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Product Details of [ 98961-97-8 ]

CAS No. :98961-97-8 MDL No. :MFCD04972523
Formula : C6H15N3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :NQZDGTYTTVHKPE-UHFFFAOYSA-N
M.W : 193.27 Pubchem ID :1094966
Synonyms :

Safety of [ 98961-97-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 98961-97-8 ]

* 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.

  • Downstream synthetic route of [ 98961-97-8 ]

[ 98961-97-8 ] Synthesis Path-Downstream   1~70

  • 1
  • [ 110-85-0 ]
  • [ 13360-57-1 ]
  • [ 98961-97-8 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In ethanol at 0℃; for 0.5h;
With sodium carbonate; chlorobenzene
The N-derivatives of piperazine such as 1-(dimethylaminocarbonyl)piperazine, and 1-(dimethylaminosulfonyl)piperazine were prepared by reacting piperazine with dimethylaminochloroformate, or dimethylaminosulfamoyl chloride, respectively.
With potassium carbonate In ethanol at 20℃;

  • 2
  • [ 98961-97-8 ]
  • [ 59943-32-7 ]
  • [ 77725-73-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In isopropyl alcohol at 20℃; for 2h;
  • 3
  • [ 98961-97-8 ]
  • [ 556-61-6 ]
  • [ 344310-57-2 ]
YieldReaction ConditionsOperation in experiment
In benzene Heating;
  • 4
  • [ 626-61-9 ]
  • [ 98961-97-8 ]
  • 4-[4'-(N,N-dimethylsulfamoyl)piperazin-1-yl]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In acetic acid at 110℃; for 6h;
  • 5
  • [ 19235-89-3 ]
  • [ 98961-97-8 ]
  • 2-cyano-4-[4'-(N,N-dimethylsulfamoyl)piperazin-1-yl]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% at 80℃; for 3h;
  • 6
  • [ 99586-65-9 ]
  • [ 98961-97-8 ]
  • 4-[4'-(N,N-dimethylsulfamoyl)piperazin-1-yl]picolinamide [ No CAS ]
  • 7
  • [ 24484-93-3 ]
  • [ 98961-97-8 ]
  • 2-[4-(N,N-dimethylsulfamoyl)piperazin-1-ylcarbonyl]-4-chloropyridine [ No CAS ]
  • 2-[4'-(N,N-dimethylsulfamoyl)piperazin-1-ylcarbonyl]-4-[4'-(N,N-dimethylsulfamoyl)piperazin-1-yl]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 35% 2: 21% at 100℃; for 5h;
  • 9
  • [ 3934-20-1 ]
  • [ 98961-97-8 ]
  • [ 357951-07-6 ]
YieldReaction ConditionsOperation in experiment
With TEA In N,N-dimethyl-formamide
  • 10
  • [ 98961-97-8 ]
  • [ 299396-96-6 ]
  • [ 299396-97-7 ]
YieldReaction ConditionsOperation in experiment
59% With triethylamine In tetrahydrofuran for 15h; Heating;
59% With sodium hydrogencarbonate; triethylamine In tetrahydrofuran; methanol; water; ethyl acetate 1.F Step F. Step F. (R)-4-[2-(1-Methoxy-ethyl)-pyrimidin-4-yl]-piperazine-1-sulfonic acid dimethylamide To a solution of (R)-2-(1-methoxyethyl)-pyrimidin-4-yl-methanesulfonate (prepared according to the method of Example 1, Step E, 2.11 g, 9.1 mmol) in tetrahydrofuran (20 mL) was added dimethylsulfamoyl piperazine (prepared according to the method disclosed in U.S. Pat. No. 2,748,129, 1.94 g, 10 mmol) followed by triethylamine (1.4 mL, 10 mmol). The reaction was refluxed for 15 h, and evaporated to an oily residue. This was extracted with ethyl acetate (20 mL) and the extract was washed first with a saturated aqueous solution of sodium bicarbonate and then with water (10 mL). The ethyl acetate extract was dried over sodium sulfate, filtered, and the filtrate was evaporated to a crude product, which was chromatographed over silica gel. Elution with a mixture of 9:1 ethyl acetate and methanol and evaporation of the solvents gave the title compound of Example 1, Step F (1.75 g, 59%); mp, 65-70° C., [α]D+54.4° (c=1, methanol); 1H NMR (CDCl3, 300 MHz) δ1.48(d, 3H), 2.89(s,6H, 3.31(m, 4H), 3.37 (s, 3H), 3.78(m, 4H), 4.34(q, 1H), 6.41(d, 1H), 8.30(d, 1H).
