* 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.
Reference：
[1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 4, p. 1351 - 1359
2
[ 735266-90-7 ]
[ 66572-55-2 ]
[ 100-09-4 ]
Reference：
[1] Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 238 - 249
3
[ 100-09-4 ]
[ 829-35-6 ]
Reference：
[1] Angewandte Chemie - International Edition, 2012, vol. 51, # 19, p. 4666 - 4670
[2] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 92, p. 11307 - 11309,3
[3] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 276 - 283
4
[ 79-19-6 ]
[ 100-09-4 ]
[ 1014-25-1 ]
Yield
Reaction Conditions
Operation in experiment
86.4%
at 80℃; for 2.5 h;
General procedure: A stirring mixture of benzoic acid (0.2442 g, 2.0 mmol), thiosemicarbazide (0.1823 g, 2.0 mmol) and POCl3 (1.2 ml) was heated at 80 oC for 2.5 h. After cooling down to room temperature, water (2.5 mL) was added. The reaction mixture was refluxed for 4 h. After cooling, the mixture was basified to pH 8 by the dropwise addition of 40percent NaOH solution under stirring. The precipitate was filtered and recrystallized from ethanol to yield 0.3130 g of the target compound 1a as a white solid ,Yield: 88.3percent.
82%
Stage #1: at 75℃; for 0.5 h; Stage #2: for 4 h; Reflux
General procedure: 5.1.1 5-(4-Morpholinophenyl)-1,3,4-thiadiazol-2-amine (59) A mixture of 4-morpholinobenzoic acid (5.18 g, 25 mmol) and N-aminothiourea (2.28 g, 25 mmol) in POCl3 (7 ml) was stirred vigorously at 75 °C for 0.5 h. After addition of H2O (30 ml), the reaction mixture was heated under reflux for 4 h and basified to pH 8 by 50percent NaOH solution. The mixture was filtered and the filter cake was recrystallized from ethanol to yield 3.90 g of compound 59 as a yellow crystal. Yield: 59percent; The synthetic procedures of compounds 60–81 were the same as that described above. 5.1.1.2 5-(4-Methoxyphenyl)-1,3,4-thiadiazol-2-amine (61) Yield: 82percent, mp: 219-220 °C (EtOH). ESI-MS m/z: 208.2 [M+H]+; 1H NMR (DMSO-d6) δ 3.80 (s, 3H), 7.01-7.03 (m, 2H), 7.23 (s, 2H), 7.67-7.69 (m, 2H).
81.3%
at 75℃; for 0.5 h;
General procedure: A stirring mixture of benzoic acid (7.32 g, 60 mmol), N-aminothiourea(6.38 g, 70 mmol) and POCl3 (20 ml) washeated at 75 °C for 0.5 h. After cooling down to room temperature,water was added. The reaction mixture was refluxedfor 4 h. After cooling, the mixture was basified to pH8 by the drop-wise addition of 50percent NaOH solution understirring. The precipitate was filtered and re-crystallized from ethanol
76.09%
at 85℃; for 10 h;
p-Anisic acid (3.04 g, 20 mmol) and thiosemicarbazide (1.82 g,20 mmol) were dissolved in 30 mL of phosphorus oxychloride, thereaction mixture was refluxed at 85 °C for 10 h. After the reactionfinished, the mixture was poured into ice water slowly and thensaturate NaOH solution was added to adjust the pH value to 8.0under vigorous stirring. The mixture was extracted with ethyl acetatethree times, the organic layer was washed with brine anddried over anhydrous sodium sulfate. After solvent evaporation, thecrude product was purified by recrystallization from anhydrousethanol to get 3.15 g white powder, yield: 76.09percent. Melting point:188.1-189.5 °C. FT-IR (KBr, Disc, cm1): 3409.28 (m, ν NH2), 3377.72(m,ν NH2), 3304.97 (w), 3105.35 (m), 1647.15 (m), 1608.48 (m, ν CN),1578.80 (w), 1511.49 (s, ν benzene), 1465.51(s), 1304.97 (w), 1267.34(w), 1246.65 (s, ν OCH3), 1174.54 (m, ν OCH3), 1128.97 (w), 1052.67 (w),1031.98 (m), 978.88 (w), 829.22 (m), 658.86 (w), 520.48 (w). 1HNMR (DMSO-d6, 400 MHz, ppm) δ: 7.69-7.67 (d, J= 8.0 Hz, 2H),7.28 (s, 2H, NH2), 7.03-7.01 (d, J =8.0 Hz, 2H), 3.80 (s, 3H, OCH3). 13CNMR (100 MHz, DMSO) δ 167.85, 160.24, 156.25, 127.77, 123.61,144.46, 55.27. MS (ESI) m/z: found, [M+H]+, 208.0542; molecularformula C9H9N3OS requires [M+H]+, 208.0544.
65%
Stage #1: for 5 h; Reflux Stage #2: for 7 h; Cooling; Reflux
General procedure: A mixture ofappropriate 4-n-alkoxybenzoic acid (10 mmol) and (0.91 g, 10 mmol) of thiosemicarbazidewith 5 mL of phosphorus oxychloride was refluxed gently for 5 hr. After cooling 50 mL of water was added, the mixture was then refluxed for 7 hr and filtered, neutralizedwith potassium hydroxide. The precipitate was washed with water and recrystallized fromethanol-water to give titled compound [III]n.
