Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 101987-89-7 | MDL No. : | MFCD08706388 |
Formula : | C13H8ClF2NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZHFGWIOLVRSZNQ-UHFFFAOYSA-N |
M.W : | 299.66 | Pubchem ID : | 9835941 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.23 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 68.86 |
TPSA : | 59.3 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) : | -5.74 cm/s |
Log Po/w (iLOGP) : | 1.32 |
Log Po/w (XLOGP3) : | 3.37 |
Log Po/w (WLOGP) : | 3.74 |
Log Po/w (MLOGP) : | 2.58 |
Log Po/w (SILICOS-IT) : | 3.34 |
Consensus Log Po/w : | 2.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -4.06 |
Solubility : | 0.0262 mg/ml ; 0.0000873 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.29 |
Solubility : | 0.0152 mg/ml ; 0.0000509 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.92 |
Solubility : | 0.036 mg/ml ; 0.00012 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.2 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
With hydrogenchloride; In pyridine; water; | STR20 3 g (0.01 mole) of the product from Example B are heated under reflux in 25 ml of pyridine with 4 g (0.04 mole) of 2-methyl-piperazine for 5 hours. The mixture is concentrated in vacuo, 20 ml of water are added, the pH is brought to 5 with 2N hydrochloric acid and the precipitate which separates out is recrystallized from methanol. 0.6 g (16% of theory) of 8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid of melting point 318-325 C. (with decomposition) is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With triethylamine In acetonitrile for 7.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; for 24h; | Example 70A8-Chloro-1-cyclopropyl-N-(2,4-dichlorobenzyl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide; 15.0 g of 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (for preparation see DE 3420743 or Y. Kimura et al. J. Med. Chem. 1994, 37 (20), 3344) are dissolved in 500 ml of DMF, and 31.3 g of PyBOP and 10.6 g of 2,4-dichlorobenzylamine are added. After one day the solvent is removed on a rotary evaporator and the residue is purified by flash chromatography on silica gel (toluene/ethyl acetate 95:5). 21.2 g (93% of theory) of the title compound are obtained.LC-MS (method 1): Rt=3.10 min, MS (ES+)=457 (M+H)+.1H NMR (300 MHz, DMSO-d6): delta=1.05-1.16 (m, 2H), 1.18-1.29 (m, 2H), 4.32 (m, 1H), 4.99 (d, J=6.0 Hz, 1H), 7.35-7.45 (m, 2H), 7.64 (d, J=2.0 Hz, 1H), 8.22 (dd, J=8.9, 10.0 Hz, 1H), 8.79 (s, 1H), 10.01 (t, J=6.0 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-diaza-bicyclo[2.2.2]octane; N-methyl-acetamide; acetonitrile; | EXAMPLE Z2 STR90 A. 8-Chloro-1-cyclopropyl-7-([S,S]-2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 15 g (50 mmol) of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are heated under reflux for 1 hour in a mixture consisting of 150 ml of acetonitrile/75 ml of dimethylformamide in the presence of 8.25 g (75 mmol) of 1,4-diazabicyclo[2.2.2]octane (DABCO) together with 7.0 g (55 mmol) of (+)-[S,S]-2,8-diazabicyclo[4.3.0]nonane. The solution is cooled and scratched to induce crystallisation, and the precipitate which has separated out is, after standing overnight, filtered off with suction, washed with acetonitrile and dried at 100 C. in an air-circulation drying oven. Yield: 13.5 g (66.6% of theory), Melting point: 193-196 C. (with decomposition), Rf value (silica gel; methylene chloride/methanol/17% strength aqueous NH3 =30:8:1): 0.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N-methyl-acetamide; acetonitrile; | A) A solution of 66.4 g (0.44 mol) of 3-nitrobenzaldehyde in 400 ml of acetonitrile is added to a solution of 34.4 g (0.4 mol) of <strong>[79286-79-6]3-aminopyrrolidine</strong> in 400 ml of acetonitrile and the mixture is stirred at room temperature for 1 hour. It is then diluted with 400 ml of dimethylformamide, 88 g (0.79 mol) of 1,4-diazabicyclo[2.2.2]octane and 120 g (0.4 mol) of 8-chloro-1-cyclo propyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are added and the mixture is heated under reflux (about 91 C. to 92 C.) for 1 hour. The resulting suspension is cooled on an ice bath and the precipitate which has separated out is filtered off with suction, washed with acetonitrile and dried. Yield: 168.5 g (84.5% of theory) of 8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-7-[3-(3-nitrobenzylideneamino)-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid; melting point: 204 C.-207 C. (with decomposition). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N-methyl-acetamide; acetonitrile; | A) 1.1 g (12.8 mmol) of pivalaldehyde are added to 0.86 g (10 mmol) of <strong>[79286-79-6]3-aminopyrrolidine</strong> at room temperature, during which the temperature rises from 20 C. to 30 C. After 1 hour, the mixture is diluted with 20 ml of acetonitrile and 10 ml of dimethylformamide, 3 g (10 mmol) of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 2.2 g (20 mmol) of 1,4-diazabicyclo[2.2.2]octane are then added and the mixture is heated under reflux for 1 hour. After cooling, the precipitate is filtered off with suction, washed with acetonitrile and dried at 100 C./12 mbar. Yield: 3.25 g (75% of theory) of 8-chloro-1-cyclopropyl-7-[3-(2,2-dimethylpropylideneamino)-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of melting point: 181 C. to 182 C. FAB mass spectrum: m/e 434 (100%, M+H?) |
[ 127199-27-3 ]
8-Chloro-6,7-difluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.95
[ 86393-33-1 ]
7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.91
[ 68077-26-9 ]
1-Ethyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid
Similarity: 0.88
[ 93107-30-3 ]
1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.87
[ 94695-52-0 ]
1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.86
[ 127199-27-3 ]
8-Chloro-6,7-difluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.95
[ 86393-33-1 ]
7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.91
[ 68077-26-9 ]
1-Ethyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid
Similarity: 0.88
[ 98105-79-4 ]
7-Chloro-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.83
[ 93110-13-5 ]
7-Chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.83
[ 127199-27-3 ]
8-Chloro-6,7-difluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.95
[ 86393-33-1 ]
7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.91
[ 68077-26-9 ]
1-Ethyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid
Similarity: 0.88
[ 93107-30-3 ]
1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.87
[ 94695-52-0 ]
1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.86
[ 127199-27-3 ]
8-Chloro-6,7-difluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.95
[ 86393-33-1 ]
7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.91
[ 68077-26-9 ]
1-Ethyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid
Similarity: 0.88
[ 93107-30-3 ]
1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.87
[ 94695-52-0 ]
1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.86
[ 127199-27-3 ]
8-Chloro-6,7-difluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.95
[ 86393-33-1 ]
7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.91
[ 68077-26-9 ]
1-Ethyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid
Similarity: 0.88
[ 93107-30-3 ]
1-Cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.87
[ 94695-52-0 ]
1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Similarity: 0.86