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[ CAS No. 63480-11-5 ] {[proInfo.proName]}

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Chemical Structure| 63480-11-5
Chemical Structure| 63480-11-5
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Product Details of [ 63480-11-5 ]

CAS No. :63480-11-5 MDL No. :MFCD03426400
Formula : C9H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :FTOHSJGKIFDLQU-UHFFFAOYSA-N
M.W : 177.16 Pubchem ID :12425790
Synonyms :

Calculated chemistry of [ 63480-11-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.07
TPSA : 63.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.13
Log Po/w (WLOGP) : 0.79
Log Po/w (MLOGP) : 1.33
Log Po/w (SILICOS-IT) : 2.52
Consensus Log Po/w : 1.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.07 mg/ml ; 0.00603 mol/l
Class : Soluble
Log S (Ali) : -2.05
Solubility : 1.59 mg/ml ; 0.00895 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.53
Solubility : 0.0522 mg/ml ; 0.000294 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.57

Safety of [ 63480-11-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 63480-11-5 ]

* 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 [ 63480-11-5 ]

[ 63480-11-5 ] Synthesis Path-Downstream   1~51

  • 3
  • [ 1192-07-0 ]
  • [ 63480-11-5 ]
  • [ 63480-01-3 ]
  • 4
  • [ 63480-11-5 ]
  • [ 75-03-6 ]
  • [ 50332-62-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl-formamide
  • 5
  • [ 63480-11-5 ]
  • [ 37795-78-1 ]
YieldReaction ConditionsOperation in experiment
With sulfuryl dichloride In acetic acid at 60℃;
  • 6
  • [ 63480-11-5 ]
  • [ 37795-84-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SO2Cl2 / acetic acid / 60 °C 2: H2O / Ambient temperature
  • 7
  • [ 5144-11-6 ]
  • [ 63480-11-5 ]
  • 1-(2-amino-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane; water 5.a EXAMPLE 5 (a) A solution of butyl lithium in hexane (2.5M, 20 ml) was added slowly to a stirred solution of 1,5-dimethyltetrazole (4.9 g) in dry tetrahydrofuran (100 ml) at -5° to 0° under nitrogen. After stirring for 0.5 hour, 7-methyl-1H-3,1-benzoxazine-2,4-dione (2.6 g) was added and stirring continued for 1.5 hours at room temperature and for 3 hours at 40°. The solvent was evaporated under reduced pressure at 40°-50°, water (100 ml) was added to the residue, followed by 5N hydrochloric acid dropwise until neutral to Universal pH paper. The mixture was extracted with ethyl acetate (3*50 ml) and the combined extracts were washed with 10% aqueous potassium carbonate solution (50 ml), dried over anhydrous magnesium sulphate and then evaporated under reduced pressure at 50°. The residue was triturated with ether to give a solid product which was collected by filtration and recrystallized from ethyl acetate to give the novel compound 1-(2-amino-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone, m.p. 155°-6°.
  • 8
  • triphosgene [ No CAS ]
  • [ 2305-36-4 ]
  • [ 63480-11-5 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In ethyl acetate at 20℃; for 0.25h; 105.105a To a solution of 2-amino-4-methylbenzoic acid (1.00 g, 6.62 mmol) in ethyl acetate (15.0 mL) were added potassium carbonate (0.914 g, 6.62 mmol) and triphosgene (0.883 g, 2.98 mmol). Following stirring at ambient temperature for 15 min., the reaction mixture was treated with water, filtered, washed with water and hexanes, and dried in vacuo to afford the title compound as an off- white solid (1.16 g, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.7 (s, 1 H), 7.80 (d, J=8.1 Hz, 1 H), 7.08 (dd, J=8.0, 0.9 Hz, 1 H), 6.93 (s, 1 H), 2.38 (s, 3 H). MS(ES+) m/e 178 [M+H]+
  • 10
  • [ 32315-10-9 ]
  • [ 2305-36-4 ]
  • [ 63480-11-5 ]
YieldReaction ConditionsOperation in experiment
93% In tetrahydrofuran at 0℃; for 5h; Inert atmosphere; Large scale; 11 Under electromagnetic stirring and ice-water bath cooling,Add 1j (2000mg, 13.23mmol) to a 150mL round bottom flask,Tetrahydrofuran (45 mL), wait for the reaction system to cool, and then slowly add triphosgene (1335 mg, 4.49 mmol).Under N2 protection, stir for 5h. After the reaction, the solvent was removed under reduced pressure, and an appropriate amount of petroleum ether was added and sonicated to fully suspend the precipitated solid in petroleum ether.After suction filtration and drying, 2170 mg of a gray solid of compound 2k was obtained (93% yield).
