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CAS No. : | 82964-91-8 | MDL No. : | MFCD00216486 |
Formula : | C7H7ClO4S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TYJOQICPGZGYDT-UHFFFAOYSA-N |
M.W : | 254.71 | Pubchem ID : | 2735182 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 52.62 |
TPSA : | 85.04 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.44 cm/s |
Log Po/w (iLOGP) : | 1.25 |
Log Po/w (XLOGP3) : | 0.58 |
Log Po/w (WLOGP) : | 3.18 |
Log Po/w (MLOGP) : | 1.03 |
Log Po/w (SILICOS-IT) : | 0.68 |
Consensus Log Po/w : | 1.34 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.97 |
Solubility : | 2.73 mg/ml ; 0.0107 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.94 |
Solubility : | 2.93 mg/ml ; 0.0115 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.25 |
Solubility : | 0.142 mg/ml ; 0.000556 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.31 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
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 triethylamine In dichloromethane for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In benzene for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In benzene for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With dihydrogen peroxide In acetic anhydride; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In sodium hydroxide at 60 - 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triethylamine In dichloromethane 1) 0 deg C, 1 h, 2) room temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In chloroform 1.) RT, 1 h, 2.) reflux, 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With triethylamine In pyridine for 168h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With water; chlorine In acetic acid for 0.75h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride In tetrahydrofuran Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-methylsulfinylbenzenesulfonyl chloride; 3-methyl-5-[4-tert-butoxycarbonylamino(tert-butoxycarbonylimino)methyl-aminobutoxy]phenol With diethylaminomethyl-polystyrene resin In acetonitrile for 52h; Stage #2: With aminomethyl-polystyrene resin In acetonitrile at 20 - 55℃; for 112h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at -78 - 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: 4-methylsulfinylbenzenesulfonyl chloride With sodium hydrogencarbonate; sodium sulfite In water at 100℃; for 1h; Stage #2: chlorobromomethane With tetrabutylammomium bromide In water at 75℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In methanol at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With polymer-supported 1,3,2-diazaphosphorinane derivative In acetonitrile at 150℃; for 0.25h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
433 mg | With dmap In 1,2-dichloro-ethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 18-crown-6 ether; potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; sodium sulfite In water at 80℃; for 3h; | C.2 To a solution of 0.26 g (3.2 mmol) of NaHCO3 and 0.4 g (3.2 mmol) of Na2SO3 in water (1.5 mL) were added 0.4 g (1.6 mmol) of 4-(methylsulfonyl)-benzenesulfonyl chloride. The reaction was heated at 80° C. for 3 h. The solvent was removed under reduced pressure. The crude material was suspended in boiling ethanol (20 mL) and the inorganic solids were removed by filtration. The filtrate was concentrated under reduced pressure to afford 0.14 g of 4-methanesulfonyl-benzenesulfinic acid sodium salt. | |
