Home Cart 0 Sign in  

[ CAS No. 153435-79-1 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 153435-79-1
Chemical Structure| 153435-79-1
Structure of 153435-79-1 * Storage: {[proInfo.prStorage]}

Quality Control of [ 153435-79-1 ]

Related Doc. of [ 153435-79-1 ]

SDS
Alternatived Products of [ 153435-79-1 ]
Alternatived Products of [ 153435-79-1 ]

Product Details of [ 153435-79-1 ]

CAS No. :153435-79-1 MDL No. :MFCD07363818
Formula : C7H8BrNO2S Boiling Point : 343.0±44.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :250.11 g/mol Pubchem ID :-
Synonyms :

Safety of [ 153435-79-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153435-79-1 ]

  • Downstream synthetic route of [ 153435-79-1 ]

[ 153435-79-1 ] Synthesis Path-Downstream   1~15

  • 2
  • [ 86674-12-6 ]
  • [ 67-56-1 ]
  • [ 22033-09-6 ]
  • [ 153435-79-1 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In water at 25℃; Dependence of the decomposition rate on concentration of H2SO4;
  • 3
  • [ 885702-32-9 ]
  • [ 153435-79-1 ]
  • <i>N</i>-methyl-3-[2-(3,4,5-trimethoxy-phenylamino)-pyrrolo[2,3-<i>d</i>]pyrimidin-7-yl]-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane at 100℃; for 5h;
  • 4
  • [ 2905-24-0 ]
  • [ 593-51-1 ]
  • [ 153435-79-1 ]
YieldReaction ConditionsOperation in experiment
15% With pyridine In dichloromethane at 0 - 80℃; for 24h; Schlenk technique; 3-Bromo-N-methylbenzenesulfonamide (27c) A 100 ml Schlenk tube was charged with 180 mg (2.66 mmol, 1.70 eq) methylamine hydrochloride, 600μL (7.83 mmol, 5.00 eq) pyridine and 17.2 mL abs. DCM. The solution was cooled to 0 °C before 400mg (226 μL, 1.57 mmol, 1.00 eq) 3-bromobenzene- sulfonylchloride were added. After stirring at 80 °Cfor 24 h. TLC analysis indicated full conversion of the starting material. The mixture was diluted with 30mL sat. NaHCO3 solution and 30 mL Et2O. The layers were separated and the aqueous layer wasextracted with Et2O (2 x 5 mL). The combined organic layers were washed with NaH2PO4 solution (4 x10 mL) and brine (2 x 5 mL), dried over MgSO4 and concentrated under reduced pressure. As it was still pyridine in the crude product, it was washed once more with NaH2PO4 solution (3 x 10 mL), driedand concentrated under reduced pressure. Final purification via column chromatography (CH/EtOAc3:1, size: 17.0 x 2.0 cm, 14 g silica gel) yielded the pure product as colorless solid (59 mg, 15 %).
With pyridine In dichloromethane at 0 - 20℃; for 3h; 15.B Compound 15-B-l ( 0.23Og 0.90mmol) was added to a stirred solution of methylamine hydrochloride ( 0.091g 1.35mmol) and pyridine ( 0.364ml 4.50 mmol) in dichloromethane (10 ml) at O0C. The reaction mixture was allowed to warm to room temperature and the reaction was followed by LCMS. Upon consumption of starting material (about 3hrs), the mixture was extracted twice with diethyl ether / saturated sodium bicarbonate solution. The organic solution was washed twice with an aqueous sodium dihydrogen phosphate (pH=3-4) solution, twice with brine, and then the organic solution was dried over MgSO4 and concentrated to afford the crude sulfonamide 15-B-2.
With triethylamine In dichloromethane at 20℃; for 2h; 29.1 Methylamine hydrochloride (1057 mg, 15.65 mmol) and triethylamine (3.3 mL, 23.48 mmol) were dissolved in dichloromethane (20 mL) and then 3-bromobenzene-1-sulfonyl chloride (4.0 g, 15.65 mmol) was slowly added. The reaction mixture was stirred at room temperature for 2 hours, diluted with dichloromethane, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. The resultant target compound (3.5 g, 90% yield) was used in the following reaction without purification. [0362] MS m/z: 250.32, 252.30 [M+1].
With triethylamine In dichloromethane at 20℃; for 2h; 29.1 Step 1: 3-bromo-N-methylbenzenesulfonamide Methylamine hydrochloride (1057 mg, 15.65 mmol) and triethylamine (3.3 mL, 23.48 mmol) were dissolved in dichloromethane (20 mL) and then 3-bromobenzene-1-sulfonyl chloride (4.0 g, 15.65 mmol) was slowly added. The reaction mixture was stirred at room temperature for 2 hours, diluted with dichloromethane, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. The resultant target compound (3.5 g, 90% yield) was used in the following reaction without purification. MS m/2: 250.32, 252.30 [M+1].

