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CAS No. : | 1203499-12-0 | MDL No. : | MFCD13563063 |
Formula : | C7H5ClFNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AQQNBZAKKNJYLI-UHFFFAOYSA-N |
M.W : | 173.57 | Pubchem ID : | 46318128 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 39.4 |
TPSA : | 29.96 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) : | 1.65 |
Log Po/w (XLOGP3) : | 1.6 |
Log Po/w (WLOGP) : | 2.5 |
Log Po/w (MLOGP) : | 1.16 |
Log Po/w (SILICOS-IT) : | 2.72 |
Consensus Log Po/w : | 1.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.26 |
Solubility : | 0.95 mg/ml ; 0.00547 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.84 |
Solubility : | 2.5 mg/ml ; 0.0144 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.25 |
Solubility : | 0.0972 mg/ml ; 0.00056 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.72 |
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 |
---|---|---|
86% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 5h; Inert atmosphere; | 1.1 S1, the synthesis of intermediate 1b: Compound 1a (3.47g, 20.0mmol),Pinacol diborate (5.6g, 22.0mmol),[1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.47g, 2.0mmol),Potassium acetate (3.93g, 40.0mmol) is dissolved in 1,4-dioxane (50mL),Under the protection of nitrogen, the temperature is raised to 100°C and the reaction is refluxed for 5 hours.The reaction was monitored by TLC. After the reaction was completed, it was concentrated under reduced pressure to remove the solvent.Then add 200mL purified water, extract three times with ethyl acetate,The volume of ethyl acetate used for each extraction is 50 mL,Combine the organic phases, and then wash the organic phases with 50 mL of purified water,Then wash the organic phase with 50 mL of saturated brine,Then it was dried with anhydrous sodium sulfate, concentrated under reduced pressure,Column chromatography separated 4.56g of intermediate 1b with a yield of 86.0%.Intermediate 1b is a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 3.1: ammonium hydroxide; sodium acetate / ethanol / 6 h / 60 °C 3.2: 3 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 10 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 3.1: ammonium hydroxide; sodium acetate / ethanol / 6 h / 60 °C 3.2: 3 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 10 h / 80 °C 5.1: lithium hydroxide monohydrate; water / methanol / 3 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 3.1: ammonium hydroxide; sodium acetate / ethanol / 6 h / 60 °C 3.2: 3 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 10 h / 80 °C 5.1: lithium hydroxide monohydrate; water / methanol / 3 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 3.1: ammonium hydroxide; sodium acetate / ethanol / 6 h / 60 °C 3.2: 3 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 10 h / 80 °C 5.1: lithium hydroxide monohydrate; water / methanol / 3 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 6 h / 20 °C 7.1: Kromasil AmyCoat chiral column / water; methanol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 3.1: ammonium hydroxide; sodium acetate / ethanol / 6 h / 60 °C 3.2: 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.7% | In tetrahydrofuran; methanol at -78 - 20℃; Inert atmosphere; | 5.2 1-(2-chloro-5-fluoropyridin-3-yl)ethan-1-one Dissolve 2-chloro-5-fluoro-N-methoxy-N-methylnicotinamide 5c (23g, 105.21mmol) in 250mL of anhydrous tetrahydrofuran, protect it with argon, cool to -78 at low temperature, and add methanol dropwise. Base magnesium bromide (45.6mL, 136.77mmol, 3mol/L inTHF), during the dripping process, keep the temperature between -78 and -60, and after the dripping, the temperature is naturally raised to room temperature overnight.LC-MS monitors the completion of the reaction. After cooling, it is quenched by adding saturated ammonium chloride solution.Add 200 mL of water, extract with ethyl acetate (100 mL×3), combine the organic phases, wash with saturated sodium chloride solution, dry with anhydrous sodium sulfate, and concentrate under reduced pressure. The residue obtained is further analyzed and purified by silica gel column chromatography (washing Removal: System A) to obtain 1-(2-chloro-5-fluoropyridin-3-yl)ethan-1-one 5d (15.6 g), yield: 85.7%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 20 °C 2: tetrahydrofuran; methanol / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 80 °C 2: sodium hydrogencarbonate / butan-1-ol / 100 °C 3: methanol; sodium tetrahydroborate / 1 h / 60 °C 4: water; iodine / tetrahydrofuran / 3 h / 50 °C 5: N-ethyl-N,N-diisopropylamine / butan-1-ol / 5 h / 120 °C 6: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 5 h / 50 °C 7: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C 8: N-ethyl-N,N-diisopropylamine; pentafluorophenyl diphenyl phosphate / N,N-dimethyl-formamide; dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 80 °C 2: sodium hydrogencarbonate / butan-1-ol / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 80 °C 2: sodium hydrogencarbonate / butan-1-ol / 100 °C 3: methanol; sodium tetrahydroborate / 1 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 80 °C 2: sodium hydrogencarbonate / butan-1-ol / 100 °C 3: methanol; sodium tetrahydroborate / 1 h / 60 °C 4: water; iodine / tetrahydrofuran / 3 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 80 °C 2: sodium hydrogencarbonate / butan-1-ol / 100 °C 3: methanol; sodium tetrahydroborate / 1 h / 60 °C 4: water; iodine / tetrahydrofuran / 3 h / 50 °C 5: N-ethyl-N,N-diisopropylamine / butan-1-ol / 5 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 80 °C 2: sodium hydrogencarbonate / butan-1-ol / 100 °C 3: methanol; sodium tetrahydroborate / 1 h / 60 °C 4: water; iodine / tetrahydrofuran / 3 h / 50 °C 5: N-ethyl-N,N-diisopropylamine / butan-1-ol / 5 h / 120 °C 6: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: titanium(IV) tetraethanolate / tetrahydrofuran / 80 °C 2: sodium hydrogencarbonate / butan-1-ol / 100 °C 3: methanol; sodium tetrahydroborate / 1 h / 60 °C 4: water; iodine / tetrahydrofuran / 3 h / 50 °C 5: N-ethyl-N,N-diisopropylamine / butan-1-ol / 5 h / 120 °C 6: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 5 h / 50 °C 7: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With titanium(IV) tetraethanolate In tetrahydrofuran at 80℃; | 5.3 (R,Z)-N-(1-(2-chloro-5-fluoropyridin-3-yl)ethylene)-2-methylpropane-2-sulfenamide The 1-(2-chloro-5-fluoropyridin-3-yl)ethan-1-one 5d (200mg, 1.15mmol), (R)-2-methylpropane-2-sulfenamide 1d (210mg, 1.73 mmol), tetraethyl titanate (1.05 g, 4.60 mmol) was dissolved in tetrahydrofuran, and reacted overnight at 80°C.LC-MS monitors the completion of the reaction. The reaction solution was added with 20 mL of water. The solid precipitated out. The filtrate was filtered and extracted with ethyl acetate (20 mL×3). The organic phases were combined, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was further analyzed and purified by silica gel column chromatography (eluent: system A) to obtain (R,Z)-N-(1-(2-chloro-5-fluoropyridin-3-yl)ethylene)- 2-Methylpropane-2-sulfenamide 5e (250mg), yield: 78%. |
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