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CAS No. : | 122734-32-1 | MDL No. : | MFCD06808585 |
Formula : | C8H18N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GKWGBMHXVRSFRT-UHFFFAOYSA-N |
M.W : | 174.24 | Pubchem ID : | 3435744 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.88 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 47.89 |
TPSA : | 50.36 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) : | -7.01 cm/s |
Log Po/w (iLOGP) : | 2.47 |
Log Po/w (XLOGP3) : | 0.5 |
Log Po/w (WLOGP) : | 0.73 |
Log Po/w (MLOGP) : | 0.63 |
Log Po/w (SILICOS-IT) : | 0.2 |
Consensus Log Po/w : | 0.91 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.84 |
Solubility : | 25.2 mg/ml ; 0.145 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.13 |
Solubility : | 13.0 mg/ml ; 0.0745 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.08 |
Solubility : | 1.46 mg/ml ; 0.00839 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.12 |
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 |
---|---|---|
94% | With hydrogen In methanol; water for 2.5 h; | Preparation 65 Synthesis of tert-butyl 2-(methylamino)ethylcarbamate (C) To a flask was added 20percent Pd(OH)2 on carbon (3.1 g), compound B (3.3 g, 12.5 mmol) in MeOH (200 mL) and water (10 mL), while being exposed to H2 (40 psi). After 2.5 h, the reaction mixture was filtered through celite and concentrated in vacuo. Water was then added (50 mL) and the mixture brought to pH 12 (by addition of 1 N NaOH) and extracted with DCM (3*50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give compound C (2.0 g, 11.7 mmol, 94percent) as a colorless oil. LC-MS [M+H] 686.5 (C35H51N5O7S+H, calc: 685.9). |
94% | Stage #1: With hydrogen In methanol; water for 2.5 h; Stage #2: With sodium hydroxide In methanol; water |
Preparation 65: Synthesis of tert-butyl 2-(methylamino)ethylcarbamate (C)To a flask was added 20percent Pd(OH)2 on carbon (3.1 g), compound B (3.3 g, 12.5 mmol) in MeOH (200 mL) and water (10 mL), while being exposed to 3/4 (40 psi). After 2.5 h, the reaction mixture was filtered through celite and concentrated in vacuo. Water was then added (50 mL) and the mixture brought to pH 12 (by addition of 1 N NaOH) and extracted with DCM (3 x 50 mL). The combined organic layers were dried over MgS04, filtered, and concentrated in vacuo to give compound C (2.0 g, 11.7 mmol, 94percent) as a colorless oil. LC-MS [M+H] 686.5(C35H5iN507S +H, calc: 685.9). Compound C was used without further purification. |
94% | Stage #1: With hydrogen In methanol; water for 2.5 h; Stage #2: With sodium hydroxide In water |
Preparation 65: Synthesis of tert-butyl 2-(methylamino)ethylcarbamate (C)To a flask was added 20percent Pd(OH)2 on carbon (3.1 g), compound B (3.3 g, 12.5 mmol) in MeOH (200 mL) and water (10 mL), while being exposed to 3/4 (40 psi). After 2.5 h, the reaction mixture was filtered through celite and concentrated in vacuo. Water was then added (50 mL) and the mixture brought to pH 12 (by addition of 1 N NaOH) and extracted with DCM (3 x 50 mL). The combined organic layers were dried over MgS04, filtered, and concentrated in vacuo to give compound C (2.0 g, 11.7 mmol, 94percent) as a colorless oil. LC-MS [M+H] 686.5(C35H5iN507S +H, calc: 685.9). Compound C was used without further purification. |
94% | With 20% palladium hydroxide-activated charcoal; hydrogen In methanol; water for 2.5 h; | In a flask,20percent Pd (OH) 2 on carbon (3.1 g)MeOH (200 mL)Compound B (3.3 g, 12.5 mmol)And water (10 mL) were added while exposing to H 2 (40 psi). After 2.5 h, the reaction mixture was filtered through celite and concentrated under reduced pressure. Water was then added (50 mL) and the pH of the mixture was brought to 12 (by adding 1 N NaOH) and extracted with DCM (3 × 50 mL). CombinedThe organic layer was dried over MgSO 4, filtered and concentrated under reduced pressure to give compound C (2.0 g, 11.7 mmol, 94percent) as a colorless oil. |
