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Structure of 102-92-1 * Storage: {[proInfo.prStorage]}
* 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] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 1, p. 65 - 70
3
[ 102-92-1 ]
[ 4774-24-7 ]
Reference：
[1] Acta Poloniae Pharmaceutica - Drug Research, 2018, vol. 75, # 4, p. 891 - 901
4
[ 102-92-1 ]
[ 480-11-5 ]
Reference：
[1] Chemistry and Biodiversity, 2015, vol. 12, # 2, p. 259 - 272
5
[ 102-92-1 ]
[ 480-11-5 ]
Reference：
[1] Chemical and pharmaceutical bulletin, 2003, vol. 51, # 3, p. 339 - 340
[2] Chemical and pharmaceutical bulletin, 2003, vol. 51, # 3, p. 339 - 340
6
[ 140-10-3 ]
[ 102-92-1 ]
Yield
Reaction Conditions
Operation in experiment
100%
for 2 h; Reflux
General procedure: A mixture of various carboxylic acids (1.0mmol), an excess of thionyl chrolide (5mL) was refluxed for 2h and concentrated in vacuo to give corresponding acyl chloride (quant).
100%
With thionyl chloride In N,N-dimethyl-formamide for 4 h; Reflux
General procedure: To a solution of 1.2 equiv of substituted cinnamic acid 1a–l (5 mmol) in 5 equiv of thionyl chloride(3.6 mL), a catalytic amount of DMF was added. The reaction mixture was refluxed for 4 h, andthen, solvent was evaporated under vacuum to get the product 2a–l in the form of a solid residue inquantitative yield. The solid residue was directly added partially to an ice-cold stirred solution of1.0 equiv of tert-butyl (2-aminoethyl)carbamate or tert-butyl (3-aminopropyl)carbamate and 2.0 equivtriethylamine in DCM (20 mL). After the addition, the mixture was warmed to room temperature andstirred for 2 h. Then, DCM (20 mL) was added and washed with 0.2 M HCl (40 mL), H2O (40 mL),5percent saturated. NaHCO3 (40 mL) and brine (40 mL), then dried over anhydrous magnesium sulfate.The solvent was removed in vacuo to give the corresponding cinnamamide derivatives 3a–l (65percent–75percent,from 1a–l) and 4a–g (59percent–70percent, from 1a–g) as a white solid. 3a–l, 4a–g (4 mmol) in DCM/TFA(9:1, 40 mL) were stirred at room temperature for 1 h. Solvents were removed in vacuo to yield 5a–l(100percent) and 6a–g (100percent) as a colorless oil.
99%
at 40℃; for 24 h;
Cinnamic acid 28 (18.06 mmol) and thionyl chloride (180.6 mmol) were mixed under inert argon atmosphere at 40 °C for 24 hours. Solvent was evaporated under vacuum, followed by dissolving the evaporation residue twice in dichlorom ethane and evaporation, thus giving cinnamic acid chloride 29 (yield: 99 percent).
96.4%
With thionyl chloride In N,N-dimethyl-formamide; toluene at 20℃; for 2 h; Reflux
(0.1 mol) of cinnamic acid, 150 mL of toluene and 14.3 g (0.12 mol) of thionyl chloride were sequentially added to a 250 mL three-necked flask, and 0.2 mL of N, N-dimethylformamide was added dropwise at room temperature with stirring, Reflux 2h. TLC to monitor the completion of the reaction, rotary evaporation of the solvent and excessive thionyl chloride, 16. Lg light yellow oily liquid, yield 96.4percent
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With potassium carbonate In water; acetone for 0.5 h;
In a mixed solution of acetone (8 mL) and water (16 mL),m-Methoxyaniline (1 g, 8.12 mmol), potassium carbonate (1.68 g, 12.18 mmol), cinnamoyl chloride (1.62 g, 9.74 mmoL) were added, and the mixture was stirred for 30 min.After the reaction was completed, the reaction mixture was poured into ice water and extracted with EtOAc EtOAc.Concentration under reduced pressure gave compound 3 in 98percent yield.
90%
Stage #1: With pyridine In dichloromethane for 0.5 h; Stage #2: for 2 h;
In a 1000 mL reaction flask50gM-Aminoanisole,43 mL of anhydrous pyridine,And 250 mL of dichloromethane were stirred for half an hour.71 g of cinnamoyl chloride was added to 250 mL of dichloromethane,And then slowly added to the reaction system,After dripping,The reaction was stirred for 2 hours.Add 500 mL of water to quench the reaction,The dichloromethane phase was then separated,Concentrated to dry,To obtain 107 g of N- (cinnamoyl) -3-methoxyaniline,Yield 90percent, purity 99percent.
