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CAS No. : | 7724-12-1 | MDL No. : | MFCD11040279 |
Formula : | C8H5N3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZOHSEULTWOYIMS-UHFFFAOYSA-N |
M.W : | 175.21 | Pubchem ID : | 14157112 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.74 |
TPSA : | 90.94 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.18 cm/s |
Log Po/w (iLOGP) : | 1.46 |
Log Po/w (XLOGP3) : | 1.67 |
Log Po/w (WLOGP) : | 1.76 |
Log Po/w (MLOGP) : | 0.22 |
Log Po/w (SILICOS-IT) : | 2.36 |
Consensus Log Po/w : | 1.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.53 |
Solubility : | 0.513 mg/ml ; 0.00293 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.19 |
Solubility : | 0.112 mg/ml ; 0.00064 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.69 |
Solubility : | 0.354 mg/ml ; 0.00202 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
71% | at 20℃; for 24 h; | Iron powder (68.05 g, 1218.55 mmol) was added to a suspension of 6-nitro-1,3-benzothiazole-2-carbonitrile (13, 5.00 g,24.37 mmol) in acetic acid (500 mL). The reaction mixture was stirred at room temperature for 24 h, diluted with water (1 L)and unreacted iron was removed by filtration through celite.The aqueous solution was extracted with EtOAc (4 × 500 mL).The combined organic layers were washed with brine (2 ×300 mL), dried (Na2SO4) and concentrated in vacuo. The crudeproduct was loaded onto a short plug of silica gel, flushedthrough with CHCl3(ca. 1 L) and concentrated in vacuo to give8as yellow microcrystals (3.02 g, 17.24 mmol, 71percent). A sample of 13was crystallised from EtOH for melting point analysis.Rf0.2 (SiO2, DCM); mp 219–220 °C (EtOH); 1H NMR(500 MHz, CDCl3) δ7.95 (d, J= 8.9 Hz, 1H, CH-4), 7.08 (d, J= 2.2 Hz, 1H, CH-7), 6.95 (dd, J= 8.8, 2.2 Hz, 1H, CH-5), 4.14(s, 2H, NH2); 13C NMR (125 MHz, CDCl3) δ147.8 (C-6),145.7 (C-7a), 138.3 (C-3a), 131.2(C-2), 126.1 (CH-4), 117.8(CH-5), 113.7 (C≡N), 104.0 (CH-7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | at 120℃; | (C) Synthesis of 2-cyano-6-aminobenzothiazole (4) Potassium cyanide (1.29 g, 19.7 mmol) was added to dimethyl sulfoxide (DMSO, 150 mL). After argon substitution, the mixture was refluxed overnight at 135° C. with stirring. The temperature was lowered to 120° C., and Compound 3 (1.02 g, 5.55 mmol) dissolved in DMSO (20 mL) was added. After disappearance of the starting materials was confirmed by thin layer chromatography (developing solvent: ethyl acetate/n-hexane=2/1), the reaction mixture was poured into a mixed solution of 1.0 mol/L potassium dihydrogenphosphate solution (100 mL) and diethyl ether, (150 mL), and the diethyl ether layer was separated. The aqueous layer was extracted 5 times with ethyl acetate, the organic layer was mixed with the diethyl ether layer, and this organic solvent layer was washed twice with purified water and twice with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/4 to 1/2) to obtain Compound 4 as yellow solid (521 mg, 54percent yield). 1H-NMR (300 MHz, CDCl3) δ 4.13 (br, 2H), 6.96 (dd, 1H, J=2.4, 8.9 Hz), 7.09 (d, 1H J=2.4 Hz), 7.95 (d, 1H, J=8.9 Hz). MS (ESI+) 176.0, [M+H]+. |
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