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[ CAS No. 10287-53-3 ] {[proInfo.proName]}

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Chemical Structure| 10287-53-3
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Product Details of [ 10287-53-3 ]

CAS No. :10287-53-3 MDL No. :MFCD00009115
Formula : C11H15NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FZUGPQWGEGAKET-UHFFFAOYSA-N
M.W : 193.24 Pubchem ID :25127
Synonyms :

Calculated chemistry of [ 10287-53-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.74
TPSA : 29.54 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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.58
Log Po/w (XLOGP3) : 2.66
Log Po/w (WLOGP) : 1.93
Log Po/w (MLOGP) : 2.23
Log Po/w (SILICOS-IT) : 1.66
Consensus Log Po/w : 2.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.33 mg/ml ; 0.00171 mol/l
Class : Soluble
Log S (Ali) : -2.93
Solubility : 0.226 mg/ml ; 0.00117 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.99
Solubility : 0.196 mg/ml ; 0.00102 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 10287-53-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10287-53-3 ]

* 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.

  • Downstream synthetic route of [ 10287-53-3 ]

[ 10287-53-3 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 64-17-5 ]
  • [ 619-84-1 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
88% With chloro-trimethyl-silane at 65℃; for 1h;
71% With sulfuric acid for 6h; Reflux;
With hydrogenchloride
With sulfuric acid
Heating;
With sulfuric acid Reflux;
With sulfuric acid
With sulfuric acid at 70℃; for 3h;
With sulfuric acid at 78℃; for 2h;

  • 2
  • [ 10287-53-3 ]
  • [ 74-88-4 ]
  • [ 113511-05-0 ]
YieldReaction ConditionsOperation in experiment
90% In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;
With methanol
  • 3
  • [ 10287-53-3 ]
  • [ 591-51-5 ]
  • [ 1719-05-7 ]
YieldReaction ConditionsOperation in experiment
86% In water at 25℃; for 0.00555556h; 4.2. Synthesis of alcohols 3 by addition of organolithium or Grignard reagents to esters 1 in water or DES. General procedure General procedure: In a 10mL Schlenk-like flask, aryl or alkyl ester 1 (0.5 mmol)was added to 1.0 mL of water or 1.0 g of DES, at room temperature in air,and the resulting mixture was vigorously stirred. A solution of the corresponding organolithium or Grignard reagent (2.5 equiv),handled under argon using conventional Schlenk techniques, was rapidly spread over the mixture under air and with vigorous stirring at room temperature to generate an emulsion. After 20 s, the reaction mixture was diluted with 2 mL of water, and then extracted with CPME (3.0 mL 3). The volatiles were removed under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane/EtOAc, 8/2) to provide the desired product.
  • 4
  • [ 108-89-4 ]
  • [ 10287-53-3 ]
  • [ 124066-15-5 ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: picoline With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - -10℃; Inert atmosphere; Stage #2: ethyl p-dimethyaminolbenzoate In tetrahydrofuran; hexane at -10 - 20℃; Inert atmosphere;
With sodium hexamethyldisilazane 1.) THF, from 0 deg C to 10 deg C, 30 min, 2.) THF, RT, 3 h; Multistep reaction;
  • 5
  • [ 540-88-5 ]
  • [ 10287-53-3 ]
  • [ 138714-61-1 ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide 1.) THF, -78 deg C, 0.5 h, 2.) THF, 25 deg C, 16 h; Yield given. Multistep reaction;
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
  • 6
  • [ 91842-96-5 ]
  • [ 10287-53-3 ]
  • 1-carbomethoxy-5-(4-dimethylaminophenyl)-3-phenyl-1H-pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% Stage #1: acetophenone carbomethoxyhydrazone With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 2h; Stage #2: ethyl p-dimethyaminolbenzoate In tetrahydrofuran at 0℃; for 1.5h; Stage #3: With hydrogenchloride In tetrahydrofuran for 1h; Heating;
  • 7
  • [ 10287-53-3 ]
  • [ 246229-63-0 ]
  • 2-(5-[4-dimethylaminophenyl]-1H-pyrazol-3-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: (1-[2-hydroxyphenyl]-ethylidene)hydrazinecarboxylic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 2h; Stage #2: ethyl p-dimethyaminolbenzoate In tetrahydrofuran at 0℃; for 1.5h; Stage #3: With hydrogenchloride In tetrahydrofuran for 97h; Heating;
  • 8
  • [ 10287-53-3 ]
  • [ 246229-63-0 ]
  • 2-(1-carbomethoxy-5-[4-dimethylaminophenyl]-1H-pyrazol-3-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: (1-[2-hydroxyphenyl]-ethylidene)hydrazinecarboxylic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 2h; Stage #2: ethyl p-dimethyaminolbenzoate In tetrahydrofuran at 0℃; for 1.5h; Stage #3: With hydrogenchloride In tetrahydrofuran for 1h; Heating;
  • 9
  • [ 68253-36-1 ]
  • [ 10287-53-3 ]
  • [4-(4,5-dihydro-naphtho[1,2-<i>c</i>]isoxazol-3-yl)-phenyl]-dimethyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 1-tetralone oxime With lithium diisopropyl amide In tetrahydrofuran Stage #2: ethyl p-dimethyaminolbenzoate In tetrahydrofuran for 2.5h; Stage #3: With hydrogenchloride Heating;
  • 10
  • [ 10287-53-3 ]
  • [ 124915-09-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl p-dimethyaminolbenzoate With methyl trifluoromethanesulfonate Stage #2: With [18F]F- K+ APE 2.2.2 at 90℃; for 0.05h;
Multi-step reaction with 2 steps 1: diethyl ether / 12 h / 20 °C 2: [18F]-potassium fluoride; [2.2.2]cryptande / acetonitrile / 0.17 h / 95 °C
Multi-step reaction with 2 steps 1: diethyl ether 2: K[18F]F/K222 / acetonitrile / 0.17 h / 90 °C
Multi-step reaction with 2 steps 1: dichloromethane / 3 h / 60 °C / Inert atmosphere 2: [18F]-potassium fluoride / acetonitrile; dimethyl sulfoxide / 0.17 h / 90 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: benzene / 20 °C / Reflux 2: K[18F]F-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane complex / N,N-dimethyl-formamide / 0.2 h / 90 °C
Multi-step reaction with 2 steps 1: benzene / 6 h / 85 °C 2: [18F]-potassium fluoride / acetonitrile

  • 11
  • [ 112-92-5 ]
  • [ 10287-53-3 ]
  • [ 125628-91-3 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 1-octadecanol; ethyl p-dimethyaminolbenzoate In xylene for 0.5h; Heating; Stage #2: With TiO(acac)2 In xylene for 24h; Heating;
61% With iron(III)-acetylacetonate; sodium carbonate In n-heptane at 105℃; for 24h; Inert atmosphere; 5.4. Representative transesterification procedure catalyzed by Fe(acac)3 and Na2CO3 as additive General procedure: To a 25 mL, one-necked, round-bottomed flask was placed Fe(acac)3 (36 mg, 0.10 mmol, 5 mol %), benzyl alcohol (216 mg, 208 μL, 2 mmol), and Na2CO3 (10.6 mg, 0.10 mmol, 5 mol %) in 10 mL heptane at room temperature under nitrogen atmosphere. A solution of methyl benzoate (272 mg, 256 μL, 2 mmol) in heptane (10 mL) was added via syringe. The resulting mixture was heated to reflux with the removal of the methanol by Dean-Stark apparatus and the reaction progress was monitored by TLC, 1H NMR spectroscopy, and GC analysis until completion of the reaction (6 h). The reaction mixture was then gradually cooled to room temperature and quenched with saturated aqueous NH4Cl solution (5 mL), then extracted with 20 mL ethyl acetate. The combined organic layer was dried (anhydrous MgSO4), filtered, and evaporated to give a crude product that was purified by column chromatography on silica gel (hexane/AcOEt=50/1) to provide the pure benzyl benzoate product 412 mg, 97% yield.
  • 12
  • [ 104-76-7 ]
  • [ 10287-53-3 ]
  • [ 21245-02-3 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 2-Ethylhexyl alcohol; ethyl p-dimethyaminolbenzoate In xylene for 0.233333h; Heating; Stage #2: With TiO(acac)2 In xylene for 30h; Heating;
  • 13
  • [ 3955-65-5 ]
  • [ 10287-53-3 ]
  • 1-(4-dimethylaminophenyl)-2-(5H-phenanthridine-6-ylidene)-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 6-methylphenanthridine With phenyllithium In diethyl ether for 0.5h; Stage #2: ethyl p-dimethyaminolbenzoate In diethyl ether for 5h; Heating; Further stages.;
10.5% With phenyllithium In diethyl ether for 2h; Heating;
  • 14
  • [ 10287-53-3 ]
  • [ 93-08-3 ]
  • [ 236106-22-2 ]
YieldReaction ConditionsOperation in experiment
58% With sodium hydride In tetrahydrofuran for 24h; Heating;
  • 15
  • [ 64-17-5 ]
  • [ 100-10-7 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
80% With manganese(IV) oxide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 24h; Inert atmosphere; 4.2 General procedure for oxidative esterification of aldehydes General procedure: In a typical procedure, a capped vessel was charged with ionic liquid BmimBF4 (0.5 mL) and put under positive pressure of nitrogen. DBU (0.5 mmol) and Cs2CO3 (1.5 mmol) were added followed by the aldehyde (0.5 mmol) and MnO2 (1.5 mmol). The reaction mixture was stirred for a few minutes and alcohol (1.5 mmol) was added. The reaction mixture was stirred at ambient temperature for 24 h. The mixture was then filtered through a thin pad of silica, which was washed with ethyl acetate (30 mL). The filtrate was analyzed by TLC and 1H NMR and then concentrated under vacuum. The resulting residue was purified by flash chromatography on silica gel where needed.
