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CAS No. : | 1203099-07-3 | MDL No. : | MFCD11101353 |
Formula : | C11H15ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IUCDRWXBDJDFQP-UHFFFAOYSA-N |
M.W : | 242.70 | Pubchem ID : | 44828568 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 66.68 |
TPSA : | 50.36 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.61 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.65 |
Log Po/w (WLOGP) : | 1.15 |
Log Po/w (MLOGP) : | 1.14 |
Log Po/w (SILICOS-IT) : | 1.15 |
Consensus Log Po/w : | 1.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.33 |
Solubility : | 1.13 mg/ml ; 0.00466 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.32 |
Solubility : | 1.16 mg/ml ; 0.00478 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.2 |
Solubility : | 0.153 mg/ml ; 0.000631 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.08 |
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 |
---|---|---|
34% | With N-ethyl-N,N-diisopropylamine In acetonitrile at 135℃; for 2.5h; Microwave irradiation; | A A. Benzyl (1 -(4-cyanopyridin-2-yl)azetidin-3-yl)carbamate To benzyl azetidin-3-ylcarbamate hydrochloride (400 mg, 1 .65 mmol) in acetonitrile (10 mL), 2-chloroisonicotinonitrile (274 mg, 1 .98 mmol) and N,N-diisopropylethylamine (0.72 mL, 4.1 mmol) were added. The mixture was heated in a microwave at 135 °C for 2.5 h. The reaction was concentrated, and the residue was purified on silica gel eluting with a 20%-90% EtOAc in hexanes gradient. The appropriate fractions were combined, evaporated under reduced pressure and placed in vacuo to give the title compound as a white solid (185 mg, 34%). 1H NMR (400 MHz, CD3OD) δ 3.91 (dd, J = 8, 6 Hz, 2 H), 4.34 (t, J = 8 Hz, 2 H), 4.56- 4.64 (m, 1 H), 5.09 (s, 2 H), 6.72 (s, 1 H), 6.84 (d, J = 5 Hz, 1 H), 7.17-7.45 (m, 5 H), 8.17 (d, J = 5 Hz, 1 H); LC-MS (LC-ES) M+H = 309. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 85℃; | A A. Benzyl (1 -(pyridin-2-yl)azetidin-3-yl)carbamate To a reaction vial with benzyl azetidin-3-ylcarbamate hydrochloride (800 mg, 3.30 mmol) in DMF (3 mL) was added 2-fluoropyrimidine (320 mg, 3.30 mmol) and N,N- diisopropylethylamine (1 .15 mL, 6.59 mmol). The mixture was heated at 85 °C overnight, cooled, diluted with EtOAc and washed (2X) with water. The aqueous layers were extracted with EtOAc, the combined organic layers washed with water (3X) and brine, dried over MgSC>4 , filtered and concentrated. The residue was purified on silica gel eluting with a 20%-70% EtOAc- hexanes gradient. The appropriate fractions were combined, evaporated under reduced pressure and placed in vacuo to give the title compound (160 mg, 17%) as a white solid. 1H NMR (400 MHz, CDC ) δ 3.81 -3.89 (m, 2 H), 4.31 -4.41 (m, 2 H), 4.69 (br s, 1 H), 5.13 (s, 2 H), 5.24 (br s, 1 H), 6.31 (d, J = 8 Hz, 1 H), 6.59-6.70 (m, 1 H), 7.30-7.42 (m, 5 H), 7.44-7.55 (m, 1 H), 8.15 (d, J = 4 Hz, 1 H); LC-MS (LC-ES) M+H = 284. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 155℃; for 5h;Microwave irradiation; | To a microwave reaction vial with benzyl azetidin-3-ylcarbamate hydrochloride (500 mg, 2.0 mmol) in acetonitrile (8 mL) was added <strong>[62802-42-0]2-chloro-5-fluoropyrimidine</strong> (546 mg, 4.1 mmol) and N,N-diisopropylethylamine (1 .1 mL, 6.2 mmol). The mixture was heated with a heating gun to form a solution and heated in a microwave at 155 C for 5 h. The solvent was concentrated in vacuo and the residue purified on silica gel eluting with a 0%-60% EtOAc/EtOH (3:1 ) in hexanes gradient. The appropriate fractions were combined, evaporated under reduced pressure and placed in vacuo to give the title compound (560 mg, 90%). 1H NMR (400 MHz, CDC ) delta 3.81 - 3.85 (m, 2 H), 4.31 -4.36 (m, 2 H), 4.55-4.62 (m, 1 H), 5.03 (s, 2 H), 5.09-5.17 (m, 1 H), 7.19- 7.32 (m, 5 H), 8.1 1 (s, 2 H); LC-MS (LC-ES) M+H = 303. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98 mg | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 4 (1-(2,3-Difluoropropyl)azetidin-3-yl)carbamic acid benzyl ester (I-100'-1-d) I-100'-1-c (100 mg),Azetidine-3-ylcarbamic acid benzyl ester hydrochloride(CAS: 914348-04-2; 100 mg)It was mixed with diisopropylethylamine (138 mg) in 1 ml of DMF; the reaction was stirred at room temperature overnight.The reaction mixture was quenched with aqueous solution and extracted with ethyl acetate. The ethyl acetate layer was collected, then washed twice with aq.Concentration and column purification gave the product I-100'-1-d (98 mg). |
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