Reference：
[1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6663 - 6668
[2] Tetrahedron, 2018, vol. 74, # 31, p. 4161 - 4167
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5766 - 5775
[4] Medicinal Chemistry, 2014, vol. 10, # 4, p. 376 - 381
[5] Medicinal Chemistry Research, 2012, vol. 21, # 6, p. 816 - 824
[6] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 8, p. 2345 - 2350
[7] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 1011 - 1016
[8] Dyes and Pigments, 2017, vol. 145, p. 152 - 159
[9] Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5289 - 5296
[10] Journal of Chemical Research, 2014, vol. 38, # 6, p. 347 - 350
[11] Molecular Crystals and Liquid Crystals, 2014, vol. 593, # 1, p. 34 - 42
[12] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 2, p. 637 - 638
[13] Heterocyclic Communications, 2007, vol. 13, # 6, p. 387 - 392
[14] European Journal of Medicinal Chemistry, 2009, vol. 44, # 7, p. 2782 - 2786
[15] Journal of Chemical Research, 2009, # 11, p. 674 - 676
[16] Journal of Chemical Research, 2009, # 11, p. 671 - 673
[17] Chinese Chemical Letters, 2010, vol. 21, # 3, p. 301 - 304
[18] Journal of Chemical Research, 2010, vol. 34, # 12, p. 719 - 721
[19] Synthetic Communications, 2011, vol. 41, # 6, p. 864 - 870
[20] Journal of Chemical Research, 2011, vol. 35, # 8, p. 442 - 443
[21] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 3, p. 1181 - 1187
[22] Oriental Journal of Chemistry, 2011, vol. 27, # 2, p. 373 - 383
[23] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 9, p. 2789 - 2795
[24] Asian Journal of Chemistry, 2012, vol. 24, # 6, p. 2739 - 2743
[25] Journal of Chemical Research, 2012, vol. 36, # 4, p. 218 - 221
[26] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 56 - 69,14
[27] Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 4, p. 403 - 404
[28] RSC Advances, 2014, vol. 4, # 99, p. 55827 - 55831
[29] Letters in Drug Design and Discovery, 2015, vol. 12, # 4, p. 314 - 318
[30] RSC Advances, 2014, vol. 4, # 27, p. 14248 - 14253
[31] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 524 - 527
[32] Oriental Journal of Chemistry, 2015, vol. 31, # 4, p. 1873 - 1885
[33] Pharmazie, 2018, vol. 73, # 3, p. 123 - 127
[34] Bioorganic Chemistry, 2018, vol. 81, p. 88 - 92
[35] Molecules, 2018, vol. 23, # 10,
5
[ 100-09-4 ]
[ 2746-25-0 ]
Reference：
[1] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 2092 - 2098
6
[ 100-09-4 ]
[ 3290-99-1 ]
Yield
Reaction Conditions
Operation in experiment
87%
at 250℃; Microwave irradiation
General procedure: Acyl hydrazides were synthesized in excellent yields from thereaction of substituted aryl acids (0.010 mol) with hydrazine hydrate(0.012 mol) in absence of organic solvents under microwaveirradiation (300 W, 250 C) for 4e8 min. Spectral analysis of thesynthesized hydrazides are consistent with the proposed structuresand with those reported [58].
Reference：
[1] Journal of Chemical Research - Part S, 2003, # 12, p. 768 - 769
[2] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 396 - 406
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 4, p. 526 - 531
[4] European Journal of Medicinal Chemistry, 2014, vol. 77, p. 231 - 242
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2011, vol. 66, # 12, p. 1202 - 1208
[6] Heterocyclic Communications, 2002, vol. 8, # 6, p. 601 - 606
[7] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 4, p. 838 - 845
[8] Journal of Chemical Research, 2010, vol. 34, # 12, p. 680 - 683
[9] Journal of Chemical Research, 2011, vol. 35, # 4, p. 234 - 237
[10] Journal of Chemical Research, 2011, vol. 35, # 6, p. 364 - 367
[11] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6293 - 6301
[12] Journal of Molecular Structure, 2011, vol. 1003, # 1-3, p. 52 - 61
[13] Journal of Molecular Structure, 2012, vol. 1011, p. 121 - 127
[14] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7246 - 7250
[15] Arzneimittel-Forschung/Drug Research, 2011, vol. 61, # 8, p. 452 - 457
[16] Letters in Drug Design and Discovery, 2012, vol. 9, # 3, p. 276 - 281
[17] Angewandte Chemie - International Edition, 2012, vol. 51, # 19, p. 4666 - 4670
[18] Molecules, 2012, vol. 17, # 5, p. 5095 - 5107
[19] Journal of Chemical Research, 2012, vol. 36, # 7, p. 383 - 386
[20] Journal of the Indian Chemical Society, 2012, vol. 89, # 2, p. 281 - 285
[21] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 92, p. 11307 - 11309,3
[22] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 47, p. 11649 - 11656
[23] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40
[24] Journal of the Brazilian Chemical Society, 2013, vol. 24, # 1, p. 115 - 120
[25] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297
[26] Journal of the Chilean Chemical Society, 2012, vol. 57, # 4, p. 1492 - 1496
[27] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3839 - 3849
[28] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5395 - 5406
[29] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 3943 - 3949
[30] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 4180 - 4184
[31] Medicinal Chemistry Research, 2013, vol. 22, # 10, p. 4980 - 4991
[32] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 276 - 283
[33] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 185 - 198