  • 5
  • [ 153435-79-1 ]
  • [ 73183-34-3 ]
  • [ 1293987-69-5 ]
YieldReaction ConditionsOperation in experiment
86% With potassium acetate In dimethyl sulfoxide at 80℃; for 6h; 29.2 3-Bromo-N-methylbenzenesulfonamide (1.6 g, 6.39 mmol) was dissolved in anhydrous DMSO (21 mL) and then potassium acetate (1.57 g, 15.99 mmol) and bis(pinacolato)diboron (1.63 g, 6.39 mmol) were added. After flowing nitrogen to the reaction mixture for 10 minutes, Pd(dppf)2Cl2 (522 mg, 0.64 mmol) was added. The reaction mixture was stirred at 80 °C for 6 hours, diluted with ethyl acetate, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (10% ethyl acetate/hexane) yielded the target compound (1.65 g, 86% yield). [0366] MS m/z: 298.52 [M+1].
69% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 6h;
69% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 6h; 2-2 N-methyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzenesulfonamide (SMY-1283) 3-bromo-N-methylbenzenesulfonamide (SMY-1277; 730 mg, 2.9 mmol) obtained in Synthesis Example 2-1,Potassium acetate (AcOK; 716 mg, 7.3 mmol),Dichloro [1,1'-bis (diphenylphosphino) ferrocene] palladium.dichloromethane (PdCl 2 (dppf) · CH 2 Cl 2; 238 mg, 0.29 mmol),And bis pinacolate diboron (B 2 pin 2; 741 mg, 2.9 mmol)Of dimethylsulfoxide (DMSO; 10 mL)Was heated at 80 ° C. for 6 hours.After cooling to room temperature, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (20 mL).Insolubles were filtered through celite. The filtrate was extracted with ethyl acetate (15 mL × 2).The combined organic layers were washed with water (20 mL × 1) and brine (20 mL × 1)Dry with Na 2 SO 4, filter and concentrate under vacuum.The obtained residue was purified by MPLC (hexane / ethyl acetate = 3: 1 to 15: 85)The target compound was obtained as a white solid (602 mg, 69%).
65% With sodium acetate In 1,4-dioxane at 80℃; Inert atmosphere; PREPARATION 1/V-methyl-3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzenesulfonamideA mixture of 3-bromo-/V-methylbenzenesulfonamide (2.3 g, 9.0 mmol), 6/'s(pinacolato)diboron (2.5 g, 10.0 mmol), Pd(dppf)CI2 (0.725 g, 0.9 mmol), KOAc (2.6 g, 27 mmol), and dppf (0.700 g, 1 .26 mmol) in 1 ,4-dioxane was heated to 80 °C and stirred overnight under nitrogen. In the morning, the reaction mixture was filtered and concentrated in vacuo. The crude product was then purified via flash column chromatography (4:1 petroleum ether/EtOAc) to give A/-methyl-3-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzenesulfonamide as a white solid (1 .7 g, 65%).
With potassium acetate In N,N-dimethyl-formamide at 80℃; 15.B The crude 15-B-2 (0.05Og, 0.20 mmol ), potassium acetate (0.059g O.Ommol), bis(pinacolato)diboron (0.046g, 0.18 mmol) and PdCl2(dppf) (0.016g 0.020mmol) were added to a round bottom flask. Dry DMF (3 ml) was then added, and the flask was flushed with nitrogen, then capped. The resultant mixture was stirred and placed into an 8O0C oil bath. The reaction was followed by LCMS. Upon consumption of starting material, the reaction mixture was extracted with ethyl acetate / water 3-4 times, then washed with brine twice. The resultant organic solution was dried over MgSO4 and concentrated to afford crude boronate ester 15-B-3 which was used directly for the Suzuki coupling without further purification, to provide Example 15-35. The Suzuki coupling was carried out using the standard conditions already described with the Boykin catalyst.
With potassium acetate In dimethyl sulfoxide at 80℃; for 6h; 29.2 Step 2: N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 3-Bromo-N-methylbenzenesulfonamide (1.6 g, 6.39 mmol) was dissolved in anhydrous DMSO (21 mL) and then potassium acetate (1.57 g, 15.99 mmol) and bis(pinacolato)diboron (1.63 g, 6.39 mmol) were added. After flowing nitrogen to the reaction mixture for 10 minutes, Pd(dppf)2Cl2 (522 mg, 0.64 mmol) was added. The reaction mixture was stirred at 80° C. for 6 hours, diluted with ethyl acetate, and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (10% ethyl acetate/hexane) yielded the target compound (1.65 g, 86% yield). MS m/z: 298.52 [M+1].