Reference：
[1] Patent: CN108101926, 2018, A, . Location in patent: Paragraph 0030; 0031; 0032
[2] Tetrahedron Letters, 1999, vol. 40, # 24, p. 4505 - 4506
[3] Patent: CN107098855, 2017, A, . Location in patent: Paragraph 0036; 0037
[4] Zhurnal Obshchei Khimii, 1940, vol. 10, p. 43,50[5] Chem. Zentralbl., 1940, vol. 111, # II, p. 202
[6] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1721 - 1728
[7] Patent: WO2008/24481, 2008, A2, . Location in patent: Page/Page column 32
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5561 - 5578
With sodium hydrogencarbonate; In water; ethyl acetate; at 0℃;
Examples 12 and 13 2-({4-[(6,7-Dihydro[l,4]dioxino[2,3-c]pyridazin-3- yImethyI)amino]-l-piperidinyl}methyl)-9-fluoro-l,2-dihydro-4H-pyrrolo[3,2,l- i/]quinoIin-4-one hydrochloride, Enantiomers 1 and 2 <n="41"/>(a) (2SJS)- 1 , 1 -Dimethylethyl { 1 -[(9-fluoro-4-oxo- 1 ,2-dihydro-4H-pyrrolo[3,2, 1 - ij]quinolin-2-yl)methyl]-4-piperidinyl}carbamateMethod A(1) (2E)-N-(3-Fluoro-2-methylphenyl)-3-phenyl-2-propenamide; A solution of cinnamyl chloride (100 g, 610 mmol) in ethyl acetate (400 ml) was added to a vigorously-stirred mixture of <strong>[443-86-7]3-fluoro-2-methylaniline</strong> (75 g, 400 mmol), saturated aqueous sodium bicarbonate (850 ml), ice (ca 100 g) and ethyl acetate (400 ml). After 1 hour the mixture was concentrated on a rotary evaporator (removing most of the ethyl acetate) and filtered, washing with water. The resulting white solid was dried in vacuo (-160 g, 100percent).MS (+ve ion electrospray) m/z 256 (MH+).
100%
With sodium hydrogencarbonate; In water; ethyl acetate; for 0.283333h;
(a) (2E)-N-(3-Fluoro-2-methylphenyl)-3-phenyl-2-propenamideA solution of cinnamyl chloride (100 g, 610 mmol) in ethyl acetate (400 ml) was added to a vigorously-stirred mixture of <strong>[443-86-7]3-fluoro-2-methylaniline</strong> (75 g, 600 mmol), saturated aqueous sodium bicarbonate (850 ml), ice (ca 100 g) and ethyl acetate (400 ml) over 2 min. After 0.25 hour the mixture was filtered, washing with water, more solids coming out of the filtrate and so refiltered. The resulting solid was dried in vacuo (160 g, 100percent).MS (+ve ion electrospray) m/z 256 (MH+).
N-(2-(2-tert-butylphenoxy)pyridin-3-yl)cinnamamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Cinnamoyl chloride (300 mg, 1.8 mmol) was added to a solution of <strong>[861673-68-9]2-(2-tert-butylphenoxy)pyridin-3-amine</strong> (385 mg, 1.6 mmol) and 4-dimethylaminopyridine (20 mg) in pyridine (8.0 mL) at room temperature under argon. The mixture was stirred at rt for 16 h, and a saturated ammonium chloride solution was added (10 mL) along with dichloromethane (20 mL). The separated aqueous layer was extracted with dichloromethane (3×20 mL) and the combined organic layers were washed with brine, dried (anhydrous sodium sulfate), filtered and evaporated to yield an oily residue which was purified using flash-chromatography (dichloromethane with linear increments of triethylamine) to afford the title compound. Alternatively, Example 1 and related analogs could be prepared using standard peptide coupling protocols with (in this case) cinnamic acid, EDCI and HOBt in dichloromethane, albeit in lower yield. (M+H)=373. 1H nmr (400 MHz, CDCl3) delta ppm: 1.44 (s, 9H), 6.58 (d, J=15.4 Hz, 1H), 6.00 (dd, J=7.8, 1.4 Hz, 1H), 7.07 (dd, J=8.0, 5.0 Hz, 1H), 7.23 (m, 1H), 7.42 (m, 2H), 7.51 (dd, J=7.8, 1.8 Hz, 1H), 7.59 (m, 2H), 7.81 (d, J=15.4 Hz, 1H), 7.90 (dd, J=5.0, 1.7 Hz, 1H), 8.02 (s, 1H), 8.92 (dd, J=7.8, 1.5 Hz, 1H).