  • 11
  • [ 98961-97-8 ]
  • [ 300553-70-2 ]
  • [ 299397-02-7 ]
YieldReaction ConditionsOperation in experiment
87% With triethylamine In tetrahydrofuran at 20℃; for 2h;
  • 12
  • [ 98961-97-8 ]
  • [ 203660-02-0 ]
  • N,N-[3-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)-3-azapentamethylene]-N',N'-dimethylsulfamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;
  • 13
  • [ 611-35-8 ]
  • [ 98961-97-8 ]
  • 4-[4-(N,N-dimethylsulfamoyl)piperazin-1-yl]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% at 140℃; for 1h;
  • 14
  • [ 57334-36-8 ]
  • [ 98961-97-8 ]
  • 8-hydroxy-4-[4-(N,N-dimethylsulfamoyl)piperazin-1-yl]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% at 130℃; for 4h; Heating;
  • 15
  • [ 16778-21-5 ]
  • [ 98961-97-8 ]
  • 8-methoxy-4-[4-(N,N-dimethylsulfamoyl)piperazin-1-yl]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% at 80℃; for 2h; Heating;
  • 16
  • [ 98961-97-8 ]
  • [ 15733-82-1 ]
  • 2-carboxy-4-[4-(N,N-dimethylsulfamoyl)piperazin-1-yl]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% at 110℃; for 0.5h; Heating;
  • 17
  • [ 98961-97-8 ]
  • [ 535921-56-3 ]
  • 2-hydroxymethyl-4-[4-(N,N-dimethylsulfamoyl)piperazin-1-yl]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% at 110℃; for 0.1h;
  • 18
  • [ 98961-97-8 ]
  • [ 4295-06-1 ]
  • [ 71-36-3 ]
  • [ 92250-29-8 ]
  • [ 535921-55-2 ]
YieldReaction ConditionsOperation in experiment
1: 66% 2: 17% With triethylamine Heating;
  • 19
  • [ 98961-97-8 ]
  • [ 4295-06-1 ]
  • [ 535921-55-2 ]
YieldReaction ConditionsOperation in experiment
77% at 140℃; for 1h;
  • 20
  • [ 98961-97-8 ]
  • [ 79-44-7 ]
  • [ 465530-87-4 ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine In tetrahydrofuran at 20℃; for 2h;
88% With triethylamine In tetrahydrofuran at 20℃; for 2h;
  • 21
  • [ 98961-97-8 ]
  • [ 654071-75-7 ]
  • [ 654071-76-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;
  • 22
  • [ 871018-32-5 ]
  • [ 98961-97-8 ]
  • C30H27F3N6O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 20℃;
  • 23
  • [ 98961-97-8 ]
  • [ 271253-94-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 43 percent / Et3N / Heating 2: MnO2 / CHCl3 / 1.5 h / Heating
Multi-step reaction with 2 steps 1: 45 percent / xylene / 4 h / Heating 2: 50 percent / MnO2 / 1,2-dimethoxy-ethane / 24 h / 20 °C
  • 24
  • [ 98961-97-8 ]
  • [ 654071-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 43 percent / Et3N / Heating 2: MnO2 / CHCl3 / 1.5 h / Heating 3: 30 percent / diethyl ether; tetrahydrofuran / 3 h / Heating
  • 25
  • [ 98961-97-8 ]
  • 4-(4-hydroxymethyl-[1,3,5]triazin-2-yl)-piperazine-1-sulfonic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 88 percent / Et3N / tetrahydrofuran / 2 h / 20 °C 2: POCl3 / 0.5 h / 110 °C 3: 58 percent / acetonitrile / 2 h / Heating 4: 70 percent / NaOAc; H2 / Pd/C / ethanol / 1 h 5: 68 percent / BBr3 / CH2Cl2 / 2 h / cooling
  • 26
  • [ 98961-97-8 ]
  • [ 465530-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 88 percent / Et3N / tetrahydrofuran / 2 h / 20 °C 2: POCl3 / 0.5 h / 110 °C 3: 58 percent / acetonitrile / 2 h / Heating 4: 70 percent / NaOAc; H2 / Pd/C / ethanol / 1 h
  • 27
  • [ 98961-97-8 ]
  • 4-[2-((S)-1-Hydroxy-ethyl)-pyridin-4-yl]-piperazine-1-sulfonic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 43 percent / Et3N / Heating 2: MnO2 / CHCl3 / 1.5 h / Heating 3: 30 percent / diethyl ether; tetrahydrofuran / 3 h / Heating 4: 84 percent / Lipase P30 / dioxane / 96 h / 45 °C 5: 55 percent / aq. NaOH / dioxane; methanol / 1 h / 20 °C
  • 28
  • [ 98961-97-8 ]
  • 4-[4-((R)-1-Hydroxy-ethyl)-[1,3,5]triazin-2-yl]-piperazine-1-sulfonic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaHCO3 / dimethylformamide / 20 °C 2: HCl; ammonium formate / Pd/C / diethyl ether; propan-2-ol / 2 h / 90 °C
  • 29
  • [ 98961-97-8 ]
  • [ 465530-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 88 percent / Et3N / tetrahydrofuran / 2 h / 20 °C 2: POCl3 / 0.5 h / 110 °C 3: 58 percent / acetonitrile / 2 h / Heating
  • 30
  • [ 98961-97-8 ]
  • acetic acid 1-[4-(4-dimethylsulfamoyl-piperazin-1-yl)-pyridin-2-yl]-(R)-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 43 percent / Et3N / Heating 2: MnO2 / CHCl3 / 1.5 h / Heating 3: 30 percent / diethyl ether; tetrahydrofuran / 3 h / Heating 4: 84 percent / Lipase P30 / dioxane / 96 h / 45 °C
  • 31
  • [ 98961-97-8 ]
  • 4-(chloro-dimethylamino-methylene)-piperazine-1-sulfonic acid dimethylamide chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / Et3N / tetrahydrofuran / 2 h / 20 °C 2: POCl3 / 0.5 h / 110 °C
  • 32
  • [ 98961-97-8 ]
  • [ 535921-58-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 17 percent / NEt3 / Heating 2: 55 percent / selenium dioxide / dioxane / 1 h / Heating
Multi-step reaction with 2 steps 1: 77 percent / 1 h / 140 °C 2: 55 percent / selenium dioxide / dioxane / 1 h / Heating
  • 33
  • [ 98961-97-8 ]
  • 2-hydroxymethyl-4-[4-(N,N-dimethylsulfamoyl)piperazin-1-yl]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 17 percent / NEt3 / Heating 2: 55 percent / selenium dioxide / dioxane / 1 h / Heating 3: 90 percent / sodium borohydride / ethanol / 0.5 h / Heating
Multi-step reaction with 3 steps 1: 77 percent / 1 h / 140 °C 2: 55 percent / selenium dioxide / dioxane / 1 h / Heating 3: 90 percent / sodium borohydride / ethanol / 0.5 h / Heating
  • 34
  • [ 98961-97-8 ]
