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CAS No. : | 98548-01-7 | MDL No. : | MFCD11226322 |
Formula : | C7H9N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZVBFSYSSUMGOKQ-UHFFFAOYSA-N |
M.W : | 167.17 | Pubchem ID : | 25067380 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.52 |
TPSA : | 78.1 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) : | -8.16 cm/s |
Log Po/w (iLOGP) : | 1.51 |
Log Po/w (XLOGP3) : | -1.19 |
Log Po/w (WLOGP) : | 0.24 |
Log Po/w (MLOGP) : | 0.13 |
Log Po/w (SILICOS-IT) : | 0.32 |
Consensus Log Po/w : | 0.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.3 |
Solubility : | 84.0 mg/ml ; 0.503 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.04 |
Solubility : | 185.0 mg/ml ; 1.11 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -1.77 |
Solubility : | 2.86 mg/ml ; 0.0171 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.0 |
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 |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; for 20h;Reflux; | A mixture of crude tert-butyl (1 -{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate that was prepared in a manner analgous to that described for Intermediate Example lnt-1 -A (3.3 g, -80% purity, 5.79 mmol), <strong>[98548-01-7]ethyl 6-aminopyridazine-3-carboxylate</strong> (CAS-Nr. 98548-01 -7, 1 g, 5.57 mmol), N,N-diisopropylethylamine (0.97 mL, 5.57 mmol) and activated 3A molecular sieves in isopropanol (30.4 mL) was heated for 20 hours under reflux. On cooling the mixture was partitioned between DCM and water, stirred vigorously and filtered through a silicone coated filter paper. The filtrate was concentrated in vacuo, taken up in DCM and washed with dilute aqueous hydrochloric acid (1 N) and brine, dried and concentrated in vacuo to give the crude title compound. Purification was achieved by chromatography on silica (gradient elution: Hexane:EtOAc 9:1 to Hexane:EtOAc 1 :1 ) to give the title compound (2.80 g, 92% purity, 90% yield).UPLC-MS (Method 3): RT = 1 .51 min; m/z = 51 3.41 (M+H).1 H-NMR (400 MHz, d6-DMSO): delta = 8.29 (d, 1 H), 7.74 (d, 1 H), 7.50 - 7.56 (m, 8H), 7.31 (d, 2H), 4.33 (q, 2H), 2.28 - 2.39 (m, 4H), 1 .88 - 1 .99 (m, 1 H), 1 .68 - 1 .80 (m, 1 H), 1 .26 - 1 .29 (m, 9H), 1 .08 (br s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In dimethyl sulfoxide; at 120℃; for 2h; | General procedure: A round bottom flask equipped with reflux condenser and magnetic stirring bar was charged with substituted heteroaryl chloride (5 mmol), sodium azide (10 mmol), triphenylphosphine (10 mmol) and DMSO (40 ml). The reaction mixture was stirred at 120 C. Reaction progress was monitored by TLC. In 3-5 hours starting material was disappeared and new product was confirmed by TLC. 1N HCl (8 mL) was added to the reaction mixture and continued to stir at 120 C for additional 1-2 hour. Reaction mixture was cooled to room temperature and diluted with 1N HCl (8 mL). The resulting mixture was poured into distilled water (100 mL) and aqueous layer was washed with EtOAc (2 X 50 mL) to remove triphenylphosphine oxide. Aqueous layer was slowly neutralized with saturated aqueous NaHCO3 solution and extracted with EtOAc (2 X 50 mL). The combined organic layers were washed with water (40 mL), brine(40 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford substituted heteroaryl amine with high purity without column purification (purity was achieved in some products by washing solid compound with n-Pantane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Slowly adding sodium (7.2 g) in ethanol (800 mL), and stirred for 2 hours at room temperature.After confirming that all the sodium had dissolved, the mixture was further stirred at room temperature for 1 hour added the commercially available methyl 6-amino-pyridazine-3-carboxylate (40.0g).Hydrogen chloride to the reaction solution (4.0mol / L ethyl acetate solution, about 80mL) was adjusted to dropped about pH5 a.The resulting reaction solution was concentrated to dryness, filtered after suspending further washed with distilled water, by air drying, to give the title compound 39.9g (99%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | 2-Bromo-1,1-diethoxy-ethane (16.55 g, 12.63 mL, 84 mmol) was dissolved in hydrogen bromide (3.52 mL of 48% w/v, 20.88 mmol) and stirred at 120 C for 30 minutes. The reaction mixture was allowed to cool to ambient temperature and EtOH (100 mL) was added, followed by NaHCO3 (3.196 g, 38.04 mmol) and <strong>[98548-01-7]ethyl 6-aminopyridazine-3-carboxylate</strong> (2 g, 12 mmol). The resulting mixture was stirred at 80 C for 1.5 hours. The dark brown reaction mixture was allowed to cool to ambient temperature and concentrated under reduced pressure to give a dark brown gum. This material was partitioned between EtOAc and water, the aqueous layer was extracted with further EtOAc (3 x 20mL) and the combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to give a brown oil which was purified by column chromatography (silica, 3% MeOH in EtOAc) to give a brown solid. This material was recrystallised from EtOAc/hexane mixtures to give ethyl imidazo[1,2-b]pyridazine-6-carboxylate as a light brown powder (1.1 g, 48%); 1H NMR (400 MHz, DMSO-d6) delta 8.52 (s, 1H), 8.28 (d, J = 9.5 Hz, 1H), 7.98 (d, J = 1.2 Hz, 1H), 7.73 (d, J = 9.5 Hz, 1H), 4.43 (q, J = 7.1 Hz, 2H), 1.37 (t, J = 7.1 Hz, 3H). |
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