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[ CAS No. 555-16-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 555-16-8
Chemical Structure| 555-16-8
Chemical Structure| 555-16-8
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Agarwal, Devesh S. ; Beteck, Richard M. ; Ilbeigi, Kayhan , et al. DOI: PubMed ID:

Abstract: A library of imidazo[1,2-a]pyridine-appended chalcones were synthesized and characterized using 1H NMR,13C NMR and HRMS. The synthesized analogs were screened for their antikinetoplastid activity against Trypanosoma cruzi, Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense and Leishmania infantum. The analogs were also tested for their cytotoxicity activity against human lung fibroblasts and primary mouse macrophages. Among all screened derivatives, (E)-N-(4-(3-(2-chlorophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active against T. cruzi and T. b. brucei exhibiting IC50 values of 8.5 and 1.35 μM, resp. Against T. b. rhodesiense, (E)-N-(4-(3-(4-bromophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active with an IC50 value of 1.13 μM. All synthesized active analogs were found to be non-cytotoxic against MRC-5 and PMM with selectivity indexes of up to more than 50.

Keywords: antikinetoplastid ; chalcone ; drug likeliness properties ; imidazo[1,2-a]pyridine ; neglected tropical diseases (NTDs) ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Jan Nowak ; Michał Tryniszewski ; Michał Barbasiewicz DOI:

Abstract: Heteroatom-based olefinating reagents (e.g., organic phosphonates, sulfonates, etc.) are used to transform carbonyl compounds into alkenes, and their mechanism of action involves aldol-type addition, cyclization, and fragmentation of four-membered ring intermediates. We have developed an analogous process using ethyl 1,1,1,3,3,3-hexafluoroisopropyl methylmalonate, which converts electrophilic aryl aldehydes into α-methylcinnamates in up to 70% yield. The reaction plausibly proceeds through the formation of β-lactone that spontaneously decarboxylates under the reaction conditions. The results shed light on the Knoevenagel–Doebner olefination, for which decarboxylative anti-fragmentation of aldol-type adducts is usually considered.

Keywords: olefination ; carbonyl compounds ; reaction mechanism ; lactones ; malonates ; Knoevenagel ; Doebner reaction

Purchased from AmBeed: ; ; ; ; ; ;

Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong , et al. DOI: PubMed ID:

Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

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Product Details of [ 555-16-8 ]

CAS No. :555-16-8 MDL No. :MFCD00007346
Formula : C7H5NO3 Boiling Point : -
Linear Structure Formula :C6H4(NO2)(CHO) InChI Key :BXRFQSNOROATLV-UHFFFAOYSA-N
M.W : 151.12 Pubchem ID :541
Synonyms :

Calculated chemistry of [ 555-16-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.65
TPSA : 62.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.99
Log Po/w (XLOGP3) : 1.56
Log Po/w (WLOGP) : 1.41
Log Po/w (MLOGP) : 0.26
Log Po/w (SILICOS-IT) : -0.18
Consensus Log Po/w : 0.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.41 mg/ml ; 0.0093 mol/l
Class : Soluble
Log S (Ali) : -2.49
Solubility : 0.488 mg/ml ; 0.00323 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.71
Solubility : 2.95 mg/ml ; 0.0195 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.32

Safety of [ 555-16-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P273-P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362 UN#:N/A
Hazard Statements:H317-H319-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 555-16-8 ]

* 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.