With sodium hydrogencarbonate; sodium sulfite In water at 80℃; for 3h; | E.1 Synthesis of 2-(4-Methanesulfonyl-benzenesulfonyl)-2-methyl-propionic acid Step 1: Synthesis of Sodium 4-methanesulfonyl-benzenesulfinate Prepared as described by adaptation of the following references: Faucher, A.-M. et al. J. Med. Chem. 2004, 47, 19-21; Binsiti, C. Eur. J. Med. Chem. Chim. Ther. 2001, 36, 809-828.Field, L.; Clark, R.D. Org. Synth. 1958, 38, 62-64.To a solution of 0.57 g of NaHC03 (7.1 mmol) and 1.1 g of Na2S03 (8.8 mmol) in water (5.0 mL) were added 1.0 g (3.9 mmol) of 4-methanesulfonyl-benzenesulfonyl chloride. The reaction was heated at 80 °C for 3 h. The solvent was removed under reduced pressure. The filtrate was concentrated under reduced pressure to give sodium 4-methanesulfonyl-benzenesulfinate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11 3-Fluoro-4-(3-chloro-5-pyridyloxy)aniline (310 mg, see Example 9) and 4-methylthiobenzenesulfonyl chloride (298 mg, prepared as described in Burton, et al., J. Chem. Soc., 604-5 (1948)), were combined in a manner similar to that described in Example 3. The crude product was purified by flash chromatography on silica, eluting with ethyl acetate/hexanes/dichloromethane (1:5:4). The product fractions were concentrated and the solid was recrystallized from hexanes/diethyl ether to provide the title compound as a white solid (315 mg, 57%), mp 130-131° C. The title compound was oxidized with mCPBA to the corresponding sulfoxide (11.2, mp 140-144 CC). The corresponding sulfone (11.3) was prepared using 4-(methylsulfonyl)benzenesulfonyl chloride (mp 165-168° C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With pyridine In tetrahydrofuran at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In dichloromethane at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / pyridine / tetrahydrofuran / 25 °C 2: 23 percent / diisopropylamine / tetrakis(triphenylphosphine)palladium; copper iodide / N,N-dimethyl-acetamide; H2O / 0.17 h / 100 °C / microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 98 percent / DABCO / CH2Cl2 / 5 h / 20 °C 2: 87 percent / Dowex 50 x 20-200 ion-exchange resin / methanol / 16 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 75 percent / KOH / ethanol / 3 h / Heating 2.1: hydrochloric acid; NaNO2 / acetic acid; H2O / -10 °C 2.2: SO2; CuCl2 / acetic acid; H2O / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / CH2Cl2 / 3 h / 20 °C 2: hydrochloric acid / acetone; H2O / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / CH2Cl2 / 3 h / 20 °C 2: hydrochloric acid / acetone; H2O / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 40 percent / NaHCO3 / H2O / 20 h / Heating 2.1: 75 percent / KOH / ethanol / 3 h / Heating 3.1: hydrochloric acid; NaNO2 / acetic acid; H2O / -10 °C 3.2: SO2; CuCl2 / acetic acid; H2O / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 100 percent / Na2SO3; NaHCO3 / H2O / 3 h / 90 °C 2.1: 40 percent / NaHCO3 / H2O / 20 h / Heating 3.1: 75 percent / KOH / ethanol / 3 h / Heating 4.1: hydrochloric acid; NaNO2 / acetic acid; H2O / -10 °C 4.2: SO2; CuCl2 / acetic acid; H2O / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / CHCl3 / 1.) RT, 1 h, 2.) reflux, 1 h 2: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, overnight |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Et3N / CHCl3 / 1.) RT, 1 h, 2.) reflux, 1 h 2: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, overnight 3: HONH2*HCl, NaOMe / methanol / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine In tetrahydrofuran at 20℃; for 1h; | 102.1 1) To a solution (10 mL) of tert-butyl [5-(aminomethyl)-2- isobutyl-6-methyl-4- (4-methylphenyl) pyridin-3- yl] methyl} carbamate (290 mg, 0.729 mmol) and triethylamine (0.15 mL, 1.09 mmol) in tetrahydrofuran was added 4- (methylsulfonyl) benzenesulfonyl chloride (223 mg, 0.875 mmol) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate (100 mL) and washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained yellow solid was washed with diisopropyl ether to give tert-butyl ( {2-isobutyl-6- methyl-4- (4-methylphenyl)-5- [ ( { [4- (methylsulfonyl) phenyl] sulfonyl} amino) methyl] pyridin-3- yl} methyl) carbamate (391 mg, yield 87%) as a yellow powder. 1 H-NMR (CDC13) 8 : 0. 95 (6H, d, J = 6.6 Hz), 1. 