* 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 the Chemical Society, 1953, p. 2822,2827
3
[ 3395-03-7 ]
[ 27841-33-4 ]
Yield
Reaction Conditions
Operation in experiment
99%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 6 h;
Compound 27 (5 g, 21.9 mmol) was reacted withAfter dissolving in methanol (147 ml)10percent Pd / C (639 mg) was added,And the mixture was stirred at room temperature for 6 hours in the presence of hydrogen gas.After completion of the reaction, the reaction mixture was filtered through celite and the filtrate was distilled under reduced pressure. Compound 28 was obtained without any purification from the residue.
Reference：
[1] Patent: KR101840674, 2018, B1, . Location in patent: Paragraph 0684-0686
[2] RSC Advances, 2016, vol. 6, # 30, p. 25203 - 25214
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 331 - 342
[4] European Journal of Organic Chemistry, 2011, # 28, p. 5427 - 5440
[5] Chemistry - A European Journal, 2017, vol. 23, # 41, p. 9888 - 9896
[6] Journal of Materials Chemistry C, 2018, vol. 6, # 40, p. 10902 - 10909
[7] European Journal of Inorganic Chemistry, 2001, # 3, p. 761 - 777
[8] Journal of Organic Chemistry, 1947, vol. 12, p. 522,529
[9] Journal of Organic Chemistry, 1959, vol. 24, p. 1451,1452, 1453
[10] Journal of the American Chemical Society, 1958, vol. 80, p. 1662
[11] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1897, vol. 125, p. 33
[12] Monatshefte fuer Chemie, 1894, vol. 15, p. 233
[13] Helvetica Chimica Acta, 1966, vol. 49, p. 913 - 939
[14] Synthesis, 1983, # 12, p. 1033 - 1036
[15] European Journal of Medicinal Chemistry, 1991, vol. 26, # 6, p. 633 - 642
[16] Journal of the American Chemical Society, 1991, vol. 113, # 22, p. 8419 - 8425
[17] Pharmaceutical Chemistry Journal, 1980, vol. 14, # 2, p. 130 - 133[18] Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 5, p. 58 - 61
[19] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1986, vol. 25, p. 267 - 270
[20] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1993, vol. 335, # 2, p. 176 - 180
[21] Journal of Chemical Research, Miniprint, 1982, # 3, p. 834 - 851
[22] Tetrahedron Letters, 1995, vol. 36, # 42, p. 7583 - 7586
[23] Journal of Medicinal Chemistry, 1996, vol. 39, # 11, p. 2170 - 2177
[24] Tetrahedron Letters, 2003, vol. 44, # 7, p. 1477 - 1480
[25] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 18, p. 3097 - 3100
[26] Journal of the American Chemical Society, 2006, vol. 128, # 26, p. 8569 - 8574
[27] Patent: US2007/203210, 2007, A1, . Location in patent: Page/Page column 41
[28] Journal of Natural Products, 2008, vol. 71, # 9, p. 1561 - 1563
[29] Patent: WO2005/92899, 2005, A1, . Location in patent: Page/Page column 125; 127
[30] Journal of Medicinal Chemistry, 2013, vol. 56, # 16, p. 6330 - 6338
[31] ChemMedChem, 2015, vol. 10, # 3, p. 511 - 522
[32] Dalton Transactions, 2015, vol. 44, # 40, p. 17453 - 17461
[33] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1949 - 1956
[34] Patent: WO2006/134378, 2006, A1, . Location in patent: Page/Page column 139
4
[ 709-09-1 ]
[ 27841-33-4 ]
Reference：
[1] Journal of the American Chemical Society, 1991, vol. 113, # 22, p. 8419 - 8425
[2] European Journal of Medicinal Chemistry, 1991, vol. 26, # 6, p. 633 - 642
[3] Helvetica Chimica Acta, 1966, vol. 49, p. 913 - 939
[4] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1949 - 1956
5
[ 7595-31-5 ]
[ 27841-33-4 ]
Reference：
[1] Journal of the American Chemical Society, 1943, vol. 65, p. 2432
[2] Synthesis, 1983, # 12, p. 1033 - 1036
6
[ 3395-03-7 ]
[ 102-51-2 ]
[ 27841-33-4 ]
Reference：
[1] Patent: US6218415, 2001, B1,
7
[ 91-16-7 ]
[ 27841-33-4 ]
Reference：
[1] European Journal of Inorganic Chemistry, 2001, # 3, p. 761 - 777
[2] Journal of Organic Chemistry, 1947, vol. 12, p. 522,529
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1897, vol. 125, p. 33
[4] European Journal of Organic Chemistry, 2011, # 28, p. 5427 - 5440
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 16, p. 6330 - 6338
[6] RSC Advances, 2016, vol. 6, # 30, p. 25203 - 25214
[7] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1949 - 1956
[8] Journal of Materials Chemistry C, 2018, vol. 6, # 40, p. 10902 - 10909
