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. : | 84973-05-7 | MDL No. : | MFCD18253966 |
Formula : | C9H5BrClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AULIHGFJRSSSKE-UHFFFAOYSA-N |
M.W : | 242.50 | Pubchem ID : | 14555933 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.45 |
TPSA : | 12.89 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) : | -5.18 cm/s |
Log Po/w (iLOGP) : | 2.36 |
Log Po/w (XLOGP3) : | 3.66 |
Log Po/w (WLOGP) : | 3.65 |
Log Po/w (MLOGP) : | 3.12 |
Log Po/w (SILICOS-IT) : | 3.76 |
Consensus Log Po/w : | 3.31 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.27 |
Solubility : | 0.0131 mg/ml ; 0.0000542 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.62 |
Solubility : | 0.0582 mg/ml ; 0.00024 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.17 |
Solubility : | 0.00162 mg/ml ; 0.00000668 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.42 |
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 |
---|---|---|
In N,N-dimethyl-formamide at 150℃; | 9.A Step A: 7-chloroquinoline-3-carbonitrile Step A: 7-chloroquinoline-3-carbonitrile: To a flask containing a stir bar was added 3-bromo-7- chloroquinoline (1.0 g, 4.1 mmol), CuCN (0.55 g, 6.2 mmol) followed by addition of DMF (25 mL). The resulting mixture was then heated to 150 °C overnight. When the reaction was complete as evidenced by LC analyisis, the reaction flask was taken out of the oil bath and cooled to RT. To the reaction mixture was then poured DCM (20 mL) and a precipitate formed immediately, which was filtered. The filtrated was washed with aq. NH4CI, dried over sodium sulfate, and purified by flash chromatography. LC-MS (IE, m/z) 189 [M + 1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 150 °C 2: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 100 °C / Inert atmosphere 3: trifluoroacetic acid / 0.33 h / 20 °C 4: ethanol / 2 h / 140 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 150 °C 2: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 150 °C 2: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 100 °C / Inert atmosphere 3: trifluoroacetic acid / 0.33 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane / 2 h / 80 °C 2: bis-triphenylphosphine-palladium(II) chloride; potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 2 h / 95 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane / 2 h / 80 °C 2: bis-triphenylphosphine-palladium(II) chloride; potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 2 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane / 2 h / 80 °C 2: bis-triphenylphosphine-palladium(II) chloride; potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 2 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,2-dimethoxyethane at 80℃; for 2h; | Intermediate 11 7-chloroquinoline-3-pentanoylboronic acid 7-Chloro-3-bromoquinoline (3.58 mmol), divaleryl diboron (4.62 mmol)1,1'-bis(diphenylphosphino)ferrocene-palladium dichloride (0.39 mmol)And potassium acetate (7.7 mmol) was dissolved in 16 ml of ethylene glycol dimethyl ether, heated to 80 ° C, stirred for 2 hours, filtered, added with water and EA extraction, concentrated under reduced pressure, flash silica gel column chromatography to afford intermediate 11. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetic acid; nitric acid / 125 °C 2.1: trichlorophosphate / 115 °C 3.1: toluene-4-sulfonic acid hydrazide / chloroform / 24 h / 20 °C 3.2: 1 h / 80 °C 4.1: stannous chloride dihydrate / methanol / 100 °C 5.1: copper(ll) bromide; isopentyl nitrite / ethylene dibromide / 3 h / 70 °C | ||
Multi-step reaction with 5 steps 1.1: acetic acid; nitric acid / 125 °C 2.1: trichlorophosphate / 115 °C 3.1: toluene-4-sulfonic acid hydrazide / chloroform / 24 h / 20 °C 3.2: 1 h / 80 °C 4.1: tin(II) chloride dihdyrate / methanol / 100 °C 5.1: copper(ll) bromide; tert.-butylnitrite / ethylene dibromide / 3 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid hydrazide / chloroform / 24 h / 20 °C 1.2: 1 h / 80 °C 2.1: stannous chloride dihydrate / methanol / 100 °C 3.1: copper(ll) bromide; isopentyl nitrite / ethylene dibromide / 3 h / 70 °C | ||
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid hydrazide / chloroform / 24 h / 20 °C 1.2: 1 h / 80 °C 2.1: tin(II) chloride dihdyrate / methanol / 100 °C 3.1: copper(ll) bromide; tert.-butylnitrite / ethylene dibromide / 3 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: stannous chloride dihydrate / methanol / 100 °C 2: copper(ll) bromide; isopentyl nitrite / ethylene dibromide / 3 h / 70 °C | ||
Multi-step reaction with 2 steps 1: tin(II) chloride dihdyrate / methanol / 100 °C 2: copper(ll) bromide; tert.-butylnitrite / ethylene dibromide / 3 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(ll) bromide; isopentyl nitrite In ethylene dibromide at 70℃; for 3h; | 216 Example 30[00625] Synthesis of 4-((4'-chloro-3'-(trifluoromethoxy)-[l,l,-biphenyl]-4-yl)thio)-lH-l,2,3-triazole-5-carboxylic acid (30) General procedure: A mixture of isoamyl nitrite (4 mL, 30 mmol), copper (II) chloride (3.22 g, 24 mmol) and 4-bromo-2-(trifluoromethoxy)aniline (Compound 30A) (5.1 g, 20 mmol) in acetonitrile (80 mL) was heated at 70 °C for 3 hours. The mixture was poured into an aqueous HC1 solution (0.5 M, 50 mL) and extracted with ethyl acetate (50 mL x 2). The combined extracts were washed with water (50 mL x 4) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (petroleum ether) to afford Compound 30B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used. ‘H-NIVIR (DMSO-d6, 400 IVII{z): 5 (ppm) 7.33-7.3 5 (m, 1H), 7.37-7.40 (m, 1H), 7.48 (t, J= 1.6 Hz, 1H). | |
With tert.-butylnitrite; copper(ll) bromide In ethylene dibromide at 70℃; for 3h; | 216 Synthesis of 4-((4'-chloro-3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)thio)-1H- 1,2,3-triazole-5-carboxylic acid (30) General procedure: A mixture of isoamyl nitrite (4 mL, 30 mmol), copper (II) chloride (3.22 g, 24 mmol) and 4-bromo-2-(trifluoromethoxy)aniline (Compound 30A) (5.1 g, 20 mmol) in acetonitrile (80 mL) was heated at 70 oC for 3 hours. The mixture was poured into an aqueous HCl solution (0.5 M, 50 mL) and extracted with ethyl acetate (50 mL x 2). The combined extracts were washed with water (50 mL x 4) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (petroleum ether) to afford Compound 30B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.1H-NMR (DMSO-d6, 400 MHz): d (ppm) 7.33-7.35 (m, 1H), 7.37-7.40 (m, 1H), 7.48 (t, J = 1.6 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; lithium hexamethyldisilazane In toluene at 110℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; lithium hexamethyldisilazane / toluene / 2 h / 110 °C 2: Cs2CO3; caesium fluoride / N,N-dimethyl-formamide / 1.5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; lithium hexamethyldisilazane / toluene / 2 h / 110 °C 2: Cs2CO3; caesium fluoride / N,N-dimethyl-formamide / 1.5 h / 50 °C 3: chloro-trimethyl-silane; sodium iodide / acetonitrile / 1 h / 60 °C |