36 (9H, s), 2.13- 2.22 (1H, m), 2.41 (3H, s), 2.61 (3H, s), 2.73 (2H, d, J = 7.4 Hz), 3.08 (3H, s), 3.83 (2H, d, J = 5.8 Hz), 3.97 (2H, d, J = 4.9 Hz), 4.11-4. 20 (2H, m), 6.84 (2H, d, J = 8.1 Hz), 7.13 (2H, d, J = 7.7 Hz), 7.77 (2H, d, J = 8.7 Hz), 7.98 (2H, d, J = 8.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 20℃; for 16h; | 1 Example 1 This Example illustrates the preparation OFV- [ (L- { (3)-3- (3, 5-DIFLUOROPHENYL)-3- [4- (methylsulfonyl) PHEILYLJPROPYL} PIPERIDIN-4-YL) METHYL]-4-(METHYLSULFONYL) BENZENESULFONAMIDE (Compound 1, Table IS) 4-Methanesulphonylbenzenesulphonyl chloride (135 mg) was added to a solution of N- [ (1-1 (3R)-3- (3, 5-DIFLUOROPHONYL)-3- [4- (METHYLSULPHONYL) phenyl] propyl} piperidin-4- yl) methylamine dihydrochloride (250 mg) and triethylamine (162 mg) in dichloromethane (10 ml) and the mixture was stirred at 20°C for 16 hours. The reaction mixture was washed with water (2x 10 ml), dried and evaporated to dryness. The residue was passed down a Bond Elut column eluting with a solvent gradient (ethyl ACETATE-30% methanol/ethyl acetate) to give the title compound, yield 176 mg, MH+ 641. NMR (DMSOd6): 1.02 (q, 2H), 1.29 (m, 1H), 1.55 (d, 2H), 1.73 (t, 2H), 2.03-2. 27 (m, 3H), 2.6-2. 78 (m, 3H), 3.27 (s, 6H), 4.17 (t, 1H), 7.0 (m, 1H), 7.10 (d, 2H), 7.6 (d, 2H), 7.80 (m, 3H), 8.0 (d, 2H), 8.13 (d, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23 4-(Methylsulfonyl)-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]-benzenesulfonamide Hydrochloride (Scheme 2, Method 4) Example 23 4-(Methylsulfonyl)-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)phenyl]-benzenesulfonamide Hydrochloride (Scheme 2, Method 4) 4-(Methylsulfonyl)-N-[2-[(phenylsulfonyl)amino]-4-(1-piperazinyl)-phenyl]benzenesulfonamide was synthesised from N-{2-amino-5-(4-t-butyloxycarbonyl-piperazinyl)-phenyl}benzenesulfonamide and 4-methylsulfonylbenzenesulfonylchloride (61 mg, 0.455 mmol) according to general method 3 to give 70 mg of a purple solid. MS (posES-FIA) m/z=Found: 551.2; Caled: 551.10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66 N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-4-(methylsulfonyl)benzenesulfonamide Hydrochloride (Scheme 3) Example 66 N-{4-(1,4-diazepan-1-yl)-2-[(phenylsulfonyl)amino]phenyl}-4-(methylsulfonyl)benzenesulfonamide Hydrochloride (Scheme 3) The compound was synthesised from of N-{2-amino-5-(4-t-butyloxycarbonyl-1,4-diazepan-1-yl)-phenyl}benzenesulfonamide and 4-methylsulfonylbenzenesulfonylchloride (69 mg, 0.269 mmole) to give 38 mg as purple solid. M+1 565.3 Calcd 565.12; 1H-NMR δ 8.08-7.48 (m, 9H), 6.76 (d, 1H), 6.48 (dd, 1H), 6.32 (d, 1H), 3.61 (app t, 2H), 3.38 (app t, 2H), 3.21 (app t, 2H), 3.17 (app t, 2H), 3.14 (app t, 2H), 2.08-2.00 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.1% | With dmap; triethylamine In tetrahydrofuran at 20℃; for 3h; | 9 Compound 8. To a stirring mixture of compound 7 (0.050 g, 0.0986 mmoL), triethylamine (0.110 mL, 0.788 mmoL), and DMAP (0.006 g, 0.049 mmoL) in 2 mL of anhydrous THF was added dropwise by syringe 4-methanesulfonyl-benzenesulfonyl chloride (0.075 g, 0.295 mmoL) in 1 mL of THF. After stirring at room temperature for 3 hours, the reaction mixture was diluted with EtOAc (30 mL). The organic solution was washed with 1.0 N HCl aqueous solution (1*20 mL), water and brine, dried over Na2SO4, and concentrated. The crude product was purified on a silica gel flash column (20% EtOAc in Hexane) to give 0.061 g (0.083 mmoL, 81.1%) as a light yellow solid. MS (API-ES) at m/z 725, 727, 729. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With pyridine In dichloromethane at 20℃; for 6h; | Intermediate 7; 4-(4-Methanesulfonyl-benzenesulfonyIamino)-benzoic acid methyl ester; To a stirring solution of 4-amino-benzoic acid methyl ester (0.594 g, 3.93 mmol) in a mixture of dichloromethane (15 niL) / pyridine (15 mL) is added 4-methanesulfonyl benzenesulfonyl chloride (1.0 g, 3.93 mmol) and the mixture is allowed to react for 6 h at ambient temperature. The reaction is diluted with ethyl acetate and washed with IN HCl. The organic layer is separated and dried over sodium sulfate, filtered, and concentrated to give 1.26 g (87%) of the title compound. MS (ES-) (m/e) 368.0 (M-I)". |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | Stage #1: 5-phenyl-1H pyrrole-3-carboxaldehyde With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With 15-crown-5 In tetrahydrofuran for 0.5h; Stage #3: 4-methylsulfinylbenzenesulfonyl chloride In tetrahydrofuran for 1h; | |
21% | Stage #1: 5-phenyl-1H pyrrole-3-carboxaldehyde With sodium hydride In tetrahydrofuran; mineral oil at 10 - 35℃; for 0.5h; Stage #2: With 15-crown-5 In tetrahydrofuran; mineral oil for 0.5h; Stage #3: 4-methylsulfinylbenzenesulfonyl chloride In tetrahydrofuran; mineral oil for 1h; | 231 1-[4-(Methylsulfonyl)phenyl]sulfonyl}-5-phenyl-1H-pyrrole-3-carbaldehyde Reference Example 231 1-[4-(Methylsulfonyl)phenyl]sulfonyl}-5-phenyl-1H-pyrrole-3-carbaldehyde To a solution (14 mL) of 5-phenyl-1H-pyrrole-3-carbaldehyde (140 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 66 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (361 mg) was added dropwise and the mixture was stirred for 30 min, [4-(methylsulfonyl)benzene]sulfonyl chloride (313 mg) was added, and the mixture was further stirred for 1 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3→1:1), crystallized from ethyl acetate·diisopropyl ether mixed solvent (1:1) to give the title compound as yellow crystals (yield 67 mg, 21%). 1H-NMR (CDCl3)δ: 3.05 (3H, s), 6.61 (1H, d, J=1.8 Hz), 7.14-7.17 (2H, m), 7.30-7.35 (2H, m), 7.41-7.52 (3H, m), 7.87-7.91 (2H, m), 8.12 (1H, d, J=1.8 Hz), 9.90 (1H, s). |
In tetrahydrofuran | R.231 1-[4-(Methylsulfonyl)phenyl]sulfonyl}-5-phenyl-1H-pyrrole-3-carbaldehyde Reference Example 231 1-[4-(Methylsulfonyl)phenyl]sulfonyl}-5-phenyl-1H-pyrrole-3-carbaldehyde To a solution (14 mL) of 5-phenyl-1H-pyrrole-3-carbaldehyde (140 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 66 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (361 mg) was added dropwise and the mixture was stirred for 30 min, [4-(methylsulfonyl)benzene]sulfonyl chloride (313 mg) was added, and the mixture was further stirred for 1 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3→1:1), crystallized from ethyl acetate·diisopropyl ether mixed solvent (1:1) to give the title compound as yellow crystals (yield 67 mg, 21%). 1H-NMR (CDCl3)δ: 3.05 (3H, s), 6.61 (1H, d, J=1.8 Hz), 7.14-7.17 (2H, m), 7.30-7.35 (2H, m), 7.41-7.52 (3H, m), 7.87-7.91 (2H, m), 8.12 (1H, d, J=1.8 Hz), 9.90 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In chloroform at 70℃; for 7h; | 8.33 Berberrubine (200 mg, 0.56 mmol) was dissolved in 30 mL CHCl3 at 70° C. Then 4-(methylsulfonyl)benzene-1-sulfonyl chloride (350 mg, 1.37 mmol) was added to the solution and stirred for 7 hours at 70° C. Then product was filtered, washed by CHCl3 and dried. 200 mg product was obtained as yellow solid. (yield: 62%) The intermediate compound 113 was used directly without further purification. |
62% | In chloroform at 70℃; for 7h; | 2.18 18. Preparation of Compound I13 from Berberrubine. Berberrubine (200 mg, 0.56 mmol) was dissolved in 30 mL CHCl3 at 70° C. Then 4-(methylsulfonyl)benzene-1-sulfonyl chloride (350 mg, 1.37 mmol) was added to the solution and stirred for 7 hours at 70° C. Then product was filtered, washed by CHCl3 and dried. 200 mg product was obtained as yellow solid. (yield: 62%) The intermediate compound 113 was used directly without further purification. |
