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CAS No. : | 100841-00-7 | MDL No. : | MFCD05053658 |
Formula : | C10H15NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NCGAPYLHHZMWPI-UHFFFAOYSA-N |
M.W : | 181.23 | Pubchem ID : | 3152109 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.75 |
TPSA : | 44.48 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) : | -6.5 cm/s |
Log Po/w (iLOGP) : | 2.36 |
Log Po/w (XLOGP3) : | 1.28 |
Log Po/w (WLOGP) : | 1.42 |
Log Po/w (MLOGP) : | 1.22 |
Log Po/w (SILICOS-IT) : | 1.66 |
Consensus Log Po/w : | 1.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.78 |
Solubility : | 3.0 mg/ml ; 0.0165 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.81 |
Solubility : | 2.78 mg/ml ; 0.0154 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.12 |
Solubility : | 0.137 mg/ml ; 0.000759 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.35 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338-P280 | UN#: | N/A |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
58% | With methylamine In methanol at 20℃; for 4h; | |
With hydrazine hydrate In ethanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate 1.) EtOH, 1.5 h, reflux, 2.) EtOH, ice water, 1 h, room temp.; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In ethanol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine at 65℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: n-butyl (R)-2-(3-formylphenoxy)butyrate; 3-(4-methoxyphenoxy)propan-1-amine In methanol at 20 - 80℃; for 12h; Stage #2: With sodium tetrahydroborate In methanol; water at 20℃; for 0.5h; | 1 3-(4-Methoxyphenoxy)propylamine (34 mg) was dissolved in methanol (3 mL), and a solution (2 mL) of n-butyl (R)-2-(3-formylphenoxy)butyrate (50 mg) in methanol was added thereto under stirring at room temperature. The mixture was further stirred at 80°C for 12 hours. Subsequently, an aqueous solution (0.5 mL) of sodium borohydride (7 mg) was added to the solution at room temperature, and the mixture was stirred for 30 minutes. The reaction solution was concentrated under reduced pressure, and chloroform was added to the concentrated product. The formed organic layer was washed with water. The washed organic layer was dried over sodium sulfate anhydrate, and concentrated under reduced pressure, to thereby yield 81 mg of a pale yellow, oily substance. The entirety of the substance was employed in the following reaction without any further treatment. 1H-NMR (400 MHz, CDCl3) δ ppm: 0.87(t, J=7 Hz, 3H), 1.07(t, J=7 Hz, 3H), 1.29(sextet, J=7 Hz, 2H), 1.60(quintet, J=7 Hz, 2H), 1.91-2.01(m, 5H), 2.79(t, J=7 Hz, 2H), 3.75(s, 3H), 3.76(s, 2H), 3.98(t, J=6 Hz, 2H), 4.00-4.19(m, 2H), 4.56(t, J=6 Hz, 1H), 6.75(dd, J=8.2 Hz, 1H), 6.79-6.85(m, 4H), 6.88-6.95(m, 2H), 7.20(t, J=8 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With borane-THF In tetrahydrofuran at 65℃; for 5h; | |
79% | Stage #1: 2-(4-Methoxyphenoxy)cyanoethane With borane-THF In tetrahydrofuran at 80℃; for 3.16667h; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0 - 80℃; for 12.4h; | |
79% | With sodium hydroxide In tetrahydrofuran; toluene | P.2 Synthesis of 3-(4-methoxyphenoxy)propylamine PREPARATIVE EXAMPLE 2 Synthesis of 3-(4-methoxyphenoxy)propylamine Under an argon atmosphere, 3-(4-methoxyphenoxy)propionitrile (5.0 g) was dissolved in tetrahydrofuran (20 mL), and borane-tetrahydrofuran complex (1.02 mol/L, 30.0 mL) was added dropwise at 80°C for 10 minutes. After stirring for 3 hours at the same temperature, the reaction liquor was returned to room temperature. In an ice-cold bath, a 4 N aqueous sodium hydroxide solution (30 mL) was added for 10 minutes. After 10 minutes, the mixture was stirred at room temperature for 5 minutes, and then stirred at 80°C for 12 hours. The mixture was returned to room temperature, and toluene (100 mL) was added, and the mixture was stirred for 1 hour, and then insoluble material was removed using Celite. An organic layer was isolated, and washed with water (100 mL x 2 times) and saturated brine (100 mL), and then dried over anhydrous sodium sulfate (80 g). The resultant was filtered, and then the filtrate was concentrated under reduced pressure to obtain a white solid (4.0 g, 79.0%). 1H-NMR (400MHz, CD3OD) δ: 2.05 (quintet, J=7Hz, 2H), 3.07(t, J=7Hz, 2H), 3.71(s, 3H), 4.01(t, J=6Hz, 2H), 6.79-6.85(m,4H). |