[34] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 115, p. 683 - 689
[35] Chemical Biology and Drug Design, 2013, vol. 82, # 5, p. 546 - 556
[36] European Journal of Medicinal Chemistry, 2014, vol. 74, p. 73 - 84
[37] Tetrahedron, 2014, vol. 70, # 12, p. 2190 - 2194
[38] Journal of the Brazilian Chemical Society, 2014, vol. 25, # 1, p. 104 - 111
[39] Medicinal Chemistry Research, 2014, vol. 23, # 4, p. 2080 - 2092
[40] Dalton Transactions, 2014, vol. 43, # 20, p. 7554 - 7560
[41] Medicinal Chemistry Research, 2014, vol. 23, # 4, p. 1661 - 1671
[42] Molecules, 2014, vol. 19, # 3, p. 3436 - 3439
[43] Archives of Pharmacal Research, 2014, vol. 37, # 7, p. 852 - 861
[44] Synthetic Communications, 2014, vol. 44, # 18, p. 2724 - 2737
[45] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4629 - 4636
[46] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4629 - 4636
[47] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 22, p. 5154 - 5156
[48] RSC Advances, 2015, vol. 5, # 17, p. 12807 - 12820
[49] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 7, p. 1045 - 1055
[50] Chemical Communications, 2015, vol. 51, # 76, p. 14365 - 14368
[51] Letters in Organic Chemistry, 2015, vol. 12, # 9, p. 637 - 644
[52] Medicinal Chemistry Research, 2015, vol. 24, # 12, p. 4166 - 4180
[53] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6014 - 6024
[54] Comptes Rendus Chimie, 2015, vol. 18, # 12, p. 1320 - 1327
[55] RSC Advances, 2015, vol. 5, # 118, p. 97089 - 97101
[56] Asian Journal of Chemistry, 2016, vol. 28, # 3, p. 639 - 643
[57] Bioorganic Chemistry, 2016, vol. 65, p. 126 - 136
[58] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 627 - 643
[59] Molecules, 2016, vol. 21, # 5,
[60] Bioorganic Chemistry, 2016, vol. 69, p. 48 - 63
[61] Oriental Journal of Chemistry, 2016, vol. 32, # 4, p. 2155 - 2161
[62] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5611 - 5617
[63] Letters in Drug Design and Discovery, 2016, vol. 13, # 9, p. 968 - 981
[64] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 213 - 220
[65] Chemical Biology and Drug Design, 2017, vol. 89, # 1, p. 47 - 60
[66] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 2, p. 207 - 212
[67] Arkivoc, 2016, vol. 2017, # 2, p. 87 - 106
[68] Tetrahedron, 2017, vol. 73, # 14, p. 1867 - 1872
[69] Oriental Journal of Chemistry, 2017, vol. 33, # 1, p. 335 - 345
[70] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1423 - 1429
[71] Journal of Molecular Structure, 2017, vol. 1138, p. 177 - 191
[72] Patent: CN106543098, 2017, A,
[73] Synlett, 2017, vol. 28, # 11, p. 1373 - 1377
[74] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 140 - 151
[75] Chemical Biology and Drug Design, 2017, vol. 90, # 2, p. 236 - 243
[76] Patent: KR101697220, 2017, B1,
[77] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5652 - 5661
[78] Acta Poloniae Pharmaceutica - Drug Research, 2017, vol. 74, # 5, p. 1405 - 1411
[79] Oriental Journal of Chemistry, 2017, vol. 33, # 2, p. 971 - 978
[80] Oriental Journal of Chemistry, 2017, vol. 33, # 6, p. 2930 - 2936
[81] Pharmaceutical Chemistry Journal, 2018, vol. 51, # 10, p. 907 - 917
[82] European Journal of Medicinal Chemistry, 2018, vol. 151, p. 705 - 722
[83] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1971 - 1985
[84] Molecular Crystals and Liquid Crystals, 2018, vol. 664, # 1, p. 85 - 94
[85] Journal of the Chemical Society of Pakistan, 2018, vol. 40, # 4, p. 773 - 781
[86] Chemistry and Biodiversity, 2018, vol. 15, # 9,
[87] Bioorganic Chemistry, 2019, vol. 84, p. 150 - 163
7
[ 100-09-4 ]
[ 13214-64-7 ]
Reference：
[1] Journal of the Chinese Chemical Society, 2016, vol. 63, # 11, p. 909 - 916
[2] Patent: CN107216282, 2017, A,
Reference：
[1] Chem. Zentralbl., 1897, vol. 68, # II, p. 616
[2] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 3, p. 924 - 928
11
[ 87932-34-1 ]
[ 501-94-0 ]
[ 100-09-4 ]
Reference：
[1] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 8, p. 2712 - 2717
[2] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 8, p. 2712 - 2717
Stage #1: With bromine; sodium hydroxide In water at 0 - 5℃; for 1 h; Stage #2: With hydrogenchloride; sodium sulfite In water; toluene at 70℃; for 1 h;
After putting 152.3 g (1.0 mol) of 4-methoxyben- zoic acid was into a 2,000 mE four-necked flask equipped with a stirrer, a thermometer, and a reflux cooling tube, 800g of water was added thereto and stirred so as to disperse 4-methoxybenzoic acid. Subsequently, 273.3 g (2.05 mol) of a 30percent sodium hydroxide aqueous solution was added. The liquid temperature was then reduced to 0° C., and 167.8 g (1.05 mol) of bromine was added dropwise at a liquid temperature of 0 to 5° C. Completion of the dropwise addition was followed by stirring for one hour at a liquid temperature of 0 to 5° C. Afier completion of the reaction, 1.28 g (0.01 mol) of sodium sulfite was added followed by addition of 100 g of toluene and raising the liquid temperature to 70° C. The organic phase was removed by a liquid separation operation, and 104.2 g (1.0 mol) of 35percent hydrochloric acid was added dropwise to the acquired aqueous phase and stirred for one hour. Precipitated crystals were collected by filtration and dried under reduced pressure to acquire 238.9 g (99.9percent purity, 91.4percent yield) of 2-bromo-4- methoxybenzoic acid.
