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CAS No. : | 86873-60-1 | MDL No. : | MFCD04114192 |
Formula : | C6H4ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GJLOKYIYZIOIPN-UHFFFAOYSA-N |
M.W : | 157.55 | Pubchem ID : | 2762872 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.21 |
TPSA : | 50.19 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) : | -6.31 cm/s |
Log Po/w (iLOGP) : | 1.08 |
Log Po/w (XLOGP3) : | 1.34 |
Log Po/w (WLOGP) : | 1.43 |
Log Po/w (MLOGP) : | -0.51 |
Log Po/w (SILICOS-IT) : | 1.39 |
Consensus Log Po/w : | 0.95 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.04 |
Solubility : | 1.44 mg/ml ; 0.00914 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.0 |
Solubility : | 1.59 mg/ml ; 0.0101 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.0 |
Solubility : | 1.57 mg/ml ; 0.00998 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.38 |
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 |
---|---|---|
81.4% | With water; sodium hydroxide In ethanol at 90 - 100℃; for 1.5 h; | 1000ml four-necked flask, fitted with a stirrer, thermometer, reflux condenser, is added 5-chloro-2-cyano-pyridine (27.7g, 0.2mo), 277 mg of the ethanol, and dissolved with stirring, an aqueous solution of 10percent NaOH was added 277ml, heated to 90 ~ 100 stirred at reflux for 1.5h, TLC TLC [discriminating the end of reaction conditions to expand (butanol - acetic acid - water = 5: 2: 2)], the reaction is complete, cooled to room temperature under stirring, the pH was adjusted to 2 with 2NHCl ~ 3, and concentrated under reduced pressure to a volume of 100ml, methanol was added to 200ml, cooled to 0 ~ 5 , filtered, the solid out, and the filtrate was concentrated to dryness under reduced pressure, the residue was added 450ml of dichloromethane and 50ml of methanol, stirred for 1h, filtered and the solid with the amount of 10percent methanol - methylene chloride mixture was washed, 60 ~ 65 vacuum oven vacuum drying 2h, as a white solid intermediate 525.5g, a yield of 81.4percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.6% | Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 2 h; Inert atmosphere Stage #2: for 2 h; |
Compound 17 (4.54 g, 23.6 mmol) was suspended in dried Et2O (100 mL) under argon atmosphere. To the suspension was added 1.54 M n-butyllithium solution in hexane (16.9 mL, 26.0 mmol) at -78 °C, and the mixture was stirred for 2 h to obtain a brown solution. Carbon dioxide gas (ca. 2 L) was blown into the solution, and the mixture was stirred for 2 h. After warming to room temperature, the solvent was distilled off in vacuo. Obtained brown solid was washed with hexane and suspended in water (50 mL). After 1 M HCl (30 mL) was added to this suspension, the mixture was concentrated in vacuo. Obtained yellow solid was washed with Et2O to obtain the title compound (358 mg, 2.27 mmol, 9.6percent) as a yellow solid. 1H NMR (DMSO-d6) δ: 8.05 (2H, d, J = 8.4 Hz), 8.12 (1H, dd, J = 8.4, 2.3 Hz), 8.76 (1H, d, J = 2.3 Hz). ESI-MS m/z: 158 [(M+H)+, 35Cl], 160 [(M+H)+, 37Cl]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.6% | With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 16 h; | To a solution of 5-chloropicolinic acid (5 g, 31 .7 mmol) in tetrahydrofuran (50 mL) was added borane-dimethylsulfide complex (10 mL) at 0°C and resulting reaction mixture was maintained at rt for 16 h. Cooled the reaction mass to 0°C, excess borane-dimethylsulfide complex was quenched with methanol (15 mL), refluxed for 1 h, concentrated the reaction, diluted in ethyl acetate (150 mL), washed with water (2 x 50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated to afford 3 g (66.6percent yield) of (5-Chloropyridin-2-yl)methanol as a white solid.1H NMR (400 MHz, CDCI3): δ ppm 3.75 (br.s, 1 H), 4.75 (s, 2H), 7.25 (d, J = 8.8 Hz, 1 H), 7.67 (dd, J = 2.2, 6.1 Hz 1 H), 8.53 (d, J = 8.8 Hz, 1 H). |
45% | Stage #1: With borane-THF In tetrahydrofuran at 20 - 70℃; for 5 h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 2 h; |
EXAMPLE 9; (5-Chloropyridin-2-yl)methyl 4-isopropyl-l,4,6,7-tetrahydro-5H-imidazo[4,5-c]- pyridine-5-carboxylate; 5-Chloropyridine-2-carboxylic acid (2.00 g, 12.7 mmol) was dissolved in THF (12 mL) at 0 0C and added to a solution of borane-THF (19.0 mL, 1 M in THF, 19.0 mmol). THF (10 mL) was added and the reaction mixture was warmed to room temperature, stirred for 2 h and heated under reflux at 70 0C for 3 h. The reaction mixture was cooled to 0 0C, quenched with aq 6 M HCl solution (4 mL) and the solution was stirred for 2 h and concentrated in vacuo. The residue was partitioned between H2O (75 mL) and DCM (75 mL). The aq layer was washed with DCM (3 x 75 mL), adjusted to pH 9 with 4 M aqNaOH (3 mL) and extracted with DCM (3 x 75 mL). The organic layers were combined, - -dried (MgSO4) and concentrated in vacuo to give 5-chloropyridine-2-methanol (0.83 g, 45percent) as a brown gum.Analytical HPLC: purity 79.5percent (System B, Rτ = 3.04 min); Analytical LCMS: purity 85percent (System A, Rτ = 1.15 min), ES+: 143.97 [35ClMH]+ and 145.98 [MH 37Cl]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: at 80℃; for 16 h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate |
A mixture of 5-chloro-2-pyridinecarboxylic acid (1.0 g, 6.35 mmol) and cone. H2SO4 (0.1 ml) was heated in EtOH (10 ml) at 80 0C for 16 hours. After cooling and concentrating at reduced pressure, the residue was dissolved in EtOAc (50 ml), washed with saturated NaHCO3 (25 ml) and brine (25 ml), dried (MgSO4), filtered and re-concentrated at reduced pressure giving the title compound (990 mg, 84percent).LCMS data: Calculated MH+ (186); Found 98percent (MH+) m/z 186, Rt = 1.13 min. NMR data: 1H NMR (250 MHz, CDCl3) δ ppm 8.63 - 8.76 (1 H, m), 8.10 (1 H, d, J=8.4 Hz), 7.82 (1 H, dd, J=8.5, 2.4 Hz), 4.49 (2 H, q, J=7.2 Hz), 1.45 (3 H, t, J=7.2 Hz). |
76.6% | With hydrogenchloride In 1,4-dioxane at 90℃; for 20 h; | 5-Chloro-pyridine-2-carboxylic acid ethyl ester (146 mg, 76. [3percent)] was obtained obtained as described in Example 11 from 5-chloro-pyridine-2-carboxylic acid (200 mg, 1.03 mmol) with ethanol (3 mL) and 4M [HC1] in dioxane (0.5 mL) at 90 [°C] for 20 h. 5-Chloro-pyridine-2-carbaldehyde (58 mg, 52percent) was obtained as described in Example 11 from 5-chloro-pyridine-2-carboxylic acid ethyl ester (146 mg, 0.786 mmol) with 1 M DIBAL in toluene (1.74 mL, 1.74 mmol) in dichloromethane (4.0 mL) 20 min. GC-MS [(M+)] : 141 |
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