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CAS No. : | 577967-81-8 | MDL No. : | MFCD08899105 |
Formula : | C12H12ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GQKKWBQAXORHHB-UHFFFAOYSA-N |
M.W : | 237.68 | Pubchem ID : | 18524412 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 64.7 |
TPSA : | 31.35 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.29 cm/s |
Log Po/w (iLOGP) : | 2.76 |
Log Po/w (XLOGP3) : | 3.46 |
Log Po/w (WLOGP) : | 3.21 |
Log Po/w (MLOGP) : | 1.99 |
Log Po/w (SILICOS-IT) : | 3.54 |
Consensus Log Po/w : | 2.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.82 |
Solubility : | 0.0357 mg/ml ; 0.00015 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.8 |
Solubility : | 0.0377 mg/ml ; 0.000158 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.97 |
Solubility : | 0.00257 mg/ml ; 0.0000108 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.79 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
67% | With N,N-dimethyl-formamide; trichlorophosphate In N,N-dimethyl-formamide at 20 - 75℃; for 2 h; | The required 2-chloro-6,7-dimethoxy-3-methylquinoline was prepared according to the procedure published in Tetrahedron Letters 1979, 4885, in the following way: [0812] To a solution of 3,4-dimethoxyaniline (4.70 g, 30.7 mmol) in dichloromethane (50 ml) were added pyridine (8.0 ml, 3 equivalents) and then dropwise propionyl chloride (3.5 ml, 40.5 mmol). After stirring at room temperature for 1 h and 50 min the mixture was poured into a mixture of water (200 ml) and concentrated hydrochloric acid (8 ml). The phases were separated, and the aqueous phase was extracted once with dichloromethane. Washing of the combined organic phases with brine, drying with magnesium sulfate, and concentration yielded 6.89 g of an oil which crystallized after a few minutes. Recrystallization from a mixture of ethyl acetate and heptane yielded 3.60 g (49percent) of N-(3,4-dimethoxyphenyl)propionamide as dark crystals. [0813] This anilide (2.1 g, 10.0 mmol) was mixed with DMF (1.1 ml, 15 mmol), and to this mixture POCl3 (6.5 ml, 70 mmol) was dropwise added at room temperature. When the addition is finished the mixture is stirred at 75° C. for 2 h. The mixture was poured into ice-water (100 ml), stirred for 30 min, and filtered. The solid was stripped with toluene and acetonitrile, to yield 1.60 g (67percent) of 2-chloro-6,7-dimethoxy-3-methylquinoline as a solid. This product was treated with 1-cyclopropylpiperazine as described in General Procedure (B) to yield the title compound. [0814] 1H NMR (DMSO-d6) δ0.83 (m, 2H), 1.23 (m, 2H), 2.42 (s, 3H), 2.94 (m, 1H), 3.40-4.50 (m, 8H), 3.88 (s, 3H), 3.91 (s, 3H), 7.29 (s, 1H), 7.48 (br s, 1H), 8.12 (br s, 1H), 11.24 (br s, 1H); HPLC-MS: m/z 328 (MH+); Rt=1.63 min. |
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