  • Upstream synthesis route of [ 555-16-8 ]
  • Downstream synthetic route of [ 555-16-8 ]

[ 555-16-8 ] Synthesis Path-Upstream   1~53

  • 1
  • [ 555-16-8 ]
  • [ 300-87-8 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 11, p. 2177 - 2187
  • 2
  • [ 555-16-8 ]
  • [ 80-73-9 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
  • 3
  • [ 23536-26-7 ]
  • [ 67-52-7 ]
  • [ 555-16-8 ]
Reference: [1] Helvetica Chimica Acta, 2014, vol. 97, # 9, p. 1219 - 1236
  • 4
  • [ 555-16-8 ]
  • [ 29608-05-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 4, p. 989 - 994
  • 5
  • [ 555-16-8 ]
  • [ 95-54-5 ]
  • [ 2963-77-1 ]
Reference: [1] ACS Catalysis, 2015, vol. 5, # 4, p. 2062 - 2069
  • 6
  • [ 555-16-8 ]
  • [ 2963-77-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 13, p. 2441 - 2446
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  • 7
  • [ 110-91-8 ]
  • [ 555-16-8 ]
  • [ 6425-46-3 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 5, p. 1159 - 1165
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 15, p. 2239 - 2241
  • 8
  • [ 555-16-8 ]
  • [ 16687-60-8 ]
YieldReaction ConditionsOperation in experiment
68% With sodium azide; cerium(IV) tetraammonium sulfate dihydrate; hydroxylamine hydrochloride In N,N-dimethyl-formamide for 9 h; Reflux; Green chemistry General procedure: Aldehyde (1 mmol), hydroxylamine hydrochloride (2 mmol) and sodium azide (2 mmol) were added successively to a solution of (NH4)4Ce(SO4)4·2H2O (20 molpercent) in 5 mL DMF. The mixture was reflux for appropriate time (Table 2). The progress of the reaction was monitored by TLC. After completion of the reaction, the solution was treated with HCl (4N, 10  mL) and then the solution was poured into 100 mL water and extract with ethyl acetate, washed several times with water. The combined organic mixture was dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography on silica gel 60-120 mesh using petroleum ether/ethyl acetate (75:25) as eluent to afford the pure solid tetrazole. All the products were characterized by 1H NMR, 13C NMR and HRMS.
Reference: [1] RSC Advances, 2016, vol. 6, # 94, p. 91999 - 92006
[2] Applied Organometallic Chemistry, 2018, vol. 32, # 4,
[3] Synlett, 2012, vol. 23, # 20, p. 2927 - 2930
[4] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2116 - 2122
[5] Synthesis (Germany), 2013, vol. 45, # 4, p. 507 - 510
[6] Tetrahedron Letters, 2018, vol. 59, # 14, p. 1385 - 1389
[7] Synthetic Communications, 2011, vol. 41, # 14, p. 2081 - 2085
[8] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2220 - 2235
[9] Tetrahedron Letters, 2016, vol. 57, # 5, p. 523 - 524
[10] Synthetic Communications, 2017, vol. 47, # 7, p. 695 - 703
  • 9
  • [ 555-16-8 ]
  • [ 105-45-3 ]
  • [ 21829-09-4 ]
YieldReaction ConditionsOperation in experiment
95% With Er(1,3,5-benzenetricarboxylate)(aqua)(N,N-dimethylformamide)1.1; ammonium acetate In ethanol at 70℃; for 4 h; General procedure: Ammonium acetate (1 mmol), was added to the mixture of benzaldehyde (1 equiv), and ethyl acetoacetate (1.1 equiv) in Ethanol (1.5 mL) along with an appropriate amount of Er-MOF as catalyst (20 mg). The mixture was stirred at 70 °C for 4 h. After completion of the reaction, the catalyst was removed by centrifuge. Then brine (5 mL) and EtOAc (5 mL) was added. The mixture was extracted with EtOAc and the combined organic phase were washed with saturated aqueous solution of NaHCO3 (10 mL), and brine(10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. After removal of the solvent under vacuum, the crude product was purified by column chromatography to afford the desired product, Table 1. It is found that the Er-MOF catalyst can be recovered and reused five times without considerable loss of catalyticactivity.
