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CAS No. : | 95652-81-6 | MDL No. : | MFCD11847276 |
Formula : | C7H6ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AVBARORPQMEWPR-UHFFFAOYSA-N |
M.W : | 171.58 | Pubchem ID : | 10855945 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.13 |
TPSA : | 39.19 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.22 cm/s |
Log Po/w (iLOGP) : | 1.86 |
Log Po/w (XLOGP3) : | 1.58 |
Log Po/w (WLOGP) : | 1.56 |
Log Po/w (MLOGP) : | 0.52 |
Log Po/w (SILICOS-IT) : | 2.12 |
Consensus Log Po/w : | 1.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.17 |
Solubility : | 1.16 mg/ml ; 0.00675 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.01 |
Solubility : | 1.66 mg/ml ; 0.00969 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.71 |
Solubility : | 0.333 mg/ml ; 0.00194 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.71 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H317-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 |
---|---|---|
65% | Stage #1: With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1 h; Stage #2: at -78℃; for 2 h; |
To a solution of 2-chloro-6-methoxypyridine (5 g, 34.82 mmol) in THF (100 mL), cooled to −78° C. was added tBuLi (1.7 M) (18.5 mL, 31.34 mmol) and stirred for 1 h; DMF (92.2 g, 31.34 mmol) was then added at −78° C. and stirred for 2 h. The reaction mixture was quenched with acetic acid and poured in to ice cold water, basified with sat NaHCO3 and extracted with EtOAc (2×500 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to get crude product, which was purified by silica gel column (eluting with pet ether: ethyl acetate=10:1) to afford 6-chloro-2-methoxynicotinaldehyde as an off white solid (3.8 g, 65percent). ES+, m/z 172 [M+H]; [C7H6ClNO2], 1H NMR (300 MHz, CDCl3) δ 10.17 (s, 1H), 8.07 (d, J=8.04 Hz, 1H), 7.03 (d, J=8.04 Hz, 1H), 3.79 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tert.-butyl lithium In tetrahydrofuran; <i>N</i>-methyl-acetamide; acetic acid; pentane | EXAMPLE 1 6-Chloro-2-methoxy-3-pyridinecarboxaldehyde To a solution of tert-butyllithium (1.7M in pentane, 48.5 mL, 83.0 mmol) in 150 mL of THF at -78° C. was added 6-chloro-2-methoxypyridine (8.94 mL, 75.0 mmol) over 5 min. The reaction mixture was stirred at -78° C. for 1 h, then dimethylformamide (7.55 mL, 97 mmol) was added and the mixture was stirred at this temperature for 1.5 h. After the addition of glacial acetic acid (8.6 mL, 150 mmol), the reaction mixture was allowed to warm to room temperature over a 30- min period, then diluted with ether (200 mL). The organic phase was washed with saturated aqueous NaHCO3 (100 mL) and brine (100 mL), and was dried over MgSO4. Concentration afforded the crude product as a light yellow solid which was recrystallized from hexanes to give 9.6 g (75percent) of 6-chloro-2-methoxy-3-pyridinecarboxaldehyde as a white solid: mp 80°-81° C. (mp 62°-64° C.) (See Dainter, R. S.; Suschitzky, H.; Wakefield, B. J. Tetrahedron Lett. 1984, 25, 5693.). 1 H NMR (300 MHz, CDCl3) δ 10.31 (s,1H), 8.07 (d, 1H, J=9 Hz), 7.03 (d, 1H, J=9 Hz), 4.09 (s, 3H); IR (nujol) 1685, 1580, 1565, 1270, 1140, 1090, 1005, 905, 820, 755 cm-1. |
75% | With tert.-butyl lithium In tetrahydrofuran; <i>N</i>-methyl-acetamide; acetic acid; pentane | EXAMPLE 1 6-Chloro-2-methoxy-3-pyridinecarboxaldehyde To a solution of tert-butyllithium (1.7M in pentane, 48.5 mL, 83.0 mmol) in 150 mL of THF at -78° C. was added 6-chloro-2-methoxypyridine (8.94 mL, 75.0 mmol) over 5 min. The reaction mixture was stirred at -78° C. for 1 h, then dimethylformamide (7.55 mL, 97 mmol) was added and the mixture was stirred at this temperature for 1.5 h. After the addition of glacial acetic acid (8.6 mL, 150 mmol), the reaction mixture was allowed to warm to room temperature over a 30- min period, then diluted with ether (200 mL). The organic phase was washed with saturated aqueous NaHCO3 (100 mL) and brine (100 mL), and was dried over MgSO4. Concentration afforded the crude product as a light yellow solid which was recrystallized from hexanes to give 9.6 g (75percent) of 6-chloro-2-methoxy-3-pyridinecarboxaldehyde as a white solid: mp 80°-81° C. (mp 62°-64° C.)(See Dainter, R. S.; Suschitzky, H.; Wakefield, B. J. Tetrahedron Lett. 1984, 25, 5693.). 1 H NMR (300 MHz, CDCl3) δ 10.31 (s, 1H), 8.07 (d, 1H, J=9 Hz), 7.03 (d, 1H, J=9 Hz), 4.09 (s, 3H); IR (nujol) 1685, 1580, 1565, 1270, 1140, 1090, 1005, 905, 820, 755 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.3% | at 55℃; for 3 h; | 2,6-Dichloronicotinaldehyde (1 g, 5.68 mmol) was diluted with sodium methoxide (11.4 mL, 5.68 mmol) (solution in methanol) and heated to 55°C. After stirring for 3 hours, the reaction was loaded directly onto a silica gel column and eluted with 5percent ethyl acetate/hexanes to 50percent ethyl acetate/hexanes to yield 6-chloro-2- methoxynicotinaldehyde (0.695 g, 4.05 mmol, 71.3 percent yield). |
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