residue was dissolved in ethylacetate and washed with water and brine, but when it does not separate easily, small amount of 1N HCl and saturated NaHCO3 was used. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-(Aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (167 mg) was obtained as 64percent yield.[0562]Step 7: To a stirred solution of 2-(4-(aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (167 mg, 0.39 mmol) in dichloromethane the intermediate (A) (117 mg, 0.39 mmol) and triethylamine (0.20 mL, 0.56 mmol) was added was stirred for overnight. The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with dichloromethane and washed with water, brine, dried over magnesium sulfate and filtered. The filtrate was evaporated and the residue was purified by column chromatography. Tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate (118 mg) was obtained as 50percent yield.[0563]Step 8: To a stirred solution of tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate (118 mg, 0.19 mmol) in dichloromethane (5 mL) cooled by ice bath and trifluoroacetic acid (4.0 mL) was added. The reaction mixture was stirred for overnight. The mixture was diluted with dichloromethane and then washed with NaHCO3, brine, dried over magnesium sulfate and filtered. The filtrate was evaporated and purified by column chromatography. 2-(4-((Sulfamoylamino)methyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 88) (79 mg) was obtained as 79percent yield.[0564]1H NMR (300 MHz, CDCl3) δ 7.76 (d, 1H, J=7.86 Hz), 7.58 (s, 1H, J=7.86 Hz), 7.27-7.32 (m, 3H), 7.10-7.24 (m, 5H), 5.59 (bs, 1H), 4.69 (bs, 1H), 4.58 (s, 2H), 4.44 (d, 2H, J=6.03 Hz), 4.26 (d, 2H, J=6.21 Hz), 3.50 (m, 1H), 2.38 (s, 3H), 1.46 (d, 3H, J=7.14 Hz).
91% Reflux Step 1 : To a stirred solution of 2-(4-bromophenyl)acetic acid (2 g, 9.3 mmol) in ethanol (10 mL) were added sulfuric acid (0.3 mL). The reaction mixture was refluxed for overnight and cooled to room temperature. The solvent was evaporated. The residue was dissolved with ethylacetate and neutralized with NaHC03. The organic layer was washed with water two times, then dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography, ethyl 2-(4-bromophenyl)acetate (2.1 g) was obtained as 91 percent yield.
80% for 8 h; Reflux A solution of 63 grams (0.29 mole) of 4-bromophenyl acetic acid and 50 milliliters of concentrated sulfuric acid in 500 milliliters of absolute ethanol was refluxed for 8 hours then allowed to stand overnight.
After pouring over 600 grams of ice, the mixture was extracted with ether/hexanes.
The ether extracts were washed thoroughly with water and sodium bicarbonate solution then dried over anhydrous sodium sulfate.
Removal of the solvent by rotary evaporation yielded 57 grams (0.24 mole, 80percent isolated yield) of an oil which crystallized upon cooling.
Filtration and washing with hexane afforded pure product.
74% Reflux 4-Bromophenylacetic acid, 7-c, (30 g, 0.14 mol) was dissolved in ethanol (150 mL) at reflux along with p-toluenesulphonic acid (2.4 g, 0.014mol). The reaction mixture was then stirred overnight. The ethanol was the removed in vacuo and the residue was taken up in EA. Combined organic layers were washed with water and the aqueous layer was re-extracted with EA. Combined organic layers were then dried over Na2S04 and concentrated to afford the titled compound, 12-a, (25 g, 74percent).1H NMR (300 MHz, CDCI3) δ 1.23-1.29 (m, 3H), 3.56 (s, 2H), 4.11-4.18 (m, 2H), 7.16 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H). LC-MS (M+H)+243, 245
74% Reflux Step A: Ethyl 2-(4-bromophenyl)acetate (12-a 4-Bromophenylacetic acid, 7-c, (30 g, 0.14 mol) was dissolved in ethanol (150 mL) at reflux along with p-toluenesulphonic acid (2.4 g, 0.014mol). The reaction mixture was then stirred overnight. The ethanol was the removed in vacuo and the residue was taken up in EA. Combined organic layers were washed with water and the aqueous layer was re-extracted with EA. Combined organic layers were then dried over Na2S04 and concentrated to afford the titled compound, 12-a, (25 g, 74percent).1H NMR (300 MHz, CDCI3) δ 1.23-1.29 (m, 3H), 3.56 (s, 2H), 4.1 1-4.18 (m, 2H), 7.16 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H). LC-MS (M+H)+ 243, 245