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; benzyl chloride at 90℃; for 0.5h; Microwave irradiation; General procedure: A 10 mL reaction vessel was charged in air with Pd(PPh3)4 (6 mg, 1 mol %), aldehyde (0.5 mmol), K2CO3 (207 mg, 1.5 mmol), benzyl chloride (70 μL, 0.6 mmol) and EtOH (1 mL). The vessel was sealed and submitted to microwave irradiation for 30 min at 90 °C, using an initial power of 30 W. (Microwave reactions were carried out with a CEM Discover 300 W monomode microwave instrument. The closed vessels used were special glass tubes with self-sealing septa that controlled pressure with appropriate sensors on the top (outside the vial). The temperature was monitored through a non-contact infrared sensor centrally located beneath the cavity floor.) The mixture was then allowed to cool to room temperature, filtered over a pad of Celite and rinsed with EtOH (5 mL). The filtrate was concentrated in vacuo and the product was purified by flash chromatography on silica gel (CH2Cl2/hexane).
80 % Turnov. With 1,2-dimethylindazolium-3-carboxylate for 3h; Heating;
  • 16
  • [ 75-97-8 ]
  • [ 10287-53-3 ]
  • 1-(4-(dimethylamino)phenyl)-4,4-dimethyl-1,3-pentanedione [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With hydrogenchloride In tetrahydrofuran 16 Synthesis of 1-(4-dimethylaminophenyl)-4,4-dimethylpentane-1,3-dione Example 16 Synthesis of 1-(4-dimethylaminophenyl)-4,4-dimethylpentane-1,3-dione Into a 100 ml three-necked flask equipped with a stirrer, a dropping funnel, a reflux condenser, and a nitogen-inlet tube, were charged 2.08 gm (31 mmol) of 60% sodium hydride and 5.0 gm (26 mmol) of ethyl 4-dimethylaminobenzoate. The mixture was dispersed in 40 ml of tetrahydrofuran and heated under refluxing. To the mixture was dropwise added 3.0 gm (30 mmol) of pinacolone and the mixture was heated with stirring for 3 hours. After cooling, 50 ml of 1N hydrochloric acid was added to the reaction mixture, and the organic layer was extracted twice with chloroform. The extract was thoroughly washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation to obtain an yellow oil. The oily substance was submitted to the Kugelrohr distillation 150° C., 1 mmHg, and crystallized from hexane to give 4.5 gm (yield: 70%) of yellow solid product. Melting Point: 61.5°-61.8° C. IR(νKBr, cm-1): 2960, 2940, 1610, 1570, 1520, 1440, 1380, 1300, 1190, 1130, 1070, 1030, 930, 850, 830, 800, 720, 690, 600. 1 H-NMR(CDCl4, δ): 1.23(9H, s, t-C4 H9), 3.03(6H, s, N-CH3), 6.20(1H, s), 6.65(2H, d, J=9Hz, Aromatic), 7.83(2H, d, J=9Hz, Aromatic), 16.87(1H, bs).
70% In tetrahydrofuran 2 EXAMPLE 2 EXAMPLE 2 Synthesis of 1-(4-dimethylaminophenyl)-4,4-dimethylpentane-1,3-dione (a compound of formula (1) in which R2 is 4-(CH3)2 N and n is 0. (Compound (1b)): A 100 ml three-necked flask equipped with a stirrer, a dropping funnel, a reflux condenser and a nitrogen-introducing tube was charged with 2.08 g (31 mmol) of a 60% sodium hydride and 5.0 g (26 mmol) of ethyl 4-dimethylaminobenzoate, and these compounds were mixed and dispersed in 40 ml of tetrahydrofuran. After reflux by heating, 3.0 g (30 mmol) of pinacolone was added dropwise carefully to the thus prepared mixture, followed by 3 hours of heating with agitation. After spontaneous cooling, the resulting reaction mixture was poured in 50 ml of a 1N hydrochloric acid and organic materials were extracted twice with chloroform. Thus extracted materials were washed thoroughly with water and then dried over anhydrous magnesium sulfate. A yellow oily material was obtained by solvent removal. Thereafter, the thus obtained yellow oily material was subjected to Kugelrohr distillation at 150° C. under 1 mmHg and the resulting sample was crystallized from hexane to obtain 4.50 g (70% in yield) of the compound of interest as a yellow solid substance. This compound is hereinafter referred to as Compound (1b). Melting point: 61.5°-61.8° C. IR (ν KBr, cm-1): 2960, 2940, 1610, 1570, 1520, 1440, 1380, 1300, 1190, 1130, 1070, 1030, 930, 850, 830, 800, 720, 690, 600 1 H-NMR (CCl4,δ): 1.23 (9H, s, t-Bu), 3.03 (6H, s, N--CH3), 6.20 (1H, s), 6.65 (2H, d, J=9 Hz, Aromatic), 7.83 (2H, d, J=9 Hz, Aromatic), 16.87 (1H, bs)
  • 17
  • [ 784-04-3 ]
  • [ 10287-53-3 ]
  • [ 157522-94-6 ]
  • [ 157522-95-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In hexane; tert-butyl methyl ether; ethyl acetate; EXAMPLE 8 Preparation of (3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol Diacetate A solution of 16.4 g (34.3 mmol) (3beta)-cholesta-5,7,16-trien-23-yne-3,25-diol diacetate and 1.64 g ethyl 4-dimethylaminobenzoate in 1.7 L of tert-butyl methyl ether at -20 C. was irradiated with a 450 W medium pressure lamp through a quartz immersion well. During the photolysis, the arc housing was constantly purged with a slow current of nitrogen. After 8 hr of irradiation at 0 to -20 C., a uranium filter was inserted in the arc housing, and then 66 mg of <strong>[784-04-3]9-acetylanthracene</strong> was added to the solution. After 1 hr 45 min of irradiation through the filter at 0 to -20 C., the solution was allowed to warm to room temperature overnight, and then washed four times with a total of 400 mL of 3N HCl. The organic layer was then washed with 200 mL of saturated aqueous NaHCO3 and dried over Na2 SO4. The solution was concentrated to dryness. Then the residual oil was purified by chromatography on silica gel, eluding with 3 L of 7% ethyl acetate in hexane. After discarding about 0.8 L of eluent, the desired fractions were combined and concentrated to give about 13 g of a clear oil.
  • 18
  • [ 10287-53-3 ]
  • [ 109-55-7 ]
  • N-(3-Dimethylaminopropyl)-p-dimethylamino benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In water 1 Preparation of N- (3-Dimethylaminopropyl)-p-dimethylamino benzamide EXAMPLE 1 Preparation of N- (3-Dimethylaminopropyl)-p-dimethylamino benzamide Ethyl-p-dimethylaminobenzoate (164.9 g, 0.85 mole), 3-dimethylaminopropylamine (95.9 g, 0.94 mole) and sodium methoxide (2.8 g, 0.054 mole) were introduced into a 4-neck, 500 ml glass reactor, equipped with stirrer, heater, nitrogen purge and deflegmator with a Dean-Stark device. The charged reactor was flushed with dry nitrogen for 15 minutes at ambient temperature and was then heated to 150° C. under vigorous stirring. After about 15 minutes accumulation of distillate, the reactor temperature was gradually increased to 170° C. in 5° increments over a period of 1 hour and was then maintained at 170° C. for an additional hour, whereupon a sample of the product, analyzed by glass chromatography (GC) indicated 99+% conversion of the ester. The resulting mixture was then cooled to 95° C. and washed twice with 200 ml of hot water after which the aqueous phase was cooled to room temperature and precipitated crystals recovered by filtration. These crystals were then combined with the organic phase in the reactor. A vacuum of about 10-20 mm Hg was then applied to the product in the reactor which was heated to 90°-95° C. for 30 minutes. The resulting distillate containing water and light products was discarded. The residue was cooled to room temperature and was identified by elemental analysis, 1 H and 13 NMR and FTIR spectra, as N-(3-dimethylamino- propyl)-p-dimethylaminobenzamide. The product yield was 205 g (96.9% of theoretical based on ethyl-p-dimethylamino-benzoate).
