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CAS No. : | 442514-22-9 | MDL No. : | MFCD06808586 |
Formula : | C9H20N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YIMSPDZAVBIXRT-UHFFFAOYSA-N |
M.W : | 188.27 | Pubchem ID : | 11309987 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.89 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 52.69 |
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) : | -6.84 cm/s |
Log Po/w (iLOGP) : | 2.63 |
Log Po/w (XLOGP3) : | 0.86 |
Log Po/w (WLOGP) : | 1.12 |
Log Po/w (MLOGP) : | 0.95 |
Log Po/w (SILICOS-IT) : | 0.62 |
Consensus Log Po/w : | 1.24 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.09 |
Solubility : | 15.4 mg/ml ; 0.0818 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.5 |
Solubility : | 5.94 mg/ml ; 0.0315 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.49 |
Solubility : | 0.613 mg/ml ; 0.00326 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.19 |
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: |
* 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 |
---|---|---|
65% | With hydrogen In methanol for 0.75 h; | Preparation 20 (12 g, 0.037 mol) was hydrogenated 45 min in 100 ml of MeOH in the presence of 0.5 g of 5percent Pd/C at 60 PSI of hydrogen. The catalyst was filtered off and the solvent was removed under reduced pressure to yield the depicted product as a colorless oil (6 g, 65percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | at 20℃; for 4 h; | (3-Bromo-propyl)-carbamic acid tert-butyl ester (11.2 g, 47.0 mmol) was combined with 2.0 M Methylamine in THF (100 mL, 200 mmol) and was stirred at room temperature for 4 h. After this period, a precipitate formed in the solution. The solution was filtered and concentrated under reduced pressure to yield 7.58 g (86percent) of (3-methylamino-propyl)-carbamic acid tert-butyl ester as a clear oil. [M+H]+ 188.94. |
86% | at 20℃; for 4 h; | Step 1 Preparation of Example 5a: (3-Methylamino-propyl)-carbamic Acid tert-butyl Ester Methylamine (100 mL of a 2.00 M solution in THF, 200 mmol) was added to (3-bromo-propyl)-carbamic acid tert-butyl ester (11.2 g, 47.0 mmol) at room temperature under nitrogen and the solution was stirred for 4 h. The resulting suspension was filtered and concentrated under reduced pressure to give 7.58 g (86percent) of (3-methylamino-propyl)-carbamic acid tert-butyl ester (5a) as a clear oil. [M+H]+188.94. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | at 60℃; for 3 h; | Synthesis of fert-Butyl (3-(methylamino)propyl)carbamate. A mixture of potassium hydroxide powder (20 molpercent, 168 mg, 3 mmol), di(lH-imidazol-l-yl)methanone (2.43 g, 15 mmol,), and tert-butyl alcohol (15 mmol, 1.112 g) in dry toluene (76 mL) was heated at 60 °C (oil bath) with stirring for 3 hours under argon atmosphere. Then N- methyl-l,3-diaminopropane (15 mmol, 1.322 g, 1.566 mL) was added dropwise. The resulting mixture was heated at 60 °C for another 3 hours. After allowing the reaction mixture to cool to room temperature, water was added to the mixture. Two layers were separated and the organic layer was washed with brine, dried over sodium sulfate and concentrated to dryness, affording slightly yellow oil (0.966 g). The aqueous phase was extracted with dichloromethane (3 χ 30 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to afford slightly yellow oil (0.941 g). The two fractions were combined to afford 1.9 g of desired product (10 mmol, 67percent). The product was used in the next synthetic step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.5% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 25 h; | To a solution of N-methyl-1,3-propanediamine 7 (5.00 g, 56.7 mmol, 1.0 eq.) in anhydrous THF (40 mL), triethylamine (15.8 mL, 113 mmol, 2.0 eq.) was added under Ar atmosphere at room temperature. A solution of di-t-butyl dicarbonate (13.7 g, 62.4 mmol, 1.1 eq.) in anhydrous THF (100 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 24 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: 4.5percent) 1H-NMR (300 MHz; CDCl3, r.t., TMS, d/ppm) 1.46 (s, 9 H, -C(CH3)3), 1.70 (m, 2 H, -CH2CH2CH2-), 2.73 (t, 2 H, J = 6.90 Hz, -CH2CH2NHCH3), 2.84 (s, 3 H, - NHCH3), 3.31 (m, 2 H, -CONHCH2CH2-). TLC; Rf = 0.3 (br, chloroform: methanol =10:1, v/v) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | at 0 - 20℃; for 18 h; | tert-Butyl (3-(methylami no)propyl)carbamate A solution of N-methyl-i ,3-propanediamine (6 g, 67.9 mmol) in THF (50 mL) was cooled to 0 °C, and a solution of di-tert-butyl dicarbonate (4.6 mL, 20.3 mmol) in THF (50 mL) was added dropwise. The reaction mixture was allowed to come to room temperature, further stirred for 18 h, and concentrated under reduced pressure. Thecrude product was purified by flash column chromatography (silica gel 230-400 mesh, eluent 10percent MeOH in CHCI3 to get the undesired regioisomer tert-butyl (3- aminopropyl)(methyl)carbamate, followed by 15percent MeOH in CHCI3 to get the desired product) to afford tert-butyl (3-(methylamino)propyl)carbamate (1 g, yield 8percent) as a viscous light-yellow liquid. 1H NMR (400MHz, CDCI3) 65.06 (br s, 1H), 3.22—3.20 (m, 2H), 2.682.65 (t, J = 6.7 Hz, 2H), 2.44 (s, 3H), 2.23 (br s, 1 H), 1.72 — 1.66 (m, 2H), 1.45 (s, 9H). MS (ESI) m/z: Calculated for C9H20N202: 188.15; found: 189.2 (M-f-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | at 0 - 20℃; for 18 h; | tert-Butyl (3-(methylami no)propyl)carbamate A solution of N-methyl-i ,3-propanediamine (6 g, 67.9 mmol) in THF (50 mL) was cooled to 0 °C, and a solution of di-tert-butyl dicarbonate (4.6 mL, 20.3 mmol) in THF (50 mL) was added dropwise. The reaction mixture was allowed to come to room temperature, further stirred for 18 h, and concentrated under reduced pressure. Thecrude product was purified by flash column chromatography (silica gel 230-400 mesh, eluent 10percent MeOH in CHCI3 to get the undesired regioisomer tert-butyl (3- aminopropyl)(methyl)carbamate, followed by 15percent MeOH in CHCI3 to get the desired product) to afford tert-butyl (3-(methylamino)propyl)carbamate (1 g, yield 8percent) as a viscous light-yellow liquid. 1H NMR (400MHz, CDCI3) 65.06 (br s, 1H), 3.22—3.20 (m, 2H), 2.682.65 (t, J = 6.7 Hz, 2H), 2.44 (s, 3H), 2.23 (br s, 1 H), 1.72 — 1.66 (m, 2H), 1.45 (s, 9H). MS (ESI) m/z: Calculated for C9H20N202: 188.15; found: 189.2 (M-f-H). |
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