8
[ 99069-17-7 ]
[ 27841-33-4 ]
Reference：
[1] Journal of the American Chemical Society, 1943, vol. 65, p. 2432
9
[ 3395-03-7 ]
[ 7595-30-4 ]
[ 27841-33-4 ]
Reference：
[1] Current Science, 1940, vol. 9, p. 118
10
[ 27841-33-4 ]
[ 216699-86-4 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 18, p. 3097 - 3100
With triphenylantimony In dichloromethane at 20℃; for 24 h;
General procedure: Triphenylstibane(35.5 mg, 0.1 mmol, 10 molpercent) and diamine 2 (1.2 mmol) were added to a solution of -hydroxy ketone 1(1 mmol) in toluene (6 mL) under air. The solution was stirred at room temperature and monitored byTLC. The reaction mixture was concentrated under reduced pressure and the residue was purified bycolumn chromatography (CH2Cl2) on silica gel. The products were confirmed by comparison of mp,NMR data, and MS spectra with that in the literature. 822:
(1α,2β,5β,6α,17α,18β,21β,22α)-8,15,24.31-tetraaza-1,6,17,22-tetrachloro-11,12,27,28,33,33,34,34-octamethoxynonacyclo[20.10.1.16,17.02,21.05,18.07,10.09,14.023,32.025,30]tetratriacontane-7(10),8,10,12,14,23(32),24,26,28,30-decaene[ No CAS ]
(1α,2β,4β,5α,8α,9β,11β,12α)-14,21-diaza-1,5,8,12-tetrachloro-17,18,23,23,24,24-hexamethoxyheptacyclo[10.10.1.15,8.02,11.04,9.013,22.015,20]tetracosane-13(22),14,16,18,20-pentaene-6,7-dione[ No CAS ]
(1α,2β,4β,5α,16α,17β,19β,20α)-7,14,22,29-tetraaza-1,5,16,20-tetrachloro-10,11,25,26,31,31,32,32-octamethoxynonacyclo[18.10.1.15,16.02,19.04,17.06,15.08,13.021,30.023,29]dotriacontane-6(15),7,9,11,13,21(30),22,24,26,28-decaene[ No CAS ]
In tetrahydrofuran; methanol; glacial AcOH; ethyl acetate; toluene;
a 2-[[N-(Benzyloxycarbonyl)-N-methyl]aminomethyl]-5,6-dimethoxybenzimidazole Cbz-sarcosine (1.4 g, 6.1 mmol) was dissolved in dry THF in a 100 mL roundbottom flask, and Et3 N (1.5 mL, 10.8 mmol) was added, followed by isobutylchloroformate (0.80 mL, 6.17 mmol). The reaction was stirred at RT, then was added to a solution of 4,5-dimethoxyphenylenediamine (6.06 mmol) in dry THF at -25 C. The Cbz-sarcosine, mixed-anhydride solution was added to the cooled phenylenediamine solution. The reaction was stirred at -25 C. for 10 min, then was allowed to warm to RT. After 20 h, the reaction was concentrated under vacuum. The residue was taken up in EtOAc and washed with 1.0 N NaHCO3. The organic layer was dried (MgSO4), filtered, concentrated under vacuum, and reconcentrated from toluene. The residue was dissolved in glacial AcOH (100 mL) and heated in an oil bath heated set at 110 C. After 24 h, the reaction was concentrated under vacuum. Flash chromatography (silica gel, step gradient, 2% MeOH/CHCl3, 5% MeOH/CHCl3) gave the title compound (1.7 g, 81%): 1 H NMR (250 MHz, CDCl3) delta 7.33 (s, 5H), 7.05 (s, 2H), 5.15 (s, 2H), 4.64 (s, 2H), 3.88 (s, 6H), 3.04 (s, 3H); MS (ES) m/e 356.2 (M+H)+.
With triphenylantimony; In dichloromethane; at 20.0℃; for 24.0h;
General procedure: Triphenylstibane(35.5 mg, 0.1 mmol, 10 mol%) and diamine 2 (1.2 mmol) were added to a solution of -hydroxy ketone 1(1 mmol) in toluene (6 mL) under air. The solution was stirred at room temperature and monitored byTLC. The reaction mixture was concentrated under reduced pressure and the residue was purified bycolumn chromatography (CH2Cl2) on silica gel. The products were confirmed by comparison of mp,NMR data, and MS spectra with that in the literature. 822:
An equimolar solution of the corresponding aldehyde and phenylenediamine (1 mmol) in EtOH (4 mL) was heated under reflux until all starting material was converted to the imine intermediate (ca.l.5 h). After addition of DDQ (395 mg, 1.1 mmol) the reaction mixture was heated at reflux until the imine intermediate was completely converted to the benzimidazole product (typically 30-60 min). The reaction mixture was then cooled to room temperature, diluted with saturated aqueous NaHC03, and the product was extracted twice with ethyl acetate. The combined organic extracts were dried with anhydrous MgS04, filtered, and concentrated under reduced pressure. The crude product was purified by Flash column chromatography on silica to give the corresponding pure benzimidazole
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
