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CAS No. : | 15855-06-8 | MDL No. : | MFCD00173928 |
Formula : | C7H6ClNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PJQBTHQTVJMCFX-UHFFFAOYSA-N |
M.W : | 187.58 | Pubchem ID : | 2782124 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.7 |
TPSA : | 59.42 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) : | -6.28 cm/s |
Log Po/w (iLOGP) : | 1.35 |
Log Po/w (XLOGP3) : | 1.64 |
Log Po/w (WLOGP) : | 1.44 |
Log Po/w (MLOGP) : | -0.36 |
Log Po/w (SILICOS-IT) : | 1.37 |
Consensus Log Po/w : | 1.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.27 |
Solubility : | 0.998 mg/ml ; 0.00532 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.5 |
Solubility : | 0.592 mg/ml ; 0.00316 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.14 |
Solubility : | 1.35 mg/ml ; 0.00718 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.94 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
78% | With hydrogen; triethylamine In methanol at 20℃; | To a suspension of the title compound of Preparation 22 (1.94 g, 6.49 mmol) in acetonitrile (150 mL), sodium iodide (4.90 g, 32.69 mmol) and trimethylsilyl chloride (4.10 mL, 32.42 mmol) were added. The resulting suspension was stirred under nitrogen atmosphere at 400C for 3 days. The mixture was cooled to O0C and the solid was filtered off, washed with acetonitrile and dried to yield 1.66 g (90percent) of the title compound.LRMS: m/z 285(M+1 )+ Retention time: 2.86min (method B) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
183 g | With sodium hydroxide In water at 70℃; for 4 h; | a) To a solution of 2,6-dichloroisonicotinic acid (200 g, 1.04 mol) in methanol (3 L), 32percent aq. NaOH (770 mL) is added. The stirred mixture becomes warm (34° C.) and is then heated to 70° C. for 4 h before it is cooled to rt. The mixture is neutralised by adding 32percent aq. HCl (100 mL) and 25percent aq. HCl (700 mL). The mixture is stirred at rt overnight. The white precipitate that forms is collected, washed with methanol and dried. The filtrate is evaporated and the residue is suspended in water (200 mL). The resulting mixture is heated to 60° C. Solid material is collected, washed with water and dried. The combined crops give 2-chloro-6-methoxy-isonicotinic acid (183 g) as a white solid; LC-MS: tR=0.80 min, [M+1]+=187.93. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | for 24 h; Heating / reflux | Freshly prepared sodium methoxide (from 1.5 g sodium in 15 mL dry methanol) was added dropwise to a solution of Example 16 (5.0 g, 26 mmol) in dry methanol (25 mL). The reaction mixture was refluxed for 24 h, allowed to cool to RT and poured in aqueous HCl (10percent, 100 mL). A pinkish solid separated and was collected on a filter, washed with water and air-dried (4.0 g, 82percent). IH NMR (400 MHz, DMSO-d6) 5 3.89 (s, 3H) 7.17 (s, 1H) 7.39 (s, 1H) 13.96 (br s, OH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Stage #1: With borane-THF In tetrahydrofuran for 3 h; Heating / reflux Stage #2: With water; sodium carbonate In tetrahydrofuranHeating / reflux |
BH3. DMS (1.0 mL, 10.66 mmol) was refluxed in THF (20 mL) for 30 min (formation of BH3. THF). At RT, Example 17 (2.0 g, 10.66 mmol in 10 mL THF) was added dropwise, and then the reaction mixture was heated to reflux for 3 h. The solution was allowed to cool to ambient temperature, solid sodium carbonate (0.5 g) and water (5 mL). The resulting mixture was heated for a short while and poored in water (50 mL). Extraction with ethyl acetate (3 x 50 mL), drying of the combined organic layers (Na2SO4) and evaporation in vacuo gave a 1: 1 mixture of starting material and product. Purification by flash column chromatography over silica gel eluting with ethyl acetate gave 780 mg (42 percent) of an off-white solid. IH NMR (400 MHz, CDC13) 8 3.92 (s, 3H) 4.66 (s, 2H) 6.64 (s, 1H) 6.89 (s, 1H). |
2 g | With borane-THF In tetrahydrofuran at 0 - 20℃; for 20.5 h; Inert atmosphere | To a solution of 2-chloro-6-methoxyisonicotinic acid (2.5 g) in dry tetrahydrofuran (50 ml) at 0°C under nitrogen was added dropwise a solution of borane- tetrahydrofuran complex (1.0M solution in tetrahydrofuran; 40 ml) over fifteen minutes. After the addition was complete, the cooling bath was removed and the mixture allowed to warm to room temperature. After three hours, the mixture was cooled to 0°C and borane-tetrahydrofuran complex (1.0M solution in tetrahydrofuran; 40 ml) was addedover fifteen minutes. After the addition was complete, the cooling bath was removed and the mixture allowed to warm to room temperature and stirred for seventeen hours. The reaction mixture was cooled to 0°C, quenched with 1.0M aqueous sodium hydroxide solution (30 ml), diluted with saturated aqueous ammonium chloride solution (50 ml) and extracted with diethyl ether (2 x 100 ml), the combined organic layer washed with brine then dried (Na2SC"4) and evaporated. The residue was triturated with hexane and filtered to afford (2-chloro-6-methoxypyridin-4-yl)methanol (2.0 g) as a white solid. LCMS: Rt 1.16 min, m/z 174/176 [M+H]+. 1H-NMR (400 MHz, CDC13) δ (ppm): 1.96 (t, 1 H) 3.94 (s, 3 H) 4.67 (d, J=3.67 Hz, 2 H) 6.65 (d, J=0.86 Hz, 1 H) 6.91 (s, 1 H) |
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