62% | In chloroform at 70℃; for 7h; | 8.33 33. Preparation of Compound 113 from Berberrubine. [00232] Berberrubine (200 mg, 0.56 mmol) was dissolved in 30 mL CHCb at 70°C. Then 4-(methylsulfonyl) benzene- 1-sulfonyl chloride (350 mg, 1.37 mmol) was added to the solution and stirred for 7 hours at 70°C. Then product was filtered, washed by CHCb and dried. 200 mg product was obtained as yellow solid. (yield:62%) The intermediate compound 113 was used directly without further purification. |
In chloroform at 70℃; for 7h; | 8.33 Berberrubine (200 mg, 0 56 mmol) was dissolved m 30 mL CHCl3 at 700CThen 4-(methylsulfonyl) benzene-1 -sulfonyl chloride (350 mg, 1 37 mmol) was added to the solution and stirred for 7 hours at 70QC Then product was filtered, washed by CHCI3 and dned 200 mg product was obtained as yellow solid (yield 62%) The intermediate compound 113 was used directly without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 1h; | A.1 Preparation #A.1: Methyl 2-(5-methyl-6-(4-(methylsulfonyl)phenylsulfonyl)-6H-thieno[2,3-b]pyrrol-4-yl)acetate To a solution of methyl 2-(5-methyl-6H-thieno[2,3-b]pyrrol-4-yl)acetate (0.059 g, 0.282 mmol) in THF at about 0° C. was added tBuOK (0.044 g, 0.395 mmol), followed by the 4-(methylsulfonyl)-benzene-1-sulfonyl chloride (0.086 g, 0.338 mmol). The reaction mixture was stirred at ambient temperature for about 1 h to give the crude title compound, which was used without further purification. LC/MS (Table 1, Method b) Rt=2.25 min; MS m/z 428 (M+H)+. | |
Stage #1: methyl 2-(5-methyl-6H-thieno[2,3-b]pyrrol-4-yl)acetate With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; Stage #2: 4-methylsulfinylbenzenesulfonyl chloride at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With pyridine at 130℃; for 0.05h; Microwave irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With pyridine at 130℃; for 0.05h; Microwave irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With pyridine at 20℃; for 18h; | Preparation of Compound C0009 Compound C0009To a solution of compound C0009-2 (570 mg, 1.58 mmol) in pyridine (20 mL) was added 4-methyl-sulfonyl-benzene sulfonyl chloride (604 mg, 2.37 mmol). The mixture was then stirred overnight (about 18 hours) at room temperature. The solvent was then removed under reduced pressure. The crude product was then diluted with CH2Cl2 (250 mL) and washed with 1M HCl (100mL×2), and the aqueous layer was extracted with CH2Cl2 (100 mL). The organic phase was then dried over anhydrous Na2SO4 and concentrated and then the crude product was recrystallized from DCN to give 150 mg purified product as a light yellow solid (1H-NMR and MS confirmed, HPLC: 96%). The solution was then evaporated to give 200 mg of the purified product. The pure product was then re-purified with silica gel column to give C0009 as a light yellow solid (180 mg, yield: 33%, 1H-NMR and MS confirmed, HPLC: 96%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 2-(3,5-dimethyl-6H-thieno[2,3-b]pyrrol-4-yl)acetate With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; Stage #2: 4-methylsulfinylbenzenesulfonyl chloride at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With 18-crown-6 ether; potassium <i>tert</i>-butylate at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 30℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In tetrahydrofuran at 60℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With triethylamine In dichloromethane at 20℃; | |
With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 2h; | 24 Example 24 - Synthesis of N-(3-(3-chloro-10,l l-dihydro-5H-dibenzo[b,fjazepin-5- yl)propyl)-4-(methylsulfonyl)benzenesulfonamide [00109] A solution of 3-(3-chloro-10,l l-dihydro-5H-dibenzo[i )azepin-5-yl)propan- 1 -amine hydrochloride (0.0800 g, 0.247 mmol) in DMF (1.0 mL) was cooled to 0 °C, treated with Ets (72 μί, 0.520 mmol), and 4-(methylsulfonyl)benzenesulfonyl chloride (0.0690 g, 0.272 mmol). The mixture was warmed to 25 °C, and stirred for 2 h. The mixture was partitioned between saturated aqueous NaCI (50 mL), and CH2CI2 (100 mL). The organic layer was