  • 2-carboxy-4-[4-(N,N-dimethylsulfamoyl)piperazin-1-yl]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 17 percent / NEt3 / Heating 2: 55 percent / selenium dioxide / dioxane / 1 h / Heating 3: 32 percent / potassium permanganate / acetone / 2 h / 20 °C
Multi-step reaction with 2 steps 1: 17 percent / NEt3 / Heating 2: 30 percent / selenium dioxide / dioxane / Heating
Multi-step reaction with 3 steps 1: 77 percent / 1 h / 140 °C 2: 55 percent / selenium dioxide / dioxane / 1 h / Heating 3: 32 percent / potassium permanganate / acetone / 2 h / 20 °C
Multi-step reaction with 2 steps 1: 77 percent / 1 h / 140 °C 2: 30 percent / selenium dioxide / dioxane / Heating

  • 35
  • [ 98961-97-8 ]
  • [ 357951-09-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: TEA / dimethylformamide 2: AIBN / 80 °C 3: OsO4; NaIO4 / dioxane; H2O
  • 36
  • [ 98961-97-8 ]
  • 4-(4-hydroxymethyl-pyrimidin-2-yl)-piperazine-1-sulfonic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: TEA / dimethylformamide 2: AIBN / 80 °C 3: OsO4; NaIO4 / dioxane; H2O 4: NaBH4 / ethanol
  • 37
  • [ 98961-97-8 ]
  • 4-[2-((R)-1-Hydroxy-ethyl)-pyrimidin-4-yl]-piperazine-1-sulfonic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / Et3N / tetrahydrofuran / 15 h / Heating 2: 38 percent / boron tribromide / CH2Cl2 / 1 h / cooling
Multi-step reaction with 2 steps 1: 87 percent / Et3N / tetrahydrofuran / 2 h / 20 °C 2: conc. HCl / 6 h / 20 °C
  • 38
  • [ 98961-97-8 ]
  • [ 357951-08-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: TEA / dimethylformamide 2: AIBN / 80 °C
  • 39
  • [ 98961-97-8 ]
  • [ 85671-93-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: benzene / Heating 2: CHCl3 / Heating 3: propan-2-ol / Heating 4: conc. HCl / propan-2-ol / Heating
  • 40
  • [ 98961-97-8 ]
  • N-(2,2-Diethoxy-ethyl)-4-dimethylsulfamoyl-N'-methyl-piperazine-1-carboxamidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: benzene / Heating 2: CHCl3 / Heating 3: propan-2-ol / Heating
  • 41
  • [ 98961-97-8 ]
  • [ 85672-28-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: benzene / Heating 2: CHCl3 / Heating 3: propan-2-ol / Heating 4: conc. HCl / propan-2-ol / Heating 5: 21 percent / nitric acid (d=1.42) / acetic acid / 0.5 h / 10 - 15 °C
  • 42
  • [ 98961-97-8 ]
  • 4-Dimethylsulfamoyl-N-methyl-piperazine-1-carboximidothioic acid methyl ester; hydriodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene / Heating 2: CHCl3 / Heating
  • 43
  • 2,4-dichloro-6-(1-benzyloxyethyl)-[1,3,5]triazine [ No CAS ]
  • [ 98961-97-8 ]
  • 4-[4-(1-benzyloxy-ethyl)-6-chloro-[1,3,5]triazin-2-yl]-piperazine-1-sulfonic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydrogencarbonate In water; ethyl acetate; N,N-dimethyl-formamide 5 4-[4-(1-Hydroxy-ethyl)-[1,3,5]triazin-2-yl]-piperazine-1-sulfonic Acid Dimethylamide A mixture of 2-(1-benzyloxy-ethyl)-4,6-dichloro-[1,3,5]triazine (0.75 mmol, 212 mg), NN-dimethylsulfamoyl piperazine (0.75 mmol, 144 mg), sodium bicarbonate (1.5 mmol, 125 mg), and DMF (3 mL) was stirred overnight at room temperature. EtOAc (15 mL) and water (20 mL) were added and the EtOAc extract was collected and washed with water (2*10 mL). The EtOAc layer was collected, dried and filtered, and the filtrate was evaporated to obtain 4-[4-(1-benzyloxy-ethyl)-6-chloro-[1,3,5]triazin-2-yl]-piperazine-1-sulfonic acid dimethylamide (97%, 320 mg); mass spectrum, m/e 441.
97% With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 20℃;
  • 44
  • [ 373354-56-4 ]
  • [ 98961-97-8 ]
  • [ 373355-36-3 ]
YieldReaction ConditionsOperation in experiment
100 Examples 75-192 Following the procedure of Example 74 using 5,5-Dioxo-2-(4-nitrobenzoxy-carbonylamino)dibenzothiophene (Example 24) and the appropriate amine the following compounds were prepared.
  • 45
  • [ 253176-45-3 ]
  • [ 98961-97-8 ]
YieldReaction ConditionsOperation in experiment
87.33% With trifluoroacetic acid In dichloromethane at 20℃; General procedure for the synthesis of intermediates 4 and 5 General procedure: Under an inert atmosphere (N2), amixture of Boc-piperazine1-1carboxylate (1eq), Dimethyl-sulfamoylchloride (1eq), and N-ethyl-N-isopropylpropan-2-amine (1eq) in DCMwas stirred at room temperature for 24h. The reaction mixture was diluted into100ml of water, and then extracted with DCM (10ml ×6). The organic layers werecombined then dried over Na2SO4 and concentrated invacuum to provide the wanted intermediate 4(yield of 100%) which was further reacted in DCM/TFA (7:3) at room temperature.After the reaction was completed, the solution was diluted in water, and then 1NKOH was used to make the solution slightly basic. The wanted compound 5 was obtained after extraction from the solution byDCM and drying under reduced pressure; to be used directly in the next stepwithout further purification
With trifluoroacetic acid In dichloromethane 119.B STEP B The product from Step A above, was dissolved in a 30% trifluoroacetic ACID/DICHLOROMETHANE solution and stirred overnight. After this time the reaction was diluted with water and 1 N potassium hydroxide was used to make the aqueous layer slightly basic. The aqueous layer was extracted a total of seven times with dichloromethane. The organic fractions were combined and dried over sodium sulfate. Filtration and concentration provided the product (2.96g). 1H NMR (CDC13, 300 MHz) 2.03 (s, 1 H), 2.83 (s, 6H), 2.92 (m, 4H), 3.23 (m, 4H). MS: calculated: 193.09, found: 194.1.
