* 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] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1110 - 1116
[2] Recueil des Travaux Chimiques des Pays-Bas, 1941, vol. 60, p. 811,813, 815
[3] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 7, p. 925 - 930
2
[ 623-03-0 ]
[ 939-80-0 ]
Yield
Reaction Conditions
Operation in experiment
75.47%
With nitronium tetrafluoborate In acetonitrile at 0 - 20℃; for 20 h;
In dry acetonitrile (40 ml) was dissolved 4-chlorobenzonitrile (4g, 29.2 mmol), and nitronium tetrafluoroborate (7.7g, 58.39 mmol) was added therto at 0 °C. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into cold water. The white solid precipitated out was collected by filtration, and the filterate was washed with water and dried. The compound (4.0g, 75.47percent) thus obtained was used for next step without purification.
Reference：
[1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1252 - 1257
[2] Patent: WO2014/24056, 2014, A1, . Location in patent: Page/Page column 40
[3] MedChemComm, 2017, vol. 8, # 10, p. 2003 - 2011
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1110 - 1116
[5] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 36
[6] Journal of the Chemical Society, 1927, p. 1117
[7] Journal of the Chemical Society, 1934, p. 1672,1676
[8] Journal of the American Chemical Society, 1961, vol. 83, p. 4564 - 4571
[9] Journal of the American Chemical Society, 1962, vol. 84, p. 1026 - 1032
[10] RSC Advances, 2016, vol. 6, # 27, p. 23038 - 23047
3
[ 16588-06-0 ]
[ 939-80-0 ]
Reference：
[1] Synthetic Communications, 1989, vol. 19, # 7,8, p. 1431 - 1436
[2] Journal of the Chemical Society, 1934, p. 1672,1676
[3] Patent: WO2011/56635, 2011, A1, . Location in patent: Page/Page column 145-146
4
[ 59670-78-9 ]
[ 939-80-0 ]
[ 7684-30-2 ]
Reference：
[1] Synthesis, 1985, # 2, p. 201 - 202
5
[ 79-24-3 ]
[ 16588-34-4 ]
[ 939-80-0 ]
[ 66399-01-7 ]
[ 134538-49-1 ]
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991, vol. 40, # 2.2, p. 366 - 372[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991, # 2, p. 426 - 433
6
[ 96-99-1 ]
[ 939-80-0 ]
Reference：
[1] Patent: WO2011/56635, 2011, A1,
7
[ 16588-34-4 ]
[ 939-80-0 ]
Reference：
[1] Chinese Journal of Chemistry, 2010, vol. 28, # 6, p. 993 - 996
8
[ 38818-50-7 ]
[ 939-80-0 ]
Reference：
[1] Journal of the Chemical Society, 1934, p. 1672,1676
[2] Patent: WO2011/56635, 2011, A1,
Reference：
[1] Journal of the Chemical Society, 1927, p. 1117
12
[ 3272-08-0 ]
[ 98-59-9 ]
[ 91-66-7 ]
[ 939-80-0 ]
Reference：
[1] Chemische Berichte, 1917, vol. 50, p. 1354
13
[ 89-73-6 ]
[ 939-80-0 ]
[ 59-49-4 ]
[ 3272-08-0 ]
Yield
Reaction Conditions
Operation in experiment
84%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18 h;
General procedure: To a solution of N-hydroxysalicylamide (0.5 g, 3.26 mmol) in anhydrous DMF (5 ml) was added 2a or 2b (3.26 mmol) and freshly calcinated K2CO3 (1.35 g, 9.78 mmol) and the mixture was kept, with stirring at the room temperature overnight. DMF was removed in vacuo and the residue was treated with water (10 ml) and then extracted with CH2Cl2 (5 ml). The organic layer was separated, washed with water, dried over anhydrous CaCl2, and purified by flesh chromatography on silica gel using CH2Cl2 as eluent. Dichloromethane was evaporated in vacuo. The resulting residue was benzo[d]oxazol-2(3H)-one 11. The water layer was acidify by hydrochloric acid, filtered and washed with water. The resulting residue was compound 12a(b).
Reference：
[1] Journal of Fluorine Chemistry, 1999, vol. 94, # 1, p. 51 - 55
22
[ 939-80-0 ]
[ 53312-79-1 ]
Yield
Reaction Conditions
Operation in experiment
97%
With sodium hydrogen sulfide In tetrahydrofuran; water at 45℃;
Example 1; Preparation of N-(1-(5-cyano-2-(3,5-dichlorophenoxy)phenylsulfonyl)piperidin-4-yl)-3-fluorobenzenesulfonamide (25) Commercially available 4-chloro-3-benzonitrile was dissolved in 4 parts THF. One part water was added with sodium hydrosulfide (3 eq.) and stirred overnight at 45° C. TLC (25percent EtOAc in hexanes) confirmed completion of the reaction. THF was evaporated in vacuo and the product precipitated. The white solid was collected via vacuum filtration, washed with water and dried in a vacuum oven with gentle heating (97.0percent yield).