  • 19
  • [ 10287-53-3 ]
  • [ 40700-40-1 ]
YieldReaction ConditionsOperation in experiment
In sulfuric acid 47 Example 47 Example 47 Preparation of ethyl 4-dimethylamino-3-nitrobenzoate ([5]-(52)-591) Ethyl 4-dimethylaminobenzoate (9.10 g) was dissolved in sulfuric acid (14 ml), and mixed acid (concentrated sulfuric acid/concentrated nitric acid=1/1) (9.0 ml) was added dropwise at room temperature. The reaction solution was stirred for 4 hours while maintaining at 5° C.-10° C. The reaction solution was poured into ice water (100 g). The precipitated crystals were filtered, and washed with water. The resulting crystals were recrystallized from water/methanol to obtain the above-captioned compound ([5]-(52)-591) (10.56 g) as yellow needle crystals. Melting point: 78.5°-79.0° C. 1 H-NMR (500 MHz, CDCl3) δ: 1.38 (t, 3H), 2.99 (s, 6H), 4.35 (q, 2H), 6.97 (d, 1H), 8.01 (dd, 1H), 8.44 (d, 1H)
  • 20
  • (1α,3β)-cholesta-5,7,16-trien-23-yne-1,3,25-triol [ No CAS ]
  • [ 784-04-3 ]
  • [ 10287-53-3 ]
  • Ro 23-7553 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; hexane; tert-butyl methyl ether; EXAMPLE 11 (1alpha,3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-1,3,25-triol A 2-L photoreactor was charged with 10 g (24.4 mmol) of (1alpha,3beta)-cholesta-5,7,16-trien-23-yne-1,3,25-triol, 1 g of ethyl 4-dimethylaminobenzoate, 1.45 L of methanol, and 250 mL of tert-butyl methyl ether. After cooling to -10 C., the solution was irradiated with a 450 W medium pressure Hg lamp at -10 to -30 C. for 7.5 hr. A uranium filter was inserted to the arc housing, and 50 mg of <strong>[784-04-3]9-acetylanthracene</strong> in 2 mL of tert-butyl methyl ether was added. The mixture was irradiated with the same lamp through the filter at -10 to -30 C. for 1.5 hr. The mixture was allowed to warm to from temperature overnight. The solution was concentrated to about 1 L, and then refluxed for 4 hr. The mixture was allowed to cool to room temperature overnight, and concentrated to dryness. The residue was purified repeatedly by chromatography on silica gel, eluding with 60% EtOAc in hexane. The desired fractions were combined and concentrated to dryness. The residue was then recrystallized from aqueous methanol to afford (1alpha,3beta,5Z,7E)-9,10-secocholesta-5,7,10(19),16-tetraen-23-yne-1,3,25-triol.
  • 21
  • [ 3040-44-6 ]
  • [ 10287-53-3 ]
  • 4-dimethylamino-benzoic acid-(2-piperidino-ethyl ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di(n-butyl)tin oxide at 160℃; for 8h; 1 A reaction mixture containing 17.4 g of N-piperidine ethanol (10), 8.7 g of ethyl-4-dimethylaminobenzoaat (6) and 0.67 g of dibutyltin oxide (Bu2SnO) was heated at 160 0C and stirred for about 8 hours. Meanwhile the formed ethanol was distilled off. The reaction mixture was diluted with 70 ml of toluene and extracted with 70 ml of distilled water. The aqueous layer was separated and extracted with toluene. The organic layers were collected and dried over MgSO4. After evaporation of the solvent, the product was purified on a Flash Column using dichloromethane/ethanol (90/10) as eluent, to obtain 10.2 g of COMPCOINI-03 (12) as a pale yellow solid.
  • 22
  • [ 10287-53-3 ]
  • [ 100-37-8 ]
  • [ 10367-92-7 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate at 150℃; for 24h; 1 A reaction mixture containing 15.9 g of N,N-diethyl ethanolamine (9), 8.7 g of ethyl-4-dimethylaminobenzoate (6) and 0.146 g of a 30 wt% solution of sodium methylate (NaOMe) in methanol was heated to 150 0C and stirred for about 24 hours. Meanwhile the formed ethanol was distilled off. The mixture was filtered to remove the formed precipitate. The filtrate was diluted with 70 ml of toluene (70 ml) and extracted with 50 ml of distilled water. The organic layer was separated, washed with water and dried over MgSO4. After evaporation of the solvent, the product was purified on a Flash Column using as eluent dichloromethane/ethanol (90/10). 1.97 g of COMPCOINI-02 (10) was obtained as a yellow oil.
  • 23
  • [ 108-01-0 ]
  • [ 10287-53-3 ]
  • 2-dimethylamino Ethyl p-dimethylamino Benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate at 136℃; for 24h; 1 A reaction mixture containing 12.0 g N,N-dimethylaminoethanol (7), 8.7 g ethyl-4-dimethylaminobenzoate (6) and 0.146 g of a 30 wt% solution of sodium methylate (NaOMe) in methanol was heated to 136 0C and stirred for about 24 hours. Meanwhile the formed ethanol was distilled off. The mixture was filtered to remove the formed precipitate. The filtrate was diluted with 70 ml of toluene and extracted with 50 ml of distilled water. The organic layer was separated, washed with water and dried over MgSO4. After evaporation of the solvent, the residue was recrystallized from n-hexane. After filtration, 2.9 g of COMPCOINI-01 (8) was obtained as a pale yellow solid.
  • 24
  • [ 10287-53-3 ]
  • [ 2124-31-4 ]
  • [ 122065-71-8 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 4'-dimethylaminoacetophenone With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: ethyl p-dimethyaminolbenzoate In tetrahydrofuran at 0 - 20℃; for 7h; Reflux; Inert atmosphere;
  • 25
  • [ 10287-53-3 ]
  • [ 19353-92-5 ]
YieldReaction ConditionsOperation in experiment
91% With hydrazine hydrate In ethanol for 12h; Reflux; Inert atmosphere; Schlenk technique; General Procedure for the synthesis of the compounds 2A. General procedure: Hydrazine monohydrate (5 mmol) was added dropwise to a solution of compounds 1A-C (1mmol) in EtOH. The mixture was refluxed for 12 h, and then the solvent was removed by rotary evaporation. The residue was treated with water and extracted with CH2Cl2. The organic layer was washed with water and dried over magnesium sulfate. The solvent was removed by rotary evaporation. The residue was purified by recrystallization.
75% With hydrazine In ethanol for 48h; Reflux;
With hydrazine hydrate In ethanol Reflux;
With hydrazine hydrate In ethanol Reflux;
With H4N2*5H2O In ethanol at 70℃; for 6h;
With hydrazine hydrate In ethanol at 90℃; Inert atmosphere; 1.b b. In product A, 80% hydrazine hydrate and 95% ethanol are added in a 1:20 molar ratio. The reaction is refluxed under a nitrogen atmosphere at 90 ° C. The reaction is completed and the column is purified (mobile phase dichloromethane: methanol = 20: 1) to give product B.
With hydrazine hydrate In ethanol for 16h; Reflux; 2.2. Synthesis of Compound 1 As shown in Scheme 1, the reflux of 4-dimethylamino-benzoic acidethyl ester (0.3584 g, 2 mmol) and hydrazine hydrate (85%,0.5 mL) in25 mL of ethanol solution were removed until the complete consumptionof imidazole-2-formaldehyde, which was monitored by TLC(about 16 h). 4-Dimethylamino-benzoic acid hydrazide (0.1791 g, 1.0mmol) and imidazole-2-formaldehyde (0.096 g, 1.0mmol)were solvedin 25 mL ethanol and kept refluxing until complete consumption of imidazole-2-formaldehyde, which was monitored by TLC (about 12 h).The reaction mixture was cooled to room temperature and a whiteprecipitate was obtained through recrystallization. The white precipitatewas collected by filtration and washed three times withmethanol to get purified precipitate, and the total yield was up to73%. Ultimately, a white solid of compound 1 was obtained by thevacuum dryer and was characterized by NMR, Elemental analysesand ESI mass data, which were consistent with the proposedformulation.Compound 1: 1H NMR (400 MHz, DMSO-d6): δ (ppm) 12.73 (s, 1H),8.30 (s, 1H), 7.78(d, J=12 Hz, 2H), 7.10(s, 1H), 6.96(d, J=8 Hz, 2H),6.73(d, J = 8 Hz, 2H), 2.98(s, 6H); 13C NMR (400 MHz, DMSO-d6) δ(ppm): 167.94, 152.59, 143.49, 132.93, 129.55, 123.84, 119.60, 111.30,39.91; ESI-MS m/z [M - H]+: calcd, 258.13 found, 258.14; ElementAnal.: calcd. for C13H15N5O: C, 60.69; H, 5.88; N, 27.22%, found: C,61.28; H, 5.62; N, 26.65%.
