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CAS No. : | 519032-08-7 | MDL No. : | MFCD12026362 |
Formula : | C17H19N3O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NIVUTAZNLHLBAN-UHFFFAOYSA-N |
M.W : | 361.35 | Pubchem ID : | 135446261 |
Synonyms : |
|
Num. heavy atoms : | 26 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 8.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 90.4 |
TPSA : | 130.87 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.94 cm/s |
Log Po/w (iLOGP) : | 2.75 |
Log Po/w (XLOGP3) : | 2.2 |
Log Po/w (WLOGP) : | 1.58 |
Log Po/w (MLOGP) : | 0.52 |
Log Po/w (SILICOS-IT) : | 1.26 |
Consensus Log Po/w : | 1.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.28 |
Solubility : | 0.19 mg/ml ; 0.000525 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.58 |
Solubility : | 0.00945 mg/ml ; 0.0000262 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.02 |
Solubility : | 0.0347 mg/ml ; 0.0000959 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.32 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
58% | Stage #1: at 20℃; for 2 h; Stage #2: With xylene In methanol at 90 - 120℃; for 16 h; Inert atmosphere |
Benzyl 2-amino-2-(hydroxyimino)-1,1-dimethylethylcarbamate (2.0 g, 8.0 mmol) was dissolved in 30 mL MeOH, dimethyl acetylenedicarboxylate (DMAD, 1.1 mL, 9.0 mmol) was added slowly. The mixture was stirred for 2 h at room temperature, and then concentrated under reduced pressure to give a white oil. The mixture of the oil and 80 mL xylene was stirred at 90 °C for 2 h and 120 °C for 2 h, then refluxed for 12 h under nitrogen, concentrated to yield the crude product. The crude product was recrystallized with 2 mL MeOH and 10 mL tert-butyl methyl ether to afford 5 as a yellow solid (1.7 g, 58 percent): 1H-NMR (DMSO-d6) δ: 7.35 (m, 5H), 5.00 (s, 2H), 3.83 (s, 3H), 1.48 (s, 6H); ESI-MS m/z 360 (M)-, 384 (M+Na) +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triethylamine In methanol at 65 - 68℃; for 7 h; | A round bottom flask was charged with methyl 2-(l-[(benzyloxy)carbonyl]amino}-l-methylethyl)-5,6-dihydroxypyrimidine-4-carboxylate (Compound I; 1 eq.) and methanol (-1.6 mL per gram of Compound 1). The slurry was warmed to 55°C, after which triethylamine (1.2 eqs.) was added in one portion. The solution was then warmed to 65°C and 4-fluorobenzylamine (1.2 eqs) was added at 65-68°C. The mixture was then aged at reflux for 7 hours. The solution was cooled to 550C5 and acetic acid (2 eqs.) was added in one portion. Water was added followed by seed crystals of 2. (Note: Crystallization would occur without seed, but seeding provides a more reliable method of crystal growth.) The resultant slurry was aged at 6O0C with the addition of more water during the ageing. The slurry was then cooled to 2O0C5 filtered, washed with 1 : 1 methanol:water, and dried in a nitrogen stream to give compound 2 (96 wt.percent purity by HPLC assay, 1.75 wt.percent water by Karl Fisher titration), 98percent overall yield (corrected for purity). Compound 2: lH NMR (600.13 MHz, CDCI3) δ 12.37 (br s, 2H), 7.95 (br t, J~6 Hz, IH), 735-7.31 (m, 2H)57.25-7.19 ( br m, 5H), 7.08-7.04 (m, 2H), 6.49 (s, IH)5 4.96 (s, 2H)5 4.58 (d, 3=6.0 Hz, 2H)5 1.64 (s, 6H).13C NMR (150.92 MHz, CDCI3) δ 168.5, 162.6 (d, JcF=246.6 Hz), 160.O5 155.35 154.1, 147.9, 136.5, 133.1 (d, JCF=3-1 Hz), 129.7 (d, JCF^7.9 Hz), 128.6, 128.1, 127.9, 127.1, 116.0 (d5 JCF=22.0 Hz), 66.8, 55.5, 42.7, 26.7. |
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