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CAS No. : | 1314987-79-5 | MDL No. : | MFCD14155811 |
Formula : | C11H16N4O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IOGPBTPTPJYTFK-UHFFFAOYSA-N |
M.W : | 268.27 | Pubchem ID : | 56777239 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.64 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 72.37 |
TPSA : | 93.18 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.45 cm/s |
Log Po/w (iLOGP) : | 2.2 |
Log Po/w (XLOGP3) : | 0.69 |
Log Po/w (WLOGP) : | 1.2 |
Log Po/w (MLOGP) : | -0.05 |
Log Po/w (SILICOS-IT) : | -1.93 |
Consensus Log Po/w : | 0.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.8 |
Solubility : | 4.23 mg/ml ; 0.0158 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.22 |
Solubility : | 1.6 mg/ml ; 0.00597 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.63 |
Solubility : | 63.3 mg/ml ; 0.236 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.66 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
85% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 16 h; Inert atmosphere | [0229j DIAD (3.92 mL, 19.9 mmmol, 1.5 equiv) was added dropwise to a stirred solution of 4-nitro-1H-pyrazole (1.5 g, 13.27 mmol), 1-Boc-3-Hydroxyazetidine (2.3 g, 13.27 mmol, 1 equiv) and triphenyiphosphine (5.22 g, 19.9 mmol, 1.5 equiv) in THF (30 mL) placed an ice-bath under N2. The mixture was stirred at 0 °C for 10 mm and allowed to warm to rt and stirred for 16 h. After diluted with EA (100 mL), the mixture was washed with water (40 mL), brine (30 mL x 2). The combined organic layer was dried, concentrated. The crude was purified through silica gel column chromatography (petroleum ether/EtOAc = 1/10) to give tert-butyl 3-(4-nitro-1H- pyrazol-1-yl)azetidine-1-carboxylate as light yellow solid (3 g, yield: 85percent). ESI-MS (M+H-56) : 213.1. ‘H NMR (400 MHz, CDC13)(5: 8.28 (s, 1H), 8.16 (s, 1H), 5.07-5.04 (m, 1H), 4.44-4.40 (m, 2H), 4.34-4.30 (m, 2H), 1.47 (s, 9H). |
5.3 g | With di-tert-butyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran at 10 - 35℃; | A) tert-butyl 3-(4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate To a solution of 4-nitro-1H-pyrazole (2.0 g), tert-butyl 3-hydroxyazetidine-1-carboxylate (3.1 g) and triphenylphosphine (5.6 g) in tetrahydrofuran (20 mL) was added di-tert-butyl (E)-diazene-1,2-dicarboxylate (5.3 g) at room temperature, and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (5.3 g). 1H NMR(300 MHz, CDCl3)δ1.47 (9H, s), 4.28-4.37 (2H, m), 4.38-4.47 (2H, m), 5.05 (1H, tt, J = 7.9, 5.1 Hz), 8.16 (1H, s), 8.27 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 12 h; | Compound 54-c (4.9 g, 15 mmol) and cesium carbonate (6.5 g, 2 mmol) were added to a solution of 4-nitropyrazole (1.13 g, 10 mmol) in DMF (15 mL) in sequence, and then the mixture was heated to 120° C. and stirred for 12 hours. After cooled to room temperature, the mixture was treated with water (60 mL), extracted with ethyl acetate (30 mL×3). The organic layers were combined, dried over anhydrous sodium sulfate, then filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate=5:1) to give compound 54-b (1.1 g, yield: 41percent). LC-MS (ESI): m/z=291 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 12 h; | Under hydrogen (1 atm), to a solution of compound 54-b (1.33 g, 5 mmol) in methanol (10 mL) was added 10percent Pd—C (0.1 g). The mixture was stirred at 25° C. for 12 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give compound 65-b (940 mg, yield: 79percent), which was used directly for the next step without purification. LC-MS (ESI): m/z=261 [M-+Na]+. |
2.1 g | With 5%-palladium/activated carbon; hydrogen In ethanol at 10 - 35℃; for 2 h; | B) tert-butyl 3-(4-amino-1H-pyrazol-1-yl)azetidine-1-carboxylate To a solution of tert-butyl 3-(4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate (5.3 g) obtained in Step B of Example 131 in ethanol (30 mL) was added 5percent palladium-carbon (4.2 g), and the mixture was stirred at room temperature for 2 hr under hydrogen atmosphere (at normal pressures). The palladium-carbon was removed by filtration through Celite, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (2.1 g). 1H NMR(300 MHz, DMSO-d6)δ1.39 (9H, s), 3.89 (2H, s), 3.98-4.08 (2H, m), 4.14-4.26 (2H, m), 4.92-5.06 (1H, m), 7.03 (1H, s), 7.13 (1H, d, J = 0.8 Hz). |
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