79% | Stage #1: 2-(4-Methoxyphenoxy)cyanoethane With borane-THF In tetrahydrofuran at 80℃; for 3.16h; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 0 - 80℃; for 12.25h; | 3 In an argon atmosphere, 3-(4-methoxyphenoxy)propionitrile (5.0 g) was dissolved in tetrahydrofuran (20 mL), and a borane-tetrahydrofuran complex (1.02 mol/L, 30.0 mL) was added dropwise to the resultant solution at 80°C over 10 minutes. The mixture was stirred for 3 hours at 80°C. Thereafter, the reaction mixture was cooled to room temperature. Under cooling on ice, 4N aqueous sodium hydroxide solution (30 mL) was added thereto over 10 minutes. Ten minutes after, the mixture was stirred at room temperature for 5 minutes, and further stirred at 80°C for 12 hours. The mixture was cooled to room temperature, and toluene (100 mL) was added thereto, followed by stirring for 1 hour. Subsequently, after removal of insoluble matter through filtration by means of Celite, the organic layer was collected and washed sequentially with water (100 mL × 2) and saturated brine (100 mL), followed by drying over sodium sulfate anhydrate (80 g). After filtration, the filtrate was concentrated under reduced pressure, to thereby yield 4.0 g of a white solid (79.0%). 1H-NMR(400 MHz, CD3OD) δ ppm: 2.05 (quintet, J=7 Hz, 2H), 3.07(t, J=7 Hz, 2H), 3.71(s, 3H), 4.01(t, J=6 Hz, 2H), 6.79-6.85(m, 4H). |
With borane-THF In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multistep reaction.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Triton B / acetonitrile 2: BH3*THF / tetrahydrofuran | ||
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; dimethylformamide / 1 h / 20 °C 1.2: 49 percent / tetrahydrofuran; dimethylformamide / 20 °C 2.1: 58 percent / methylamine / methanol / 4 h / 20 °C | ||
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) Me2SO, 25 deg C, 3 h, 2.) Me2SO, 25 deg C, 72 h 2: hydrazine hydrate / aq. ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2.) NaBH4 / 1.) EtOH, 1.5 h, reflux, 2.) EtOH, ice water, 1 h, room temp. 2: 50 percent / HCOOH / H2O / 1 h / 90 - 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde; 3-(4-methoxyphenoxy)propan-1-amine In 1,2-dichloro-ethane for 0.333333h; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; | 24 Synthesis of N-3-(4-Methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine Production Example 24 Synthesis of N-3-(4-Methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine 3-tert-Butyldimethylsilyloxybenzaldehyde (1.5 g, 6.34 mmol) was dissolved in 1,2-dichloroethane (10.0 mL). Subsequently, 3-(4-methoxyphenoxy)propylamine (1.5 g, 8.25 mmol) was added thereto, and the resultant mixture was stirred for 20 minutes. At room temperature, sodium triacetoxyborohydride (1.75 g, 8.25 mmol) and acetic acid (495 mg, 8.25 mmol) were added thereto, and the mixture was stirred overnight. A saturated aqueous sodium hydrogencarbonate solution was added thereto. The reaction mixture was extracted with chloroform, and the organic layer was washed with brine. The resultant mixture was subjected to drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound was obtained (1.9 g, 78%). 1H-NMR (400 MHz, CDCl3) δ 0.00 (s, 6H), 0.73 (s, 9H), 1.81 (m, 2H), 2.66 (br. s, 2H), 3.58 (s, 3H), 3.61 (s, 2H), 3.81 (t, J=6 Hz, 2H), 6.55 (d, J=7 Hz, 1H), 6.63 (br. s, 5H), 6.73 (d, J=7 Hz, 1H), 6.99 (t, J=7 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.4% | Stage #1: meta-hydroxybenzaldehyde; 3-(4-methoxyphenoxy)propan-1-amine In methanol at 20℃; for 20.1h; Stage #2: With sodium tetrahydroborate; water In methanol at 20℃; for 12.1h; | |