Reference：
[1] Journal of Organic Chemistry, 2007, vol. 72, # 9, p. 3419 - 3429
21
[ 77184-81-7 ]
[ 5722-93-0 ]
[ 77184-89-5 ]
[ 100-09-4 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 9, p. 2630 - 2633
22
[ 100-09-4 ]
[ 54435-09-5 ]
Reference：
[1] Journal of Organic Chemistry, 2007, vol. 72, # 9, p. 3419 - 3429
[2] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1983, vol. 22, # 9, p. 770 - 773
23
[ 100-09-4 ]
[ 23676-09-7 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1867, vol. 141, p. 258
24
[ 100-09-4 ]
[ 37934-89-7 ]
Reference：
[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 28, p. 7317 - 7320[2] Angew. Chem., 2013, vol. 125, # 28, p. 7458 - 7461,4
25
[ 100-09-4 ]
[ 21971-21-1 ]
Reference：
[1] Journal of Organic Chemistry, 2007, vol. 72, # 9, p. 3419 - 3429
26
[ 20714-90-3 ]
[ 20714-89-0 ]
[ 100-09-4 ]
Reference：
[1] Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7234 - 7242
27
[ 616-45-5 ]
[ 100-09-4 ]
[ 72432-10-1 ]
Yield
Reaction Conditions
Operation in experiment
91%
With silica gel In tolueneReflux
Into a 250 mL four-necked flask, 150 mL of toluene, p-methoxybenzoic acid (34 g, 0.2 mol), α-pyrrolidone (17 g, 0.2 mol), silica (6 g, 10 mmol) were refluxed, and methanol was distilled off. . Methanol was evaporated and cooled to 15°C to precipitate a solid. Filter to obtain a solid cake. Dissolve with 95percent ethanol, decolorize the activated carbon, filter it while hot, crystallization after cold, filter and filter cake to obtain dried aniracetam finished product 39.5g. (Yield is 91percent)
79%
With zirconyl chloride octahydrate In chlorobenzene at 131℃; for 18 h; Dean-Stark
General procedure: In a typical reaction, a round-bottom flask equipped with a Dean-Stark apparatus, a magnetic stirring bar and temperature controller was charged with 2-pyrrolidone (5.8 mmol), palmitic acid (5.8 mmol), ZrOCl2.8H2O (0.58 mmol) and mesitylene (20 ml). When methyl palmitate was used as acylating agent, the Dean-Stark bridge was filled with 4Å molecular sieves to remove methanol from the reaction mixture. The set-up was flushed with gaseous nitrogen for 10 min before the onset of the reaction. The reaction vessel was then heated and kept for 18 h under reflux conditions.
Reference：
[1] Patent: CN107840816, 2018, A, . Location in patent: Paragraph 0036-0049
[2] Tetrahedron Letters, 2018, vol. 59, # 17, p. 1646 - 1650
[3] Patent: EP2604592, 2014, B1, . Location in patent: Paragraph 0018
28
[ 100-09-4 ]
[ 133865-89-1 ]
Reference：
[1] Patent: CN107915657, 2018, A,
29
[ 100-09-4 ]
[ 133238-87-6 ]
[ 141627-42-1 ]
Yield
Reaction Conditions
Operation in experiment
72.7%
Stage #1: With Methyltrichlorosilane In chlorobenzene at 20 - 40℃; for 4 h; Stage #2: With ethanol In chlorobenzene at 0℃;
EXAMPLE 133.94 g of chlorobenzene (35 mmol, 7 eq.), 1.05 g of iron chloride (6.5 mmol, 1.3 eq.) and 0.80 g of para-anisic acid (5.25 mmol, 1.05 eq.) are introduced into a 30 ml Schott tube with magnetic stirring at 500 rpm and at ambient temperature.1.09 g of 2-n-butyl-5-nitrobenzofuran (5 mmol, 1 eq.) and 1.12 g of trichloromethylsilane (7.5 mmol, 1.5 eq.) are then added dropwise, and then the reaction mixture is put, with stirring, at a temperature of 40° C. for 4 hours.The reaction mixture is then cooled to 0° C. by means of an ice-bath, and 3 ml of ethanol are added.The mixture is diluted with 25 ml of chlorobenzene and filtered over sintered glass of no. 2 porosity.The filtrate (organic phase) is then washed three times with 25 ml of a 1 N hydrochloric acid solution.The organic phase is dried over magnesium sulfate and then concentrated under reduced pressure.The product is isolated from the crude reaction mixture by separation on a column of silica (silica gel 60 of diameter 0.2 to 0.5 mm), the eluant being a heptane/ethyl acetate mixture going from a ratio of 95:5 to 80:20 during the elution.1.28 g of 2-n-butyl-5-nitro-8-(4'-methoxy)acetophenonebenzofuran (3.64 mmol, which corresponds to a yield of 72.7percent) in the form of a white solid (m.p.=94.7° C.) are then obtained.The NMR characteristics of the resulting product are as follows:1H NMR (200 MHz, CDCl3): δ (ppm)=0.87-0.92 (t, 3H, J=7.2 Hz); 1.30-1.42 (m, 2H); 1.72-1.82 (m, 2H); 2.90-2.95 (t, 2H, J=7.9 Hz); 3.13 (s, 3H); 6.98-7.01 (d, 2H, J=9.3 Hz); 7.55-7.58 (d, 1H, J=9.6 Hz); 7.82-7.85 (d, 2H, J=9 Hz); 8.20-8.24 (dd, 1H, J2=9.2 Hz, J2=2.4 Hz); 8.33-8.34 (d, 1H, J=2.7 Hz).