washed with saturated aqueous NaCI (2 x 50 mL), dried (Na2S04), and concentrated in vacuo. The residue was dissolved in a minimal amount of CH2CI2 and purified by flash chromatography (Si02, 0-25% hexanes-Ethyl acetate) to afford the title compound as a white solid (0.1170 g, 94%). Ή NMR (600 MHz, CDCI3) δ 8.01 (2H, d, J= 7.9 Hz), 7.91 (211, d, J= 7.67 Hz), 7.13-7.17 (2H, m), 7.00 (3H, m), 6.97 (IH, s).6.91 (1H, d, ./= 8.2 Hz), 4.57 (1H, br s), 3.72 (2H, t, J = 5.8 Hz), 3.10 (3H, br s), 3.08 (2H, m), 3.06 (4H, br s), 1.76 (2H, quintet, 7= 6.2 Hz); l3C NMR (150 MHz, CDCI3) δ 148.8, 147.4, 145.5, 144.3, 135.1, 131.84, 131.83, 131.7, 130.0, 128.5, 128.1, 127.0, 124.0, 122.8, 120.2, 119.7, 47.5,44.5,41.5, 32.1, 31.5, 27.6; LCMS m/z 505.0598 ([M + H+], C24H25CIN2O4S2 requires 505.1017). |
94% | With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 2h; | RTC-44:N-(3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-4-(methylsulfonyl)benzenesulfonamide A solution of 3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propan-1-amine hydrochloride (0.0800 g, 0.247 mmol) in DMF (1.0 mL) was cooled to 0 C, treated with triethylamine (72 L, 0.520 mmol), and 4-(methylsulfonyl)benzenesulfonyl chloride (0.0690 g, 0.272 mmol). The mixture was warmed to 25 C, and stirred for 2 h. The mixture was partitioned between saturated aqueous NaCl (50 mL), and CH2Cl2 (100 mL). The organic layer was washed with saturated aqueous NaCl (2 50 mL), dried (Na2SO4), and concentrated in vacuo. The residue was dissolved in a minimal amount of CH2Cl2 and purified by flash chromatography (SiO2, 0-25% ethyl acetate-hexanes) to afford the title compound as a white solid (0.117 g, 94%). 1H NMR (600 MHz, CDCl3) 8.01 (2H, d, J = 7.9 Hz), 7.91 (2H, d, J = 7.7 Hz), 7.13-7.17 (2H, m), 7.00 (3H, m), 6.97 (1H, s), 6.91 (1H, d, J = 8.2 Hz), 4.57 (1H, br s), 3.72 (2H, t, J = 5.8 Hz), 3.10 (3H, br s), 3.08 (2H, m), 3.06 (4H, br s), 1.76 (2H, quintet, J = 6.2 Hz); 13C NMR (150 MHz, CDCl3) 148.8, 147.4, 145.5, 144.3, 135.1, 131.84, 131.83, 131.7, 130.0, 128.5, 128.1, 127.0, 124.0, 122.8, 120.2, 119.7, 47.5, 44.5, 41.5, 32.1, 31.5, 27.6; LCMS m/z 505.1 ([M + H+], C24H25ClN2O4S2 requires 505.1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With triethylamine In acetonitrile at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 50℃; for 0.166667h; Flow reactor; | 307 Example 307 N-[4-(2,4-difluorophenoxy)-3-(4-ethoxy-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]-4-(methylsulfonyl)benzenesulfonamide General procedure: Example 307 N-[4-(2,4-difluorophenoxy)-3-(4-ethoxy-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]-4-(methylsulfonyl)benzenesulfonamide [1170] A stock solution of Example 406B and diisopropylethylamine (0.11 M and 0.2 M in dimethyl acetamide, respectively, 375 μL, 0.40 mmol Example 406B (1.0 equivalent) and 0.80 mmol diisopropylethylamine (2 equivalents)) and 4-(methylsulfonyl)benzenesulfonyl chloride (0.40 M in dimethyl acetamide, 232 μL, 0.92 mmol, 2.3 equivalents) were mixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 50° C., and passed through the reactor at 180 μL per minute (10 minute residence time). Upon exiting the reactor, the reaction mixture was loaded directly into an injection loop and purified by preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 AXIA column (50 mm×21.2 mm) eluting with a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) at a flow rate of 30 mL/min (0-0.5 min 5% A, 0.5-6.5 min linear gradient 5-100% A, 6.5-8.5 min 100% A, 8.5-9.0 min linear gradient 100-5% A, 9.0-10 min 5% A) to provide the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) δ 8.16-8.09 (m, 2H), 8.02-7.96 (m, 2H), 7.45 (s, 1H), 7.36-7.27 (m, 1H), 7.07 (dd, J=8.7, 2.7 Hz, 1H), 7.06-6.91 (m, 3H), 6.85-6.79 (m, 1H), 5.80 (s, 1H), 3.89 (q, J=7.0 Hz, 2H), 3.35 (s, 3H), 3.27 (s, 3H), 1.26-1.06 (m, 3H). MS (APCI+) m/z 590.9 