In tetrahydrofuran at 20℃;
In tetrahydrofuran at -5℃; for 5h;
Stage #1: 2-amino-4-methyl benzoic acid In 1,4-dioxane Reflux; Stage #2: bis(trichloromethyl) carbonate In 1,4-dioxane Reflux; Step 4: General procedure: The mixture of 2-aminobenzoic acid (1 equivalent) and 1,4-dioxane were heatedat reflux. Then, a solution of triphosgene (BTC, 0.4 equivalent) in 1,4-dioxane wasadded dropwise to the above mixture over 30 min. After that, this solution was refluxovernight. Then the solvent was removed under reduced pressure, and PE/EA = 2:1was added to the obtained residue with vigorous stirring. The precipitate wascollected by filtration, washed with Petroleum ether, and dried to give the isotaicanhydride as a solid in theoretical yield.
In tetrahydrofuran at 20℃; for 6h; 4.1.1. Synthetic procedure for 2 General procedure: To a solution of different 2-aminobenzoic acid (5.0 mmol) in 20 mLanhydrous tetrahydrofuran (THF) was added triphosgene (BTC, 0.445 g,1.67 mmol) in batches. The reaction mixture was stirred at room temperaturefor 6 h and then poured into ice water. The resulting solid werefiltrated to obtain compounds 1, which were dissolved in 10 mL ofanhydrous N,N-dimethyl formamide (DMF), and then sodium hydride(NaH, 0.096 g, 4.0 mmol) was added in batches at 0. The reactionmixture was stirred at 0 for 30 min, and then methyl iodide (CH3I,0.469 g, 3.3 mmol) was added dropwise. The reaction was detected byTLC. After completion, the reaction mixture was poured into the icewater. The resulting solid were filtrated to obtain compounds 2.
In tetrahydrofuran at 20℃; for 6h;

  • 11
  • [ 63480-11-5 ]
  • C12H14N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4.5 h / 20 - 60 °C / Inert atmosphere 2: 200 °C / Microwave irradiation; Acidic conditions
  • 12
  • [ 63480-11-5 ]
  • C12H13ClN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4.5 h / 20 - 60 °C / Inert atmosphere 2: 200 °C / Microwave irradiation; Acidic conditions 3: chlorosulfonic acid / 16 h / 65 °C
  • 13
  • [ 63480-11-5 ]
  • C19H18F3N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4.5 h / 20 - 60 °C / Inert atmosphere 2: 200 °C / Microwave irradiation; Acidic conditions 3: chlorosulfonic acid / 16 h / 65 °C 4: pyridine / dichloromethane / 16 h / 20 °C
  • 14
  • [ 63480-11-5 ]
  • [ 15028-41-8 ]
  • C13H18N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 60℃; for 4.5h; Inert atmosphere; regioselective reaction;
  • 15
  • [ 63480-11-5 ]
  • 3-((4-chlorophenyl)(phenyl)methyl)-1,7-dimethylquinazoline-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; urea / N,N-dimethyl acetamide / 1.25 h / 250 °C / Microwave irradiation 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C
  • 16
  • [ 63480-11-5 ]
  • [ 5267-39-0 ]
  • 3-((4-chlorophenyl)(phenyl)methyl)-7-methylquinazoline-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
30 mg With triethylamine; urea In N,N-dimethyl acetamide at 250℃; for 1.25h; Microwave irradiation; 20 3-((4-Chlorophenyl)(phenyl)methyl)-7-methylquinazoline-2,4(lH,3H)-dione 4-Methylisatoic anhydride (80 mg; 0.45 mmol), (4-chlorophenyl)(phenyl)methanamine hydrochloride (138 mg; 0.54 mmol), urea (40.7 mg; 0.68 mmol), TEA (0.076 ml; 0.54 mmol), and 0.5 ml of DMA were charged in a microwave tube and heated for 15 min at 250 °C. The microwave reaction was run again for the same time at the same temperature and then for 60 min at 250 °C. The reaction mixture was cooled to rt, mixed with 5 ml of water, and extracted twice with 5 ml of EtOAc. Combined organic phases were dried over Na2S04 and evaporated to dryness. The crude product was purified with CombiFlash (0402) (EtOAc:heptane; normal phase silica) to yield 30 mg of 3-((4- chlorophenyl)(phenyl)methyl)-7-methylquinazoline-2,4(lH,3H)-dione. LC-MS (ES-) [M- 1]: 375.03.