With N-chloro-succinimide; trifluoroacetic acid; at 70℃; for 3h;
A mixture of 4-methoxybenzoic acid (0.46 g; 3 mmol) and N-chlorosuccinimide (NCS) (0.36 g; 2.7 mmol) in trifluoroacetic acid (5 ml) was stirred for 3 h at -70 0C. After removing solvent under reduced pressure the residue was treated with H2O (10 ml). The solid was filtered off and purified by FCC (SiO2; EtOAc) to give the title compound (0.38 g; 68%) as a colourless solid. 1 H-NMR (CDCI3) 3.97 (s, 3H); 6.96 (d, 1 H, J = 8.7 Hz); 8.0 (dd, 1 H, J = 2; 8.7 Hz); 8.1 1 (d, 1 H, J = 2Hz).
With N-Bromosuccinimide; iodine; In acetonitrile; for 12h;Darkness;
General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)
68%
With iodine pentoxide; potassium bromide; In water; at 20℃; for 23h;
General procedure: A mixture of arene (0.5 mmol), I2O5 (334 mg, 1.0 mmol), and KBr (148 mg, 1.25 mmol) was dissolved in 2mL of H2O. The reaction was complete after stirring for the indicated time at room temperature. The mixture was extracted by ethyl acetate and concentrated under reduced pressure, and the mixture was purified by flash column chromatography (silica gel) to afford the desired product.
With bromine; In tetrachloromethane; at 50℃; for 24h;
General procedure: SO2Cl2 (10 mL) and 4-methoxybenzoic acid (5.0 g) was added to the reaction bulb, and then stirred at 50C for 24 h. After concentration under reduced pressure, the residue was re-crystallized from boiling water to give 3-chloro-4,5-dimethoxybenzoic acid 5a as white needles. To perform bromide of methoxybenzoic acid, we used Br2 in CCl4. A solution of 4-methoxybenzoic acid 5a (1.0 g) and DMF (catalytic amount) in thionyl chloride (5 mL) was stirred at 80-90C for 2h. After reclaimed the thionyl chloride under reduced pressure, 4-methoxybenzoyl chloride 6a was yielded. 4-methoxybenzoyl chloride 6a was dissolved in dried CH2Cl2 and reacted with excess furan (5mL) catalyzed by AlCl3. The reaction mixture was stirred at 0C for 2 h and then warmed to room temperature and stirred for additional 12 h. After the reaction was completed, the reaction was quenched by carefully pouring the mixture into iced water (100 mL) and the resultant compound was collected by filtration. Then, the filtrate was extracted with CH2Cl2 (320mL), and dried with anhydrous Na2SO4. The solvent was removed under reduced pressure to yield brown solid. The brown solid was purified by silica gel column chromatography (Petroleum ether/EtOAc 80:20, v/v) to give compound 7a as light yellow solid. 10% (eq) BBr3 (5 mL) was added to a solution of compound 7a (0.5 g) in CH2Cl2 (20 mL). The reaction mixture was stirred at -78C for 30 min and then warmed to room temperature and stirred for additional 3.5 h. After the reaction was completed, it was quenched by carefully pouring the mixture into iced water (100 mL), extraction of the aqueous layer three times with EtOAc, washing with 5% NaHSO3 (40 mL) and water (100 mL), and drying with anhydrous Na2SO4. The solvent was removed under reduced pressure to yield a light red solid 8a (0.551 g, 50% yield).
General procedure: A solution of NHMe(OMe) (0.360 g, 6.0 mmol) and benzoic acid (0.244 g, 2.0 mmol) was stirred in dry toluene (10 mL) at 0 C for 10 min. A solution of PCl3 (0.137 g, 1.0 mmol) in dry toluene (2 mL) was then added dropwise to the mixture. The mixture was warmed to r.t. slowly and then stirred at 60 C for 0.5 h. When the reaction was complete (TLC monitoring), the mixture was cooled to r.t. The mixture was then quenched with sat. NaHCO3 soln (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried (anhyd MgSO4). The solvent was removed in vacuo.The product was purified by column chromatography (silica gel, petroleum ether-EtOAc, 3:2) to give pure 3a as a colorless oil; yield: 320 mg (97%).