95% With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10 h; In the 100 ml flask is added in a single port 0.01 µM percent Lewis acid-base dual function catalyst I (wherein Rf=CF3; R1, R2, R3, R4, R5, R6=F), 0.1 µM to the nitrobenzene formaldehyde (R7=4 - NO2- Ph), 0.1 µM methyl acetoacetate (R8=Me; R9=Me), 0.1 µM ammonium acetate, 10 ml toluene, the reaction in the 100 °C stirring for 10 hours, TLC tracking reaction to the reaction is complete. The reaction result is: product II (R7=4 - NO2- Ph; R8=Me; R9=Me) of the yield is 94percent; catalyst system used repeatedly 10 times, its catalytic performance did not decline
95% at 100℃; for 0.333333 h; Green chemistry General procedure: To a glassy reactor equipped with a magnetic stir bar, amixture of aromatic aldehyde (1.0 mmol), β-keto ester(2 mmol), ammonium acetate (1.5 mmol) and n-Fe3O4(at)ZrO2/HPW (0.003 g, 15 mol percent) was added. The reactorwas put in an oil bath with the temperature of 100 °C andthe reaction was carried out under solvent-free condition.The progress of the reaction was monitored using TLCplates. When the reaction was completed, the mixture wasallowed to cool to room temperature. Afterwards, the mixturewas triturated with 5mL ethyl acetate and the catalystwas separated by the help of an external magnet. Then thesolvent was evaporated and the crude product was recrystallizedfrom EtOH/H2O to offer the pure product.
94% for 2.25 h; Heating; Green chemistry General procedure: A mixture of aldehyde 1 (1 mmol), 1,3-dicarbonyl compound 2 (2 mmol), and nitrogen source 3 (3 mmol) were mixed and heated in the presence of a low-melting sugar mixture.The progress of the reaction was monitored by thin-layer chromatography (TLC) using n-hexane–ethyl acetate (7:3) as the solvent system. The Rf values of the product spots ranged from 0.5 to 0.6. After completion of the reaction, water was added to the reaction mixture to obtain the solid product as a precipitate. In cases where the product was obtained as a melt, several washings with water followed by bicarbonate solution gave crystalline products. The solids were filtered and washed with cold water. In most of the cases, the product obtained was pure, and when impure, the product was recrystallized from hot ethanol. Further two products were obtained as oils (Table 5, entries 4w and 4x). These products were extracted with ethyl acetate and dried over anhydrous Na2SO4. Evaporation of the solvent gave the pure product as an oil.
92% at 55℃; for 4 h; Green chemistry General procedure: A mixture of aldehyde (1 mmol), β-dicarbonyl compound (1or 2 mmol), NH4OAc (2.5 mmol), dimedone (1 mmol, whenused), and SBA-15/NHSO3H (5 molpercent) was stirred at 55 °C.After complete disappearance of starting material asindicated by TLC, the resulting mixture was diluted with hotEtOAc (10 mL) and filtered. The catalyst was completelyrecovered from the residue.
82% at 80℃; for 0.15 h; General procedure: A mixture of the alkyl or aryl aldehyde (1 mmol), -dicarbonyl(2 mmol) and ammonium acetate (1.5 mmol) in the presence ofFe3O4NPs (0.024 g, equal to 10 molpercent) was heated at 80C, withstirring. The progress of the reaction was monitored by TLC (elu-ent: EtOAc:n-hexane). After completion of the reaction, the mixturewas cooled to room temperature and then ethanol was added tothe resulting mixture and separated Fe3O4NPs by a normal mag-net. After evaporation of solvent, the solid product was filtered andrecrystallized from ethanol to give the pure products in 72–95percentyields based on the starting aldehyde.