With 2,6-dimethylpyridine; In dichloromethane; at 0 - 26℃;
A mixture of (3-fluoro-2-methoxyphenyl)amine (5 g, 35.4 mmol) and 2,6-lutidine (7.4 mL, 64 mmol) in dichloromethane (20 mL) was treated at O0C dropwise with a solution of cinnamoylchloride (7.08 g, 42.5 mmol) in dichloromethane (30 mL). The reaction mixture was allowed to reach room temperature and was stirred over night. It was quenched with potassium phosphate buffer (50 mL, IM, pH 7) and stirred for 15 minutes. Dichloromethane was removed under reduced pressure and it was extracted with ethyl acetate. The organic phase was washed with phosphate buffer (like above, 100 mL), dried over sodium sulfate and concentrated to dryness. The residue was crystallized from ethyl acetate/ hexanes and then recrystallized from hexanes to give the product as colorless solid (6.21 g, 65%), mp 8O0C. MS (ESP^; 272 (MH+) for C16H14FNO21H-NMR (DMSO-AO delta: 3.88 (s, 3H); 6.97-7.12 (m, 2H); 7.23 (d, IH); 7.38-7.48 (m, 3H); 7.56-7.65 (m, 3H); 8.05 (m, IH); 9.61 (s, IH).
With sodium hydrogencarbonate; In water; ethyl acetate; at 0℃; for 0.25h;
A solution of cinnamyl chloride (100 g, 610 mmol) in ethyl acetate (400 ml) was added to a vigorously-stirred mixture of <strong>[443-86-7]3-fluoro-2-methylaniline</strong> (75 g, 600 mmol), saturated aqueous sodium bicarbonate (850 ml), ice (ca 100 g) and ethyl acetate (400 ml) over 2 min. After 0.25 hour the mixture was filtered, washing with water, more solids coming out of the filtrate and so refltered. The resulting solid was dried in vacuo (-160 g, 100percent). MS (+ve ion electrospray) m/z 256 (MH+).
With pyridine; In dichloromethane; at 0 - 20℃; for 2h;
To <strong>[7149-75-9]4-chloro-3-methylaniline</strong> (3.33 g, 19.98 mmole) in dichloromethane (100 mL) and pyridine (20 mL) was added cinnamoyl chloride (2.83 g, 19.98 mmole) at 00C. The mixture was stirred at room temperature for 2 h. Solvent and pyridine were removed by rotary evaporator under reduced pressure. The residue was diluted with ethyl acetate and washed IN HCl (2 x 100 mL), water (2 x 100 mL), sodium bicarbonate solution (2 x 10OmL) and dried over sodium sulfate. After removing solvent a white solid was recovered (5.38 g, 99percent yield). The product was used for the next step without further purification. 1H NMR (400 MHz, DMSOd6): delta 7.76-7.24 (m, 10H), 6.58(d, IH), 2.55 (s, 3H); MS (ESI) m/z: Calculated for C16H14ClNO: 271.1; found: 272 (M+H)+.
99%
With pyridine; In dichloromethane; at 20℃; for 2h;
N-(4-Chloro-3-methylphenyl)cinnamamide To <strong>[7149-75-9]4-chloro-3-methylaniline</strong> (3.33 g, 19.98 mmole) in dichloromethane (100 mL) and pyridine (20 mL) was added cinnamoyl chloride (2.83 g, 19.98 mmole) at 0° C. The mixture was stirred at room temperature for 2 h. Solvent and pyridine were removed by rotary evaporator under reduced pressure. The residue was diluted with ethyl acetate and washed 1N HCl (2*100 mL), water (2*100 mL), sodium bicarbonate solution (2*100 mL) and dried over sodium sulfate. After removing solvent a white solid was recovered (5.38 g, 99percent yield). The product was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6): delta 7.76-7.24 (m, 10H), 6.58 (d, 1H), 2.55 (s, 3H); MS (ESI) m/z: Calculated for C16H14ClNO: 271.1. found: 272 (M+H)+.