89%
With Bromotrichloromethane; 4-(diphenylphosphino)-benzyltrimethylammonium bromide; triethylamine; In tetrahydrofuran; at 60℃; for 6h;Inert atmosphere;
General procedure: IS-PPh3 (746 mg, 1.8 mmol) was dried by a vacuum pump for 2 h at 70 C. To a flask containing IS-PPh3 were added 4-methoxycarboxylic acid (152 mg, 1.0 mmol), BrCCl3 (357 mg, 1.8 mmol), benzylamine (129 mg, 1.2 mmol), triethylamine (0.14 mL, 1.0 mmol), and THF (4 mL). The obtained mixture was stirred for 6 h at 60 C under Ar atmosphere. After the reaction, diethyl ether (10 mL) and aq HCl (1 M, 2 mL) were added at 0 C and the obtained mixture was stirred for 15-30 min at room temperature. Then, the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with diethyl ether (10 mL×4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzyl-4-methoxybenzamide was obtained in 93% yield with 99% purity, as estimated by 1H NMR measurement. For cinnamic and aliphatic amides (entries 18-25 in Table 2) and indole-2-carboxamide (entry 16 in Table 2), the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with chloroform (10 mL×4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzylamide was obtained. or the recovery of IS-Ph3PO, NaCl (5.0 g) was added to the aqueous layer. The aqueous solution was extracted with CHCl3 (10 mL×5) and the combined organic layer was dried over NaSO4. After removal of the solvent, IS-Ph3PO containing a trace amount of IS-Ph3P was obtained in 95% yield.
General procedure: To a solution of acid 1 (1.0g, 8.9 mmol) in THF (15 mL) was added Et3N (3.1 mL, 22.2 mmol), and T3P (50% solution in EtOAc, 10.6mL, 17.7 mmol) at 0-5 C and the solution was stirred for about 10 min under a nitrogen atmosphere. Then N,O-dimethylhydroxylaminehydrochloride salt (1.1g, 13.3 mmol) was added to the reaction mixture at 0-5 C and the heterogeneous mixture was allowed to stir at room temperature till the completion of the reactionas indicated by TLC (see Table S-1). The mixture was then diluted with water(20 mL) followed by ethyl acetate (20 mL) and stirred for about 10 min. The separated organic layer was collected, washed with 5% citric acid (2 x10 mL),5% Na2CO3 (2 x 10 mL), and then brine solution. The collected organic layer was dried over anhydrous Na2SO4, filtered and concentrated under low vacuum. The crude product obtainedwas purified by flash column chromatography over silicagel (100-200 mesh) using 12-15% EtOAc / n-hexane as eluent to affordthe desired compound.
86%
To 4-methoxybenzoic acid (100 g, 657.89 mmol) was added SOCl2 (200 g, 1.68 mol). To the solution was added a solution of N-methoxymethanamine hydrochloride (71.5 g, 729.59 mmol) in 500 mL of DCM. The mixture was stirred 2 hours with refluxing. To the mixture was added Et3N (300 g, 2.97 mol). The solution was allowed to react, with stirring, for 30 minutes while the temperature was maintained at room temperature. When the reaction was completed, it was quenched by 500 mL water and extracted by DCM. Removal of solvent followed by purification by flash column chromatography on silica gel gave 110 g (86%) of N,4-dimethoxy-N-methylbenzamide as a yellow liquid.
81%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 3h;
General procedure: To a solution of 3-cyanobenzoic acid 8a (3.0 g, 19.7 mmol) in DMF was added N,O-dimethylhydroxylamine hydrochloride (2.0 g, 20.7 mmol), Et3N (2.88 mL, d = 0.73, 20.7 mmol) and EDC·HCl (4.0 g, 20.7 mmol). After the mixture was stirred for 3 h at room temperature, the solvent was removed in vacuo and the residue was dissolved in EtOAc, washed with 10% citric acid, 10% NaHCO3 and saturated NaCl, and dried over Na2SO4. Then, the solvent was removed to give a colorless oil of compound 9a (3.0 g, 79%).
With dimethyl amine; In ethanol; isopropyl alcohol;
a) 200 kg of 2-methoxyethyl acetoacetate and 185.1 kg of 3-nitrobenzaldehyde are suspended in 800 l of isopropanol. Then 5.65 kg of p-anisic acid and 5.05 kg of 33percent dimethylamine in ethanol are added, heating for about 30' at about 35° C. to obtain a solution. The reaction mixture is left to cool at 20/25° C. and then it is cooled for about 12 hours with running water and for a further 24 hours at about 0° C. with brine, then is centrifuged, washing with isopropanol. After drying, 327 kg of 2-methoxyethyl 2-(3-nitrobenzylidene) acetoacetate are obtained, in an about 91percent yield.
N-(1,8-naphthyridin-2-yl)-4-methoxybenzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With 1,1'-carbonyldiimidazole; In propan-1-ol; water;
EXAMPLE 20 The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (4.55 g), N,N'-carbonyldiimidazole (6.55 g) and <strong>[15992-83-3]2-amino-1,8-naphthyridine</strong> (5.2 g). The product produced by precipitation in water (8.35 g; m.p. 85 C., viscous) is filtered and then dissolved in boiling 1-propanol (50 cc). After 1 hour's cooling at 4 C., the crystallized solid is separated by filtration, washed with 1-propanol (2*5 cc) and dried at 35 C. under reduced pressure (0.067 kPa). N-(1,8-naphthyridin-2-yl)-4-methoxybenzamide (6.9 g) is produced, m.p. 150 C. 2-Amino-1,8-naphthyridine can be prepared according to U.S. Pat. No. 3,948,917.