Reference：
[1] Patent: US2011/230487, 2011, A1, . Location in patent: Page/Page column 35
[2] Synlett, 2010, # 20, p. 3019 - 3022
[3] Patent: US2012/196824, 2012, A1,
[4] Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 369[5] Chem.Abstr., 1948, vol. 42, p. 148
[6] Patent: US2003/139390, 2003, A1,
[7] Chemical Communications, 2015, vol. 51, # 61, p. 12197 - 12200
[8] Chemical Communications, 2015, vol. 51, # 66, p. 13086 - 13089
[9] RSC Advances, 2016, vol. 6, # 27, p. 23038 - 23047
[10] ACS Catalysis, 2016, vol. 6, # 11, p. 7844 - 7854
23
[ 939-80-0 ]
[ 7732-18-5 ]
[ 53312-79-1 ]
Reference：
[1] Patent: US5744643, 1998, A,
[2] Patent: US5744643, 1998, A,
3'-methoxy-2-nitro[1,1'-biphenyl]-4-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
77%
With potassium carbonate;[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; In 1,4-dioxane; at 60℃; for 18h;Product distribution / selectivity;
In air, a vial was charged with complex Ih (6.8 mg, 0.01 mmol), potassium carbonate (207 mg, 1.50 mmol), the boronic acid (0.6 mmol) and the organohalide (0.5 mmol). The vial was sealed with a septum and purged with argon (3×). Dioxane (2.0 mL) was added and the contents were stirred at 60 C. for the specified period of time. The reaction was then diluted with diethyl ether (2 mL) and transferred to a round bottom flask. The reaction vial was rinsed with additional diethyl ether (2 mL) and combined with the previous dilution. Each reaction was performed in duplicate and the contents were combined, concentrated onto silica gel and purified by flash chromatography.
2-(3,4-dichloro-phenyl)-<i>N</i>-isopropyl-1-naphthalen-1-ylmethyl-1<i>H</i>-benzoimidazole-5-carboxamidine; compound with GENERIC INORGANIC NEUTRAL COMPONENT[ No CAS ]
2-(3,4-dichloro-phenyl)-<i>N</i>-(3-methyl-butyl)-1-naphthalen-1-ylmethyl-1<i>H</i>-benzoimidazole-5-carboxamidine; compound with GENERIC INORGANIC NEUTRAL COMPONENT[ No CAS ]
<i>N</i>-benzyl-2-(3,4-dichloro-phenyl)-1-naphthalen-1-ylmethyl-1<i>H</i>-benzoimidazole-5-carboxamidine; compound with GENERIC INORGANIC NEUTRAL COMPONENT[ No CAS ]
4-(4-{5-cyano-1-[(1-phenyl-ethylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-{4-[5-cyano-1-(2-oxo-2-piperidin-1-yl-ethyl)-1<i>H</i>-benzoimidazol-2-ylmethoxy]-phenoxy}-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-[4-(1-phenylcarbamoylmethyl-5-thiocarbamoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy)-phenoxy]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{1-[(1-phenyl-ethylcarbamoyl)-methyl]-5-thiocarbamoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-{4-[1-(benzylcarbamoyl-methyl)-5-thiocarbamoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy]-phenoxy}-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-[4-(5-carbamimidoyl-1-phenylcarbamoylmethyl-1<i>H</i>-benzoimidazol-2-ylmethoxy)-phenoxy]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-[4-({5-cyano-1-[(1-methyl-1-phenyl-ethylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethyl}-amino)-phenoxy]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-[4-({5-cyano-1-[(1-phenyl-ethylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethyl}-amino)-phenoxy]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-[4-({5-cyano-1-[(1-phenyl-ethylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethyl}-amino)-phenoxy]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{5-carbamimidoyl-1-[(1-phenyl-ethylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-{4-[1-(2-oxo-2-piperidin-1-yl-ethyl)-5-thiocarbamoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy]-phenoxy}-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-{4-[1-(benzylcarbamoyl-methyl)-5-carbamimidoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy]-phenoxy}-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{5-cyano-1-[(3-phenyl-propylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{5-cyano-1-[(3,4-dichloro-phenylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-{4-[5-carbamimidoyl-1-(2-oxo-2-piperidin-1-yl-ethyl)-1<i>H</i>-benzoimidazol-2-ylmethoxy]-phenoxy}-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-[4-({5-cyano-1-[(3,4-dichloro-phenylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethyl}-amino)-phenoxy]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{5-cyano-1-[(cyclohexylmethyl-carbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-[4-(1-cyclohexylcarbamoylmethyl-5-thiocarbamoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy)-phenoxy]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{1-[(3,4-dichloro-phenylcarbamoyl)-methyl]-5-thiocarbamoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-[4-(5-carbamimidoyl-1-cyclohexylcarbamoylmethyl-1<i>H</i>-benzoimidazol-2-ylmethoxy)-phenoxy]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{1-[(3-phenyl-propylcarbamoyl)-methyl]-5-thiocarbamoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{5-cyano-1-[(3,4-dichloro-benzylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-[4-({5-cyano-1-[(3,4-dichloro-benzylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethyl}-amino)-phenoxy]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{5-carbamimidoyl-1-[(3,4-dichloro-phenylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{1-[(cyclohexylmethyl-carbamoyl)-methyl]-5-thiocarbamoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{5-carbamimidoyl-1-[(3-phenyl-propylcarbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{1-[(3,4-dichloro-benzylcarbamoyl)-methyl]-5-thiocarbamoyl-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
4-(4-{5-carbamimidoyl-1-[(cyclohexylmethyl-carbamoyl)-methyl]-1<i>H</i>-benzoimidazol-2-ylmethoxy}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
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