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CAS No. : | 3400-22-4 | MDL No. : | MFCD00522600 |
Formula : | C9H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SIOAPROKUUGJAQ-UHFFFAOYSA-N |
M.W : | 165.19 g/mol | Pubchem ID : | 346031 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 45.93 |
TPSA : | 38.33 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.6 cm/s |
Log Po/w (iLOGP) : | 1.91 |
Log Po/w (XLOGP3) : | 1.0 |
Log Po/w (WLOGP) : | 1.05 |
Log Po/w (MLOGP) : | 1.23 |
Log Po/w (SILICOS-IT) : | 1.38 |
Consensus Log Po/w : | 1.31 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.67 |
Solubility : | 3.56 mg/ml ; 0.0216 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.39 |
Solubility : | 6.67 mg/ml ; 0.0404 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.9 |
Solubility : | 0.206 mg/ml ; 0.00125 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
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: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; water; at 0 - 20℃; for 1h; | General procedure: Triethylamine (15 mmol), 33.3% methylamine in water (20 mmol) were added tothe solution of acid chloride (10 mmol) in CH2Cl2 (20 mL) at 0C. The reactionmixture was stirred at room temperature for 1 h and monitored by TLC until thereaction was completed. Then water (50 mL) was added to the mixture and extractedwith CH2Cl2 (30 mL). The organic phase was dried over anhydrous Na2SO4 andconcentrated under reduced pressure. The residue can be purified by silica gel flashchromatography or recrystallization, and the corresponding benzamide products canbe obtained with a yield of 80-95%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.9 g (76%) | With thionyl chloride; | EXAMPLE I N-Methyl 4-Methoxybenzimidoyl Chloride N-Methyl 4-methoxybenzamide (13.95 g, 84.5 mmole) was placed in a 50 ml round bottom flask equipped with magnetic stirrer, heating mantle, condenser and base trap. Thionyl chloride (33 g, 278 mmole) was added. The reaction was stirred and heated at reflux until gas evolution ceased (three hours). The excess thionyl chloride was distilled at ca. 15 mm Hg, and the product distilled at 75-80 C. (0.1 mm Hg) to yield 11.9 g (76%) of the title compound as a clear colorless liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-methoxy-N-methylbenzamide With n-butyllithium In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; Stage #2: cresyl-glicidyl ether In tetrahydrofuran; diethyl ether at -15 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
a. 4-Methoxy-N-methylbenzamide. Using a procedure similar to that described in Example 28 sub-part a, except replacing 2-methoxybenzoyl chloride with 4-methoxybenzoyl chloride (10 g) the amide was prepared (7.22 g) as a solid: mp 111-113 C.; MS: m/z=166; NMR(CDCl3): 3.0 (d, J=4.9, 3), 3.84 (s,3), 6.90 (m,2), 7.74 (m,2). | ||
With dimethyl amine; In dichloromethane; | EXAMPLE 1 4-Methoxy-N-methyl-benzamide (8) An addition funnel containing p-anisoyl chloride (47.6 g, 279 mmol) and methylene chloride (125 mL) was attached to a 2L 3-neck round bottom flask containing 375 mL methylene chloride. The reaction flask was cooled in an ice bath and methylamine (g) was bubbled through the solvent. The contents of the addition funnel were added dropwise. A white precipitate appeared. Warmed to room temperature and stirred for 24 h. Washed with water; separated layers and dried the organic portion with sodium sulfate (anh.). Removal of the solvent in vacuo followed by trituration with hexane/ether gave 8 as a white solid (33.7 g, 204 mmol, 73.2%) 1H-NMR (CHCl3, 300 MHz) δ 7.80 (d, 2H); 6.95 (d, 2H); 6.10 (s, br, 1H); 3.85 (s, 3H), 3.00 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sec.