  • 6
  • [ 2905-24-0 ]
  • [ 74-89-5 ]
  • [ 153435-79-1 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran at 20℃; A.A15.1 Step 1. Synthesis of N-methyl-3-bromobenzenesulfonamide To a solution of 3-bromobenzenesulfonyl chloride (2.5 g, 11.2 mmol) in THF (15 mL) at 0° C. was added methylamine (2.0 M in THF; 28 mL, 56 mmol). The resulting solution was allowed to warm to room temp. and was stirred at room temp. overnight. The resulting mixture was separated between EtOAc (25 mL) and a 1 M HCl solution (25 mL). The aqueous phase was back-extracted with EtOAc (2*25 mL). The combined organic phases were sequentially washed with water (2*25 mL) and a saturated NaCl solution (25 mL), dried (MgSO4) and concentrated under reduced pressure to give N-methyl-3-bromobenzenesulfonamide as a white solid (2.8 g, 99%).
85% In tetrahydrofuran at 20℃; for 2h;
85% In tetrahydrofuran at 20℃; for 2h; 2-1 3-bromo-N-methylbenzenesulfonamide (SMY-1277) A 2 M solution of methylamine (MeNH 2) in THF (0.625 mL, 17 mmol)Was dissolved in THF (10 mL)m-Bromobenzenesulfonyl chloride (0.50 mL, 3.5 mmol)Was slowly added.The reaction mixture was stirred at room temperature for 2 hours.The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (15 mL × 2).The combined organic layers were washed with water (15 mL × 1) and brine (15 mL × 1), dried over Na 2 SO 4, filtered and concentrated in vacuo.The obtained residue was purified by MPLC (hexane / ethyl acetate = 3: 1 to 2: 3) to give the objective compound as a white solid (734 mg, 85%).
In tetrahydrofuran; ethanol for 0.0833333h; 41.a ) 3-Bromo-λ/-methylbenzenesulfonamideMeNH2 (6 ml_, 8 M solution in EtOH, 48 mmol) was added to a solution of 3- bromobenzenesulfonyl chloride (3.50 g, 13.698 mmol) in THF (60 ml_). The reaction mixture was allowed to react for 5 min and poured into H2O (200 ml_) and extracted with CH2CI2 (2x100 ml_). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated, to furnish the product as a yellow coloured solid. The crude residue was submitted to next step without purification.1H NMR (CDCI3, 250 MHz) δ ppm: 8.01 (t, J = 1.6 Hz, 1 H), 7.82-7.68 (m, 2H), 7.41 (t, J = 8.0 Hz, 1 H), 4.70 (bs, 1 H), 2.68 (d, J = 4.9 Hz, 3H).