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  • 10
  • [ 674-82-8 ]
  • [ 67-56-1 ]
  • [ 555-16-8 ]
  • [ 21829-09-4 ]
YieldReaction ConditionsOperation in experiment
80% With ammonium acetate In neat (no solvent) at 60℃; Green chemistry General procedure: In this work SBA-15 nanoreactor was synthesized by the procedure reported by Zhao et al. [6a] and then modified with mercaptopropyltrimethoxysilane (MPTMS) and oxidized to the sulfonic acid [6b] nanoparticle using hydrogen peroxide (Fig. 1). A mixture of diketene (3 mmol), aldehyde (1 mmol), enamine (1 mmol) and alcohol (4 mL) and SBA-15/SO3H (0.07 g, ~4 molpercent) was reacted under neat conditions for appropriate time (TLC). After that, 20 mL hot EtOH was added to the reaction vessel and, with simple centrifuging, the catalyst was removed as filtrate, washed and then the product recrystallized from hot ethanol. All of the products are synthesized by four-component method and were identified by their physical and spectral data (mp, IR, 1H NMR and 13C NMR).
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 8, p. 930 - 932
[2] Chinese Chemical Letters, 2013, vol. 24, # 5, p. 401 - 403
[3] Synthesis, 2010, # 23, p. 4057 - 4060
  • 11
  • [ 60-35-5 ]
  • [ 555-16-8 ]
  • [ 105-45-3 ]
  • [ 21829-09-4 ]
YieldReaction ConditionsOperation in experiment
82% With Candida antarctica lipase B immobilized on acrylic resin In tert-butyl methyl ether at 50℃; for 72 h; Aldehyde (0.125 mmol), acetamide (0.5 mmol), and CAL-B (100 mg) in the mixed solvent (1 ml, 1,3-dicarbonyl compounds/methyl tert-butyl ether=4:6, by vol) at 50 °C for 72 h. The reaction was terminated by filtering off the enzyme. The crude residue was purified by silica gel column chromatography with an eluent consisting of petroleum ether/ethyl acetate (1/1 v/v). Product-contained fractions were combined, concentrated, and dried to give the product 1,4-dihydropyridine.
Reference: [1] Tetrahedron, 2011, vol. 67, # 14, p. 2689 - 2692
  • 12
  • [ 624-45-3 ]
  • [ 555-16-8 ]
  • [ 21829-09-4 ]
YieldReaction ConditionsOperation in experiment
92% With ammonium acetate In neat (no solvent) at 55℃; for 4 h; Green chemistry General procedure: Polyhydroquinolines and DihydropyridinesA mixture of aldehyde (1 mmol), β-dicarbonyl compound (1or 2 mmol), NH4OAc (2.5 mmol), dimedone (1 mmol, whenused), and SBA-15/NHSO3H (5 molpercent) was stirred at 55 °C.After complete disappearance of starting material asindicated by TLC, the resulting mixture was diluted with hotEtOAc (10 mL) and filtered. The catalyst was completelyrecovered from the residue
Reference: [1] Synlett, 2014, vol. 25, # 19, p. 2753 - 2756
  • 13
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  • [ 126-81-8 ]
  • [ 105-45-3 ]
  • [ 3357-14-0 ]
  • [ 40588-46-3 ]
  • [ 21829-09-4 ]
YieldReaction ConditionsOperation in experiment
8% With C22H25F6N5S; ammonium acetate In dichloromethane at 20℃; for 1 h; To a mixture of 0.014 g (0.1 mol) of dimedone, 0.01 mL (0.1 mol) of methyl acetoacetate, 0.015 g (0.1 mol) of p-nitrobenzaldehyde, and 0.096 g (0.125 mmol) of ammonium acetate at room temperature was added 1 mL of methylene chloride and 5 mmol of catalyst 5–9, the mixture was stirred for 1 h, then the solution was evaporated on a rotary evaporator. From the residue the reaction products were isolated by column chromatography, eluent ethyl acetate–hexane,1 : 8. Compounds were eluted in the following order: 4, 2, 3, and 1. Yield of compound 1 64–72percent.