With hydrazine hydrate In ethanol; toluene at 70℃; for 16h;
With hydrazine hydrate In ethanol at 78℃; for 6h;

Reference: [1]Khelladi, Mustapha; Leclerc, Nicolas; Jacquemin, Denis; De Nicola, Antoinette; Ulrich, Gilles [Tetrahedron Letters, 2018, vol. 59, # 10, p. 878 - 881]
[2]Location in patent: experimental part Mu, Honglei; Gong, Rui; Ren, Lin; Zhong, Cheng; Sun, Yimin; Fu, Enqin [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 70, # 4, p. 923 - 928]
[3]Location in patent: scheme or table Zheng, Qing-Zhong; Zhang, Xiao-Min; Xu, Ying; Cheng, Kui; Jiao, Qing-Cai; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 7836 - 7841]
[4]Du, Qian-Ru; Li, Dong-Dong; Pi, Ya-Zhou; Li, Jing-Ran; Sun, Jian; Fang, Fei; Zhong, Wei-Qing; Gong, Hai-Bin; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297]
[5]Kamal, Ahmed; Srikanth; Vishnuvardhan; Kumar, G. Bharath; Suresh Babu, Korrapati; Hussaini, S.M. Ali; Kapure, Jeevak Sopanrao; Alarifi, Abdullah [Bioorganic Chemistry, 2016, vol. 65, p. 126 - 136]
[6]Current Patent Assignee: HUAZHONG UNIVERSITY OF SCIENCE & TECHNOLOGY - CN107501123, 2017, A Location in patent: Paragraph 0021
[7]Fang, Hao; Huang, Peng-Cheng; Wu, Fang-Ying [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, vol. 204, p. 568 - 575]
[8]Mahy, William; Willis, Nicky J.; Zhao, Yuguang; Woodward, Hannah L.; Svensson, Fredrik; Sipthorp, James; Vecchia, Luca; Ruza, Reinis R.; Hillier, James; Kjær, Svend; Frew, Sarah; Monaghan, Amy; Bictash, Magda; Salinas, Patricia C.; Whiting, Paul; Vincent, Jean-Paul; Jones, E. Yvonne; Fish, Paul V. [Journal of Medicinal Chemistry, 2020, vol. 63, # 21, p. 12942 - 12956]
[9]Liu, Jie; Zhang, Guang-Yu; Zhang, Zhe; Li, Bo; Chai, Fei; Wang, Qi; Zhou, Zi-Dan; Xu, Ling-Ling; Wang, Shou-Kai; Jin, Zhen; Tang, You-Zhi [Bioorganic Chemistry, 2021, vol. 112]
  • 26
  • [ 94-09-7 ]
  • [ 74-88-4 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
With tetra-(n-butyl)ammonium iodide; potassium hydroxide In water; benzene
With potassium carbonate In ethanol at 75℃; for 18h; Schlenk technique;
With potassium carbonate In acetone at 80℃; for 24h; Inert atmosphere; 1.a a, Weigh 1g of ethyl p-aminobenzoate in a two-necked round bottom flask, add 40ml of acetone to dissolve, then add3.6g of anhydrous potassium carbonate and 14.1g of methyl iodide, the reaction was stirred under nitrogen at 80 ° C under reflux for 24 hours, the reaction was completed, the reaction mixture was filtered, the filtrate was extracted with methylene chloride, the organic phase was dried over magnesium sulfate, filtered The product was purified by column chromatography (mobile phase dichloromethane: methanol = 20: 1) to give product A after removing magnesium sulfate and concentrating by evaporation.
With potassium carbonate In acetone at 80℃; for 24h; Inert atmosphere; 1.a a, Weigh 1g of ethyl p-aminobenzoate in a two-necked round bottom flask, add 40ml of acetone to dissolve, then add3.6g of anhydrous potassium carbonate and 14.1g of methyl iodide, the reaction was stirred under nitrogen at 80 ° C under reflux for 24 hours, the reaction was completed, the reaction mixture was filtered, the filtrate was extracted with methylene chloride, the organic phase was dried over magnesium sulfate, filtered The product was purified by column chromatography (mobile phase dichloromethane: methanol = 20: 1) to give product A after removing magnesium sulfate and concentrating by evaporation.

  • 27
  • [ 10287-53-3 ]
  • [ 333-27-7 ]
  • ethyl 4-(N,N,N-trimethylammonium)-1-benzoate triflate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In diethyl ether at 20℃; for 12h;
88% In dichloromethane at 20℃;
88% In dichloromethane at 60℃; for 3h; Inert atmosphere;
87% In dichloromethane at 0 - 20℃;
84% In benzene at 20℃; Reflux; 4.8. Synthesis of 4-trimethylammonium ethylbenzoate triflate To a solution of ethyl-4-dimethylaminobenzoate (0.65 g,3.36 mmol) dissolved in 12 mL of anhydrous benzene was added dropwise methyltrifluoromethanesulfonate (0.42 mL, 3.70 mmol).The mixture was heated to reflux for 6 h and was then stirred overnight at room temperature. The reaction mixture was concentratedunder reduced pressure and the resulting crude precipitate was recrystallized with diethyl ether to yield 1.01 g (84%) of white product.
48% In dichloromethane at 20℃;
In diethyl ether
In dichloromethane at 20℃; for 4h;
In dichloromethane at 20℃; Inert atmosphere;
In acetonitrile at 70℃; Inert atmosphere; Schlenk technique;
In benzene at 85℃; for 6h; 1.1 1-1: Preparation of Ethyl 4-[Trimethylammonium]Benzoate 0.64 g of ethyl 4-[dimethylamino]benzoate was dissolved in 12 ml of benzene, 0.4 ml of methyl trifluoromethanesulfonate was added, and the mixture was stirred at 85° C. for 6 hours. The reaction was allowed to cool at room temperature and the solvent was removed by distillation under reduced pressure to yield ethyl 4-[trimethylammonium] benzoate as a white product. The results of 1 H-NMR analysis of the product are shown below: 1H-NMR (300 MHz, CDCl3): 1.34 (t, 3H), 3.64 (s, 9H), 4.36 (q, 2H), 8.12-8.17 (m, 4H).

Reference: [1]Location in patent: experimental part Dissoki, Samar; Hagooly, Aviv; Elmachily, Smadar; Mishani, Eyal [Journal of labelled compounds and radiopharmaceuticals, 2011, vol. 54, # 11, p. 693 - 701]
[2]Reeves, Jonathan T.; Fandrick, Daniel R.; Tan, Zhulin; Song, Jinhua J.; Lee, Heewon; Yee, Nathan K.; Senanayake, Chris H. [Organic Letters, 2010, vol. 12, # 19, p. 4388 - 4391]
[3]Kim, Dong Hyun; Blacker, Megan; Valliant, John F. [Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3678 - 3686]
[4]He, Rong-De; Li, Chun-Ling; Pan, Qiu-Quan; Guo, Peng; Liu, Xue-Yuan; Shu, Xing-Zhong [Journal of the American Chemical Society, 2019, vol. 141, # 32, p. 12481 - 12486]
[5]Matusiak, Nathalie; Castelli, Riccardo; Tuin, Adriaan W.; Overkleeft, Herman S.; Wisastra, Rosalina; Dekker, Frank J.; Prély, Laurette M.; Bischoff, Rainer P.M.; Van Waarde, Aren; Dierckx, Rudi A.J.O.; Elsinga, Philip H. [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 1, p. 192 - 202]
[6]Location in patent: experimental part Hatanaka, Kentaro; Asai, Tomohiro; Koide, Hiroyuki; Kenjo, Eriya; Tsuzuku, Takuma; Harada, Norihiro; Tsukada, Hideo; Oku, Naoto [Bioconjugate Chemistry, 2010, vol. 21, # 4, p. 756 - 763]
[7]Hoehne, Aileen; Behera, Deepak; Parsons, William H.; James, Michelle L.; Shen, Bin; Borgohain, Preeti; Bodapati, Deepika; Prabhakar, Archana; Gambhir, Sanjiv S.; Yeomans, David C.; Biswal, Sandip; Chin, Frederick T.; Bois, J. Du [Journal of the American Chemical Society, 2013, vol. 135, # 48, p. 18012 - 18015]
[8]Zhang, Hua; Hagihara, Shinya; Itami, Kenichiro [Chemistry - A European Journal, 2015, vol. 21, # 47, p. 16796 - 16800]
[9]Wang, Dong-Yu; Morimoto, Koki; Yang, Ze-Kun; Wang, Chao; Uchiyama, Masanobu [Chemistry - An Asian Journal, 2017, vol. 12, # 19, p. 2554 - 2557]
[10]Wang, Dong-Yu; Yang, Ze-Kun; Wang, Chao; Zhang, Ao; Uchiyama, Masanobu [Angewandte Chemie - International Edition, 2018, vol. 57, # 14, p. 3641 - 3645][Angew. Chem., 2018, vol. 130, # 14, p. 3703 - 3707,5]
[11]Current Patent Assignee: CHONNAM NATIONAL UNIVERSITY - US2019/336621, 2019, A1 Location in patent: Paragraph 0040-0042
  • 28
  • [ 10287-53-3 ]
  • [ 1703-46-4 ]
  • [ 1197-19-9 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: ethyl p-dimethyaminolbenzoate With sodium diisobutyl-tert-butoxyaluminium hydride In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: With ammonia; iodine In tetrahydrofuran; water at 0 - 20℃; for 3h; 4.2. Typical procedure for conversion of aromatic ethyl esters into aromatic nitriles General procedure: NaOtBu (98% purity, 353 mg, 3.6 mmol) was dried by a vacuum pump for 30 min at room temperature. To a solution of NaOtBu in THF (3 mL) was added DIBAL-H (1.04 M, 3.27 mL, 3.4 mmol) at 0 °C under argon atmosphere and the obtained mixture was stirred for 1 h at room temperature. Then, ethyl benzoate (150.06 mg, 2.0 mmol) in THF (4 mL) was added to the solution at 0 °C, and the obtained mixture was stirred for 4 h. Finally, aq NH3 (concentration: 28.0%-30.0%, 4 mL) and I2 (2.08 g, 4.1 equiv) were added at 0 °C, and the obtained mixture was stirred for 3 h at room temperature. Then the reaction mixture was poured into saturated aq Na2SO3 solution (10 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent under reduced pressure, the residue was treated with flash short column chromatography on silica gel (eluent: hexane/ethyl acetate=9:1) to afford benzonitrile (156.7 mg, 76% yield)
  • 29
  • [ 10287-53-3 ]
  • [ 1197-19-9 ]
YieldReaction ConditionsOperation in experiment
