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CAS No. : | 6331-71-1 | MDL No. : | MFCD00523648 |
Formula : | C9H12N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QEPGWLBMAAEBCP-UHFFFAOYSA-N |
M.W : | 164.20 | Pubchem ID : | 235527 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.74 |
TPSA : | 46.33 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.08 cm/s |
Log Po/w (iLOGP) : | 1.58 |
Log Po/w (XLOGP3) : | 0.31 |
Log Po/w (WLOGP) : | 0.98 |
Log Po/w (MLOGP) : | 1.23 |
Log Po/w (SILICOS-IT) : | 0.55 |
Consensus Log Po/w : | 0.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.29 |
Solubility : | 8.39 mg/ml ; 0.0511 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.85 |
Solubility : | 23.4 mg/ml ; 0.143 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.09 |
Solubility : | 1.34 mg/ml ; 0.00815 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 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: |
* 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 |
---|---|---|
71% | With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran at 5℃; | To a 500 ml three-mouth bottle by adding 200 ml of THF, cooling to 5 °C the following add 17.3g (0.46mol, 4 . 0eq) of lithium aluminum hydride, then lower the temperature to the -5 ° C the following, the three aluminum chloride 3.0g (0.023mol, 0 . 2eq) THF slowly dropwise to the reaction in the solution, stirring for 10 min, temperature at 5 °C the following starting to drop plus step amide 19.0g (0.114mol, 1 . 0eq) in 100 ml of solution THF. Added after stirring overnight TLC inspection reaction end, cooling to 0 °C the following, starting the dropping water filtration, the filter cake is washed with dichloromethane eluviation, concentrated filtrate, vacuum distillation, to obtain colorless oily liquid 12.0g product. Yield: 71.0percent, GC: 99.9percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | for 3.16667 h; Inert atmosphere | Step 2: 4-Amino-N, V-dimethyl-benzamideTo a solution of N, N-dimethyl-4-nitro benzamide (23 g, 0.1185 mol) in MeOH (200 mL) was added Pd/C 10percent> (2.3 g) in portions and the Parr reaction vessel was purged with nitrogen for 10 min. The reaction vessel was fixed in Parr shaker at 60 psi pressure for 3 h. The reaction mixture was filtered through the Celite.(R). pad and the filtrate was concentrated under reduced pressure to afford the title compound [18.0 g, 93percent]; LC-MS (ESI): Calculated mass: 164.1; Observed mass: 165.2 [M+H]+ (RT: 0.17 min). |
65% | With palladium 10% on activated carbon; hydrogen In ethyl acetateInert atmosphere | A solution of N,N-dimethyl-4-nitrobenzamide (2.0 g, 10 mmol) in EtOAc (20 mL)was added to a flask containing 10percent Pd/C under a nitrogen atmosphere. Thereaction was placed under a hydrogen atmosphere, where it was shaken overnight. The reaction mixture was diluted with methanol (10 mL) filtered through a pad of Celite (pre-washed with EtOAc) then eluted with further EtOAc. The combined filtrate solvents were removed in vacuo to afford a light yellowsolid (1.69 g, 65percent).LC/MS (method A): RT = 0.41 mm; m/z= 165 [M+H]. Total run time 3.75 mins. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 3 h; Stage #2: With sodium carbonate In water |
The title compound from Step B above (0.46 g, 1.75 mmol) was dissolved in dichloromethane (2.2 mL) and treated with a 4 M solution of hydrochloric acid in 1,4-dioxane (2.2 mL, 8.8 mmol). The mixture was stirred at room temperature for 3 h and diluted with ethyl acetate (20 mL). Saturated aqueous sodium carbonate was then added until pH10. The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethyl acetate to afford the title compound as an off-white solid (0.16 g, 55percent).1H-NMR (400 MHz, CDCl3): δ=3.04 (s, 6H), 3.80 (br-s, 2H), 6.67 (m, 2H), 7.31 (m, 2H) |
615 mg | With hydrogenchloride In ethyl acetate at 20℃; for 5 h; | To a solution of tert-butyl 4-(dimethylcarbamoyl)phenylcarbamate (Int. 73) (1.11 g, 4.21 mmol) in AcOEt (20 ml), HCl 4M in AcOEt (18 ml, 76 mmol) was added, and the mixture stirred for 5 hours at RT. The pH was adjusted at 6/7 by adding NaHCO3 sat. sol. and aqueous phase was extracted with AcOEt (*3). Organic phase was dried over Na2SO4 and evaporated under reduced pressure to give mg 615 of the title product (Int. 74). |
615 mg | With hydrogenchloride In ethyl acetate at 20℃; for 5 h; | Step 2: Synthesis of 4-amino-N,N-dimethylbenzamide (Intermediate 74) To a solution of tert-butyl 4-(dimethylcarbamoyl)phenylcarbamate (Int. 73X1.1 1 g, 4.21 mmol) in AcOEt (20 ml), HC1 4M in AcOEt (18 ml, 76 mmol) was added and the mixture stirred for 5hrs at RT. The pH was adjusted at 6/7 by adding NaHCO3 sat. sol. and aqueous phase was extracted with AcOEt (x3). Organic phase was dried over Na2SO4 and evaporated under reduced pressure to give mg 615 of the title product (Int. 74). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: With triethylamine In dichloromethane at 10℃; for 0.166667 h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; |
To a 500 ml three-mouth bottle by adding 200 ml of methylene chloride, will be under stirring 25.0g (0.18mol, 1 . 0eq) of the P-aminobenzoic acid in reaction adds the human, cooling to 10 °C the following, then adding dimethylamine hydrochloride 17.8g (0.21mol, 1 . 2eq), triethylamine 36.1g (0.36mol, 2 . 0eq), stirring 10 min later, is added in batches EDCI40.0g (0.21mol, 1 . 2eq), after stirring at room temperature for overnight. TLC detection reaction end, in the poured into a saturated sodium bicarbonate aqueous solution, ethyl acetate extraction, combined with the phase, wash once salt water, organic phase with sodium sulfate drying, filtering, turned to the raped drying Canada petroleum ether filtration, the white solid obtained product 19.0 g. Yield: 65.0percent, MP (°C) 151.0-153.0 °C, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper(l) iodide; lithium chloride In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere | General procedure: Inan oven-dried 250 mL round-bottomed flask equipped with a stir bar was added 6.54 g of active zinc (Zn, 100.0 mmol) in 100 mL of THF. The flask was then cooled down to 0 C using an ice-bath. Next, 4-iodoaniline (10.9 g,50.0 mmol) solution dissolved in 40.0 mL of THF was can nulated into the flask at 0 C. The resulting mixture was allowed to warm up to room temperature and stirred at ambient temperature for 24 h. The whole mixture was settleddown and then the supernatant was used for the subsequent coupling reactions. (b) Cross-coupling reaction of A; Into a 25 mL round-bottomed flask was placed 4-aminophenylzinc iodide (4.0 mL, 0.25 M in THF, 1.0 mmol)under argon atmosphere, then the flask was cooled down to 0 C using an icebath. Next, 4-methoxybenzoyl chloride (0.13 g, 0.8 mmol) was added, then stirred at 0 C for 30 min., quenched with saturated NH4Cl solution, thenextracted with ethyl acetate (3 10 mL). It was washed with saturated NaHCO3, 8percent NH4OH solutions and brine, then dried over anhydrous MgSO4.Purification by recrystallization (hexanes/ethyl ether) afforded 0.13 g of (4-aminophenyl)(4-methoxyphenyl)methanone (1c) |
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