Reference: [1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 5, p. 701 - 705[2] Zh. Org. Khim., 2016, vol. 52, # 5, p. 713 - 717,5
  • 14
  • [ 105025-71-6 ]
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  • [ 21829-09-4 ]
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  • 15
  • [ 555-16-8 ]
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
  • [ 21829-09-4 ]
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  • [ 77233-99-9 ]
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  • 18
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  • [ 72324-39-1 ]
  • [ 21829-09-4 ]
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  • [ 631-61-8 ]
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  • 21
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  • 23
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  • [ 1008-95-3 ]
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  • [ 100-27-6 ]
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  • [ 15184-96-0 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 20℃; for 0.166667 h;
Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran; 1,2-dichloro-ethane at 20℃; for 1 h;
C-I) 4-Amino-dimethylbenzylamine7 g (46.3 mmol, 1 eq) 4-nitrobenzaldehyde are dissolved in 1 ,2-dichloroethane, then27.7 mL of dimethylamine (55.6 mmol, 1.2 eq, 2 molar solution in THF) are added and the solution is stirred for 10 min at RT. To this are then added, successively, 3.2 mL (55.6 mmol, 1.2 eq) acetic acid and 14.7 g (69.5 mmol, 1.5 eq) sodium trisacetoxyboro hydride and the reaction mixture is stirred for 1 h at RT. The reaction mixture is slowly poured into saturated, aqueous sodium hydrogen carbonate solution. The aqueous phase is washed twice with 100 mL of DCM and the combined organic phases are dried on magnesium sulphate. 6.9 g (38.1 mmol, 82percent) 4-nitro-dimethylbenzylamine are obtained, which is used in the following reduction without any further purification. MS-ESI+: 181 (M+H)+
Reference: [1] Synthetic Communications, 2000, vol. 30, # 11, p. 2001 - 2008
[2] Patent: WO2008/77885, 2008, A2, . Location in patent: Page/Page column 19
  • 28
  • [ 22705-32-4 ]
  • [ 555-16-8 ]
  • [ 15184-96-0 ]
Reference: [1] Synlett, 2001, # 10, p. 1617 - 1619
  • 29
  • [ 506-59-2 ]
  • [ 555-16-8 ]
  • [ 15184-96-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1320 - 1336
  • 30
  • [ 555-16-8 ]
  • [ 68-12-2 ]
  • [ 15184-96-0 ]
Reference: [1] Journal of the Indian Chemical Society, 2007, vol. 84, # 6, p. 612 - 614
  • 31
  • [ 75-52-5 ]
  • [ 555-16-8 ]
  • [ 123-08-0 ]
  • [ 3179-08-6 ]
  • [ 3156-41-0 ]
  • [ 18731-47-0 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 29, p. 7052 - 7062
  • 32
  • [ 67-56-1 ]
  • [ 555-16-8 ]
  • [ 24588-74-7 ]
  • [ 51513-29-2 ]
  • [ 2345-56-4 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 24, p. 4545 - 4556
  • 33
  • [ 20035-08-9 ]
  • [ 555-16-8 ]
  • [ 50899-03-1 ]
YieldReaction ConditionsOperation in experiment
48% With {(Pd{Fe(η5-C5H5)(η5-C5H3C(CH3)=NC6H4CH3-4)}(μ-Cl))2}; potassium carbonate In dimethyl sulfoxide at 110℃; for 12 h; Inert atmosphere General procedure: Under N2 atmosphere, a reaction vessel was charged with a mixture of sodium sulfinates 1 (0.6 mmol), nitroarenes 2 (0.3 mmol), palladacycle I (0.75 molpercent) and K2CO3 (1.0 equiv) in DMSO (2 ml) at room temperature. After that, the mixture was heated to 110 °C and incubated in an oil bath for 12 h under N2 atmosphere. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with brine three times. The combined organic solution was dried with Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by thin-layer chromatography on silica gel GF 254 (ethyl acetate/petroleum ether) to give the pure product.