17% Stage #1: ethyl p-dimethyaminolbenzoate With sodium diisobutyl-tert-butoxyaluminium hydride In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: With ammonia; iodine In tetrahydrofuran; water at 0 - 20℃; for 3h; 4.2. Typical procedure for conversion of aromatic ethyl esters into aromatic nitriles General procedure: NaOtBu (98% purity, 353 mg, 3.6 mmol) was dried by a vacuum pump for 30 min at room temperature. To a solution of NaOtBu in THF (3 mL) was added DIBAL-H (1.04 M, 3.27 mL, 3.4 mmol) at 0 °C under argon atmosphere and the obtained mixture was stirred for 1 h at room temperature. Then, ethyl benzoate (150.06 mg, 2.0 mmol) in THF (4 mL) was added to the solution at 0 °C, and the obtained mixture was stirred for 4 h. Finally, aq NH3 (concentration: 28.0%-30.0%, 4 mL) and I2 (2.08 g, 4.1 equiv) were added at 0 °C, and the obtained mixture was stirred for 3 h at room temperature. Then the reaction mixture was poured into saturated aq Na2SO3 solution (10 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent under reduced pressure, the residue was treated with flash short column chromatography on silica gel (eluent: hexane/ethyl acetate=9:1) to afford benzonitrile (156.7 mg, 76% yield)
  • 30
  • [ 10287-53-3 ]
  • [ 619-84-1 ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: ethyl p-dimethyaminolbenzoate With iron(III) chloride In tetrachloromethane at 85℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrachloromethane Inert atmosphere;
With sodium hydroxide In ethanol at 85℃; for 6h; 1.b b, a obtained in step a 10% sodium hydroxide, no reactant can be, 95% ethanol as a solvent, 85 ° C under reflux for 6 hours, with 1M hydrochloric acid to adjust PH weakly acidic, the reaction solution was concentrated , Add anhydrous acetone to dissolve, filter, take the precipitate, vacuum dried to give the product B;
  • 31
  • [ 10287-53-3 ]
  • [ 98-86-2 ]
  • [ 19743-33-0 ]
YieldReaction ConditionsOperation in experiment
36% With sodium hydride In tetrahydrofuran; mineral oil at 60℃; for 24h;
  • 32
  • [ 10287-53-3 ]
  • [ 141762-27-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: diethyl ether / 12 h / 20 °C 2: [18F]-potassium fluoride; [2.2.2]cryptande / acetonitrile / 0.17 h / 95 °C 3: sodium hydroxide / water; acetonitrile / 0.17 h / 40 - 90 °C 4: tetramethyl ammoniumhydroxide / acetonitrile / 0.03 h / 75 - 95 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: diethyl ether 2: K[18F]F/K222 / acetonitrile / 0.17 h / 90 °C 3: tetrapropylammonium hydroxide / water; acetonitrile / 0.05 h / 120 °C 4: acetonitrile / 0.08 h / 90 °C
Multi-step reaction with 4 steps 1: diethyl ether 2: K[18F]F/K222 / acetonitrile / 0.17 h / 90 °C 3: tetrapropylammonium hydroxide / water; acetonitrile / 0.05 h / 120 °C 4: acetonitrile / 0.08 h / 90 °C
Multi-step reaction with 4 steps 1: dichloromethane / 3 h / 60 °C / Inert atmosphere 2: [18F]-potassium fluoride / acetonitrile; dimethyl sulfoxide / 0.17 h / 90 °C / Inert atmosphere 3: sodium hydroxide / 0.08 h / 90 °C 4: 0.08 h / 90 °C
Multi-step reaction with 5 steps 1: benzene / 20 °C / Reflux 2: K[18F]F-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane complex / N,N-dimethyl-formamide / 0.2 h / 90 °C 3: hydrogenchloride / N,N-dimethyl-formamide; water / 0.08 h / 100 °C 4: [2.2.2]cryptande; potassium carbonate / acetonitrile; water 5: acetonitrile / 0.08 h / 90 °C
Multi-step reaction with 3 steps 1: benzene / 6 h / 85 °C 2: [18F]-potassium fluoride / acetonitrile 3: tetrapropylammonium hydroxide / acetonitrile

  • 33
  • [ 74-83-9 ]
  • [ 10287-53-3 ]
  • [ 1394949-85-9 ]
YieldReaction ConditionsOperation in experiment
98% In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Schlenk technique;
  • 34
  • [ 1202-25-1 ]
  • [ 10287-53-3 ]
  • [ 122065-71-8 ]
YieldReaction ConditionsOperation in experiment
General procedure: A flame-dried Schlenk test tubewith a magnetic stirring bar was charged with NaH (60% suspension in mineral oil) in dry THF (4 mL) at room temperature under N2 atmosphere.4-(Dimethylamino)acetophenone (250 mg, 1.53 mmol) was then added and the mixture was stirred for 10 min, followed by the addition of ethyl benzoate (340 mg, 1.76 mmol). The reaction mixture was refluxed for 8 h to give a viscous yellow suspension. The reaction was quenched with ice water(50 mL), and the pH was adjusted to 5-7 with hydrochloric acid. The light yellow precipitates formed were quickly filtrated and washed with cold water. The crude product was recrystallized with ethanol / water = 1:1 to afford the pure dibenzoylmethane derivative as light yellow needles.2 For the precursor of 3, the reaction mixture was extracted with ethyl acetate (20 mL × 3). The combined organic phase was washed with water, dried over anhydrous Na2SO4 and filtered. After removal of the volatile solvent by rotary evaporation, the crude product was obtained by flash chromatography. Recrystallization with ethanol / water = 1:1 afforded the purecompound as a yellow crystal.3
  • 35
  • [ 1202-25-1 ]
  • [ 10287-53-3 ]
  • [ 852931-76-1 ]
  • 36
  • [ 10287-53-3 ]
  • [ 75057-89-5 ]
YieldReaction ConditionsOperation in experiment
54% With hydroxylamine hydrochloride; sodium methylate In methanol at 0℃; 4.7.2 General procedure for the preparation of compounds 6a-6u General procedure: To a stirred solution of sodium methoxide (10mmol) and 6mmol of hydroxylamine hydrochloride at 0°C is added an ester (9 or 10, 3mmol). The reaction is monitored by TLC, and upon completion the reaction mixture is brought to pH 7-8 with 1M hydrochloric acid. The resulted mixture is extracted thrice with AcOEt, and the combined organic layer washes with brine. After drying over MgSO4, removement of the solvent under reduced pressure give a slight yellow oil. Compound 6 is obtained after purification with column chromatography on silica gel, eluting with AcOEt-petroleum ether.
  • 37
  • [ 10287-53-3 ]
  • [ 88284-48-4 ]
  • ethyl 4-(N-methyl-N-phenylamino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium fluoride; 18-crown-6 ether; ammonium bicarbonate In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;
  • 38
  • [ 10287-53-3 ]
  • [ 123-54-6 ]
  • C14H17NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: acetylacetone With sodium hydride In 1,2-dimethoxyethane; mineral oil for 1h; Reflux; Stage #2: ethyl p-dimethyaminolbenzoate In 1,2-dimethoxyethane; mineral oil for 4h; Reflux; 2-[4-(Dimethylamino)phenyl]-6-methyl-4H-pyran-4-one (3) A solution of acetyl acetone (560mg, 5.58mmol) in DME (5mL) was slowly added to a stirred suspension of NaH (60% in oil; 670mg, 16.74mmol) in DME (10mL) at 25°C, after which the mixture was refluxed for 1h. A solution of ethyl 4-(dimethylamino)benzoate (1.0g, 5.58mmol) in DME (5mL) was added and the reaction mixture was further refluxed for 4h. Three-quarters of the solvent was evaporated under reduced pressure. The resulting mixture was treated with water (20mL) at 0°C, neutralized with 1M hydrochloric acid and extracted with Et2O (2×). The extract was dried (MgSO4) and concentrated under reduced pressure to give a yellow solid, which was purified by column chromatography eluting with a mixture of CHCl3/ acetone (5:1) to afford the triketone 2 (1.22g, 88%). This trione 2 was dissolved in conc. H2SO4 (4mL) at 0°C. After stirring for 3h at 25°C, the mixture was poured into ice-water, neutralized with Na2CO3 and extracted with Et2O (2×). The extract was dried (MgSO4) and concentrated under reduced pressure to give the pyranone 3a (1.069g, 95%) as a yellow solid
  • 39
  • [ 10287-53-3 ]
  • [ 1703-46-4 ]
YieldReaction ConditionsOperation in experiment
12% With methylsilane; potassium <i>tert</i>-butylate In tetrahydrofuran at 70℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction;
10% With ethanol; potassium <i>tert</i>-butylate; C39H41FeMnN2O5P(1+)*Br(1-) In <i>tert</i>-butyl alcohol at 100℃; for 22h; Inert atmosphere; Schlenk technique; enantioselective reaction;
  • 40
  • [ 383-63-1 ]
  • [ 26672-80-0 ]
  • [ 360-34-9 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: ethyl trifluoroacetate, With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 1-(4-(dimethylamino)phenyl)pentan-1-one In tetrahydrofuran at 0℃; for 6h; Inert atmosphere; Schlenk technique; Reflux; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.25h; Inert atmosphere; Schlenk technique; General procedure for ‘trifluoroacetic ester/ketone metathesis’ and the preparation of TFMKs General procedure: Under Ar atmosphere in a dry Schlenk tube, a mixture of NaH (6.0 mmol) and trifluoroacetate (6.0 mmol) was stirred in THF (5 mL) at room temperature for 10 min. To this mixture enolizable ketones (5.0 mmol) in THF (5 mL) was added dropwise at 0 °C under Ar atmosphere. After stirring for 2-6 h at reaction temperature, the reaction solution was cooled to 0 °C again and quenched with 6 mL of 1 mol/L HCl. After stirring for additional 15 min, the mixture was neutralized with saturated NaHCO3 solution. After usual workup, the residue was purified by chromatography on silica gel to afford the trifluoromethyl alkyl ketone products.