  • 7
  • [ 153435-79-1 ]
  • [ 108-95-2 ]
  • 4-(3-(N-methylsulfamoyl)phenyloxy)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; CuI; potassium carbonate In N,N-dimethyl-formamide 15.2 Step 2. Step 2. Synthesis of 4-(3-(N-methylsulfamoyl)phenyloxy)benzene To a slurry of phenol (1.9 g, 20 mmol), K2CO3 (6.0 g, 40 mmol), and CuI (4 g, 20 mmol) in DMF (25 mL) was added N-methyl-3-bromobenzenesulfonamide (2.5 g, 10 mmol), and the resulting mixture was stirred at the reflux temp. overnight, cooled to room temp., and separated between EtOAc (50 mL) and a 1 N HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2*50 mL). The combined organic phases were sequentially washed with water (2*50 mL) and a saturated NaCl solution (50 mL), dried (MgSO4), and concentrated under reduced pressure. The residual oil was purified by column chromatography (30% EtOAc/70% hexane) to give 4-(3-(N-methylsulfamoyl)phenyloxy)benzene (0.30 g).
With hydrogenchloride; CuI; potassium carbonate In N,N-dimethyl-formamide 2 Step 2. Step 2. Synthesis of 4-(3-(N-methylsulfamoyl)phenyloxy)benzene To a slurry of phenol (1.9 g, 20 mmol), K2CO3 (6.0 g, 40 mmol), and CuI (4 g, 20 mmol) in DMF (25 mL) was added N-methyl-3-bromobenzenesulfonamide (2.5 g, 10 mmol), and the resulting mixture was stirred at the reflux temp. overnight, cooled to room temp., and separated between EtOAc (50 mL) and a 1 N HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2*50 mL). The combined organic phases were sequentially washed with water (2*50 mL) and a saturated NaCl solution (50 mL), dried (MgSO4), and concentrated under reduced pressure. The residual oil was purified by column chromatography (30% EtOAc/70% hexane) to give 4-(3-(N-methylsulfamoyl)phenyloxy)benzene (0.30 g).
With hydrogenchloride; CuI; potassium carbonate In N,N-dimethyl-formamide 2 Step 2. Step 2. Synthesis of 4-(3-(N-methylsulfamoyl)phenyloxy)benzene To a slurry of phenol (1.9 g, 20 mmol), K2CO3 (6.0 g, 40 mmol), and CuI (4 g, 20 mmol) in DMF (25 mL) was added N-methyl-3-bromobenzenesulfonamide (2.5 g, 10 mmol), and the resulting mixture was stirred at the reflux temp. overnight, cooled to room temp., and separated between EtOAc (50 mL) and a 1N HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2*50 mL). The combined organic phases were sequentially washed with water (2*50 mL) and a saturated NaCl solution (50 mL), dried (MgSO4), and concentrated under reduced pressure. The residual oil was purified by column chromatography (30% EtOAc/70% hexane) to give 4-(3-(N-methylsulfamoyl)phenyloxy)benzene (0.30 g).
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide Heating / reflux; A.A15.2 Step 2. Synthesis of 4-(3-(N-methylsulfamoyl)phenyloxy)benzene To a slurry of phenol (1.9 g, 20 mmol), K2CO3 (6.0 g, 40 mmol), and CuI (4 g, 20 mmol) in DMF (25 mL) was added N-methyl-3-bromobenzenesulfonamide (2.5 g, 10 mmol), and the resulting mixture was stirred at the reflux temp. overnight, cooled to room temp., and separated between EtOAc (50 mL) and a 1 N HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2*50 mL). The combined organic phases were sequentially washed with water (2*50 nL) and a saturated NaCl solution (50 mL), dried (MgSO4), and concentrated under reduced pressure. The residual oil was purified by column chromatography (30% EtOAc/70% hexane) to give 4-(3-(N-methylsulfamoyl)phenyloxy)benzene (0.30 g).

