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CAS No. : | 1195710-15-6 | MDL No. : | MFCD18382565 |
Formula : | C9H7ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | COLZTHKNBCUKOS-UHFFFAOYSA-N |
M.W : | 178.62 | Pubchem ID : | 20142091 |
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 : | 1.0 |
Molar Refractivity : | 51.16 |
TPSA : | 38.91 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) : | -5.78 cm/s |
Log Po/w (iLOGP) : | 1.63 |
Log Po/w (XLOGP3) : | 2.26 |
Log Po/w (WLOGP) : | 2.48 |
Log Po/w (MLOGP) : | 1.76 |
Log Po/w (SILICOS-IT) : | 2.36 |
Consensus Log Po/w : | 2.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.99 |
Solubility : | 0.184 mg/ml ; 0.00103 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.71 |
Solubility : | 0.345 mg/ml ; 0.00193 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.96 |
Solubility : | 0.0198 mg/ml ; 0.000111 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.43 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H312-H315-H319-H332-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 methanol; potassium hydroxide; nickel Hydrogenation; | ||
Multi-step reaction with 3 steps 1: chloroform / 24 h / 20 °C 2: sodium hydroxide / 1 h / 80 °C 3: water; tin(ll) chloride / methanol / 1 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 2 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 |
Multi-step reaction with 2 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7-Chloro-3-nitrochinolin, Fe, Reduktion; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: water; nitric acid 2: phosphoryl chloride 3: Raney nickel; methanol; KOH / Hydrogenation | ||
Multi-step reaction with 5 steps 1: nitric acid; propionic acid / 125 °C 2: trichlorophosphate / 18 h / 115 °C 3: chloroform / 24 h / 20 °C 4: sodium hydroxide / 1 h / 80 °C 5: water; tin(ll) chloride / methanol / 1 h / 80 °C / Inert atmosphere | ||
Multi-step reaction with 4 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 |
Multi-step reaction with 4 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: acetic acid / 1 h / 125 °C 2: sodium hydroxide 3: nitric acid; propionic acid / 125 °C 4: trichlorophosphate / 18 h / 115 °C 5: chloroform / 24 h / 20 °C 6: sodium hydroxide / 1 h / 80 °C 7: water; tin(ll) chloride / methanol / 1 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With water; tin(ll) chloride In methanol at 80℃; for 1h; Inert atmosphere; | |
With stannous chloride dihydrate In methanol at 100℃; | 186 To a solution of Compound 186D (200 mg, 0.96 mmol) in MeOH (10 mL) was added SnC122H2O (1.25 g, 4.8 mmol) and stirred at 100 °C overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 50% v/v) to leave a crude product, which was further purified with reverse phase chromatography using eluent (acetonitrile in water, from 0% to 20% v/v) afford Compound 186E. LC-MS (ESI) m/z: 179 [M+H] ‘HNIVIR (DMSO-d6, 400 MHz): 5 (ppm) 7.28 (s, 1H), 7.43 (d, J= 8.8 Hz, 1H),7.70-7.73 (m, 1H), 7.82 (s, 1H), 8.50(s, 1H). | |
With tin(II) chloride dihdyrate In methanol at 100℃; | 186 To a solution of Compound 186D (200 mg, 0.96 mmol) in MeOH (10 mL) was added SnCl . (3062) 22H2O (1.25 g, 4.8 mmol) and stirred at 100 oC overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 50% v/v) to leave a crude product, which was further purified with reverse phase chromatography using eluent (acetonitrile in water, from 0% to 20% v/v) afford Compound 186E. LC-MS (ESI) m/z: 179 [M+H]+; 1H- NMR (DMSO-d6, 400 MHz): d (ppm) 7.28 (s, 1H), 7.43 (d, J = 8.8 Hz, 1H),7.70-7.73 (m, 1H), 7.82 (s, 1H), 8.50(s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate; potassium phosphate / 1,4-dioxane / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate; potassium phosphate / 1,4-dioxane / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate; potassium phosphate / 1,4-dioxane / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: propan-1-ol / 4 h / 180 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate; potassium phosphate / 1,4-dioxane / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate; potassium phosphate / 1,4-dioxane / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate; potassium phosphate / 1,4-dioxane / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane / 24 h / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: propan-1-ol / 4 h / 180 °C / Inert atmosphere; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate; potassium phosphate / 1,4-dioxane / 24 h / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane / 24 h / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: bis[2-(diphenylphosphino)phenyl] ether; palladium diacetate; potassium phosphate / 1,4-dioxane / 24 h / 85 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C 3.1: propan-1-ol / 4 h / 180 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: 3-amino-7-chloroquinoline With tetrafluoroboric acid; sodium nitrite In water at 20℃; Cooling with ice; Stage #2: In 1,2-dichloro-benzene at 110℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium nitrite; tetrafluoroboric acid / water / 20 °C / Cooling with ice 1.2: 2 h / 110 °C 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 4 h / -85 - -78 °C 2.2: 2 h / -85 - -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: sodium hydroxide 2: nitric acid; propionic acid / 125 °C 3: trichlorophosphate / 18 h / 115 °C 4: chloroform / 24 h / 20 °C 5: sodium hydroxide / 1 h / 80 °C 6: water; tin(ll) chloride / methanol / 1 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / 1 h / 80 °C 2: water; tin(ll) chloride / methanol / 1 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride In ethyl acetate at 20℃; | 5 Step 5: Synthesis of 3-amino-7chloroquinoline 3-tert-Butoxycarbonylamino-7-chloroquinoline (20 g, 0.07 mol) dissolved in hydrochloric acidIn ethyl acetate solution (400 ml),Stirring at room temperature overnight, the raw materials are finished.Filtering,The filter cake was washed with ethyl acetate and then drained;The filter cake is dissolved in water, and the insoluble matter is filtered out, and then adjusted to a strong alkali with sodium hydroxide.Precipitating solid filtered solids,This is 3-amino-7-chloroquinoline (12.16 g, 95%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal / N,N-dimethyl-formamide / 48 h / 135 °C 2: tin(ll) chloride / ethanol / 4 h / 90 °C 3: sodium hydroxide; water / methanol / 3 h / 20 °C 4: diphenylphosphoranyl azide; triethylamine / 5 h / 100 °C 5: hydrogenchloride / ethyl acetate / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tin(ll) chloride / ethanol / 4 h / 90 °C 2: sodium hydroxide; water / methanol / 3 h / 20 °C 3: diphenylphosphoranyl azide; triethylamine / 5 h / 100 °C 4: hydrogenchloride / ethyl acetate / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide; water / methanol / 3 h / 20 °C 2: diphenylphosphoranyl azide; triethylamine / 5 h / 100 °C 3: hydrogenchloride / ethyl acetate / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 150℃; for 2h; Microwave irradiation; | 186 General procedure: To a solution of Compound 6A (138 mg, 0.32 mmol) in tolunen (4 mL) was added N-methylpiperazine (160 mg, 1.6 mmol), t-BuONa (61 mg, 0.64 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), and Xantphos (37 mg, 0.064 mmol) and heated in a microwave oven at 120 °C for 2 hours. The mixture was concentrated and purified by reverse phase column chromatography to afford Compound 6B. LC-MS (ESI) m/z: 440 [M+H]+. | |
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 150℃; for 2h; Microwave irradiation; | 186 General procedure: To a solution of Compound 6A (138 mg, 0.32 mmol) in tolunen (4 mL) was added N-methylpiperazine (160 mg, 1.6 mmol), t-BuONa (61 mg, 0.64 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), and Xantphos (37 mg, 0.064 mmol) and heated in a microwave oven at 120 oC for 2 hours. The mixture was concentrated and purified by reverse phase column (2208) chromatography to afford Compound 6B. LC-MS (ESI) m/z: 440 [M+H]+. |
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). |