EXAMPLE 133.94 g of chlorobenzene (35 mmol, 7 eq.), 1.05 g of iron chloride (6.5 mmol, 1.3 eq.) and 0.80 g of para-anisic acid (5.25 mmol, 1.05 eq.) are introduced into a 30 ml Schott tube with magnetic stirring at 500 rpm and at ambient temperature.1.09 g of 2-n-butyl-5-nitrobenzofuran (5 mmol, 1 eq.) and 1.12 g of trichloromethylsilane (7.5 mmol, 1.5 eq.) are then added dropwise, and then the reaction mixture is put, with stirring, at a temperature of 40 C. for 4 hours.The reaction mixture is then cooled to 0 C. by means of an ice-bath, and 3 ml of ethanol are added.The mixture is diluted with 25 ml of chlorobenzene and filtered over sintered glass of no. 2 porosity.The filtrate (organic phase) is then washed three times with 25 ml of a 1 N hydrochloric acid solution.The organic phase is dried over magnesium sulfate and then concentrated under reduced pressure.The product is isolated from the crude reaction mixture by separation on a column of silica (silica gel 60 of diameter 0.2 to 0.5 mm), the eluant being a heptane/ethyl acetate mixture going from a ratio of 95:5 to 80:20 during the elution.1.28 g of 2-n-butyl-5-nitro-8-(4'-methoxy)acetophenonebenzofuran (3.64 mmol, which corresponds to a yield of 72.7%) in the form of a white solid (m.p.=94.7 C.) are then obtained.The NMR characteristics of the resulting product are as follows:1H NMR (200 MHz, CDCl3): delta (ppm)=0.87-0.92 (t, 3H, J=7.2 Hz); 1.30-1.42 (m, 2H); 1.72-1.82 (m, 2H); 2.90-2.95 (t, 2H, J=7.9 Hz); 3.13 (s, 3H); 6.98-7.01 (d, 2H, J=9.3 Hz); 7.55-7.58 (d, 1H, J=9.6 Hz); 7.82-7.85 (d, 2H, J=9 Hz); 8.20-8.24 (dd, 1H, J2=9.2 Hz, J2=2.4 Hz); 8.33-8.34 (d, 1H, J=2.7 Hz).
General procedure: To a solution of carboxylic acid (1.3 mmol) in dry CH3CN (3 mL), were added the isatin derivative (1.00 mmol), cyclohexyl isocyanide (1.0 mmol), and sufficiently activated 4 A MS (100 mg). The resultant mixture was stirred at 80 C for the appropriate time as specified in Table 3 and was monitored by TLC. After completion of the reaction, for compounds 4a-o, the solvent was removed under reduced pressure and the residue dissolved in dry CH2Cl2. The 4 A MS was recovered by simple filtration and addition of n-hexane to the filtrate yielded the pure solid products. For compound 4o, the solvent was removed under reduced pressure and the residue was washed with dry CH2Cl2. The solid residue was then dissolved in EtOH, the 4 A MS was recovered by simple filtration, and the filtrate crystallized from ethanol to yield the pure product 4o in 60% yield.
4-methoxy-N-[4-(1,3-oxazol-5-yl)phenyl]benzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
39%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 72h;
The title compound was prepared from 4-methoxybenzoic acid and 4-(oxazol-5-yl) aniline according to the above procedure to afford the title compound as a yellow solid (65 mg) in 39% yield. 4-methoxybenzoic acid (86.2 mg, 0.567 mmol) and <strong>[1008-95-3]4-(1,3-oxazol-5-yl)aniline</strong> (100 mg, 0.624 mmol) were dissolved in 2 ml DMF. HATU (474 mg, 1.25 mmol) was added followed by diisopropylethylamine (402 mg, 0.542 ml, 3.12 mmol). The reaction was stirred at room temperature for 72 h. The reaction mixture was diluted with ethyl acetate, shaken with 50% saturated NaHCO3 then brine. The pure product precipitated in the course of the workup. After the brine wash, the 2-phase mixture was filtered on paper (1.5-cm disc), washed twice with water, then twice with ether to afford the product (65.3 mg, 39%).
General procedure: To a solution of 2-Methylbenzoic acid (1.36 g, 10 mmol) in DCM (50 mL), Et3N (1.12 g, 11 mmol) and TBTU (3.60 g,11 mmol) were added in turn. After 20 min, compound b (n =4, 1.17 g, 5 mmol) and Et3N (0.50 g, 5 mmol) were added. The reaction solution was stirred at room temperature for 8 h.Then, the solvent was evaporated with the residue being takenup in EtOAc (50 mL). the EtOAc solution was washed with saturated citric acid (3 × 20 mL), NaHCO3 (3 × 20 mL), and brine (3 × 20 mL), dried over MgSO4, and evaporated under vacuum. The desired compound c (1.50 g, 76 percent yield) was derived by crystallization in EtOAc/petroleum ether (1/4) as white powder. ESI-MS: m/z: 397.8 [M+H]+.
With 4-methyl-morpholine; In 1,4-dioxane; water; at 20℃; for 0.25h;
General procedure: To a solution of benzoic acid 1a (2.2 g, 18.0 mmol) and N-methylmorpholine (396 muL, 3.60 mmol) in 1,4-dioxane/H2O(100 mL:50 mL) was added DMT-MM (5.23 g, 18.9 mmol) at room temperature. After stirring for 15 min, a solution ofalanine 2a (1.76 g, 19.8 mmol) and aq 1 M NaOH (19.8 mL, 19.8 mmol) was added. After the reaction was completed(monitored by TLC), N-methylmorpholine (3.96 mL, 36.0 mmol) and DMT-MM (14.9 g, 54 mmol) were added in order.After stirring for 3 h, the reaction mixture was diluted in EtOAc (100 mL) and washed with aq 1 M HCl (40 mL), sat. aqNaHCO3 (40 mL), and brine (30 mL). The organic layer was dried over Na2SO4, filtered, and evaporated under reducedpressure. The residue was purified by column chromatography (EtOAc:hexane = 7:3) to give oxazole 3aa in 78% yield.5-((4,6-Dimethoxy-1,3,5-triazin-2-yl)oxy)-4-methyl-2-phenyloxazole (3aa) Yield: 78%. White solid.