  • 41
  • [ 112-60-7 ]
  • [ 10287-53-3 ]
  • C26H36N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With titanium(IV) isopropylate at 80 - 170℃; for 3h; Inert atmosphere; 1 Synthesis of an oligomeric difunctional aminobenzoate 20.4g (0.105 mol) of tetraethylene glycol was dissolved in 38.6 (0.20 mol) of N,Ndimethylaminobenzoic acid ethylester (EDB) at 80-100°C. Then, 1.0 ml of titanium isopropylate was added and the reaction mixture was heated under Nitrogen to 170°C for three hours. Then vacuum (20 KPa) was applied for 30 minutes. A brown clear liquid remained. After several days, the liquid crystallized to a pale amber solid. Yield: 47.2g (96%)Characterization:Molecular weight: Number average: 478; Weight average: 492Purity: 98 area% (GPC)Melting point: 48-52°CAbsorption maximum: 308 nm
  • 42
  • [ 10287-53-3 ]
  • C39H53N3O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.8 g With titanium(IV) isopropylate at 60 - 170℃; Inert atmosphere; 2 Synthesis of oligomeric trifunctional aminobenzoate 55.0 g of N,N-dimethylaminobenzoic acid ethylester (EDB) and 45.Og of ethoxylated trimethylolpropane (Mw average 450) were charged into a 250 ml flask, equipped with thermometer, mechanical stirrer, nitrogen inlet tube, condenser and receiver. Nitrogen was introduced at a rate of three bubbles/sec. Then, the mixture was heated to 60°C until the EDB was completely into solution. Then, l.5g of titanium iso-propylate (Tyzor TPT) was added, the mixture was heated to 150-170°C, and ethanol was distilled off. After the ethanol formation subsided, the reaction was resumed for another 3-5 hours at 170°C to minimize the residual amount of EDB.Yield: 87.8g.Characterization:Residual: EDB 0.1% determined by quantitative GC Molecular weight: Number average 943; Weight average 973 Purity: 96 area %(GPC)Viscosity: 20.5 Pas25°C (D = 50 1/s) Absorption maximum: 310 nm
  • 43
  • [ 41532-84-7 ]
  • [ 10287-53-3 ]
  • (Z)-2-(1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)-1-(4(dimethylamino) phenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With sodium hydride In toluene; mineral oil for 24h; Reflux; Synthesis of (Z)-2-(1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)-1-phenylethanone (3a) General procedure: Sodium hydride (60 wt% in oil, 1.6 g, 40 mmol) was added to a toluene (100 mL) solution of 1,1,2-trimethyl-1H-benzo[e]indole 1 (2.1 g, 10 mmol and ethyl benzoate 2a (1.5 g, 10 mmol) at room temperature. The solution was refluxed for 1 day. After cooling to 0-5 °C, aq. NH4Cl was added to the reaction mixture and extracted with ethyl acetate. The extract was dried over MgSO4 and concentrated in vacuo. Column chromatography of the residue on silica gel gave 1 (2.6 g, 72%) as a yellow solid. mp (110-112 °C).
  • 44
  • [ 64-18-6 ]
  • [ 53033-82-2 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
68% With tris(pentafluorophenyl)borate In dibutyl ether at 100℃; Schlenk technique; Inert atmosphere;
  • 45
  • [ 6265-94-7 ]
  • [ 10287-53-3 ]
  • C23H20N2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With sodium hydride In toluene; mineral oil Reflux; 2.2.1 Synthesis of 7a General procedure: To the toluene (50mL) solution of 2-benzylbenzo[d]oxazole (2.09g, 10mmol) and ethyl benzoate (1.5g, 10mmol), sodium hydride (60wt% in oil, 1.6g, 40mmol) was added in at room temperature. The solution was refluxed for overnight. After cooling to 0-5°C, aq. NH4Cl was added to the reaction mixture and the product extracted with ethyl acetate. The extract was dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product obtained was purified by column chromatography using silica gel to give 7a (1.8g, 57%) as a pale yellow solid.
  • 46
  • [ 2008-07-3 ]
  • [ 10287-53-3 ]
  • C23H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydride In toluene; mineral oil Reflux; 2.2.1 Synthesis of 7a General procedure: To the toluene (50mL) solution of 2-benzylbenzo[d]oxazole (2.09g, 10mmol) and ethyl benzoate (1.5g, 10mmol), sodium hydride (60wt% in oil, 1.6g, 40mmol) was added in at room temperature. The solution was refluxed for overnight. After cooling to 0-5°C, aq. NH4Cl was added to the reaction mixture and the product extracted with ethyl acetate. The extract was dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product obtained was purified by column chromatography using silica gel to give 7a (1.8g, 57%) as a pale yellow solid.
  • 47
  • [ 3955-65-5 ]
  • [ 10287-53-3 ]
  • C23H20N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 6-methylphenanthridine With n-butyllithium In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: ethyl p-dimethyaminolbenzoate In tetrahydrofuran at 20 - 45℃; Inert atmosphere;
  • 48
  • [ 10287-53-3 ]
  • [ 88284-48-4 ]
  • [ 105-07-7 ]
  • ethyl-4-((4-cyanophenyl)(2-(dimethylamino)phenyl)methoxy)benzoate [ No CAS ]
  • ethyl 4-(N-methyl-N-phenylamino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 63% 2: 23% Stage #1: ethyl p-dimethyaminolbenzoate; 4-cyanobenzaldehyde With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at -10℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-(trimethylsilyl)phenyl trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
  • 49
  • [ 10287-53-3 ]
  • [ 536-74-3 ]
  • ethyl 4-[methyl(3-phenylprop-2-yn-1-yl)amino]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With tert.-butylhydroperoxide; oxygen In water at 100℃;
  • 50
  • [ 124-38-9 ]
  • [ 10541-82-9 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
72% With diphenylsilane; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In N,N-dimethyl-formamide at 50℃; chemoselective reaction;
69% With phenylsilane In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique;
41 %Spectr. With diphenylsilane; betaine In acetonitrile at 70℃; for 12h; Inert atmosphere;
  • 51
  • [ 613-90-1 ]
  • [ 10287-53-3 ]
  • [ 1569293-72-6 ]
YieldReaction ConditionsOperation in experiment
82% With tert.-butylhydroperoxide; ferrous(II) sulfate heptahydrate In methanol for 24h; Reflux; 4.2. Typical procedure for the synthesis of 2a General procedure: Method A: The mixture of FeSO47H2O (6.95 mg, 0.025 mmol),N,N-dimethylaniline (60.55 mg, 0.5 mmol), benzoyl cyanide (78.62 mg, 0.6 mmol) in CH3OH (2.0 mL) was stirred under an oxygen atmosphere at room temperature for 16 h. After the tertiary amine was completely consumed (checked by TLC), the reaction mixture was filtrated and concentrated under reduced pressure. The residue was then purified by column chromatography on silicagel (petroleum ether/ethyl acetate, 4:1) to afford 2a (66.5 mg, 91%yield) as a yellow oil. Method B: The mixture of FeSO47H2O (6.95 mg, 0.025 mmol),N,N-dimethylaniline (60.55 mg, 0.5 mmol), benzoyl cyanide (78.62 mg, 0.6 mmol), and TBHP (70% aqueous solution, 108 mL,0.75 mmol) in CH3OH (2.0 mL) was stirred under air at room temperature for 16 h. After the tertiary amine was completely consumed, the reaction mixture was filtrated and concentrated under reduced pressure. The residue was then purified by columnchromatography on silica gel (petroleum ether/ethyl acetate, 4:1) to afford 2a (64.3 mg, 88% yield) as a yellow oil.
  • 52
  • [ 504-29-0 ]
  • [ 10287-53-3 ]
  • 4-(dimethylamino)-N-(pyridin-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 2-aminopyridine With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere; Stage #2: ethyl p-dimethyaminolbenzoate In tetrahydrofuran; mineral oil Reflux; Inert atmosphere;
  • 53
  • [ 10287-53-3 ]
  • [ 569-72-2 ]
  • ethyl 4-((2-fluoro-3,3-diphenylallyl)(methyl)amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; sodium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Irradiation;
  • 54
  • [ 64-18-6 ]
  • [ 10541-82-9 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
91% With platinum on carbon; phenylsilane In toluene at 80℃; for 15h;
91% With platinum on activated charcoal; phenylsilane In toluene at 80℃; for 15h; Schlenk technique; Inert atmosphere; 15 Preparation of compound IV-9 An activated carbon supported platinum catalyst (Pt / C, 0.06 mg platinum, 0.0003 mmol, 0.1 mol%) was added to a 10 mL Schlenk tube. After evacuating the argon gas, 1 mL of solvent (toluene) was added.Under the protection of argon, to the above system, phenylsilane (78.9 mg, 0.75 mmol) was successively added successively,III-9 (R2 = p-adiphenyl, R3 = methyl) (53.8 mg, 0.3 mmol) and formic acid (27.6 mg, 0.6 mmol).The reaction was carried out at 80 ° C with stirring for 15 hours.After completion of the reaction, 3 mL of ethyl acetate was added to the system and the reaction was quenched with aqueous sodium hydroxide solution (3 mol / L, 3 mL)Ethyl acetate (3 x 10 mL), the organic phase was separated, dried over anhydrous Na2SO4, filtered,The solvent was removed by rotary evaporation.The residue was purified by column chromatography on ethyl acetate / petroleum ether = 1: 50 mixed solvent,The product was isolated and purified to give the target product IV-952.8 mg, yield 91%.