Stage #1: (S)-6'-chloro-N-((R)-hept-6-en-3-ylsulfonyl)-5-((2-((S)-1-hydroxyallyl)-2-methylcyclobutyl)methyl)-3',4,4',5-tetrahydro-2H,2’H-spiro[benzo[b][1,4]oxazepine-3,1’-naphthalene]-7-carboxamide With trifluoroacetic acid In dichloromethane Stage #2: With potassium hydroxide In dichloromethane; water 119.B Step B The product from Step A above, was dissolved in a 30% trifluoroacetic acid/dichloromethane solution and stirred overnight. After this time the reaction was diluted with water and IN potassium hydroxide was used to make the aqueous layer slightly basic. The aqueous layer was extracted a total of seven times with dichloromethane. The organic fractions were combined and dried over sodium sulfate. Filtration and concentration provided the product (2.96 g).[1311] ^ NMR (CDC13, 300 MHz) 2.03 (s, 1H), 2.83 (s, 6H), 2.92 (m, 4H), 3.23 (m, 4H).[1312] MS: calculated: 193.09, found: 194.1.
Stage #1: (S)-6'-chloro-N-((R)-hept-6-en-3-ylsulfonyl)-5-((2-((S)-1-hydroxyallyl)-2-methylcyclobutyl)methyl)-3',4,4',5-tetrahydro-2H,2’H-spiro[benzo[b][1,4]oxazepine-3,1’-naphthalene]-7-carboxamide In dichloromethane; trifluoroacetic acid Stage #2: With potassium hydroxide In H20 119 Preparative example 119 The product from Step A above, was dissolved in a 30% trifluoroacetic acid/dichloromethane solution and stirred overnight. After this time the reaction was diluted with water and 1 N potassium hydroxide was used to make the aqueous layer slightly basic. The aqueous layer was extracted a total of seven times with dichloromethane. The organic fractions were combined and dried over sodium sulfate. Filtration and concentration provided the product (2.96 g).
With trifluoroacetic acid In dichloromethane 119.B The product from Step A above, was dissolved in a 30% trifluoroacetic acid/dichloromethane solution and stirred overnight. After this time the reaction was diluted with water and 1 N potassium hydroxide was used to make the aqueous layer slightly basic. The aqueous layer was extracted a total of seven times with dichloromethane. The organic fractions were combined and dried over sodium sulfate. Filtration and concentration provided the product (2.96g). 'H NMR (CDCI3, 300 MHz) 2.03 (s, 1H), 2.83 (s, 6H), 2.92 (m, 4H), 3.23 (m, 4H). MS: calculated : 193.09, found: 194.1.

  • 46
  • [ 13360-57-1 ]
  • [ 57260-71-6 ]
  • [ 98961-97-8 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: dimethylamino sulfonyl chloride; 1-t-Butoxycarbonylpiperazine With triethylamine In tetrahydrofuran at 0℃; for 1h; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 48h; Stage #3: With sodium hydroxide In dichloromethane; water 400.400A Example 400; [3-(4-Carboxypiperidin-1-yl)phenyl][2,3-dichloro-4-(E-[(4-(dimethylaminosulfamoyl)piperazin-1-yl)carbonyl]ethenyl)phenyl]sulfide; Example 400A; N,N-Dimethyl Piperazinylsulfamide To a solution of tert-butyl 1-piperazinecarboxylate (2.5 g. 13.42 mmol) in tetrahydrofuran (21.5 ml, 0.25 M) at 0° C. was added triethylamine (2.25 ML, 16.11 mmol) followed by dimethylsulfamoyl chloride (1.73 ML, 16.11 mmol).The reaction mixture was stirred at 0° C. for 1 h, diluted with ethyl acetate (100 ML) and washed with saturated NaHCO3 solution (2*30 ML), followed by brine (2*30 ML).The dried (Na2SO4) organic layer was evaporated to dryness under reduced pressure and the residue obtained was treated with 10% trifluoroacetic acid in methylene chloride (20 ML) at ambient temperature.After 48 h, methylene chloride was evaporated in vacuo to obtain a colorless syrup.This crude material was made basic (1 N NaOH, 50 ML), and the mixture was extracted sequentially with ethyl acetate (2*20 ML) and methylene chloride (2*30 ML).The combined organic layers were dried (Na2SO4) and evaporated to dryness under reduced pressure to obtain the title compound in quantitative yield. 1H NMR (300 MHz, DMSO-d6) δ 2.77 (s, 3H), 2.79 (s, 3H), 3.12-3.20 (m, 7H), 3.3 (m, 1H), 8.86 (br s, 1H); MS (ESI) m/e 194 (M+H)+.
  • 47
  • [ 98961-97-8 ]
  • dimethylaminocarbamoyl chloride [ No CAS ]
  • [ 465530-87-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran; hexane; ethyl acetate 1.1 4-Dimethylsulfamoyl-piperazine-1-carboxylic Acid Dimethylamide Step 1 4-Dimethylsulfamoyl-piperazine-1-carboxylic Acid Dimethylamide To a solution of N-N-dimethylsulfamoyl-piperazine (5.2 mmol, 1.0 g) in THF (10 mL) and triethylamine (0.75 mL) was added N,N-dimethylaminocarbamoyl chloride (0.5 mL) and the reaction was stirred for 2 h at room temperature. The precipitated triethylamine hydrochloride was filtered off and the filtrate was evaporated to obtain a white solid, which was crystallized from a 1:1 mixture of EtOAc and n-hexane to yield the title compound of Step 1 (88%).