  • 17
  • [ 63480-11-5 ]
  • [ 74-89-5 ]
  • [ 1201935-73-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-methyl-2H-3,1-benzoxazine-2,4(1H)-dione With acetic acid In water; acetonitrile at 60℃; for 0.333333h; Reflux; Stage #2: methylamine In water; acetonitrile for 1.5h; 1.3 Example 1 15 g of 3-nitro-4-methylbenzoic acid and 9 g of sodium hydroxide were weighed into a 500 mL three-necked flask and 100 mLDistilled water, and then add 2g of ferric chloride and 5g of activated carbon, water bath heated to 70 , and then dropping 12g hydrazine hydrateReaction 1h, filtered to obtain light yellow powder;Into a 500 mL three-necked flask, 15 g of the above-prepared light was addedYellow powder and 1 g of pyridine and 100 mL of acetonitrile were added and the temperature was raised to 50 ° C while stirring.Dropping speed was controlled so that the dropping was completed in 1 hour, and the reaction was kept for 4 hours and cooled to room temperature.To the aboveStep in the three-neck flask by adding 1g mass concentration of 80% acetic acid solution, start the mixer,Stirring at 300r / min for 20min. After stirring, the mixture is poured into a refluxing device and heated to60 ° C, and 10 mL of a 40% aqueous solution of methylamine was dropwise added thereto to control the dropping speed,30min within the drop is completed, insulation reaction 1h;To the mixed solution after the completion of the above reaction, 50 mL of distilled water was addedWater, stirring 10min and then into the separatory funnel, put it aside 1h layered, separated from the organic phase, spare;The organic phase was transferred to a 500 mL three-necked flask, heated in a water bath to 40 ° C,20g of sulfonyl chloride and 10mL of acetonitrile were added under stirring. The dropping rate was controlled so as to be added dropwise within 1 hour, and the reaction was kept for 3 hours.To room temperature, filtered to filter residue, into the oven, at 105 drying in the 3-amino-6-chloro-N,Methylbenzamide.