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With dmap In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With pyridine In 1,2-dichloro-ethane at 20℃; Cooling with ice; Inert atmosphere; | 1.2.9. Procedure J: Synthesis of sulfonamides General procedure: To a stirred solution of amine derivative (1.0 equivalence) in 2 mL of anhydrous pyridine under ice cooling, was added a solution of arylsulfonylchloride (1.2 equivalence) in dichloroethane (2 mL) dropwise. The reaction mixture was stirred at room temperature under the nitrogen atmosphere for overnight. After completion of the reaction (monitored by TLC), reaction mixture was diluted with chloroform (20 mL) and quenched with water (10 mL), extracted with chloroform (3x50 mL), the organic layer was washed with 1N HCl (50 mL), then with water (50 mL), dried over Na2SO4, concentrated in rota-vap and purified by flash column chromatography (elutent: EtOAc/Petroleum ether) to give desired products (27-35). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine Sealed tube; | 401 Example 401N-(2-[2-Amino-6-(2, 3-dimethylphenyl)pyrimidin-4-yl]amino}ethyl)-4-methanesulfonylbenzene-1-sulfonamide. General procedure: General procedure 10: A mixture of an 4-N-(aminoalkyl)-6-(2,3- dimethylphenyl)pyrimidine-2,4-diamine (1.0 equiv.), a suitable sulfonyl chloride (1.2 equiv.), and triethylamine (1.5 equiv.) in DCM or MeCN (1.0 mL) is stirred in a sealed tube at rt or 50 00 After completion the crude mixture is concentratedand purified by preparative HPLC or by silica gel chromatography.Example 401N-(2-[2-Amino-6-(2, 3-dimethylphenyl)pyrimidin-4-yl]amino}ethyl)-4-methanesulfonylbenzene-1-sulfonamide.Prepared according to general procedure 10 from 4-methanesulfonylbenzene-1-sulfonyl chloride and 4-N-(2-aminoethyl)-6-(2,3-dimethylphenyl)pyrimidine-2,4-diamine. LCMS [M+H] 476; 1H NMR (400 MHz, CD3OD) OH ppm 8.10 - 8.14 (m,3 H), 8.05 - 8.09 (m, 3 H), 7.16 - 7.20 (m, 1 H), 7.09 - 7.14 (m, 1 H), 7.05 - 7.08(m, 1H), 5.73-5.76 (m, 1 H), 3.42-3.49 (m, 2 H), 3.14 (s, 6 H), 2.31 (s, 4 H),2.18 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | In dichloromethane at 20℃; for 1h; | S1.1.3. N'-(3-Methylphenyl)-4-(methylsulfonyl)benzenesulfonyl hydrazide (1d) To a suspension of m-tolyl hydrazine (48.8 mg, 0.40 mmol) in CH2Cl2 (0.20 mL) was added 4-(methylsulfonyl)benzenesulfonyl chloride (50.9 mg, 0.20 mmol). The reaction was stirred at room temperature for 1 h. After the reaction was completed, CH2Cl2 was removed under reduced pressure and the residue was washed with MeOH to give N'-(3-methylphenyl)-4-(methylsulfonyl)benzenesulfonyl hydrazide (22.0 mg, 32 %) as a powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With dmap; triethylamine In dichloromethane at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: cyclopentyl 3-(2-methoxy-4-(piperazine-1-carbonyl)benzyl)-1-methyl-1H-indol-5-ylcarbamate With triethylamine In tetrahydrofuran at 0 - 5℃; for 0.166667h; Stage #2: 4-methylsulfinylbenzenesulfonyl chloride In tetrahydrofuran at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In dichloromethane at 0 - 20℃; for 96h; | General procedure for the preparation of 3-(1H-imidazol-1-ylmethyl)piperidine derivatives (3a-x) General procedure: To a suspension of 3-(1H-imidazol-1-ylmethyl)piperidine*chloridrate 1 (1 g, 4.20 mmol) and triethylamine (1.245 g, 12.60 mmol) in dry dichloromethane, at 0 °C, was added, dropwise, a solution of the properly arylsulfonyl chloride 2a-x (5.04 mmol) in dry dichloromethane. The reaction mixture was stirred at 0 °C for about 2h and at room temperature for 4 days (completion of the reaction was monitored by TLC). The reaction was quenched with distilled water (10 mL) and extracted with dichloromethane (3 x 10 mL). The combined organic layer was washed with distilled water again, dried over anhydrous Na2SO4 and solvent evaporated in vacuum. The crude