  • 48
  • [ 98961-97-8 ]
  • [ 105950-89-8 ]
  • [ 140687-49-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran 1.c (c) (c) 4-[4-(N,N-Dimethylsulfamoyl)piperazino]-2-methyloxymethylpyrimidine hydrochloride 3.70 g (23.3 mmol) of 4-chloro-2-methyloxymethylpyrimidine (from stage b), 4.75 g (24.6 mmol) of N,N-dimethylsulfamoylpiperazine and 3.4 ml of triethylamine in 15.4 ml of dry tetrahydrofuran are heated to reflux for 7 hours. After the reaction mixture has been cooled to room temperature, the precipitated triethylammonium chloride is filtered off with suction and washed with ethyl acetate, and the filtrate is evaporated in vacuo. The remaining crude product is chromatographed on silica gel (ethyl acetate/methanol 9:1). 5.90 g of oily product are obtained. 1 H NMR (270 MHz/CDCl3): δ=8.28 (d, J=6Hz, 1H) δ=6.41 (d, J=6Hz, 1H); δ=4.48 (s, 2H); δ=3.75 (t, J=5Hz, 4H); δ=3.33(t, J=5Hz, 4H); δ=2.86 (s, 6H)
  • 49
  • [ 6320-15-6 ]
  • [ 98961-97-8 ]
  • 4-((4-N,N-dimethylsulfamoyl)piperazino)-2,6-dimethoxypyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.6% With triethylamine; In tetrahydrofuran; Example 1 Triethylamine (15.3 ml, 0.11 mol) was added to a solution of 4-chloro-2,6-dimethoxypyrimidine (17.46 g, 0.1 mol) and l-dimethylsulfamoylpiperazine (21.26 g, 0.11 mol) in tetrahydrofuran, and the mixture was refluxed for 40 hours. After standing to cooling, deposited crystals were removed by filtration and the filtrate was concentrated and then purified by silica gel column-chromatography to give 4-((4-N,N-dimethylsulfamoyl)piperazino)-2,6-dimethoxypyrimidine (21.7 g, 65.6%). 1H-NMR (CDCl3) 2.86 (s, 6H, -N-CH3), 3.30 (m, 4H, piperazine ring), 3.91 (s, 3H, -O-CH3), 3.92 (s, 3H, -O-CH3), 5.52 (s, aromatic).
  • 50
  • [ 98961-97-8 ]
  • [ 33034-67-2 ]
  • 2-((4-N,N-dimethylsulfamoyl)piperazino)-4-trifluoromethylpyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.4% With triethylamine In tetrahydrofuran; hexane; water 2 Example 2 Example 2 To a solution of 2-chloro-4-trifluoromethylpyrimidine (10 g, 0.55 mol) and dimethylsulfamoylpiperazine (11.21 g, 0.058 mol) tetrahydrofuran (70 ml), was added triethylamine (7.82 ml, 0.056 mol) and the solution was refluxed for 8 hours. After cooling by standing, the reaction mixture was poured into cool water and extracted by ethyl acetate. The extract solution was washed with water and then saturated saline, and dried on magnesium sulfate, followed by solvent removal by distillation under reduced pressure. The residue was recrystallized in ethyl acetate:hexane (1:1) to give 2-((4-N,N-dimethylsulfamoyl)piperazino)-4-trifluoromethylpyrimidine (12.2 g, 65.4 %). 1H-NMR (CDCl3) 2.86 (s, 6H, -N-CH3), 3.32 (m, 4H, piperazine ring), 4.00 (m, 4H, piperazine ring), 6.82 (s, 1H, J=4.6 Hz, aromatic), 8.52 (s, 1H, J=4.6 Hz, aromatic).
  • 51
  • [ 1722-12-9 ]
  • [ 98961-97-8 ]
  • [ 99191-22-7 ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine In tetrahydrofuran for 40h; Reflux;
I This compound was synthesised as previously described (Kador et al. (2004) J. Ocul. Pharmacol. Ther., 20:333-44). Briefly, piperazine was converted to piperazine-1-sulfonic acid dimethylamide which was then reacted with 2-chloropyrimide to give JHX-1 in 75% yield. The structure was confirmed by 1H-NMR, 13C-NMR, ESI-MS and elemental analysis.
  • 52
  • [ 98961-97-8 ]
  • [ 13223-25-1 ]
  • [ 1146543-70-5 ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine; In tetrahydrofuran; for 40h;Heating / reflux; Synthesis of 1-N,N'-dimethylsulfamoyl-4-(4,6-dimethoxy-2-pyrimidyl)piperazine (JHX-5) Et3N (0.73 mL, 5.2 mmol) was added to 1.0 g of piperazine-1-sulfonic acid dimethylamide (5.2 mmol) in 20 mL of THF. <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (0.9 g, 5.2 mmol) in 5 mL of THF was then added and the mixture was refluxed with stirring for 40 hours. After cooling, THF was removed under vacuum and the remaining yellow solid was dissolved in 300 mL of CHCl3, washed with brine, dried over Na2SO4 and filtered. Solvent removal and CC with 1:1 CHCl3:hexane gave 1.4 g (81%) of white JHX-5, mp 103-105 C. The structure was confirmed by 1H-NMR, 13C-NMR, EI-MS, and elemental analysis. 1H NMR (CDCl3) delta5.41 (s, 1H), 3.86 (s, 6H), 3.89-3.86 (m, 4H), 3.28 (appt, J=4.88 Hz, 4H), 2.86 (s, 6H); EI-MS (m/z) 331 (M+).
  • 53
  • [ 10320-42-0 ]
  • [ 98961-97-8 ]
  • [ 1146543-74-9 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In tetrahydrofuran; at 20℃; for 24h; Triethylamine (7.2 mL, 51.8 mmol) was added to a solution of piperazine-1-sulfonic acid dimethyl amide (10 g, 51.8 mmol) dissolved in 400 mL of THF. <strong>[10320-42-0]2-chloro-5-nitropyrimidine</strong> (7.7 g, 48.3 mmol) dissolved in 20 mL of THF was added to the stirred mixture. After 24 hours stirring at room temperature (RT), THF was removed under vacuum and 600 mL of CHCl3 was added to the residue. The CHCl3 layer was washed with 0.5 N HCl and brine, dried over Na2SO4, and filtered. Solvent evaporation gave 14.1 g (92percent) of straw yellow solid 1-N,N'-dimethylsulfamoyl-4-(2-(5-nitropyrimidyl)piperazine. The structure was confirmed by 1H-NMR. 1H NMR (CDCl3) delta9.08 (s, 2H), 4.09 (appt, J=5.13 Hz, 4H), 3.35 (appt, J=5.13 Hz, 4H), 2.87 (s, 6H).