  • 8
  • [ 2905-24-0 ]
  • [ 153435-79-1 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride; methylamine In tetrahydrofuran 1 Step 1. Step 1. Synthesis of N-methyl-3-bromobenzenesulfonamide To a solution of 3-bromobenzenesulfonyl chloride (2.5 g, 11.2 mmol) in THF (15 mL) at 0° C. was added methylamine (2.0 M in THF; 28 mL, 56 mmol). The resulting solution was allowed to warm to room temp. and was stirred at room temp. overnight. The resulting mixture was separated between EtOAc (25 mL) and a 1 M HCl solution (25 mL). The aqueous phase was back-extracted with EtOAc (2*25 mL). The combined organic phases were sequentially washed with water (2*25 mL) and a saturated NaCl solution (25 mL), dried (MgSO4) and concentrated under reduced pressure to give N-methyl-3-bromobenzenesulfonamide as a white solid (2.8 g, 99%).
99% With hydrogenchloride; methylamine In tetrahydrofuran 15.1 Step 1. Step 1. Synthesis of N-methyl-3-bromobenzenesulfonamide To a solution of 3-bromobenzenesulfonyl chloride (2.5 g, 11.2 mmol) in THF (15 mL) at 0° C. was added methylamine (2.0 M in THF; 28 mL, 56 mmol). The resulting solution was allowed to warm to room temp. and was stirred at room temp. overnight. The resulting mixture was separated between EtOAc (25 mL) and a 1 M HCl solution (25 mL). The aqueous phase was back-extracted with EtOAc (2*25 mL). The combined organic phases were sequentially washed with water (2*25 mL) and a saturated NaCl solution (25 mL), dried (MgSO4) and concentrated under reduced pressure to give N-methyl-3-bromobenzenesulfonamide as a white solid (2.8 g, 99%).
99% With hydrogenchloride; methylamine In tetrahydrofuran 1 Step 1. Step 1. Synthesis of N-methyl-3-bromobenzenesulfonamide To a solution of 3-bromobenzenesulfonyl chloride (2.5 g, 11.2 mmol) in THF (15 mL) at 0° C. was added methylamine (2.0 M in THF; 28 mL, 56 mmol). The resulting solution was allowed to warrn to room temp. and was stirred at room temp. overnight. The resulting mixture was separated between EtOAc (25 mL) and a 1 M HCl solution (25 mL). The aqueous phase was back-extracted with EtOAc (2*25 mL). The combined organic phases were sequentially washed with water (2*25 mL) and a saturated NaCl solution (25 mL), dried (MgSO4) and concentrated under reduced pressure to give N-methyl-3-bromobenzenesulfonamide as a white solid (2.8 g, 99%).
99% With hydrogenchloride; methylamine In tetrahydrofuran 1 Step 1. Step 1. Synthesis of N-methyl-3-bromobenzenesulfonamide To a solution of 3-bromobenzenesulfonyl chloride (2.5 g, 11.2 mmol) in THF (15 mL) at 0° C. was added methylamine (2.0M in THF; 28 mL, 56 mmol). The resulting solution was allowed to warm to room temp. and was stirred at room temp. overnight. The resulting mixture was separated between EtOAc (25 mL) and a 1M HCl solution (25 mL). The aqueous phase was back-extracted with EtOAc (2*25 mL). The combined organic phases were sequentially washed with water (2*25 mL) and a saturated NaCl solution (25 mL), dried (MgSO4) and concentrated under reduced pressure to give N-methyl-3-bromobenzenesulfonamide as a white solid (2.8 g, 99%).
With methylamine In tetrahydrofuran 19.a a a 3-Bromo-N-methyl-benzenesulfonamide Methylamine was bubbled through a solution of 3-bromobenzenesulfonyl chloride (5.0 g) in tetrahydrofuran (50 ml) at 0° C. The resulting suspension was stirred for 3 hours, filtered and concentrated at reduced pressure. The residue was triturated with hexane and filtered to afford the sub-titled compound as a solid (4.52 g). m.p. 88-89° C. MS (APCI) 250 (M+H)+(free base) 1H NMR (DMSO) 8.02(1H, m); 7.80(1H, m); 7.72(1H, m) 7.42(1H, t); 4.44(1H, bm); 2.70(3H, d).
With methylamine In methanol; water 98.b b b Methyl 3-bromobenzenesulfonamide 3-Bromobenzenesulfonyl chloride (0.33 g) was added to a saturated solution of methylamine in methanol (50 ml). After 10 minutes, the solution was concentrated under reduced pressure. Water (20 ml) was added to the residue and the resulting solid filtered and dried in vacuo to give the sub-title compound (0.32 g). 1 H NMR (DMSO-d6) 7.95-7.84(2 H, m); 7.79(1 H, m); 7.65(1 H, br); 2.43(3 H, s).

