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CAS No. : | 1103234-56-5 | MDL No. : | MFCD18157658 |
Formula : | C10H11F2NO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RTAWCKGXCGSFJI-UHFFFAOYSA-N |
M.W : | 279.26 | Pubchem ID : | 46192923 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 61.2 |
TPSA : | 91.85 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.93 cm/s |
Log Po/w (iLOGP) : | 0.66 |
Log Po/w (XLOGP3) : | 1.51 |
Log Po/w (WLOGP) : | 3.55 |
Log Po/w (MLOGP) : | 0.62 |
Log Po/w (SILICOS-IT) : | 1.4 |
Consensus Log Po/w : | 1.55 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.44 |
Solubility : | 1.02 mg/ml ; 0.00364 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.05 |
Solubility : | 0.251 mg/ml ; 0.000897 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.5 |
Solubility : | 0.0881 mg/ml ; 0.000316 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.36 |
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 |
---|---|---|
77% | Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Stage #2: With aluminum (III) chloride In dichloromethane at 20℃; |
General procedure: The carboxylic acid (1.1 eq.) was suspended in dry DCM (0.5 m), oxalyl chloride (1 .05 eq.) and a few drops of DMF were added successively. After the gas formation stopped the resulting solution was added dropwise to a suspension of the azaindole (1 eq.) and AICI3(5 eq.) in dry DCM (0.5 m). The mixture was stirred at room temperature for 0.5 - 3h.Saturated, aqueous NH4CI solution was added to quench the reaction. The water phase was extracted with EtOAc (3x), the combined organic layers were dried over Na2S04and the solvent was evaporated under reduced pressure. The product was purified via flash chromatography (Si02, nHex/EtOAc 1 :1 or DCM/MeOH (content of MeOH increased in 0.5percent- steps from 0 to 3percent (v/v)) to yield the titled compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; Stage #2: With hydrogenchloride In water |
Example C2,6-Difluoro-3-(propylsulfonamido)benzoic acidA IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(/V-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was washed with Et2O (4 X 15 mL) to give 2,6-difiuoro- 3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, d6- DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J= 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0. |
77% | Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; Stage #2: With hydrogenchloride In water |
A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight.The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C).IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 x 50 mL). The material was then washed with Et2O (4 x 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400MHz, DMSO- d6) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J= 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0. |
77% | Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; Stage #2: With hydrogenchloride In water |
A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 x 50 mL). The material was then washed with Et2O (4 x 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, DMSO- J6) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J= 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0. |
77% | Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran; methanol |
Example C2,6-Difluoro-3 -(propylsulfonamido)benzoic acid; [00238] A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(jV-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, (4-DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79- 1.69 (m, 2H), 0.98 (t, J= 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0. |
77% | Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water |
Intermediate Example B2,6-difluoro-3 -(propylsulfonamido)benzoic acid[00178] A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 350C). IN HCl (150 niL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was then washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, (CDg)2SO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06(m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0. |
77% | With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; | A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were removed in vacuo (water bath temperature 35°C). IN HC1 (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was washed with Et20 (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, (CD3)2SO) δ 9.74 (s, 1H), 7.57-7.50 (m, 1H), 7.23-7.17 (m, 1H), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J - 7.4 Hz, 3H). m/z (APCI-neg) M-l = 278.0. |
77% | Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; Stage #2: With hydrogenchloride In water |
A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was then washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, d6-DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0. |
77% | Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water |
2,6-difluoro-3 -(propylsulfonamido)benzoic acid <n="40"/>[00188] A IN aqueous NaOH solution (150 niL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)-benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 niL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was then washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, d6-DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H). m/z (APCI-neg) M-I = 278.0. |
77% | Stage #1: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; Stage #2: With hydrogenchloride In water |
A IN aqueous NaOH solution (150 mL, 150 mmol) was added to a solution of methyl 2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate (20.0 g, 50.1 mmol) in 4:1 THF/MeOH (250 mL, 0.2M). The reaction mixture was stirred at room temperature overnight. The majority of the organic solvents were then removed in vacuo (water bath temperature 35°C). IN HCl (150 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with water (4 X 50 mL). The material was then washed with Et2O (4 X 15 mL) to give 2,6-difluoro-3-(propylsulfonamido)benzoic acid as a solid (10.7 g, 77percent yield). 1H NMR (400 MHz, d6-DMSO) δ 9.74 (s, IH), 7.57-7.50 (m, IH), 7.23-7.17 (m, IH), 3.11-3.06 (m, 2H), 1.79-1.69 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H). m/z (APCI-neg) M-I == 278.0. |
55% | With sodium hydroxide In tetrahydrofuran; methanol; water at 0 - 20℃; | General procedure: The ester / disulfonamide was dissolved in THF/MeOH (1 m, 4:1 ), cooled to 0°C and treated with NaOHaq(2 M, 2 - 3 eq.). After 10 min. the ice bath was removed and the reaction was stirred at room temperature until complete hydrolysis. THF/MeOH was removed in vacuo, the residual was treated with HCq(2 m) upon precipitating of the product. The precipitate was filtered of, dried and was used without any further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With water; lithium hydroxide In tetrahydrofuran at 20℃; | Step 6: 2,6-difluoro-3-(propylsulfonamido)benzoic acid To a solution of methyl 2,6-difluoro-3-(propylsulfonamido)benzoate (22.3 g, 76 mmol) in THF (100 mL) was added LiOH aqueous (2.5 eq.) and the resulting reaction mixture was stirred at room temperature for overnight. The solvent was removed in vacuo and the residue was neutralized with HCl (6N) to pH1H NMR (DMSC i): ? 9.73 (1H, s), 7.55-7.49 (1H, m), 7.21-7.17 (1H, m), 3.09-3.05 (2H, m), 1.77-1.64 (2H, m), 0.96 (3H, t, J = 7.2 Hz). |
96% | With lithium hydroxide In tetrahydrofuran; water at 20℃; | To a solution of 2,6-difluoro-3-propanesulfonamidobenzoate (22.3 g, 76 mmol) in tetrahydrofenasilane was added an aqueous solution of lithium hydroxide (2.5 equivalents), and the resulting mixture was stirred at room temperature overnight. Vacuum concentration to remove most of the solvent, slowly dropping 6N hydrochloric acid to pH The filter cake was washed with a large amount of water and dried to give the title compound (20.4 g, 96percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With Oxone In N,N-dimethyl-formamide at 20℃; | To a reaction flask, propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (43, 3.00 g, 11.4 mmol) and oxone (9.10 g, 14.8 mmol) and 30 mL of anhydrous NN-dimethylformamide were added under nitrogen. The mixture was stirred at room temperature overnight, then quenched with 250 mL of 1 M hydrochloric acid solution and extracted with 250 mL of ethyl acetate. The organic layers were washed with 3 x 100 mL of IM hydrochloric acid solution and dried over magnesium sulfate. After removal of drying agent and solvent, the residue was dried in vacuo to provide the desired compound (45, 2.9g, 91percent). |
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