With triethylamine; In dichloromethane; for 0.25h;
General procedure: <strong>[19840-99-4]7-amino-4-methylquinolin-2(1H)-one</strong> (1.00 eq)was dissolved in dichloromethane and stirred for 15 min at ambient temperature, meanwhile the triethylamine (1.05 eq) was added. After 15 min the proper cinnamoyl chloride (1.05 eq) was added dropwise (cinnamoyl chloride for compound 13; 3,4-diace-toxycinnamoyl chloride for compound 14; 3-methoxy-4-acetoxycinnamoyl chloride for compound 15). The course of the reaction was monitored by TLC. After 15 min product was filtrated and recrystallized from CH2Cl2: (CH3)2CO 1 : 1
General procedure: To a cold (0-5 °C) stirred suspension of aminobenzamides 2a-g (0.016 mol) in pyridine (13 ml), 0.016 mol of the appropriate cinnamoyl chloride 3a-e, 3-phenylpropioloyl chloride 3f-k and 3-phenylpropanoyl chloride 3l-o was added over 30 min. After addition was complete, the solution was stirred for 24 h and then poured onto crushed ice. The precipitate was removed by filtration, washed with water, and crystallized from the appropriate solvent.
With pyridine; In dichloromethane; at 0℃; for 3h;Inert atmosphere;
General procedure: 1 equiv of piperazinyl amine was dissolved in pyridine (20 ml/g)and stirred at 0 C under inert atmosphere. 1.2 equiv of cinnamoylchloride derivative was dissolved in dry DCM (10 ml/g) and addeddropwise to above stirred solution at 0 C. The reaction mixturewasstirred for 3 h and was monitored by TLC. After completion of thereaction, the reaction mixturewas diluted withwater (20 ml/g) andethyl acetate (30 ml/g) followed by 2 N HCl to make it acidic. Theprecipitate came out which was filtered as yellow solid and furtherwashed with 2 N HCl and then water. The precipitate was suspendedin saturated bicarbonate solution and stirred vigorously toremove acid impurities. The crude compound was purified eitherby column chromatography or by recrystallization from ethyl acetateand hexane.
With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 1h;
The embodiment 1 in the prepared 15g (0.121mol) 5-norbornene-2-methanol, 61.2g (0.605mol) triethylamine (Aldrich Company) and 20mlTHF into the 250 ml flask push, then in the 0 C in ice under stirring. The addition of soluble flask 60mlTHF of in 22.1g (0.133mol) cinnamomun acyl chloride is slowly added to the prepared in a mixture of 10 minutes. Next, the rise of the temperature of the reactants to the room temperature, then stirring 1 hour. The use of acetic acid ethyl ester dilution of the solution. The diluted solution into the separatory funnel, water and NaHCO 3 washing several times, then the distillation to remove solvent under reduced pressure. The use of column chromatography (hexane: ethyl acetate = 20:1) refining the product, in order to get the product. (Yield: 88%).
(E)-N-(4-(6-methoxyquinolin-8-ylamino)pentyl)-3-phenylacrylamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
General procedure: Method A: A suspension of PQ diphosphate (1 equiv.) and TEA (3 equiv.) in dry dichloromethanewas stirred at room temperature. After 15 min, a solution of chloride 4 (1.25 equiv.) in drydichloromethane was added dropwise. The reaction mixture was stirred at room temperature, lightprotected. After 0.5-3 h, solvent was removed under reduced pressure and the residue was dissolvedin ethyl acetate/5% NaOH mixture (1:1). The organic layer was extracted with 5% NaOH solution andwater, dried over anhydrous sodium sulfate, filtered and evaporated. The crude product was purifiedby column chromatography.
2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-yl (2E)-3-phenylprop-2-enoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
25%
General procedure: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.39 mmol, 100 mg) was suspended in dry CH3CN (10 mL), then NaH (10.3 mg, 0.43 mmol) was added. The corresponding suspension was kept at RT for 2 h. Cinnamoyl chloride (0.78 mmol, 65 mg) was added and the reaction was stirred overnight at RT. The solvent was removed under vacuum; the residue was then taken up in CH2Cl2 (3x5mL) obtaining a suspension; the mother liquor was filtered off from the solid (inorganic phase), washed with saturated Na2CO3 solution (3x10mL); the organic phase, dried over Na2SO4, was evaporated under vacuum and purified by silica gel column chromatography (CH2Cl2/MeOH 90:10) to give 7 (Rf = 0.56) as a waxy solid (45 mg, 30%) that has to be stored under an inert gas (N2).