  • 54
  • [ 110-85-0 ]
  • [ 98961-97-8 ]
YieldReaction ConditionsOperation in experiment
I Synthesis of 1-N,N'-dimethylsulfamoyl-4-(2-pyrimidyl)piperazine (JHX-1) Synthesis of 1-N,N'-dimethylsulfamoyl-4-(2-pyrimidyl)piperazine (JHX-1) This compound was synthesised as previously described (Kador et al. (2004) J. Ocul. Pharmacol. Ther., 20:333-44). Briefly, piperazine was converted to piperazine-1-sulfonic acid dimethylamide which was then reacted with 2-chloropyrimide to give JHX-1 in 75% yield. The structure was confirmed by 1H-NMR, 13C-NMR, ESI-MS and elemental analysis.
  • 55
  • [ 98961-97-8 ]
  • [ 1189852-16-1 ]
  • [ 1190058-16-2 ]
YieldReaction ConditionsOperation in experiment
81% In N,N-dimethyl-formamide at 100℃; for 2h; 263 A solution of N-(7-chloro-2-methylpyrazolo[l ,5-α]pyrimidin-5-yl)-4-(2- hydroxypropan-2-yl)benzamide (2F, 86 mg, 0.25 mmol) and λ/,λ/-dimethylpiperazine-l- sulfonamide (145 mg, 0.75 mmol) in DMF (1.0 mL) was stirred at 100 0C for 2h. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC (35-60% MeCN/H2O gradient + 0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (101.3 mg, 81%). 1H NMR (DMSO-de) δ: 10.90 (s, IH), 8.00 (d, J = 8.8 Hz, 2H), 7.60 (d, J = 8.6 Hz, 2H), 7.36 (s, IH), 6.20 (s, IH), 3.79 - 3.82 (m, 4H), 3.39 - 3.48 (m, 4H), 3.07 - 3.16 (m, 2H), 2.39 (s, 3H), 1.66 - 1.82 (m, 2H), 1.45 (s, 6H), 1.01 (t, 3H); ESI-MS: m/z 502.3 (M+H)+.
  • 56
  • [ 98961-97-8 ]
  • 1-(2-(dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
  • 4-(1-(2-(dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; 154 To a solution of l-(2-(dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-l ,4-dihydroquinoline-3-carboxylic acid (Example 153, 80 mg, 0.14 mmol) in dimethylformamide (0.5 mL) was added HATU (78.4 mg, 0.20 mmol) then diisopropylethylamine (95.2 uL, 0.55 mmol). This was followed by N ,N- dimethylpiperazine-1 -sulfonamide (52.7 mg, 0.27 mmol) and the reaction was stirred at room temperature for 1 h. The solvent was removed under reduced pressure and the residue purified by prep HPLC (Water-methanol-0.1% Formic acid). MS (ESP): 764.4 (MH+) for C34H42F3N9O7S21H NMR (300 MHz, CD3OD): δ 0.99 (t, 3H), 1.63 (m, 2H), 2.43 (s, 6H), 2.85 (s, 6H), 2.92 (t, 2H), 3.32 (brs, 6H), 3.47 (brs, 2H), 3.81 (brs, 2H), 4.55 (t, 2H), 7.67 (d, IH), 7.84 (s, IH), 7.87 (d, IH), 8.18 (s, IH), 8.29 (s, IH), 8.32 (s, 2H).
  • 57
  • [ 98961-97-8 ]
  • [ 4983-28-2 ]
  • [ 1146543-67-0 ]
  • 59
  • [ 98961-97-8 ]
  • [ 846060-70-6 ]
  • [ 1280479-82-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (1S,2R)-1-(3,4-dichlorophenyl)-2-hydroxymethylcyclopropanecarboxylic acid (4-fluorobenzyl)methylamide Stage #2: piperazine-1-sulfonic acid dimethylamide
  • 60
  • [ 98961-97-8 ]
  • [ 1445720-44-4 ]
  • [ 1445902-10-2 ]
YieldReaction ConditionsOperation in experiment
118 mg With chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct; sodium t-butanolate; ruphos In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; 9.3 Step 3 : 4- {4-[(S)- 1 -(Isobutyl-phenylmethanesulfonyl-amino)-ethyl]-phenyl} -piperazine- 1 -sulfonic acid dimethylamide Step 3 : 4- {4-[(S)- 1 -(Isobutyl-phenylmethanesulfonyl-amino)-ethyl]-phenyl} -piperazine- 1 -sulfonic acid dimethylamide In a vial, (^-N-(l -(4-bromophenyl)ethyl)-N-isobutyl(phenyl)methanesulfonamide (150 mg, 0.36 mmol) N,N-dimethylpiperazine-l -sulfonamide (106 mg, 0.54 mmol), 2- dicyclohexylphosphino-2',6'-di-i-propoxy-l, -biphenyl (9 mg, 0.018 mmol), chloro(2- dicyclohexylphosphino-2',6'-di-i-propoxy-l ,l '-biphenyl)[2-(2 aminoethylphenyl)]palladium(II), methyl-t-butylether adduct (13 mg, 0.018 mmol) and sodium teri-butoxide (54 mg, 0.54 mmol) were combined and the vial was purged with nitrogen. 1 ,4-Dioxane (3 mL) was added and the reaction was stirred at 100 °C for 16 hours. The reaction was filtered through diatomaceous earth, concentrated and purified by preparative reverse phase HPLC to yield 1 18 mg of 4-{4-[()-l -(Isobutyl- phenylmethanesulfonyl-amino)-ethyl]-phenyl} -piperazine- 1 -sulfonic acid dimethylamide11 H NMR (400 MHz, DMSO) δ 7.40 - 7.34 (m, 5H), 7.34 - 7.29 (m, 2H), 6.99 - 6.90 (m, 2H), 4.94 (q, J= 7.2 Hz, 1H), 4.32 (d, J= 13.4 Hz, 1H), 4.21 (d, J= 13.5 Hz, 1H), 3.32 - 3.24 (m, 4H), 3.23 - 3.16 (m, 4H), 2.90 - 2.70 (m, 8H), 1.66 - 1.53 (m, 1H), 1.50 (d, J= 7.1 Hz, 3H), 0.64 (dd, J= 13.7, 6.6 Hz, 6H); LCMS (m/z) ES+ 523.2 [M+l]+.