  • 18
  • [ 75-05-8 ]
  • [ 2305-36-4 ]
  • [ 63480-11-5 ]
YieldReaction ConditionsOperation in experiment
With pyridine In water at 50℃; for 4h; 1.2 Example 1 15 g of 3-nitro-4-methylbenzoic acid and 9 g of sodium hydroxide were weighed into a 500 mL three-necked flask and 100 mLDistilled water, and then add 2g of ferric chloride and 5g of activated carbon, water bath heated to 70 , and then dropping 12g hydrazine hydrateReaction 1h, filtered to obtain light yellow powder;Into a 500 mL three-necked flask, 15 g of the above-prepared light was addedYellow powder and 1 g of pyridine and 100 mL of acetonitrile were added and the temperature was raised to 50 ° C while stirring.Dropping speed was controlled so that the dropping was completed in 1 hour, and the reaction was kept for 4 hours and cooled to room temperature.To the aboveStep in the three-neck flask by adding 1g mass concentration of 80% acetic acid solution, start the mixer,Stirring at 300r / min for 20min. After stirring, the mixture is poured into a refluxing device and heated to60 ° C, and 10 mL of a 40% aqueous solution of methylamine was dropwise added thereto to control the dropping speed,30min within the drop is completed, insulation reaction 1h;To the mixed solution after the completion of the above reaction, 50 mL of distilled water was addedWater, stirring 10min and then into the separatory funnel, put it aside 1h layered, separated from the organic phase, spare;The organic phase was transferred to a 500 mL three-necked flask, heated in a water bath to 40 ° C,20g of sulfonyl chloride and 10mL of acetonitrile were added under stirring. The dropping rate was controlled so as to be added dropwise within 1 hour, and the reaction was kept for 3 hours.To room temperature, filtered to filter residue, into the oven, at 105 drying in the 3-amino-6-chloro-N,Methylbenzamide.
  • 19
  • [ 27329-27-7 ]
  • [ 63480-11-5 ]
  • 20
  • [ 63480-11-5 ]
  • [ 501-65-5 ]
  • 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In N,N-dimethyl-formamide at 110℃; for 24h; Sealed tube; regioselective reaction;
  • 21
  • [ 63480-11-5 ]
  • [ 928-49-4 ]
  • 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In N,N-dimethyl-formamide at 110℃; for 24h; Sealed tube; regioselective reaction;
  • 22
  • [ 63480-11-5 ]
  • C17H14F3NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: C20H22N3O2(1+)*BF4(1-); potassium hexamethylsilazane / toluene / 48 h / 50 °C / Inert atmosphere; Molecular sieve; Sealed tube
  • 23
  • [ 63480-11-5 ]
  • [ 74-88-4 ]
  • [ 1403614-53-8 ]
YieldReaction ConditionsOperation in experiment
91% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; 1,7-dimethyl-2H-3,1-benzoxazine-2,4(1H)-dione To a solution of 4.78 g 7-methyl-2H-3,1-benzoxazine-2,4(1 H)-dione (27 mmol, CAS 63480-11- 5) and 9.4 ml. N,N-diisopropylethylamine (54 mmol) in 45 ml. DMF was added 5.1 mL iodomethane (81 mmol) and was stirred overnight at rt. To the mixture was added ice water (300 ml). The solid that precipitated from this procedure was collected by filtration, washed with water and hexane and dried in vacuum to give 4.92 g of the title compound (95 % purity, 91 % yield).1H NMR (DMSO-d6) d: 7.89 (d, 1 H), 7.29 (s, 1 H), 7.15-7.19 (m, 1 H), 3.45 (s, 3H), 2.46 (s, 3H). LC-MS (Method 1 ): R, = 0.87 min; MS (ESIpos): m/z = 192.1 [M+H]+
91% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; 1,7-dimethyl-2H-3,1-benzoxazine-2,4(1H)-dione To a solution of 4.78 g 7-methyl-2H-3,1-benzoxazine-2,4(1H)-dione (27 mmol, CAS 63480-11-5) and 9.4 ml. N,N-diisopropylethylamine (54 mmol) in 45 ml. DMF was added 5.1 mL iodomethane (81 mmol) and was stirred overnight at rt. To the mixture was added ice water (300 ml). The solid that precipitated from this procedure was collected by filtration, washed with water and hexane and dried in vacuum to give 4.92 g of the title compound (95 % purity, 91 % yield). 1H NMR (DMSO-de) d: 7.89 (d, 1H), 7.29 (s, 1H), 7.15-7.19 (m, 1H), 3.45 (s, 3H), 2.46 (s, 3H). LC-MS (Method 1): R, = 0.87 min; MS (ESIpos): m/z = 192.1 [M+H]+
56% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;
Stage #1: 4-methylisatoic anhydride With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: iodomethane In N,N-dimethyl-d<SUB>6</SUB>-formamide at 0℃; 4.1.1. Synthetic procedure for 2 General procedure: To a solution of different 2-aminobenzoic acid (5.0 mmol) in 20 mLanhydrous tetrahydrofuran (THF) was added triphosgene (BTC, 0.445 g,1.67 mmol) in batches. The reaction mixture was stirred at room temperaturefor 6 h and then poured into ice water. The resulting solid werefiltrated to obtain compounds 1, which were dissolved in 10 mL ofanhydrous N,N-dimethyl formamide (DMF), and then sodium hydride(NaH, 0.096 g, 4.0 mmol) was added in batches at 0. The reactionmixture was stirred at 0 for 30 min, and then methyl iodide (CH3I,0.469 g, 3.3 mmol) was added dropwise. The reaction was detected byTLC. After completion, the reaction mixture was poured into the icewater. The resulting solid were filtrated to obtain compounds 2.

