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CAS No. : | 103766-25-2 | MDL No. : | MFCD08458352 |
Formula : | C5H4ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZPLQIPFOCGIIHV-UHFFFAOYSA-N |
M.W : | 145.54 | Pubchem ID : | 54679224 |
Synonyms : |
Gimestat;CDHP;chlorodihydroxypyridine. Abbreviation: CDHP.;5-Chlorodihydropyrimidine
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 34.1 |
TPSA : | 53.09 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.24 cm/s |
Log Po/w (iLOGP) : | 1.02 |
Log Po/w (XLOGP3) : | -0.08 |
Log Po/w (WLOGP) : | 0.73 |
Log Po/w (MLOGP) : | 0.24 |
Log Po/w (SILICOS-IT) : | 1.73 |
Consensus Log Po/w : | 0.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.19 |
Solubility : | 9.5 mg/ml ; 0.0653 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.58 |
Solubility : | 38.0 mg/ml ; 0.261 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.95 |
Solubility : | 1.63 mg/ml ; 0.0112 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.61 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-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 |
---|---|---|
86% | With acetic acid; sodium iodide In acetonitrile at 60℃; for 8 h; | A mixture of compound 6 (8.0 g, 44 mmol), acetonitrile (100 mL), acetic acid (3 mL)and sodium iodide (13.2 g, 88 mmol) was heated for 8 h at 60 °C. Then the mixture was cooled to room temperature and poured into 10percent sodium thiosulfate solution (200 mL) to precipitate a colourless solid, which was recrystallised from water to give pure compound 2: Yield 5.6 g (86percent); m.p.272–273 °C (lit.7 273–274 °C); 1H NMR (400 MHz, DMSO-d6): δ 5.70(s, 1H), 7.51 (s, 1H), 11.29 (br, 2H) ; 13C NMR (100 MHz, DMSO-d6): δ163.5, 163.2, 134.6, 105.6, 98.7; LRMS (ESI) m/z (percent): 146 (100) [M (35Cl+ 1]+, 148 (30) [M (37Cl) + 1]+; HRMS (ESI) m/z calcd for C5H535ClNO2:[M + H]+: 146.0003; found: 146.0012; calcd for C5H537ClNO2: [M + H]+:147.9975; found: 147.9975. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.4% | Stage #1: at 128 - 130℃; for 0.666667 h; Stage #2: With acetyl chloride In ethanol at 20℃; for 1 h; |
Xylene (40 mL) was added to 2,2-cyclohexyl-5-chloro-1,3-dioxin-4-one (4.25 g, 0.021 mol), produced in Referential Example 2, and ketene diethyl ether (2.91 g, 0.025 mol), and the mixture was stirred under heating at 128 to 130°C (internal temperature) for 40 minutes. The reaction mixture was cooled to room temperature, and concentrated. The residue was dissolved in ethanol (60 mL), and at room temperature, acetyl chloride (0.17 g, 0.0022 mol) was added to the solution, followed by stirring for one hour. To the reaction mixture, concentrated ammonia (28percent) (4.2 mL) was added, followed by stirring at room temperature for four hours. A 30percent aqueous solution of sodium hydroxide (3 g, 0.0225 mol) was added to the reaction mixture, followed by stirring at room temperature for 12 hours. The precipitated crystals were collected through filtration, washed with ethanol (10 mL, two times), and dried under reduced pressure at room temperature for five hours, to thereby yield 3.04 g of a product as crystals. The thus-obtained crystals were dissolved in water (30 mL) under heating, and the solution was cooled to room temperature. 6N Aqueous hydrochloric acid (4.5 g) was added to the solution, followed by stirring at room temperature for five hours. The precipitated crystals were collected through filtration, washed with water, and dried under reduced pressure at 40 to 45°C for 18 hours, to thereby yield 2.21 g of the title compound (yield with respect to 2,2-cyclohexyl-5-chloro-1,3-dioxin-4-one: 72.4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | Stage #1: With acetyl chloride In ethanol at 20℃; for 1 h; Stage #2: With ammonia In ethanol; water at 20℃; for 15 h; |
The compound (0.23 g, 0.001 mol) was dissolved in ethanol (5 mL), and acetyl chloride (0.1 mL) was added to the solution at room temperature, followed by stirring for one hour. The reaction mixture was concentrated, and the residue was dissolved in ethanol (5 mL). Concentrated aqueous ammonia (28percent) (1 mL) was added to the solution, and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated, and water (1.4 mL) and acetic acid (0.14 mL) were added to the residue, followed by stirring at room temperature for two hours. The precipitated crystals were collected through filtration, washed with water, and dried under reduced pressure at 40 to 45°C for 18 hours, to thereby yield 0.05 g of the title compound (yield with respect to 5-chloro-2,2-diethoxy-2,3-dihydropyran-4-one: 33.0percent, yield with respect to 5-chloro-2,2-dimethyl-1,3-dioxin-4-one: 29.4percent). |