ethyl 6-fluoro-3-(4-methoxybenzoyl)-1H-indole-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
71.8%
To a 100 mL flask was added (4-methoxybenzoic acid)(976 mg, 6.41 mmol) and acetonitrile (11 mL) were added and dissolved,85% Phosphoric Acid (0.125 mL, 6.41 mmol) and trifluoroacetic anhydride (3 mL, 21.39 mmol) were added and stirred for 10 minutes.Then, <strong>[348-37-8]ethyl-6-fluoro-1H-indole-2-carboxylate</strong> (1.1 g, 4.28 mmol) synthesized in the above Step 2 was added,Stir for 10 hours.After completion of the reaction, the organic layer was separated using ethyl acetate and water, and the organic layer was further treated with saturated sodium hydrogencarbonate and sodium chloride, and water was removed with magnesium sulfate.After filtration, the mixture was purified by column chromatography (EA / n-Hex = 1: 4) to give ethyl 6-fluoro-3- (4- methoxybenzoyl) -1H-indole- Rate(1.2 g, 3.06 mmol, 71.8%).
In 5 ml of quartz optical reaction tube, adding 0.05 mmol <strong>[92409-15-9]2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)-1,3-propanediol</strong>, 5 mg mpg-C3N4Catalyst, magneton, and add 1 ml solvent acetonitrile (substrate concentration is 0.05 mol/L). Air above the oxygen displacement reaction tube, and the opening is sealed, is arranged in the integrated light in the reaction device, the rotating speed of 500 r/min, the illumination wavelength is 405 nm (the power of 6 W), temperature constant at 40C, reaction 8 h. After the reaction, gas chromatography - mass spectrum detecting the product, and for high performance liquid chromatography quantitative, substrate conversion and product yield is shown in table 1.
A mixture of 4-methoxybenzoic acid (5.0 g, 33 mmol, 1.0 eq), EDCI (7.6 g, 39 mmol, 1.2 eq), HOBt (6.7 g, 49mmol, 1.5 eq) and TEA (6.7 g, 66 mmol, 9.1 mL, 2.0 eq) in 75 mL of DMF was stirred for 10 mm, then N-methoxymethanamine hydrochloride (3.9 g, 39.4 mmol, 1.2 eq) was added. The mixture was stirred at 15 C for another 12 hours under N2 atmosphere. The reaction mixture was partitioned between 100 mL of water and 100 mL of EtOAc. The organic phase was separated, washed three times with 150 mL of water and 50 mL of brine, dried over Na2SO4,filtered and concentrated under reduced pressure to give 5 g of crude N,4-dimethoxy-N- methylbenzamide as colorless liquid which was used into the next step without further purification
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide;
General procedure: To a solution of corresponding acids (RCOOH, 0.63 mmol), HOBt (170 mg, 1.26 mmol), EDCI (242 mg, 1.26 mmol), and DIPEA (0.208 mL, 1.26 mmol) were added to DMA (60 mL), and then 4 (186 mg, 1.26mmol) were added, the mixture was stirred overnight. The mixture was dissolved in water, then the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to give N-(4-nitrophenethyl)amide (5) in a good yield. And to a solution of 5 in MeOH was added 10% Pd/C under H2 at reflux overnight, then the mixture was dissolved in water, then the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to give N-(4-aminophenethyl)amide (6) in a good yield. Then the mixture of 3 and 6 was added NaCNBH3 in MeOH and the solution was stirred under reflux overnight. After reaction completed, the solvent was removed under reduced pressure and the residue was dissolved in water, the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to afford the corresponding compounds (7-26) in good yields.
With tetrakis(triphenylphosphine) palladium(0); triethylamine; In 1,4-dioxane; at 100℃; for 8h;
At room temperature, 761 mg (5 mmol) of p-methoxybenzoic acid 1d, 625 mg (6 mmol) of styrene 2a, and 721 mg (5 mmol) of <strong>[580-19-8]7-aminoquinoline</strong> 3a were added to a 25 mL round bottom flask, and then 578 mg (0.5 mmol) of tetratriphenylphosphine palladium, 15 mL of 1,4-dioxane, and 1010 mg (10 mmol) of triethylamine were stirred at 100 C. for 8 hours. After the reaction was completed, 15 mL of a saturated sodium chloride aqueous solution was added to the system, and extracted three times with 10 mL of ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off. Silica gel column chromatography of 200-300 mesh 4d pure product was obtained (1608mg, yield 85%, pale yellow solid).
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;
General procedure: A mixture of 2 or 3 (0.50 mmol), the corresponding acids RCOOH (0.60 mmol),DCC (0.60 mmol), DMAP (0.1 mmol) in dry dichloromethane (15 mL) was stirred atroom temperature. When the reaction was completed, and checked by TLC, the mixturewas filtered to remove urea from the reaction, and the filtrate was diluted bydichloromethane (45 mL). Subsequently, the diluted organic phase was washed bysaturated aqueous NaHCO3 (30 mL), and brine (30 mL), dried over anhydrousNa2SO4, concentrated in vacuo, and purified by CC to give the pure 9R/S-acyloxyderivatives of cinchonidine and cinchonine 5a-j,l-o and 6a,c,e-o [17-19]. The dataof target compounds are shown as follows.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