70% at 80℃; for 15 h; Cooling with ice To an ice cooled solution of 2-(3-bromophenyl)acetic acid (2.5 g, 11.62 mmol) in EtOH (25 mL), thionyl chloride (1.6 mL, 23.24 mmol) was added dropwise. The reaction mixture was heated at 80° C. for 15 h. The reaction was monitored by TLC and after completion of the reaction, the reaction mixture was concentrated under vacuum and water was added to the residue. A saturated aqueous solution of NaHCO3 was added to the solution until the pH of the solution was 9. Then, the aqueous solution was extracted with EtOAc, the organic layer was dried over Na2SO4, concentrated under vacuum, and purified by column chromatography (silica gel) to yield ethyl 2-(3-bromophenyl)acetate (2 g, 70percent).LCMS: 99.80percent (254 nm, R.T.=2.99)

Reference: [1] Patent: WO2010/86820, 2010, A1, . Location in patent: Page/Page column 53
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 21, p. 6665 - 6681
[3] Patent: US2013/79320, 2013, A1, . Location in patent: Paragraph 0473; 0474
[4] Patent: WO2013/45451, 2013, A1, . Location in patent: Paragraph 51
[5] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 714 - 723
[6] Chemical Communications, 2018, vol. 54, # 26, p. 3231 - 3234
[7] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1586 - 1605
[8] Patent: US2013/79377, 2013, A1, . Location in patent: Paragraph 0554; 0556
[9] Patent: WO2013/45447, 2013, A1, . Location in patent: Page/Page column 82
[10] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6640 - 6658
[11] Patent: EP1476416, 2015, B1, . Location in patent: Paragraph 0053
[12] Patent: WO2013/40790, 2013, A1, . Location in patent: Page/Page column 59; 60
[13] Patent: WO2013/43624, 2013, A1, . Location in patent: Page/Page column 59; 60
[14] Patent: US2012/295874, 2012, A1, . Location in patent: Page/Page column 230
[15] Journal of the American Chemical Society, 2003, vol. 125, # 46, p. 13948 - 13949
[16] Journal of Organic Chemistry, 2009, vol. 74, # 14, p. 5100 - 5103
[17] Patent: US6344561, 2002, B2, . Location in patent: Page column 70
[18] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6608 - 6612
[19] Chemistry - A European Journal, 2013, vol. 19, # 36, p. 11904 - 11915
[20] Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12116 - 12127
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YieldReaction ConditionsOperation in experiment
99% With sulfuric acid In ethanol (1)
Concentrated sulfuric acid (10 ml) was added to an ethanol (300 ml) solution of 4-bromophenylacetic acid (25 g, 120 mmols), and heated under reflux for 15 hours.
The reaction mixture was concentrated under reduced pressure, and the residue was poured into water with ice, and extracted with ethyl acetate.
The extract was washed with water, and then dried with anhydrous magnesium sulfate.
This was concentrated under reduced pressure to give an oil of ethyl 4-bromophenylacetate (28 g, 99percent).
1H-NMR (CDCl3) δ: 1.25(3H,t,J=7.2Hz), 3.56(2H,s),
Reference: [1] Patent: EP1123918, 2001, A1,
[2] Patent: US5776951, 1998, A,
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YieldReaction ConditionsOperation in experiment
89% at 80℃; for 24 h; Inert atmosphere; Sealed vial General procedure: Carboxylic acid (0.5 mmol) and MImC (2a, 1.0 mmol) were placed in a dry 20 mL vial with a Teflon tape-coated thread. A magnetic stirbar was added, followed by dry MeCN (1.0 mL), and the vial was quickly sealed with a plastic cap (gas is evolved during the course of the reaction. All experiments should be performed behind a blast shield if a sealed container is used.). The reaction mixture was then stirred at 23 °C for 15 min and then heated to 80 °C using a heating block for 24 h. The mixture was cooled to room temperature and then the vial was carefully opened (CAUTION: vial under pressure.). The volatiles were removed in vacuo, the resulting residue was dissolved in diethyl ether (20 mL), and then washed with 1 M HCl (10 mL). The aqueous layer was back-extracted with diethyl ether (20 mL) and the organic fractions were combined, washed with a saturated solution of NaHCO3 and then brine, dried over MgSO4, and concentrated in vacuo to afford the desired ester.