  • 55
  • [ 64-17-5 ]
  • [ 32315-10-9 ]
  • [ 121-69-7 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: bis(trichloromethyl) carbonate; <i>N</i>,<i>N</i>-dimethyl-aniline In chlorobenzene at 65℃; for 2h; Stage #2: ethanol In chlorobenzene at 30℃; 5 Example 5: preparation of p-dimethylamino benzoic acid ethyl ester In 500 ml in four-mouth bottle, by adding N, N-dimethyl aniline (121.2g, 1 . 0mol) and 60 ml chlorobenzene, stir, the double (trichloromethyl) carbonate (29.7g, 0 . 1mol) dissolved in 120 ml chlorobenzene in, slowly dripped into N, N-dimethyl aniline in chlorobenzene solution, 2h the drop finishes, then slow heating to 65 °C, thermal reaction, TLC or GC monitoring reaction, after the reaction is complete, to temperature to 30 °C, slowly dropping 18.4g anhydrous ethanol, the drop finishes, thermal reaction, TLC or GC monitoring reaction, after the reaction, the reaction solution slowly into 150 ml water, stirring hydrolysis, and control the temperature in the 25 °C left and right, 1h rear, static hierarchical, organic phase with saturated salt water washing, drying with anhydrous sodium sulfate, vacuum distillation to recover solvent and excess raw material, and then decompress the rectification and purification ethyl dimethyl amino benzoate 47.2g (collection fraction conditions: 110-115° C/0 . 02mmHg), yield 81%, purity 99.3%.
  • 56
  • [ 124-38-9 ]
  • [ 10287-53-3 ]
  • [ 88284-48-4 ]
  • 4-(ethoxycarbonyl)phenyl 2-(dimethylamino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: carbon dioxide; ethyl p-dimethyaminolbenzoate With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at -10℃; for 0.0833333h; Sealed tube; Glovebox; Stage #2: 2-(trimethylsilyl)phenyl trifluoromethanesulfonate In tetrahydrofuran at -10℃; for 24h; Sealed tube; Glovebox;
  • 57
  • [ 124-38-9 ]
  • [ 10287-53-3 ]
  • 4,5-dimethyl-2-(trimethylsilyl)phenyl triflate [ No CAS ]
  • 4-(ethoxycarbonyl)phenyl 2-(dimethylamino)-4,5-dimethylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: carbon dioxide; ethyl p-dimethyaminolbenzoate With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at -10℃; for 0.0833333h; Sealed tube; Glovebox; Stage #2: 4,5-dimethyl-2-(trimethylsilyl)phenyl triflate In tetrahydrofuran at -10℃; for 24h; Sealed tube; Glovebox;
  • 58
  • [ 124-38-9 ]
  • [ 10287-53-3 ]
  • [ 717903-52-1 ]
  • 4-(ethoxycarbonyl)phenyl 6-(dimethylamino)benzo[d][1,3]dioxole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: carbon dioxide; ethyl p-dimethyaminolbenzoate With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at -10℃; for 0.0833333h; Sealed tube; Glovebox; Stage #2: 6-(trimethylsilyl)benzo[d][1,3]dioxol-5-yl triflate In tetrahydrofuran at -10℃; for 24h; Sealed tube; Glovebox;
  • 59
  • [ 124-38-9 ]
  • [ 10287-53-3 ]
  • [ 217813-00-8 ]
  • 4-(ethoxycarbonyl)phenyl 2-(dimethylamino)-4,5-difluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: carbon dioxide; ethyl p-dimethyaminolbenzoate With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at -10℃; for 0.0833333h; Sealed tube; Glovebox; Stage #2: 4,5-di-fluoro-2-(trimethylsilyl)phenyl trifluoromethanesulfonate In tetrahydrofuran at -10℃; for 24h; Sealed tube; Glovebox;
  • 60
  • [ 124-38-9 ]
  • [ 10287-53-3 ]
  • 2-(trimethylsilyl)naphthalen-3-yl trifluoromethanesulfonate [ No CAS ]
  • 4-(ethoxycarbonyl)phenyl 3-(dimethylamino)-2-naphthoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: carbon dioxide; ethyl p-dimethyaminolbenzoate With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at -10℃; for 0.0833333h; Sealed tube; Glovebox; Stage #2: 2-(trimethylsilyl)naphthalen-3-yl trifluoromethanesulfonate In tetrahydrofuran at -10℃; for 24h; Sealed tube; Glovebox;
  • 61
  • [ 124-38-9 ]
  • [ 10287-53-3 ]
  • [ 252054-88-9 ]
  • 4-(ethoxycarbonyl)phenyl 2-(dimethylamino)-1-naphthoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: carbon dioxide; ethyl p-dimethyaminolbenzoate With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at -10℃; for 0.0833333h; Sealed tube; Glovebox; Stage #2: 1-(trimethylsilyl)naphthalen-2-yl triflate In tetrahydrofuran at -10℃; for 24h; Sealed tube; Glovebox;
  • 62
  • [ 10287-53-3 ]
  • [ 1147550-11-5 ]
  • C12H14N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With oxygen; Nitrogen dioxide; trifluoroacetic acid In acetonitrile at 15℃; for 3h;
  • 63
  • [ 110-88-3 ]
  • [ 94-09-7 ]
  • [ 10287-53-3 ]
  • [ 10541-82-9 ]
YieldReaction ConditionsOperation in experiment
1: 37% 2: 57% With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 48h; Inert atmosphere; chemoselective reaction; N-Methylation of Aromatic Amines and N-Heterocycles; General Procedure General procedure: The N-containing substrate (1 mmol) and trioxane (270 mg, 3 mmol) were dissolved in CH2Cl2 (1.5 mL) under N2 atmosphere. To this solution were added TFA (0.75 mL) and Et3SiH (1.45 mL, 10 mmol). The reaction was monitored by TLC (eluent: see below). After 24 or 48 h (in case of incomplete conversion, after 24 h), aq 2 N NaOH (20 mL) solution was carefully added and the mixture was extracted with CH2Cl2 (3*20 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo and the residue was purified by flash column chromatography (FCC).
  • 64
  • [ 10287-53-3 ]
  • C11H13(2)H2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With [{μ-(IDipp)PH}{Ir(cod)}2{μ-Cl}][BArF4]; deuterium gas In dichloromethane at 20℃; for 16h;
97% With C53H47BF15IrN2; deuterium gas In cyclohexane at 20℃; for 16h; Inert atmosphere;
With C29H46IrN3P(1+)*C32H12BF24(1-); deuterium gas In dichloromethane at 21 - 24℃; for 1h;
  • 65
  • [ 711-79-5 ]
  • [ 10287-53-3 ]
  • C21H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% Stage #1: ethyl p-dimethyaminolbenzoate With sodium hydride In tetrahydrofuran for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 1-hydroxy-2-acetonaphthone In tetrahydrofuran at 60℃; Inert atmosphere; Schlenk technique;
  • 66
  • [ 2797-28-6 ]
  • [ 10287-53-3 ]
  • [ 100-44-7 ]
  • C18H22NO2(1+)*C24BF20(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In ethanol at 20℃; for 24h; 37 General procedure: To 2.35 g (16.8 mmol) of 4- (methylthio) phenol, 2.96 g (16.8 mmol) of chloromethyl naphthalene (1-naphthylmethyl chloride)117.8 g (16.8 mmol) of a 10% by mass aqueous solution of tetrakis (pentafluorophenyl) borate sodium salt (sodium tetrakis (pentafluorophenyl) borate) (manufactured by Nippon Shokubai Co., Ltd.)And the mixture was stirred at room temperature for 24 hours.After filtration, washing with water and drying,Washed with hexane, and again dried to obtain the target sulfonium compound.The yield was 90%. Incidentally,As the solvent used,It is only water. The sum of the Hammett substituent constants of the substituent in R -0.37.In Example 23,Except that 2.27 g (16.8 mmol) of 4- (methylthio) phenol was replaced with N, N-dimethyl-p-toluidine (manufactured by Tokyo Chemical Industry Co., Ltd.)The following compound (109) was obtained in the same manner as in Example 23. The yield was 87%. Example 37 Synthesis of Compound (113) In the same manner as in Example 35 except that 2.34 g (18.5 mmol) of benzyl chloride was used in place of 1-naphthylmethyl bromide in Example 35, the following compound 113) was obtained. The yield was 75%.