With sodium hydrogencarbonate; In dichloromethane; at 0 - 20℃;
General procedure: To a stirred solution of N-alkylanthranilaldehydes 4 (10 mmol) and sodium bicarbonate (NaHCO3) (15 mmol) in dry CH2Cl2 (15 mL) at 0-5 C, was added dropwise a solution of acryloyl chloride derivatives 5 (12 mmol) in dry CH2Cl2 (15 mL) at 0-5 C, over 45 min, which was then stirred at room temperature to 2-5 h. The organic solution was then washed with water (20 mL) and hydrogen chloride (5%) solution (20 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the residue was separated by column chromatography on a silica gel with petroleum ether/ethyl acetate (3:1) as an eluent to obtain pure N-acrylated anthranilaldehyde derivatives 1a-f.
With potassium carbonate; In water; acetone; at 0 - 20℃; for 3h;
General procedure: To a mixture of fluoroaniline and K2CO3 in acetone-water cooled in an ice bath, cinnamoyl chloride was added in small portions.The mixture was stirred at 0C for 2 h and held at 20C for 1 h. The precipitated material was filtered off, washed with water and dried.
With potassium carbonate; In water; acetone; at 0 - 20℃; for 3h;
General procedure: To a mixture of fluoroaniline and K2CO3 in acetone-water cooled in an ice bath, cinnamoyl chloride was added in small portions.The mixture was stirred at 0C for 2 h and held at 20C for 1 h. The precipitated material was filtered off, washed with water and dried.
With potassium carbonate; In water; acetone; at 0 - 20℃; for 3h;
General procedure: To a mixture of fluoroaniline and K2CO3 in acetone-water cooled in an ice bath, cinnamoyl chloride was added in small portions.The mixture was stirred at 0°C for 2 h and held at 20°C for 1 h. The precipitated material was filtered off, washed with water and dried.
With dmap; triethylamine; In dichloromethane; at 0℃; for 18h;Inert atmosphere;
To a solution of <strong>[19752-84-2]tetrahydro-2H-pyran-3-ol</strong> (compound 5) (51.0 mg, 0.5 mmol) in CH2Cl2 (2.5 mL) was added with Et3N (55.0 mg, 0.55 mmol) and DMAP (3 mg, 0.025 mmol), followed by the addition of cinnamoyl chloride (92.0 mg, 0.55 mmol) at 0 C. The mixture was stirred for 18 h then added with saturated NaHCO3 solution. The organic phase was separated and washed with brine, dried over anhydrous Na2SO4. The crude product was purified via silica gel column with PE/EtOAc (30:1-10:1) to give the title compound 6 as a white foam
To a 250 ml round bottom flask was added 7-methyl-5-bromo-lH-indole (50 mmol)Add 100 ml of toluene to mix it,Further addition of cinnamoyl chloride (60 mmol)Room temperature reaction for 1 hour,After the compound has been completely precipitated,Phenylhydrazine (60 mmol) was added,Heated to 105 C with a heating jacket,Placed on a magnetic stirrer,The reaction was heated under reflux for 6 hours,Reaction process constantly point observation,Until the raw material reaction completely after the stop heating,Remove the condensing unit.The reaction solution was distilled and concentrated, and the product was isolated by column chromatography.The crude product was recrystallized from an ethanol-water solution, dried,The product was obtained (15.2 g as a white solid, 77.5% yield).
With sodium hydride; In dichloromethane; at 20℃; for 3h;
Put 22.4g (0.1mol) of 2-hydroxy-1- (4- (2-hydroxyethoxy) phenyl) -2-methylpropane-1-one in a 250ml three-necked bottle,100 ml of dichloromethane and 2.4 g (0.1 mol) of sodium hydride were added.After stirring well, 33.2 g (0.2 mol) of cinnamoyl chloride was added, and the reaction was stirred at room temperature for 3 h.Then, the reaction solution was filtered, and the filtrate was sequentially washed with dilute hydrochloric acid (5%), saturated aqueous sodium hydrogen carbonate solution and distilled water, and then dried overnight with anhydrous sodium sulfate, and then filtered. The organic phase was distilled off under reduced pressure.Obtained pale yellow crystals, a total of 40 g, yield 83%,This product was confirmed to be the title compound by 1H-NMR spectrum.
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