68.3% | With hydrogen In methanol at 20℃; for 16 h; | A mixture of tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate (1.20 g, 4.54 mmol), 10percent Pd/C (0.90 g) and MeOH (60 ml) was stirred under a H2 atmosphere (0.8 MPa, RT, 16 h). The mixture was filtered and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel, eluding with saturated NH3 in MeOH-DCM (0-10percent) to afford tert-butyl 2-(methylamino)ethylcarbamate as a colorless oil (0.54 g, 68.3percent). 1H-NMR (CDCl3): δ3.25 (m, 2H, CH2), 2.7 (m, 2H, CH2), 2.49 (s, 3H, CH3), 1.49 (s, 9H, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.3 g | With potassium iodide In ethanol at 50℃; for 5 h; | Synthesis of tert-butyl 2-(methylainino)ethylcarbamate To a solution of tert-butyl 2-bromoethylcarbamate (9 g, 40.3 mmol) and methylamine (41.7 g, 403 rnrnol, 30percent in EtOll) in EtOll (80 mL) was added KI (140mg, 0.8 mmol). The mixture was heated to 50°C with stirring for 5 hours and then concentrated under reduce pressure, the residue was poured into water and extracted with EtOAc (3* 8OrnL). The organic phase was dried over Na2SO4, filtered and removal of solvent to give 4.3 g oil (used for next step without purification).LC-MS: CP-0007023-128: (ES, nz/z): 175 [M+ H1 |
0.67g | With potassium iodide In ethanol at 50℃; | To a solution of di-tert-butyl dicarbonate (4.80g, 22.0mmol) in dry CH2Cl2 (25mL) was added 2-bromoethylamine hydrobromide 14 (5.00g, 24.4mmol) at 0°C under argon, triethylamine (5mL, 33.0mmol) was slowly added dropwise to the flask, slowly warmed to room temperature and stirred overnight. The reaction solution was washed with saturated NH4Cl (30mL), saturated NaHCO3 (30mL) and saturated NaCl (30mL), dried over anhydrous Na2SO4. The organic phase was filtered and the solvent was removed under reduced pressure to give product without further purification. The crude product (1.0g, 4.5mmol) was dissolved in EtOH (15mL), and then methylamine (1.0g, 33percentwt., 10.2mmol) and KI (0.017g, 0.1mmol) were added. The reaction solution was stirred at 50°C until it is completed. The reaction solution was quenched with H2O (20 mL), and extracted with CH2Cl2 (40mL x 2), and the combined organic layers dried with Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel using CH3OH/CH2Cl2 (1/20, V/V) as eluent to give 9 as colorless oil (0.67g, 84percent); 1H NMR (400MHz, CDCl3) δ 5.83 (br, 1H, NH),3.57 (q, 2H, J = 5.45Hz, CH2), 3.48 (s, 1H, NH), 3.19 (t, 2H, J = 5.79Hz, CH2), 2.76 (s, 3H, CH3), 1.44 (s, 9H, (CH3)3); HRMS (ESI) m/z [M+H]+ Calcd for C8H19N2O2+: 175.1447. Found: 175.1443. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17.8% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 20 h; | To a solution of N-methylethylenediamine 1 (10.0 g, 135 mmol, 1.0 eq.) in anhydrous THF (70 mL), triethylamine (37.6 ml, 270 mmol, 2.0 eq.) was added under Ar atmosphere at room temperature. A solution of di-t-butyl dicarbonate (32.5 g, 148 mmol, 1.1 eq.) in anhydrous THF (250 mL) was added dropwise at 0°C from a dropping funnel for 30 minutes, and the resulting mixture was stirred at 0°C for 30 minutes and then at room temperature for 19 hours. The reaction mixture was filtered and the solvent was evaporated under vacuum, followed by purification of the residue by column chromatography (SiO2, chloroform: methanol: 30:1, v/v --> chloroform: methanol: triethylamine = 150:10:3, v/v) to obtain a yellow oily product (yield: 17.8percent) 1H-NMR (300 MHz; CDCl3, r.t., TMS, d/ppm) 1.33 (s, 9 H, -C(CH3)3), 2.76 (t, 2 H, J = 6.4 Hz, -CH2CH2NHCH3), 2.86 (s, 3 H, -NHCH3), 3.21 (t, 2 H, J = 6.1 Hz, - CONHCH2CH2-). ESI-TOFMS (+), m/z: 175.14[M+H]+ (calcd.. for C8H19N2O2+ 175.14) TLC; Rf = 0.3 (br, chloroform/methanol = 10:1, v/v) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | for 2 h; | Synthesis of tert-bulyl 2-(methylainino)ethylcarbaniate To a solution of compound 16 (1.3 g, 4.22 mmol) in MeOll (30 mL) was added Pd/C (150 mg, 10percent). The suspension was agitated under an H2 atmosphere with stiff ing for 2 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduce pressure to give an oil product (720 mg, 98percent).1HNMR: CP-0007023-117: ‘H-NMR (DMSO-d6, 500MHz): ö(ppm) 6.707 (s,1H), 2.999-2.962 (q, J=6.5, 12.5 Hz, 2H), 2.488-2.461 (t, J=7, 13.5 Hz, 2H), 2.247 (s,3H), 1.369 (s, 911). |
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