Reference: [1] Tetrahedron, 2014, vol. 70, # 47, p. 9107 - 9112
  • 34
  • [ 555-16-8 ]
  • [ 74-89-5 ]
  • [ 19499-60-6 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: at 0℃; for 0.25 h;
Stage #2: With sodium tetrahydroborate In methanol; water at 20℃; for 2 h;
Preparation 33A; N-methyl(4-nitrophenv0methanamiπe; O2NNp-Nitrobenzaldehyde (15.0 g, 99.3 mmol) and 40percent aqueous methylamine (17 mL) were combined in MeOH (250 mL) for 15 min at 00C for 15 min and then treated with sodium borohydride (3.77 g, 99.3 mmol). The mixture was stirred at RT for 2 h and concentrated. Water (50 mL) was added to the residue which was then extracted with DCM (3 x 250 mL). The extracts were dried and concentrated giving the title substance. Yield 15. 4 g, 94percent. 1H NMR (CDCI3) δ 8.10 (m, 2H), 7.43 (m, 2H), 3.79 (s, 2H), 2.39 (s, 3H). MS (AP+) m/e 167 (MH+).
62%
Stage #1: at 80℃; for 24 h; Molecular sieve; Sealed tube
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 24 h;
General procedure: The desired nitro-substituted benzaldehyde (1 eq, 13.2 mmol, 2.0 g), methylamine (40percent watersolution, 1.1 eq, 14.5 mmol, 0.95 mL) and molecular sieves (3A, 100 mg) were introduced in a screw cap vialand the mixture was heated at 80°C for 24h. After cooling to RT, the mixture was diluted with chloroform (3mL) and filtered. The solvent was removed by rotary evaporation and the crude obtained was redissolved inmethanol (30 mL) and cooled to 0 °C. NaBH4 (1.1 eq, 14.5 mmol, 550 mg) was added in three portions andthe resultant mixture allowed warming to RT and reacting for 24 h. The mixture was then quenched with aq.NH4OH 5percent (10 mL) and the solvent was concentrated by rotary evaporation. The obtained aqueous layer wasextracted with CH2Cl2 (3 x 10 mL). The combined organic extracts were dried over Na2SO4, filtered and thefiltrate was concentrated by rotary evaporation. The residue was purified by silica gel flash chromatographyor distillation under vacuum to give the title compound.
Reference: [1] Patent: WO2008/4117, 2008, A1, . Location in patent: Page/Page column 116
[2] Molecules, 2017, vol. 22, # 12,
  • 35
  • [ 555-16-8 ]
  • [ 19499-60-6 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 3, p. 569 - 575
[2] Chemistry - A European Journal, 2014, vol. 20, # 52, p. 17565 - 17571
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2747 - 2759
  • 36
  • [ 593-51-1 ]
  • [ 555-16-8 ]
  • [ 19499-60-6 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1987, vol. 320, # 7, p. 647 - 654
  • 37
  • [ 555-16-8 ]
  • [ 5048-82-8 ]
Reference: [1] Patent: WO2014/131855, 2014, A1,
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8967 - 9004
  • 38
  • [ 555-16-8 ]
  • [ 27914-56-3 ]
Reference: [1] Patent: JP5667058, 2015, B2,
  • 39
  • [ 141-82-2 ]
  • [ 555-16-8 ]
  • [ 102308-62-3 ]
YieldReaction ConditionsOperation in experiment