-butyllithium; benzaldehyde; In tetrahydrofuran; toluene; | EXAMPLE 3 5-Methoxy-3-phenyl-3H-isobenzofuran-1-one (9) A solution of 8 (15 g, 91 mmol) in THF was cooled to -70 C. under Argon. To this was added sec-butyllithium (147 mL, 1.3M). After stirring 0.5 h a tan suspension resulted. Added benzaldehyde (9.2 mL, 91 mmol.) and stirred 1 h. Quenched with ice then removed TiF in vacuo. Added sat. sodium bicarbonate and extracted with ethyl acetate (4*). Dried the combined organic portions with sodium sulfate (anh.) and removed the solvent in vacuo. Added toluene and heated to reflux for 1 h. Removal of the solvent in vacuo followed by trituration with hexane/ether gave unreacted starting material 8 (4.63 g). Concentration of the filtrate in vacuo followed by flash column chromatography (hexane:ethyl acetate 80:20) gave 9 as a yellow solid (12.0 g, 50.1 mmol, 55.1%) 1H-NMR(CHCl3, 300MHz) δ 7.90 (d, 1H); 7.40-7.20 (m, 4H); 7.05 (d, 1H); 6.75 (s, 1H), 6.30 (s, 1H); 3.82 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium metal trapped in the nanoscale pores of silica gel; In tetrahydrofuran; at 20℃; for 2h;Glovebox; Sealed tube; Inert atmosphere; | General procedure: In a helium-filled glove box, the desired number ofequivalents of Na-AG or Na-SG were added to a round bottom flask, along with aglass-coated stir bar, and the flask sealed with a septum. This closed systemwas then taken out of the glove box, continuously purged with nitrogen, followedby injection of the pure synthesized Weinreb amide dissolved in THF. The resulting mixture was stirred for thetime specified. After completion of the reaction, the mixture was then partitioned using ethyl acetate and brine. The organic layer was concentrated under reducedpressure using a rotary evaporator. 1H NMR of the crude product wastaken to check for reaction extent/completion and to identify the productsobtained. Crude product was fractionated and purified by columnchromatography on silica gel to afford the desired product and byproducts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sodium iodide dihydrate; palladium 10% on activated carbon; potassium acetate; caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 36h;Schlenk technique; | General procedure: A mixture of a substituted benzamide (1) (0.3 mmol, 1.0 equiv),an alkyne (2) (0.6 mmol or 0.9 mmol, 2.0 equiv or 3.0 equiv),10% Pd/C (0.03 mmol, 10 mol%, Alfa Aesar, No. 044696, eggshell,reduced), NaI·2H2O (0.6 mmol, 2.0 equiv), Cs2CO3 (0.3 mmol, 1.0equiv), and KOAc (0.6 mmol, 2.0 equiv) was weighted in a Schlenktube equipped with a stir bar. DMF (1.0 mL) was added and themixture was stirred at 120 C for 36 h under air. Afterwards, themixture was filtered and washed with H2O (30 mL) and extractedwith CH2Cl2 (3×30 mL). The combined organic phase was driedwith anhydrous Na2SO4. After removal of solvents under reducedpressure, the residue was absorbed to small amounts of silica. Thepurification was performed by flash column chromatography onsilica gel with EA:PE (Petroleum ether) = 1:5 or 1:10 as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In tert-Amyl alcohol at 100℃; for 22h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine; In dichloromethane; at 35℃; | General procedure: Methacryloyl chloride (2 equiv.) was added to a mixture of amide (1 equiv.), triethylamine (2 equiv.) and DMAP (0.1 equiv.) in dichloromethane (20 mL). The resulted mixture was stirred at 35 oC for 10-12 h. The reaction was quenched with saturated aqueous Na2CO3 (5 mL), and then the mixture was extracted with dichloromethane (3 x 5 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate as the eluent) affording the corresponding N-alkyl-N-methacryloyl benzamides 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dmap; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 0.333333h;Sealed tube; Microwave irradiation; | General procedure: To a dry microwave vial, aryl halide (Br, I) (1 eqv.) and amine (2eqv.) were taken in dry 1,4-dioxane. 5 mol% of Pd(OAc)2, 5 mol% ofXantphos and DMAP (2 eqv.) were added followed by (0.25 or 0.3) equivalents ofCo2(CO)8 and the vial was sealed immediately andmicrowave irradiated for 20 min. The reactionmixture was concentrated under reduced pressure, diluted with ethyl acetate andwater, the ethyl acetate layer separated, dried over sodium sulphate, andconcentrated. Thecrude products obtained were subjected to purification by flash chromatographyon silica gel coloumn eluting with petroleum ether and ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: Compounds 2were prepared according to modified known procedure.3 To theappropriate amide (12.5 mmol) stirred in THF (75 mL) at -78 C under argon was added BuLi (27.5 mmol). The solution was held at -78 C for 0.5 h, then allowed to warm to 0 C and kept at 0 C for 6 min. The mixture