  • 9
  • aqueous lithium chloride [ No CAS ]
  • bis(triphenylphosphine)palladium(II) dichloride [ No CAS ]
  • [ 163498-76-8 ]
  • [ 153435-79-1 ]
  • 7-(3-Methylaminosulfonylphenyl)-1-(4-methyl-1-piperazinyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; lithium chloride In N,N-dimethyl-formamide 41 7-(3-Methylaminosulfonylphenyl)-1-(4-methyl-1-piperazinyl)naphthalene EXAMPLE 41 7-(3-Methylaminosulfonylphenyl)-1-(4-methyl-1-piperazinyl)naphthalene 7-Trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene (0.25 g, 0.67 mmol), 3-methylaminosulfonyl-1-bromobenzene (0.18 g, 0.72 mmol), triethylamine (0.45 mL, 3.23 mmol), lithium chloride (0.088 g, 2.07 mmol), and bis (triphenylphosphine) palladium chloride (0.025 g, 0.036 mmol) were combined in DMF (12.5 mL) and heated to 110 to 110° C. for 45 minutes. The reaction was cooled to room temperature and 1 N aqueous lithium chloride (20 mL) was added. The mixture was extracted with ether (2*). The combined organic layer was washed with 1 N lithium chloride and brine; then it was dried over magnesium sulfate and concentrated to an orange oil. Flash chromatography on silica gel (1*6 inches) with an ethyl acetate/hexane gradient of from 50 to 75% followed by continued elution with ethyl acetate and finally 5% methanol/ethyl acetate 0.11 g (42%) of the title product. The sample was recrystallized from ethyl acetate for analysis: mp 147.5-148° C. Analysis calculated for C22H25N3O2S: C, 66.81; H, 6.31; N, 10.62. Found: C, 66.32; H. 6.16; N, 10.41.
With triethylamine; lithium chloride In N,N-dimethyl-formamide 41 7-(3-Methylaminosulfonylphenyl)-1-(4-methyl-1-piperazinyl)naphthalene EXAMPLE 41 7-(3-Methylaminosulfonylphenyl)-1-(4-methyl-1-piperazinyl)naphthalene 7-Trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene (0.25 g, 0.67 mmol), 3-methylaminosulfonyl-1-bromobenzene (0.18 g, 0.72 mmol), triethylamine (0.45 mL, 3.23 mmol), lithium chloride (0.088 g, 2.07 mmol), and bis (triphenylphosphine) palladium chloride (0.025 g, 0.036 mmol) were combined in DMF (12.5 mL) and heated to 110° to 110° C. for 45 minutes. The reaction was cooled to room temperature and 1 N aqueous lithium chloride (20 mL) was added. The mixture was extracted with ether (2x). The combined organic layer was washed with 1N lithium chloride and brine; then it was dried over magnesium sulfate and concentrated to an orange oil. Flash chromatography on silica gel (1*6 inches) with an ethyl acetate/hexane gradient of from 50 to 75% followed by continued elution with ethyl acetate and finally 5% methanol/ethyl acetate 0.11 g (42%) of the title product. The sample was recrystallized from ethyl acetate for analysis: mp 147.5°-148° C. Analysis calculated for C22 H25 N3 O2 S: C, 66.81; H, 6.31; N, 10.62. Found: C, 66.32; H, 6.16; N, 10.41.
YieldReaction ConditionsOperation in experiment
88%
  • 11
  • tetrabutylammonium fluoride monohydrate [ No CAS ]
  • [ 192376-94-6 ]
  • [ 5419-55-6 ]
  • [ 497-19-8 ]
  • [ 153435-79-1 ]
  • [ 192376-16-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium; oxalic acid In tetrahydrofuran; methanol; ethanol; water; toluene 98.c c c (2R)-1-(3'-(Methylaminosulfonyl)biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanoloxalic acid salt A solution of n-butyllithium (2.5 M in hexanes, 0.50 ml) was added to a stirred solution of (2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-(tert-butyldimethylsilyloxy)butane (0.50 g, Example 98a) in anhydrous tetrahydrofuran (5 ml) at -78° C. under nitrogen. After 15 minutes, the reaction mixture was added dropwise to a solution of triisopropyl borate (0.53 ml) in anhydrous tetrahydrofuran (5 ml) at -78° C. under nitrogen. The mixture was allowed to warm to room temperature and stirred for 30 minutes. Hydrochloric acid (2 M, 10 ml) was added and the mixture stirred for 30 minutes then concentrated under reduced pressure. A solution of methyl 3-bromobenzenesulfonamide (0.32 g) in ethanol (3 ml), tetrakis(triphenylphosphine)palladium(0) (60 mg), aqueous sodium carbonate (2 M, 3 ml) and toluene (12 ml) were added to the residual gum. The mixture was then heated at reflux, under nitrogen for 6 hours before being added to water (50 ml). The mixture was extracted with ethyl acetate (2*50 ml), the combined organic extracts dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (5 ml) and tetrabutylammonium fluoride hydrate (0.50 g) was added. The mixture was stirred for 2 hours before being added to water (30 ml). The mixture was extracted with ethyl acetate (2*50 ml), the combined organic extracts dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluding with ethyl acetate to give an oil (0.297 g). The latter was converted to the oxalate salt upon treatment with oxalic acid (excess) in ether and was recrystallized from ethyl acetate. The resulting hydroscopic solid was dissolved in methanol and the solution evaporated under reduced pressure to give the title compound as a foam (0.178 g). MS (APCI) 413.1 ((M-oxalic acid)+H)+ 1 H NMR (DMSO-d6) 8.49(1 H, s); 8.42(1 H, d); 7.96(1 H, s); 7.90(1 H, d); 7.73-7.62 (5 H, m); 7.49(1 H, q); 7.34(1 H, dd); 7.08(2 H, d); 3.95(2 H, d); 3.83-3.78(1 H, m); 2.87-2.78(1 H, m); 2.76-2.65(1 H, m); 2.44(3 H, d); 1.93-1.82(1 H, m); 1.79-1.70(1 H, m).
  • 12
  • [ 936092-52-3 ]
  • [ 153435-79-1 ]
  • N-methyl-3-{5-methyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With caesium carbonate In 1,4-dioxane; N,N-dimethyl-formamide at 160℃; for 0.333333h; Microwave irradiation; 92 [0207] A suspension of intermediate 32 (0.10 g, 0.33 mmol), 3-bromo-iV-methyl- benzenesulfonamide (0.11 g, 0.44 mmol), Pd2(dba)3 (20 mg, 0.022 mmol), Xantphos (25 mg, 0.043 mmol) and cesium carbonate (0.25 g, 0.77 mmol) in dioxane/DMF (3/1, 4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 ° C for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue triturated in a mixture of DCM/Et2O (1/5, 30 mL). After filtration, the title compound was obtained as a light brown solid (65 mg, 42%).[0208] 1H NMR (500 MHz, DMSO-d6): δ 2.11 (s, 3H), 2.23 (s, 3H), 2.44 (d, J= 5.0 Hz, 3H), 2.45-2.50 (m, 4H), 3.03 (t, J= 4.9 Hz, 4H), 6.81 (d, J= 9.1 Hz, 2H), 7.40-7.43 (m, 2H), 7.46 (d, J= 9.1 Hz, 2H), 7.52 (t, J= 8.0 Hz, IH), 7.89 (s, IH), 7.94 (t, J= 1.8 Hz, IH), 8.29 (br d, J= 8.3 Hz, IH), 8.56 (s, IH), 8.72 (s, IH). MS (ES+): m/z 468 (M+H)+.
  • 13
  • [ 24424-99-5 ]
  • [ 153435-79-1 ]
  • [ 1166183-95-4 ]
YieldReaction ConditionsOperation in experiment
89% With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.25h; 41.b ) tert-Butyl (3-bromophenyl)sulfonyl(methyl)carbamate BoC2O (3.41 g, 15.624 mmol) was added to a solution of 3-bromo-/V- methylbenzenesulfonamide (13.698 mmol), DMAP (166 mg, 1.358 mmol) and DIPEA (7.0 ml_, 40.89 mmol) in CH3CN (70 ml_). The reaction mixture was stirred at r.t. for 15 min, poured into H2O (200 ml_) and extracted with EtOAc (200 ml_). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (2→10% EtOAc/hexanes), to afford 4.72 g of tert-butyl (3- bromophenyl)sulfonyl(methyl)carbannate (white solid, yield: 89%). 1H NMR (CDCI3, 250 MHz) δ ppm: 8.04 (t, J = 1.9 Hz, 1 H), 7.89-7.71 (m, 2H), 7.40 (t, J = 8.0 Hz, 1 H), 3.35 (s, 3H), 1.37 (s, 9H).
  • 14
  • [ 337536-20-6 ]
  • [ 153435-79-1 ]
  • [ 1293981-29-9 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 16h; Reflux; Inert atmosphere; 4.20. 4'-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-N-methyl[1,1'-biphenyl]-3-carboxamide (21a) General procedure: Under N2 atmosphere a mixture of crude 19 (3.44 g), 3-bromophenyl-N-methylcarboxamide 20a (1.10 g, 5.14 mmol) and Pd(PPh3)4 (0) (210 mg, 0.18 mmol) in DME (20 mL) and 2 M Na2CO3 solution (20 mL) was refluxed for 16 h. The resulting mixture was extracted with AcOEt and the combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The residue was chromatographed on silica gel (hexane/AcOEt = 1:2) to give 21a (1.00 g, 1.69 mmol, 33%) as a pale yellow amorphous solid.
  • 15
  • [ 153435-79-1 ]
  • [ 4637-24-5 ]
  • [ 153435-80-4 ]
YieldReaction ConditionsOperation in experiment
92% In N,N-dimethyl-formamide at 20 - 80℃; for 18h;
Historical Records