  • 24
  • [ 63480-11-5 ]
  • [ 39549-79-6 ]
YieldReaction ConditionsOperation in experiment
With ammonium carbonate; In 1,4-dioxane; at 60℃; for 8h; General procedure: A suspension of substituted isatoic anhydride (35 mmol), ammonium carbonate (140 mmol), and 1,4-dioxane (150 mL) was heated at 60 C. After stirring for 8 h, the reaction mixture was cooled to room temperature and evaporated under reduced pressure, and then water (200 mL) was added to the residue, which was extracted with CH2Cl2 (380 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to give compounds 9 in yields of 63-94%.
  • 25
  • [ 63480-11-5 ]
  • 7-methylbenzo[d][1,2,3]triazin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: ammonium carbonate / 1,4-dioxane / 8 h / 60 °C 2.1: hydrogenchloride / water / 0.33 h / 0 °C 2.2: 2.67 h / 0 °C 2.3: 0.25 h / pH 8
  • 26
  • [ 63480-11-5 ]
  • C11H12BrN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ammonium carbonate / 1,4-dioxane / 8 h / 60 °C 2.1: hydrogenchloride / water / 0.33 h / 0 °C 2.2: 2.67 h / 0 °C 2.3: 0.25 h / pH 8 3.1: potassium carbonate / acetone / Reflux
  • 27
  • [ 63480-11-5 ]
  • [ 6638-79-5 ]
  • 2-amino-N-methoxy-N,4-dimethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In ethanol; water at 20℃; for 0.333333h; Stage #2: 7-methyl-2H-3,1-benzoxazine-2,4(1H)-dione In ethanol; water for 3h; Reflux; Step 5: General procedure: To a solution of N,O-dimethylhydroxylamine hydrochloride (2 equivalent) in 90%aqueous ethanol was added triethlyamine (2 equivalent) and after 20 min of stirring atroom temperature isatonic anhydride S-6 (1 equivalent) in several portions was addedinto the reaction mixture. After that, this solution was reflux for 3 h. When thereaction was complete as determined by TLC, the reaction was stopped by pouredonto an equivual volume of ice and saturated aqueous Na2CO3 and stir with a glassrod. The separated solid was filtered through a Buchner funnel. Then ethanol wasremoved under reduce pressure and the resulting aqueous mixture was extracted withEtOAc three times and the combined organic extracts were washed with brine, driedover anhydrous Na2SO4, and concentrated in vacuo. The crude was purified bycolumn chromatography (PE/EA = 2:1) on silicagel to give S-7.