was cooled to -78 C and DMF (1.280 g, 17.5 mmol) was added. The reaction mixture after 0.5 h at -78 C was warmed to room temperature and kept for 1 h. Then water (15 mL) was added. The mixture was adjusted to pH 2 with hydrochloric acid (2.0 M solution in water) and the organic layer was separated. The water layer was extracted with CHCl3/THF mixture 1:1 (3x15 mL). The combined organic solutions were dried with magnesium sulfate(VI) and evaporated to give the crude products 2. The compounds 2 were purified by crystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12%; 66% | With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; zinc dibromide; In acetonitrile; at 80℃; for 16h; | General procedure: Under air, in a 50 mL tube, ZnBr2 (20 mol %), TBAI(10 mol%), and a stirring bar was added. Then toluene (10 mmol), DMF (1 mmol), MeCN(2 mL) and TBHP (6 mmol) were injected by syringe. Then close the tube and keepthe final solution at 80 oC for 16 h. When the reaction wasfinished, the solvent was removed in vacuo, and the residue was purified byflash column (petroleum ether/ethyl acetate). All the products are commerciallyavailable. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dmap; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 0.333333h;Microwave irradiation; | General procedure: To a dry microwave vial, aryl halide (Br, I) (1 eqv.) and amine (2 eqv.)were taken in dry 1,4-dioxane. 5 mol% of Pd(OAc)2, 5 mol% ofXantphos and DMAP (2 eqv.) were added followed by (0.25 or 0.3) equivalents ofCo2(CO)8 and the vial was sealed immediately andmicrowave irradiated for 20 min. The reaction mixture was concentrated under reducedpressure, diluted with ethyl acetate and water, the ethyl acetate layerseparated, dried over sodium sulphate, and concentrated. The crude products obtained were subjected topurification by flash chromatography on silica gel coloumn eluting withpetroleum ether and ethyl acetate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; silver(I) acetate; In 1,2-dichloro-ethane; at 60℃; for 13h;Inert atmosphere; | General procedure: To a dried screw-capped vial were added benzamide 2 (0.10mmol), ethyl acrylate 3 (0.15mmol), 1b (4.8mg, 0.01mmol), AgSbF6 (6.8mg, 0.02mmol), AgOAc (41.7mg, 0.25mmol), and 1,2-dichloroethane (1.0mL) under Ar atmosphere. The vial was capped and the mixture was heated at 60C for 13h with stirring. After the mixture was cooled to room temperature, saturated EDTA·2Na aqwas added following dilution with CH2Cl2. Organic layer was separated and aqueous layer was extracted with CH2Cl2 (×2). Combined organic layers were dried over Na2SO4. After filtration and evaporation, obtained crude mixture was purified by silica gel column chromatography (CH2Cl2/EtOAc) to give product3.4.1.1 _4.1.3 (E)-Ethyl 3-(5-methoxy-2-(methylcarbamoyl)phenyl)acrylate (4c) A colorless solid; IR (KBr) ν 2985, 2942, 1715, 16,641, 1625, 1546, 1314, 1293, 1228, 1182, 1034, 974, 862 cm-1; 1H NMR (CDCl3, 400 MHz) δ 1.32 (t, J=7.3 Hz, 3H), 2.98 (d, J=5.0 Hz, 3H), 3.83 (s, 3H), 4.24 (q, J=7.3 Hz, 2H), 5.88 (br s, 1H), 6.33 (d, J=16.7 Hz, 1H), 6.89 (dd, J=2.3, 8.7 Hz, 1H), 7.06 (d, J=2.3 Hz, 1H), 7.43 (d, J=8.7 Hz, 1s), 8.02 (d, J=16.5 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 14.4, 27.1, 55.6, 60.8, 112.2, 115.4, 121.1, 129.5, 129.7, 135.0, 142.3, 161.0, 166.6, 169.2; HRMS (ESI): m/z calculated for [M+Na]+: 286.1050, found: 286.1054. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With tert.-butylhydroperoxide; iron(III) chloride; tetra-(n-butyl)ammonium iodide; In water; at 60℃; for 24h;Sealed tube; Molecular sieve; Green chemistry; | Add 4-methyl anisole (20 eq) to a clean 10 mL sealed tubeAnd methylamine 40% aqueous solution (0.24mmol),TBHP (70% water) 6 eq as oxidant,30 mol% TBAI and 15 mol% FeCl3 are used as catalysts,100 mg of 4A molecular sieve and 1.5 mL of water.React at 60 oC for 24 hours,TLC dot plate detection, after the reaction, the reaction solution is cooled to room temperature,The reaction solution was extracted with ethyl acetate (3×10 mL),Combine the organic phases and dry with anhydrous Na2SO4,The organic layer is concentrated and column chromatography to obtain pureN-methyl 4-methoxybenzamide, yellow solid, yield 78%. |
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