Related Functional Groups of
[ 153435-79-1 ]

Bromides

Chemical Structure| 703-12-8

[ 703-12-8 ]

4-Bromo-N-methylbenzenesulfonamide

Similarity: 0.98

Chemical Structure| 871269-07-7

[ 871269-07-7 ]

3-Bromo-N-ethylbenzenesulfonamide

Similarity: 0.92

Chemical Structure| 153435-80-4

[ 153435-80-4 ]

3-Bromo-N,N-dimethylbenzenesulfonamide

Similarity: 0.92

Chemical Structure| 6318-32-7

[ 6318-32-7 ]

2,5-Dibromo-N-methylbenzenesulfonamide

Similarity: 0.90

Chemical Structure| 1984-25-4

[ 1984-25-4 ]

4-Bromo-N-ethylbenzenesulfonamide

Similarity: 0.90

Sulfamides

Chemical Structure| 703-12-8

[ 703-12-8 ]

4-Bromo-N-methylbenzenesulfonamide

Similarity: 0.98

Chemical Structure| 871269-07-7

[ 871269-07-7 ]

3-Bromo-N-ethylbenzenesulfonamide

Similarity: 0.92

Chemical Structure| 153435-80-4

[ 153435-80-4 ]

3-Bromo-N,N-dimethylbenzenesulfonamide

Similarity: 0.92

Chemical Structure| 6318-32-7

[ 6318-32-7 ]

2,5-Dibromo-N-methylbenzenesulfonamide

Similarity: 0.90

Chemical Structure| 1984-25-4

[ 1984-25-4 ]

4-Bromo-N-ethylbenzenesulfonamide

Similarity: 0.90

Amines

Chemical Structure| 703-12-8

[ 703-12-8 ]

4-Bromo-N-methylbenzenesulfonamide

Similarity: 0.98

Chemical Structure| 871269-07-7

[ 871269-07-7 ]

3-Bromo-N-ethylbenzenesulfonamide

Similarity: 0.92

Chemical Structure| 153435-80-4

[ 153435-80-4 ]

3-Bromo-N,N-dimethylbenzenesulfonamide

Similarity: 0.92

Chemical Structure| 6318-32-7

[ 6318-32-7 ]

2,5-Dibromo-N-methylbenzenesulfonamide

Similarity: 0.90

Chemical Structure| 1984-25-4

[ 1984-25-4 ]

4-Bromo-N-ethylbenzenesulfonamide

Similarity: 0.90

Aryls

Chemical Structure| 703-12-8

[ 703-12-8 ]

4-Bromo-N-methylbenzenesulfonamide

Similarity: 0.98

Chemical Structure| 871269-07-7

[ 871269-07-7 ]

3-Bromo-N-ethylbenzenesulfonamide

Similarity: 0.92

Chemical Structure| 153435-80-4

[ 153435-80-4 ]

3-Bromo-N,N-dimethylbenzenesulfonamide

Similarity: 0.92

Chemical Structure| 6318-32-7

[ 6318-32-7 ]

2,5-Dibromo-N-methylbenzenesulfonamide

Similarity: 0.90

Chemical Structure| 1984-25-4

[ 1984-25-4 ]

4-Bromo-N-ethylbenzenesulfonamide

Similarity: 0.90