Reference: [1] Tetrahedron, 2011, vol. 67, # 46, p. 8851 - 8859
[2] Organic Letters, 2012, vol. 14, # 8, p. 1970 - 1973
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YieldReaction ConditionsOperation in experiment
57% With potassium carbonate In ethyl acetate; acetonitrile A.
Ethyl 4-bromophenylacetate

A solution of 25.0 g (116.3 mmol) of 4-bromophenylacetic acid, 24.1 g (174.4 mmol) of potassium carbonate and 10.2 mL (127.9 mmol) of iodoethane in 250 mL of acetonitrile was heated at 70° C. for 16 hours.
The mixture was cooled to ambient temperature, diluted with 200 mL of ethyl acetate and washed once with 200 mL of saturated aqueous sodium bicarbonate.
The organic layer was separated and the aqueous layer was extracted three times with 75 mL each of ethyl acetate.
The combined organics were dried (MgSO4), filtered and concentrated in vacuo to afford 16.2 g (57percent) of the title compound.
57% With potassium carbonate In ethyl acetate; acetonitrile A.
Ethyl 4-bromophenylacetate

A solution of 25.0 g (116.3 mmol) of 4-bromophenylacetic acid, 24.1 g (174.4 mmol) of potassium carbonate and 10.2 mL (127.9 mmol) of iodoethane in 250 mL of acetonitrile was heated at 70° C. for 16 hours.
The mixture was cooled to ambient temperature, diluted with 200 mL of ethyl acetate and washed once with 200 mL of saturated aqueous sodium bicarbonate.
The organic layer was separated and the aqueous layer was extracted three times with 75 mL each of ethyl acetate.
The combined organics were dried (MgSO4), filtered and concentrated in vacuo to afford 16.2 g (57percent) of the title compound.
Reference: [1] Patent: US6303816, 2001, B1,
[2] Patent: US6500865, 2002, B1,
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Reference: [1] Patent: US5489584, 1996, A,
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  • [ 1528-41-2 ]
Reference: [1] Patent: WO2013/45447, 2013, A1,
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  • [ 1878-68-8 ]
  • [ 19725-82-7 ]
YieldReaction ConditionsOperation in experiment
50.7% With hydrogenchloride In carbon disulfide; thionyl chloride; aqueous KOH; ethyl acetate; benzene 16A.
5-Bromo-2-carboxymethyl-benzoic acid
(4-Bromo-phenyl)-acetic acid (20 g, 93 mmol) in thionyl chloride (40 ml) was heated at 850° C. for two hours after which time thionyl chloride was removed under vacuum.
The resulting acid chloride was combined with lead thiocyanate (Pb(SCN)2, 30 g, 93 mmol) in benzene (300 ml).
The reaction mixture was refluxed for 3 hours.
After cooled to room temperature, it was filtered through celite.
The filtrate was evaporated to yield an orange liquid.
This was then dissolved in carbon disulfide (30 ml) and was added dropwise into a solution of aluminum chloride (AlCl3, 24.7 g, 186 mmol) in carbon disulfide (60 ml) at 0° C.
The reaction mixture was heated to reflux for 12 hours.
The reaction mixture was cooled to 0° C. and 1N aqueous HCl (200 ml) was added.
The resulting orange precipitate was collected and then suspended in ethyl acetate.
After filtration obtained an orange solid.
This solid was dissolved in 25percent aqueous KOH (80 ml).
The solution was heated to reflux for 15 hours.
After cooling to 0° C., the reaction mixture was adjusted to pH 3 with 6N aqueous HCl.
The aqueous solution was extracted with ethyl acetate repeatedly.
The combined organic layers were washed with brine, dried over MgSO4 and concentrated under vacuum to provide the title compound of 16A as a yellow solid (12.22 g, 50.7percent yield).
Reference: [1] Patent: US6586447, 2003, B1,
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  • [ 154825-97-5 ]
Reference: [1] Patent: EP2738174, 2014, A2,
[2] Patent: US2014/163226, 2014, A1,
[3] Patent: US2014/364413, 2014, A1,
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  • [ 149910-98-5 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 47, p. 15325 - 15329
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  • [ 146533-41-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1586 - 1605
[2] Patent: US2012/142716, 2012, A1,
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7849 - 7861
[4] Patent: WO2017/93903, 2017, A1,
[5] Monatshefte fur Chemie, 2018, vol. 149, # 3, p. 653 - 661
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