  • 61
  • [ 98961-97-8 ]
  • [ 1445720-42-2 ]
  • [ 1445902-12-4 ]
YieldReaction ConditionsOperation in experiment
124 mg With chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct; sodium t-butanolate; ruphos In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; 10.3 Step 3 : 4- {4-[(R)- 1 -(Isobutyl-phenylmethanesulfonyl-amino)-ethyl]-phenyl} - piperazine-1 -sulfonic acid dimethylamide Step 3 : 4- {4-[(R)- 1 -(Isobutyl-phenylmethanesulfonyl-amino)-ethyl]-phenyl} - piperazine-1 -sulfonic acid dimethylamide In a vial, ( ?)-N-(l-(4-bromophenyl)ethyl)-N-isobutyl(phenyl)methanesulfonamide (150 mg, 0.36 mmol) N,N-dimethylpiperazine-l -sulfonamide (106 mg, 0.54 mmol) 2- dicyclohexylphosphino-2',6'-di-i-propoxy-l, -biphenyl (9 mg, 0.018 mmol), chloro(2- dicyclohexylphosphino-2',6'-di-i-propoxy-l ,l '-biphenyl)[2-(2 aminoethylphenyl)]palladium(II), methyl-t-butylether adduct (13 mg, 0.018 mmol) and sodium teri-butoxide (54 mg, 0.54 mmol) were combined and the vial was purged with nitrogen. 1 ,4-Dioxane (3 mL) was added and the reaction was stirred at 100 °C for 16 hours. The reaction was filtered through diatomaceous earth, concentrated and purified by preparative reverse phase HPLC to yield 124 mg of 4-{4-[( ?)-l-(Isobutyl- phenylmethanesulfonyl-amino)-ethyl]-phenyl} -piperazine- 1 -sulfonic acid dimethylamide. 1H NMR (400 MHz, DMSO) δ 7.39 - 7.34 (m, 5H), 7.34 - 7.28 (m, 2H), 6.97 - 6.92 (m, 2H), 5.01 - 4.88 (m, 1H), 4.32 (d, J= 13.4 Hz, 1H), 4.21 (d, J= 13.4 Hz, 1H), 3.37 - 3.30 (m, 2H), 3.24 - 3.13 (m, 5H), 2.86 - 2.72 (m, 8H), 2.60 - 2.53 (m, 1H), 1.67 - 1.52 (m, 1H), 1.50 (d, J= 7.1 Hz, 3H), 0.64 (dd, J= 13.8, 6.6 Hz, 6H); LCMS (m/z) ES+ 523.2 [M+l]+.
  • 62
  • [ 98961-97-8 ]
  • [ 1610520-45-0 ]
  • [ 1610518-53-0 ]
YieldReaction ConditionsOperation in experiment
9.7 mg With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; 38 Example 38 To a suspension of 7-(3,4-dimethoxyphenyl)-5-methyl-4-oxo-4,5-dihydrothieno[3,2-c]pyridine-2- carbaldehyde (for a preparation see Intermediate 25, 16.5 mg, 0.05 mmol) in tetrahydrofuran (2 ml.) was added A/,A/-dimethylpiperazine-1 -sulphonamide (39 mg, 0.2 mmol) followed by sodium triacetoxyborohydride (42 mg, 0.2 mmol). The mixture was stirred at room temperature overnight. The material was loaded onto a 5 g SCX cartridge, washed with methanol and then eluted with NH3 in methanol. The eluted material was concentrated and then purified on a 10 g NH2-SPE column eluting with 99:1-90:10 dichloromethane/methanol. The eluted material was again concentrated and then purified on a 20 g silica column eluting with 95:5 - 5:1 dichloromethane/methanol. The concentrated product was dissolved in dichloromethane and MP-NCO was added and the reaction was stirred at room temperature for 2 hr. The material was again purified on a 12 g silica column using a graduating solvent system of 98:2 - 9: 1 dichloromethane/methanol. Evaporation of the solvent gave the product 4-((7-(3,4-dimethoxyphenyl)-5-methyl-4-oxo-4,5-dihydrothieno[3,2- c]pyridin-2-yl)methyl)-/V,/V-dimethylpiperazine-1-sulphonamide (9.7 mg). LCMS (2 min, Formic Acid): Rt = 0.89 min, MH+ = 507.
  • 63
  • [ 98961-97-8 ]
  • [ 325158-39-2 ]
  • 4-(3-((6-bromonaphthalen-2-yl)oxy)-2-hydroxypropyl)-N,N-dimethylpiperazine-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% In ethanol Reflux; 1 2.1.3 Synthesis of compound 1 and analoguestiteled 6a-m General procedure: Compound 1and analogues (6a-m) were obtainedby reaction of 1eq of 2-(((6-bromonaphthalen-2-yl)oxy)methyl)oxirane (intermediate 3) with the appropriate piperazinederivative (1.2eq) in EtOH (10 ml) at reflux for 5 to 8h. After concentrationunder reduced pressure of reaction mixture, the purified compounds wereobtained after purification by column chromatography using PE: EA (1:2) orrecrystallization in EtOAc.