product was purified by column chromatography on silica gel (eluent CH2Cl2:MeOH, 98:2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 20℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 20 - 45℃; Inert atmosphere; | 2 4.1.2 General procedure B: 2,4-Difluoro-N-(5-(5-(2-methyl-1-oxoisoindolin-5-yl)thiophen-2-yl)pyridin-2-yl)benzenesulfonamide (4) General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 °C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 21℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 21℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 21℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 21℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 21℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 21℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 21℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With potassium carbonate In dichloromethane at 0℃; | 5.1.2 General procedures for 12N-Benzoyl aloperine derivitatives (3a-c) General procedure: To a solution of 1 (0.5g, 2mmol) in CH2Cl2 (30mL), K2CO3 (1.8g, 6mmol) and the substituted benzoyl chloride (2mmol) were added and stirred at 0°C untill the TLC analysis showed completion of the reaction, then filterd. The filtrate was washed with water, brine, dried, filtered and concentrated. Then the residue was purified by flash column chromatography on silica gel with CH2Cl2/CH3OH as the eluent to give the title compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24.4% | With triethylamine In dichloromethane at 20℃; | 1 Example 1 Compound 1A (150 mg, 0.458 mmol) was dissolved in dichloromethane (20 mL) then triethylamine (70 μL, 0.504 mmol) was added and stirred at room temperature.1B (128 mg, 0.504 mmol) was added portionwise and the reaction was continued overnight at room temperature.The reaction solution was spin-dried, saturated aqueous sodium hydrogen carbonate and ethyl acetate were added, the layers were extracted, and the organic layer was collected, dried over anhydrous sodium sulfate, and spin-dried. The resulting residue was added to dichloromethane to precipitate a solid, which was stirred for 30 minutes and suction-filtered. After washing with dichloromethane, the cake was collected and dried to give Compound 1 as a white solid (61 mg, yield 24.4%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 60℃; for 0.333333h; Flow reactor; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-methylsulfinylbenzenesulfonyl chloride; 2-azidoethyl (5-acetamido-9-amino-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→6)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside With N-ethyl-N,N-diisopropylamine In methanol at 22℃; for 2h; Stage #2: With sodium hydroxide; trimethylphosphane In tetrahydrofuran; water at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-methylsulfinylbenzenesulfonyl chloride; 2-azidoethyl (5-acetamido-9-amino-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-6-O-sulfo-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside With N-ethyl-N,N-diisopropylamine In methanol at 22℃; for 2h; Stage #2: With sodium hydroxide; trimethylphosphane In tetrahydrofuran; water at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With indium; In acetonitrile; at 110℃; for 18h; | To a solution of <strong>[117324-58-0]methyl 2-amino-5-(trifluoromethyl)benzoate</strong> (0.261 g, 1.19 mmol) and 4-(methylsulfonyl)benzenesulfonyl chloride (0.300 g, 1.18 mmol) in 5 mL acetonitrile was added powdered indium metal (0.027 g, 0.24 mmol). The mixture was stirred at 110 C. for 18 hours. The reaction was then concentrated to a residue. The crude product was purified by silica flash chromatography to afford methyl 2-((4-(methylsulfonyl)phenyl)sulfonamido)-5-(trifluoromethyl)benzoate as a solid. LCMS-ESI- (m/z): [M-H]- calcd 436.01; found 436.18 |
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