  • 67
  • [ 132404-42-3 ]
  • [ 1458-98-6 ]
  • [ 10287-53-3 ]
  • C4F9O6S3(1-)*C15H22NO2(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In ethanol at 20℃; for 24h; 41 General procedure: To 2.35 g (16.8 mmol) of 4- (methylthio) phenol, 2.96 g (16.8 mmol) of chloromethyl naphthalene (1-naphthylmethyl chloride)117.8 g (16.8 mmol) of a 10% by mass aqueous solution of tetrakis (pentafluorophenyl) borate sodium salt (sodium tetrakis (pentafluorophenyl) borate) (manufactured by Nippon Shokubai Co., Ltd.)And the mixture was stirred at room temperature for 24 hours.After filtration, washing with water and drying,Washed with hexane, and again dried to obtain the target sulfonium compound.The yield was 90%. In Example 39,Tetrakis (pentafluorophenyl) borate sodiumA 10: 1 mass ratio solution of 9.17 mass% water: ethyl alcohol was mixed with 70.3 g of a 10: 1 mass ratio solution of 10 mass% water: ethyl alcohol of tris (trifluoromethanesulfonyl) methide lithium (manufactured by Central Glass) 16.8 mmol).The following compound (117) was obtained in the same manner as in Example 39.The yield was 70%.
  • 68
  • [ 1458-98-6 ]
  • [ 10287-53-3 ]
  • C15H22NO2(1+)*F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium hexafluoroantimonate In ethanol at 20℃; for 24h; 42 General procedure: To 2.35 g (16.8 mmol) of 4- (methylthio) phenol, 2.96 g (16.8 mmol) of chloromethyl naphthalene (1-naphthylmethyl chloride)117.8 g (16.8 mmol) of a 10% by mass aqueous solution of tetrakis (pentafluorophenyl) borate sodium salt (sodium tetrakis (pentafluorophenyl) borate) (manufactured by Nippon Shokubai Co., Ltd.)And the mixture was stirred at room temperature for 24 hours.After filtration, washing with water and drying,Washed with hexane, and again dried to obtain the target sulfonium compound.The yield was 90%. In Example 39, A 10: 1 mass ratio solution of 9.17 mass% of water: ethyl alcohol of tetrakis (pentafluorophenyl) borate was added to a 2.5 mass% aqueous solution of sodium hexafluorophosphate (manufactured by Tokyo Chemical Industry Co., Ltd.): ethyl alcohol Except that 112.9 g (16.8 mmol) of a 10: 1 mass ratio solution ofThe following compound (118) was obtained in the same manner as in Example 39. The yield was 68%.
  • 69
  • [ 10287-53-3 ]
  • [ 53892-40-3 ]
YieldReaction ConditionsOperation in experiment
78% With air In 1,2-dimethoxyethane at 20℃; Irradiation;
  • 70
  • [ 10287-53-3 ]
  • [ 118-93-4 ]
  • 1-(4-(dimethylamino)phenyl)-3-(2-hydroxyphenyl)propane-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With sodium hydride In tetrahydrofuran at 70℃; for 2h;
  • 71
  • [ 703-23-1 ]
  • [ 10287-53-3 ]
  • 1-(4-(dimethylamino)phenyl)-3-(2-hydroxy-6-methoxyphenyl)propane-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With sodium hydride In tetrahydrofuran at 70℃; for 2h;
  • 72
  • [ 64-17-5 ]
  • tert-butyl (4-(dimethylamino)benzoyl)(methyl)carbamate [ No CAS ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
88% With pyridine; [2,2]bipyridinyl; manganese; chloro-trimethyl-silane; cobalt(II) bromide In N,N-dimethyl-formamide at 60℃; for 20h; Sealed tube;
  • 73
  • [ 586-77-6 ]
  • [ 95-92-1 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
55% With dmap; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.333333h; Microwave irradiation;
  • 74
  • [ 2396-84-1 ]
  • [ 10287-53-3 ]
  • ethyl 4-((6-ethoxy-2-methyl-6-oxohex-3-en-1-yl)(methyl)amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 1,3-bis-(diphenylphosphino)propane; cesium pivalate; cobalt(II) bromide In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;
  • 75
  • [ 10287-53-3 ]
  • [ 1481-27-2 ]
  • (Z)-3-(4-(dimethylamino)phenyl)-1-(4-fluoro-2-hydroxyphenyl)-3-hydroxyprop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With sodium hydride In tetrahydrofuran at 60℃;
  • 76
  • [ 10287-53-3 ]
  • [ 111409-79-1 ]
  • ethyl 4-(dimethylamino)-2-((triisopropylsilyl)ethynyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate; sodium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 120℃; for 24h; Inert atmosphere; regioselective reaction;
  • 77
  • [ 64-17-5 ]
  • [ 1202-25-1 ]
  • [ 10287-53-3 ]
  • 78
  • [ 677-25-8 ]
  • [ 10287-53-3 ]
  • (E)-ethyl 4-(dimethylamino)-2-(2-(fluorosulfonyl)vinyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; acetic acid at 100℃; for 15h; Sealed tube;
  • 79
  • [ 64-17-5 ]
  • 3-(4-(dimethylamino)benzoyl)oxazolidin-2-one [ No CAS ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
78% With ytterbium(III) triflate In acetonitrile at 90℃; for 48h; Sealed tube; Inert atmosphere;
  • 80
  • [ 124-38-9 ]
  • [ 94-09-7 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
76% With diphenylsilane; C21H41N3NiP2 In acetonitrile at 120℃; for 24h; Autoclave;
54%Chromat. With tin(II) trifluoromethanesulfonate; hydrogen; cobalt(II) diacetate tetrahydrate; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In ethanol at 125℃; for 24h; Glovebox; Green chemistry;
  • 81
  • [ 101-82-6 ]
  • [ 10287-53-3 ]
  • C21H20N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: 2-Benzylpyridine With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: ethyl p-dimethyaminolbenzoate In tetrahydrofuran for 10h; Reflux;
  • 82
  • [ 136918-14-4 ]
  • [ 10287-53-3 ]
  • C19H18N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrabutyl ammonium fluoride; acetic acid In acetonitrile at 60℃; for 3h; Electrochemical reaction; Inert atmosphere;
  • 83
  • [ 74-83-9 ]
  • [ 94-09-7 ]
  • [ 10287-53-3 ]
YieldReaction ConditionsOperation in experiment
17 g With triethylamine In N,N-dimethyl-formamide at 75℃; for 0.133333h; 1 16.5 g (0.1 mol) of benzocaine dissolved in 200 mL of N,N-dimethylformamide, and configured as solution A;Methyl bromide (0.22 mol) and triethylamine 20 g (0.2 mol) dissolved in 200 mL of N, N-dimethylformamide, configured as solution B;The solution A and the solution B were fed into the silicon carbide reactor at a reaction temperature of 75 ° C through a tetrafluoro pump at the same flow rate of 10 mL/min.The material undergoes a substitution reaction in the microreactor, and the residence time is 8 min, and the material after the reaction is collected.The whole reaction solution was poured into water, and the reaction liquid was extracted 4 times with 300 mL of chloroform, and the organic phase was combined.After concentration, it was separated by silica gel column chromatography (PE: EA=5:1), disubstituted product N,N-dimethyl-p-carboxylate aniline 17 g;
  • 84
  • [ 2876-08-6 ]
  • [ 10287-53-3 ]
  • 1-[4-(dimethylamino)phenyl]-2-(1-methyl-1H-benzimidazol-2-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With sodium hydride In N,N-dimethyl-formamide; mineral oil; benzene Reflux; A slightly modified procedure [139] was used to prepare 1-[4-(dimethylamino)phenyl]-2-(1-methyl-1H-benzimidazol-2-yl)ethanone. A mixture of 1,2-dimethylbenzimidazole (0.29g, 2mmol), ethyl 4-(dimethylamino)benzoate (0.39g, 2mmol), dry benzene (10mL), dimethylformamide (0.5mL) and sodium hydride (0.15g, 60% suspension in mineral oil) was refluxed and stirred magnetically overnight. The reaction was quenched by addition of water (15mL) and the resulted mixture was extracted with ethyl acetate (20mL). The organic layer was subsequently washed with water (2 x 10mL) and brine (2 x 10mL) and dried with sodium sulfate. Solid impurities were filtered off, the filtrate was concentrated on the rotary evaporator. The obtained solid was recrystallized from ethanol. 1-[4-(dimethylamino)phenyl]-2-(1-methyl-1H-benzimidazol-2-yl)ethanone - Yellow solid, yield 36%, Mp 228-230∘C, and 228-230∘C [49]. In CDCl3 solution 1-[4-(dimethylamino)phenyl]-2-(1-methyl-1H-benzimidazol-2-yl)ethanone (ketimine tautomeric form) is in equilibrium with (Z)-1-[4-(dimethylamino)phenyl]-2-(1-methyl-1H-benzimidazol-2-yl)ethenol (enolimine form). 1H NMR (CDCl3 from TMS) δ: 8.02 (m, 2H), 7.68 (d, 1H, JH,H3 JH,H3 =8.80Hz), 7.74 (m, 2H), 7.30 (m, 1H), 7.24 (m, 1H), 7.18 (m, 2H), 6.73 (m, 4H), 6.66 (m, 2H), 5.81 (s, 1H), 4.61 (s, 2H), 3.78 (s, 6H), 3.03 (s, 6H), 3.01 (s, 6H). 13C NMR δ: 191.7, 170.8, 153.8, 153.5, 149.8, 142.2, 136.1, 131.9, 131.2, 127.5, 123.7, 122.4, 122.3, 122.0, 119.2, 116.8, 111.4, 110.73, 110.67, 110.4, 109.3, 74.9, 40.1, 40.0, 38.8, 30.5. 15N NMR (CDCl3 from MeNO2) δ:-136.8,-233.8,-317.3. C18H19N3O, Calcd. C 73.69, H 6.53, N 14.32. Found C 73.78, H 6.63, N 14.23.
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