69% With ammonium acetate In butan-1-olReflux General procedure: A mixture of appropriate aldehyde 2.40 g (1-15), 2.44 g ofmalonic acid and 3.54 g of ammonium acetate (1:1.1:2.3), in 200mLof the 1-butanol was refluxed for 1.5-2 h until the evolution of CO2ceased. The precipitate formed was filtered and washed withboiling 1-butanol (2 x 50 mL), boiling ethanol (2 x 50 mL) and100mL of water. Precipitates were dried at 80-100 °C for 8-10 h.Purity of product was checked by TLC, and yield obtained about65-80percent in each reaction.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 252 - 268
  • 40
  • [ 555-16-8 ]
  • [ 102308-62-3 ]
YieldReaction ConditionsOperation in experiment
14% With ammonium acetate; malonic acid In ethanol; water EXAMPLE 38
Preparation of N-(4-Cyanophenyl)-N--[3-(3-(4--nitrophenyl)propionic acid)]urea sodium salt
A stirred suspension of ammonium acetate (30.8 g, 400 mmol) and 4-nitrobenzaldehyde (30.2 g, 200 mmol) in 50 mL of 95percent ethanol was heated to 45 °C.
To the resulting thick slurry was added 75 mL of 95percent ethanol and malonic acid (20.8 g, 200 mmol).
The reaction mixture was heated at reflux for 24 h.
The cooled reaction mixture was filtered and the solid washed with copious amounts of ethanol.
The solid was air-dried to afford 42.55 g of crude product as a pale orange powder.
The crude product (35 g) was slurried in 300 mL of water, heated to 55°C, and the pH adjusted to 1 with concentrated HCl.
After cooling to RT, the slurry was filtered and the solid washed with water.
The filtrate was concentrated to approximately 250 mL and the pH adjusted to 7 with 1 N NaOH.
The resulting suspension was stirred overnight and then filtered.
The solid was dried in vacuo to afford 4.95 g (14percent) of 3-amino-3-(4--nitrophenyl)propionic acid as a white powder: 1H NMR (D2O/NaOD/TSP) δ 8.15 (d, J = 8.7 Hz, 2 H), 7.56 (d, J = 8.7 Hz, 2 H), 4.38 (t, J = 7.3 Hz, 1 H), 2.72-2.52 (m, 2 H); 13C NMR (D2O/NaOD/TSP) δ 182.2, 155.3, 149.3, 130.1, 126.6, 55.5, 49.5.
Reference: [1] Patent: EP355819, 1990, A1,
  • 41
  • [ 555-16-8 ]
  • [ 102308-62-3 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 37, p. 7449 - 7461
[2] Tetrahedron, 2002, vol. 58, # 37, p. 7449 - 7461
  • 42
  • [ 461-72-3 ]
  • [ 555-16-8 ]
  • [ 38335-24-9 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 7, p. 4203 - 4208
  • 43
  • [ 555-16-8 ]
  • [ 343239-58-7 ]
Reference: [1] Patent: CN108164387, 2018, A,
  • 44
  • [ 2689-62-5 ]
  • [ 555-16-8 ]
  • [ 40277-76-7 ]
  • [ 1530-32-1 ]
Reference: [1] Synthetic Communications, 1982, vol. 12, # 6, p. 469 - 476
  • 45
  • [ 555-16-8 ]
  • [ 70261-82-4 ]
Reference: [1] Russian Journal of Organic Chemistry, 2011, vol. 47, # 10, p. 1556 - 1563
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8801 - 8815
  • 46
  • [ 109-01-3 ]
  • [ 555-16-8 ]
  • [ 70261-81-3 ]
YieldReaction ConditionsOperation in experiment
90% With sodium tetrahydroborate; acetic acid In chloroform at 0 - 20℃; for 13 h; General procedure: AcOH (100percent) (140 mL, 2.44 ml) was added over 1 h to a flask containing stirred NaBH4 (20.0 g, 0.53 ml) and CHCl3 (220 mL) at 0-5 °. The resulting mixture was stirred at 0-5 ° for 1.5 h and 1-methylpiperazine (1) (28.0 ml, 0.25 ml) and a solution of methyl 4-formylbenzoate (2a) (43.4 g, 0.26 ml) in CHCl3 (60 mL) were added. The resulting mixture was stirred at 0-5 ° for 1 h and then for 12 h at rt. the mixture was treated with H2O (150 mL) and Na2CO3 until pH 8.0-9.0. The aqueous phase was extracted with EtOAc (2 .x. 100 ml) then both organic layers were combined, washed with H2O (1 .x. 100 ml), and dried over anhydrous Na2SO4. Filtration and evaporation of the solvents gave methyl 4-[(4-methylpiperazin-1-yl)methyl]benzoate (4a): yellowish oil; yield: 61.6 g, 99percent.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5056 - 5058