  • 28
  • [ 63480-11-5 ]
  • (2-amino-4-methylphenyl)(2-(4-(trifluoromethyl)phenethyl)phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / ethanol; water / 0.33 h / 20 °C 1.2: 3 h / Reflux 2.1: tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: 3.5 h / -78 °C / Schlenk technique; Inert atmosphere
  • 29
  • [ 63480-11-5 ]
  • 1-(2,7-dimethyl-4-(2-(4-(trifluoromethyl)phenethyl)phenyl)quinolin-3-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / ethanol; water / 0.33 h / 20 °C 1.2: 3 h / Reflux 2.1: tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: 3.5 h / -78 °C / Schlenk technique; Inert atmosphere 3.1: (R)-TRIP / benzonitrile / 20 h / 20 - 120 °C / Molecular sieve; Schlenk technique
  • 30
  • [ 123-39-7 ]
  • [ 63480-11-5 ]
  • [ 100-52-7 ]
  • 3,7-dimethyl-2-phenylquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With Trimethylacetic acid at 130℃; for 12h; Schlenk technique; 6 This example is an embodiment of the method for synthesizing quinazolinone derivatives of the present invention.The synthesis method of quinazolinone derivatives in this embodiment includes the following steps:0.25 mmol of 4-methyl-isatoic anhydride in the schlenk tube,0.375 mmol benzaldehyde,60 mg pivalic acid and 1 ml N-methylformamide,After stirring and reacting at 130°C and air for 12 hours,Stop heating and stirring, cool to room temperature,The solvent was removed by rotary evaporation under reduced pressure, and then separated and purified by column chromatography.The target product is obtained, and the stationary phase of column chromatography is silica gel,The eluent is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether: ethyl acetate = 6:1, v/v),The target product yield is 85%.
85% at 120℃; for 12h; Sealed tube; Typical experimental procedure for the synthesis of 4a General procedure: The mixture of isatoic anhydride 1a (41 mg, 0.25 mmol), benzaldehyde 2a (40 mg, 0.375 mmol), p-TSA/C (12 wt %, 90 mg, 25 mol % based on p-TSA content), and N-methylformamide 3a (1 mL) were added successively to a Schlenk tube (50 mL) equipped with a magnetic stirrer bar, the Schlenk tube was then closed and the resulting reaction mixture was heated at 120 °C for 12 h under air atmosphere. After cooling to room temperature, the reaction mixture was filtrated and then concentrated under vacuum. The residue was directly purified by preparative TLC on silica, eluting with petroleum ether (60-90°C): ethyl acetate (6:1) to give 3-methyl-2-phenylquinazolin-4(3H)-one (4a) as a white solid (52 mg, 89%).
  • 31
  • [ 63480-11-5 ]
  • [ 104-94-9 ]
  • C15H16N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In water at 80℃; for 8h; Large scale; 11 Under electromagnetic stirring, add 2k (2170mg, 12.25mmol) to a 250mL round bottom flask, and then add p-anisidine (1507mg, 12.25mmol),Finally, water (80 mL) was added. After reacting for 8h in an oil bath at 80°C, a gray solid precipitated.After suction filtration and drying, 2350 mg of gray solid of compound 3k was obtained (yield 75%).
  • 32
  • [ 63480-11-5 ]
  • C17H12N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: water / 8 h / 80 °C / Large scale 2.1: toluene-4-sulfonic acid; magnesium sulfate / tetrahydrofuran / 3 h / 20 °C / Large scale 2.2: 0.5 h / 0 °C / Large scale 3.1: silver nitrate / water; acetone / 4 h / 20 °C / Darkness 4.1: palladium diacetate; boron trifluoride diethyl etherate / chloroform / 2 h / 60 °C
  • 33
  • [ 63480-11-5 ]
  • C21H22N2O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: water / 8 h / 80 °C / Large scale 2.1: toluene-4-sulfonic acid; magnesium sulfate / tetrahydrofuran / 3 h / 20 °C / Large scale 2.2: 0.5 h / 0 °C / Large scale
  • 34
  • [ 63480-11-5 ]
  • C18H14N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: water / 8 h / 80 °C / Large scale 2.1: toluene-4-sulfonic acid; magnesium sulfate / tetrahydrofuran / 3 h / 20 °C / Large scale 2.2: 0.5 h / 0 °C / Large scale 3.1: silver nitrate / water; acetone / 4 h / 20 °C / Darkness
  • 35
  • [ 63480-11-5 ]
  • [ 627-45-2 ]
  • [ 104-87-0 ]
  • 3-ethyl-7-methyl-2-(p-tolyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% at 120℃; for 12h; Sealed tube; Typical experimental procedure for the synthesis of 4a General procedure: The mixture of isatoic anhydride 1a (41 mg, 0.25 mmol), benzaldehyde 2a (40 mg, 0.375 mmol), p-TSA/C (12 wt %, 90 mg, 25 mol % based on p-TSA content), and N-methylformamide 3a (1 mL) were added successively to a Schlenk tube (50 mL) equipped with a magnetic stirrer bar, the Schlenk tube was then closed and the resulting reaction mixture was heated at 120 °C for 12 h under air atmosphere. After cooling to room temperature, the reaction mixture was filtrated and then concentrated under vacuum. The residue was directly purified by preparative TLC on silica, eluting with petroleum ether (60-90°C): ethyl acetate (6:1) to give 3-methyl-2-phenylquinazolin-4(3H)-one (4a) as a white solid (52 mg, 89%).