With sodium borohydrid In methanol; water | P.3 Synthesis of N-(3-(4-methoxyphenoxy)propyl)-3-hydroxybenzylamine PREPARATIVE EXAMPLE 3 Synthesis of N-(3-(4-methoxyphenoxy)propyl)-3-hydroxybenzylamine 3-(4-Methoxyphenoxy)propylamine (10.0 g) was dissolved in methanol (50 mL) at room temperature, a solution of 3-hydroxybenzaldehyde (6.7 g) in methanol (50 mL) was added dropwise within 5 minutes at water temperature (about 20°C), and then the resulting mixture was stirred at room temperature for 20 hours. Then, sodium borohydride (2.1 g)/water (100 mL) was added dropwise at water temperature (about 20°C) for 5 minutes, and the mixture was stirred at room temperature for 12 hours. Precipitates were removed, washed with water and then dried under reduced pressure at 80°C for 5 hours. Pale yellow crystals were obtained (13.9 g, 87.4%). 1H-NMR (400MHz, DMSO-d6)δ: 1.82(quintet, J=7Hz, 2H), 2.60(t, J=7Hz, 2H), 3.60(s, 2H), 3.68(s, 3H), 3.95(t, J=7Hz, 2H), 6.60(d, J=8Hz, 1H), 6.73(t,J=8Hz, 1H), 6.74 (s, 1H), 6.83 (s, 4H), 7.07(t, J=8Hz, 1H). Melting point: 142.7°C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3-(4-methoxyphenoxy)propan-1-amine With hydrogenchloride In tetrahydrofuran Stage #2: cyanoguanidine hydrochloride at 20 - 140℃; | 4.1.3. Preparation of 2,N6-disubstituted 1,2-dihydro-1,3,5-triazine-4,6-diamines (16) General procedure: Hydrogen chloride gas was bubbled through a solution of the amine (12) dissolved in THF. The resultant hydrogen chloride salt (13) of the amine was filtered off and completely mixed with dicyandiamide (7, 1.2 eq.) using a spatula. The resultant mixture was slowly heated from ambient temperature until it melted (120 °C). Heating was continued until a temperature of 140 °C was reached. Stirring was continued at this temperature for 60 min during which time a clear homogeneous solution was obtained [35]. The mixture was allowed to cool down to 90 °C (caution being exercised to prevent solidification of the reaction mixture), at which point 1,4-dioxane (3 ml/mmol amine hydrochloride) was added. To this solution of the biguanide salt (14) was added the aldehyde or ketone (10, 5.0 eq.) and one drop of conc. HCl. The resulting reaction mixture was irradiated with microwave energy at 100 W and 85 °C for 30 min with air cooling. The reaction mixture was purified directly by column chromatography using dichloromethane: methanol (95:5), until all the aldehyde/ketone had eluted, and was then further chromatographed with dichloromethane: methanol (80:20) to afford the desired 2,N6-disubstituted 1,2-dihydro-1,3,5-triazine-4,6-diamine hydrochloride (16). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / tetrahydrofuran 1.2: 20 - 140 °C 2.1: hydrogenchloride / 1,4-dioxane; water / 0.5 h / 85 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: 3-bromopropylamine tert-butylcarbamate; 4-methoxy-phenol With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 17h; Inert atmosphere; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile at 20℃; for 14h; Inert atmosphere; Overall yield = 99 %; Overall yield = 4.721 g; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: montmorillonite K-10 / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation 2.1: hydrogenchloride 2.2: 0.5 h / 100 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With montmorillonite K-10 In 1,4-dioxane at 100℃; for 0.5h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanol / 12 h / 20 - 80 °C 1.2: 0.5 h / 20 °C 2.1: triethylamine / acetonitrile / 12 h / 20 - 80 °C 3.1: sodium hydroxide; water / ethanol / 1 h / 20 °C 3.2: pH 1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanol / 12 h / 20 - 80 °C 1.2: 0.5 h / 20 °C 2.1: triethylamine / acetonitrile / 12 h / 20 - 80 °C |
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