[2] Russian Journal of Organic Chemistry, 2013, vol. 49, # 4, p. 563 - 567[3] Zh. Org. Khim., 2013, vol. 49, # 4, p. 580 - 584
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8801 - 8815
[5] Russian Journal of Organic Chemistry, 2011, vol. 47, # 10, p. 1556 - 1563
  • 47
  • [ 109-01-3 ]
  • [ 555-16-8 ]
  • [ 7556-55-0 ]
  • [ 619-73-8 ]
  • [ 70261-81-3 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2007, vol. 43, # 12, p. 1540 - 1543
  • 48
  • [ 555-16-8 ]
  • [ 178265-65-1 ]
Reference: [1] Journal of Physical Organic Chemistry, 2012, vol. 25, # 9, p. 754 - 759
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 28, p. 4602 - 4612
[3] Journal of Catalysis, 2014, vol. 310, p. 37 - 44
[4] New Journal of Chemistry, 2016, vol. 40, # 7, p. 5775 - 5781
[5] Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 351, p. 231 - 239
  • 49
  • [ 555-16-8 ]
  • [ 118727-34-7 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 984 - 992
  • 50
  • [ 402-45-9 ]
  • [ 555-16-8 ]
  • [ 90035-20-4 ]
YieldReaction ConditionsOperation in experiment
69% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 5 h; Inert atmosphere; Schlenk technique; Green chemistry General procedure: Under an argon atmosphere, a Schlenk tube was charged with MCM-41-2N-Cu(OAc)2(46 mg, 0.025 mmol), nitroarene 1 (0.5 mmol), phenol 2 (1.0 mmol), Cs2CO3 (1.0 mmol) and DMF (3 mL). The reaction mixture was stirred at 100 °C for 5 h under Ar. After being cooled to room temperature, the mixture was diluted with ethyl acetate (20 mL) and filtered. The MCM-41-2N-Cu(OAc)2 catalyst was washed with distilled water (2 × 5 mL), DMF (2 × 5 mL) and EtOH (2 × 5 mL) and could be reused in the next run. The filtrate was washed with water (2 × 10 mL) and dried over anhydrous MgSO4. After removal of the solvent under reduced pressure, the residue was purified by column chromatography (EtOAc/hexane) on silica gel to afford the desired product 3.
62% With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4 h; Inert atmosphere; Schlenk technique General procedure: Under N2 atmosphere, a Schlenk tube was charged with nitroarenes 1 (0.5 mmol), phenols 2 (1.0 mmol), Cu(OAc)2·H2O (5 mol percent), and Cs2CO3 (1.0 mmol) in DMF (3 mL) at room temperature. After that, the mixture was stirred constantly at 100 °C (oil bath temperature) for 4 h. After the completion of the reaction, as monitored by TLC and GC–MS analysis, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtrated. The filtrate was concentrated under vacuum, and the resulting residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to afford the desired arylated product 3.
Reference: [1] Journal of Chemical Research, 2017, vol. 41, # 12, p. 725 - 729
[2] Tetrahedron, 2012, vol. 68, # 43, p. 8905 - 8907
  • 51
  • [ 128796-39-4 ]
  • [ 555-16-8 ]
  • [ 90035-20-4 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 7, p. 1726 - 1729
  • 52
  • [ 555-16-8 ]
  • [ 57260-71-6 ]
  • [ 130636-61-2 ]
Reference: [1] Patent: US2007/167435, 2007, A1, . Location in patent: Page/Page column 47
  • 53
  • [ 555-16-8 ]
  • [ 262368-47-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 285 - 296
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