  • 36
  • [ 63480-11-5 ]
  • [ 627-45-2 ]
  • [ 104-88-1 ]
  • 2-(4-chlorophenyl)-3-ethyl-7-methylquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% at 120℃; for 12h; Sealed tube; Typical experimental procedure for the synthesis of 4a General procedure: The mixture of isatoic anhydride 1a (41 mg, 0.25 mmol), benzaldehyde 2a (40 mg, 0.375 mmol), p-TSA/C (12 wt %, 90 mg, 25 mol % based on p-TSA content), and N-methylformamide 3a (1 mL) were added successively to a Schlenk tube (50 mL) equipped with a magnetic stirrer bar, the Schlenk tube was then closed and the resulting reaction mixture was heated at 120 °C for 12 h under air atmosphere. After cooling to room temperature, the reaction mixture was filtrated and then concentrated under vacuum. The residue was directly purified by preparative TLC on silica, eluting with petroleum ether (60-90°C): ethyl acetate (6:1) to give 3-methyl-2-phenylquinazolin-4(3H)-one (4a) as a white solid (52 mg, 89%).
  • 37
  • [ 500-22-1 ]
  • [ 63480-11-5 ]
  • [ 627-45-2 ]
  • 3-ethyl-7-methyl-2-(pyridin-3-yl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% at 120℃; for 12h; Sealed tube; Typical experimental procedure for the synthesis of 4a General procedure: The mixture of isatoic anhydride 1a (41 mg, 0.25 mmol), benzaldehyde 2a (40 mg, 0.375 mmol), p-TSA/C (12 wt %, 90 mg, 25 mol % based on p-TSA content), and N-methylformamide 3a (1 mL) were added successively to a Schlenk tube (50 mL) equipped with a magnetic stirrer bar, the Schlenk tube was then closed and the resulting reaction mixture was heated at 120 °C for 12 h under air atmosphere. After cooling to room temperature, the reaction mixture was filtrated and then concentrated under vacuum. The residue was directly purified by preparative TLC on silica, eluting with petroleum ether (60-90°C): ethyl acetate (6:1) to give 3-methyl-2-phenylquinazolin-4(3H)-one (4a) as a white solid (52 mg, 89%).
  • 38
  • [ 63480-11-5 ]
  • 4-[4-(1,3-benzoxazol-2-yl)-4-methylpiperidin-1-yl]-1,7-dimethyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: triethylamine / 2-methyltetrahydrofuran / 113 h / 80 °C 3: trichlorophosphate / 90 °C 4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 90 °C
  • 39
  • [ 63480-11-5 ]
  • 4-[4-(1,3-benzoxazol-2-yl)piperidin-1-yl]-1,7-dimethyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: triethylamine / 2-methyltetrahydrofuran / 113 h / 80 °C 3: trichlorophosphate / 90 °C 4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 90 °C
  • 40
  • [ 63480-11-5 ]
  • 1,7-dimethyl-4-[4-methyl-4-(5-methyl-1,3-benzoxazol-2-yl)piperidin-1-yl]-2-oxo-1,2-dihydroquinoline-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: triethylamine / 2-methyltetrahydrofuran / 113 h / 80 °C 3: trichlorophosphate / 90 °C 4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 90 °C
  • 41
  • [ 63480-11-5 ]
  • 1,7-dimethyl-4-[4-(5-methyl-1,3-benzoxazol-2-yl)piperidin-1-yl]-2-oxo-1,2-dihydroquinoline-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: triethylamine / 2-methyltetrahydrofuran / 113 h / 80 °C 3: trichlorophosphate / 90 °C 4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 90 °C
  • 42
  • [ 63480-11-5 ]
  • 4-[4-(1,3-benzoxazol-2-yl)-4-methylpiperidin-1-yl]-1,7-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: triethylamine / 2-methyltetrahydrofuran / 113 h / 80 °C 3: trichlorophosphate / 90 °C 4: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 2 h / 90 °C 5: (E)-acetaldoxime; palladium diacetate / ethanol / 4 h / 80 °C
  • 43
  • [ 63480-11-5 ]
  • 4-hydroxy-1,7-dimethyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: triethylamine / 2-methyltetrahydrofuran / 113 h / 80 °C
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: triethylamine / 2-methyltetrahydrofuran / 113 h / 80 °C
  • 44
  • [ 63480-11-5 ]
  • 4-chloro-1,7-dimethyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: triethylamine / 2-methyltetrahydrofuran / 113 h / 80 °C 3: trichlorophosphate / 90 °C
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: triethylamine / 2-methyltetrahydrofuran / 113 h / 80 °C 3: trichlorophosphate / 90 °C
  • 45
  • [ 63480-11-5 ]
  • [ 886-38-4 ]
  • C23H17NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With 1,1,1,3',3',3'-hexafluoro-propanol; sodium carbonate; silver(l) oxide In toluene at 100℃; for 16h; Schlenk technique; Inert atmosphere;
  • 46
  • [ 63480-11-5 ]
  • [ 100-51-6 ]
  • 7-methyl-2-phenylquinazoline-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With ammonium hydroxide; palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate; acetic acid In water at 140℃; for 16h; Sealed tube; Heating;
  • 47
  • [ 63480-11-5 ]
  • [ 74-89-5 ]
  • [ 100-51-6 ]
  • 3,7-dimethyl-2-phenylquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate; acetic acid In water at 140℃; for 16h; Sealed tube; Heating;
  • 48
  • [ 63480-11-5 ]
  • [ 886-38-4 ]
  • (E)-2-(1,2-diphenylvinyl)-7-methyl-4H-benzo[d][1,3]oxazin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With 1,1,1,3',3',3'-hexafluoro-propanol; sodium carbonate; silver(l) oxide In toluene at 100℃; for 16h; Schlenk technique; Inert atmosphere;
  • 49
  • [ 63480-11-5 ]
  • C20H19N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 0 °C 2.1: trifluoroacetic anhydride; 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl acetamide / 6 h / 100 °C / Autoclave
  • 50
  • [ 4427-96-7 ]
  • [ 63480-11-5 ]
  • (6R,15R)-3,12-dimethyl-6,15-divinyl-6,7,15,16-tetrahydrodibenzo[e,l][1,8]dioxa[4,11]diazacyclotetradecine-9,18(5H,14H)-dione [ No CAS ]
  • 3,12-dimethyl-6,15-divinyl-6,7,15,16-tetrahydrodibenzo[e,l][1,8]dioxa[4,11]diazacyclotetradecine-9,18(5H,14H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ClO4(1-)*C56H48IrNO3P(1+); triethylamine In 1,2-dichloro-ethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; Overall yield = 39 percent; Overall yield = 16 mg;
  • 51
  • [ 4894-26-2 ]
  • [ 63480-11-5 ]
  • C19H17N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 20℃;
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