  • 64
  • [ 98961-97-8 ]
  • 11-chloro-5-(dimethyl-1H-1,2,3-triazol-5-yl)-8-[(S)-(2-fluorophenyl)(oxan-4-yl)methyl]-3,8,10-triazatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,5,9,11-hexaene [ No CAS ]
  • 4-[5-(dimethyl-1H-1,2,3-triazol-5-yl)-8-[(S)-(2-fluorophenyl)(oxan-4-yl)methyl]-3,8,10-triazatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,5,9,11-hexaen-11-yl]-N,N-dimethylpiperazine-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With palladium diacetate; caesium carbonate; ruphos In 1,4-dioxane at 100℃; for 48h; Inert atmosphere; Sealed tube; 269 4-[5-(dimethyl-1H-1,2,3-triazol-5-yl)-8-[(S)-(2-fluorophenyl)(oxan-4-yl)methyl]-3,8,10-triazatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,5,9,11-hexaen-11-yl]-N,N-dimethylpiperazine-1-sulfonamide In a small pressure vessel equipped with a magnetic stirring bar was added (2C03 (19.9 mg, 0.061 mmol) was added. Argon was bubbled into the mixture with sonication for 5 min, then the vessel was capped and placed into a preheated aluminum block at 100°C, and the reaction mixture was stirred for 48 h. Solid were removed by filtration, and the filtrate was purified by preparative HPLC: Column: Waters XBridge C18, 19 x 200 mm, 5-μιτι particles; Mobile Phase A: 5:95 methanol: water with lOmM LiOAc; Mobile Phase B: 95:5 methanol: water with lOmM NftOAc; Gradient: 35-75% B over 20 min, then a 5- min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 2.7 mg (10%) of the title compound with an average purity by LC/MS analysis was 96%. Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7μτη particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50°C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 1 mL/min; Detection: UV at 220 nm. Rt= 1.85 min.; LC/MS (M+H) = 648.1. Injection 2 conditions: Column: Waters BEH CI 8, 2.0 x 50 mm, 1.7-μιη particles; Mobile Phase A: 5:95 methanol: water with 10 mM Nl UOAc; Mobile Phase B: 95:5 methanol: water with 10 mM NH4OAc; Temperature: 50°C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 0.5 rnL/min; Detection: UV at 220 nm. Rt = 3.12 min.; LC/MS (M+H) = 648.1. NMR (500MHz, DMSO-c e) δ 8.44 (s, 1H), 8.30 (d, J=8.4 Hz, 2H), 8.15 (t, J=7.5 Hz, 1H), 7.32 (d, J=6.6 Hz, 1H), 7.28 - 7.20 (m, 1H), 7.11 (t, J=9.2 Hz, 1H), 6.90 (d, J=8.8 Hz, 1H), 6.02 (br. s., 1H), 4.01 (s, 3H), 3.90 (s, 2H), 3.87 - 3.79 (m, 4H), 3.75 (d, J=10.3 Hz, 1H), 3.53 (br. s., 1H), 3.49 - 3.43 (m, 3H), 3.34 (br. s., 2H), 3.28 - 3.15 (m, 1H), 2.87 - 2.77 (m, 6H), 2.30 (s, 3H), 1.62 (d, J=12.5 Hz, 1H), 1.45 (d, J=12.1 Hz, 1H), 1.33 (d, J=8.4 Hz, 1H), 1.10 - 0.96 (m, 1H). LC/MS (M+H) = 648.3; HPLC conditions: Rt= 3.52 min: Column: (Phenomenex LUNA C18 2 x 50 mm (4 min grad) eluting with 10-90% aq MeOH containing 0.1%TFA, 0.8 rnL/min, monitoring at 254 nm); Temperature: 40°C).
  • 65
  • [ 98961-97-8 ]
  • (S)-7-chloro-3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole [ No CAS ]
  • 4-[3-(dimethyl-1H-1,2,3-triazol-5-yl)-5-[(S)-oxan-4-yl(phenyl)methyl]-5H-pyrido [3,2-b]indol-7-yl]-N,N-dimethylpiperazine-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)-palladium(II); palladium diacetate; sodium t-butanolate; ruphos In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; Sealed tube; Sonication; 50 4-[3-(Dimethyl-lH-l,2,3-triazol-5-yl)-5-[(.S)-oxan-4-yl(phenyl)methyl]-5H- pyrido [3,2-b] indol-7-yl] -AyV-dimethylpiperazine- 1-sulfonamide In a small pressure vial equipped with a magnetic stirring bar was added (5 -7- chloro-3-(l,4-dimethyl-lH-l,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4- yl)methyl)-5H-pyrido[3,2-b]indole (30 mg, 0.064 mmol), N,N-dimethylpiperazine-l- sulfonamide (18.4 mg, 0.095 mmol) and dioxane (2 mL). RuPhos precatalyst (CAS 1375325-68-0, 2.8 mg, 3.81 μπιο), Pd(OAc)2 (0.9 mg, 3.81 μπιο), RuPhos (CAS 787618-22-8, 1.8 mg, 3.81 μηιο) and sodium i-butoxide (18.3 mg, 0.191 mmol) were added. Argon was bubbled into the mixture with sonication for 5 min. The vial was sealed, placed into a preheated oil bath at 100°C and the reaction mixture was stirred for 16 h. Solids were removed by filtration, and the filtrate was purified by preparative HPLC: Column: Waters XBridge C18, 19 x 200 mm, 5-μιη particles; Mobile Phase A: 5:95 MeOH: water with lOmM NH4OAc; Mobile Phase B: 95:5 MeOH: water with lOmM NH4OAc; Gradient: 30-70% B over 20 min, then a 5 min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 9.1 mg (22%) of the title compound with an average purity by LC/MS analysis of 96%. Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-μτη particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50°C; Gradient: 0-100% B over 3 min, then a 0.75 min hold at 100% B; Flow: 1.0 mL/min; Detection: UV at 220 nm. Rt= 1.79 min.; LC/MS (M+H) = 629.1. Injection 2 conditions: Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-μιη particles; Mobile Phase A: 5:95 ACN:water with 0.1% trifluoroacetic acid; Mobile Phase B: 95:5 ACN:water with 0.1% trifluoroacetic acid; Temperature: 50°C; Gradient: 0-100% B over 3 min, then a 0.75 min hold at 100% B; Flow: 1.0 mL/min; Detection: UV at 220 nm. Rt= 1.60 min.; LC/MS (M+H) = 629.0. NMR (500MHz, DMSO-c e) δ 8.40 (s, 1H), 8.24 (br. s., 1H), 8.04 (d, J=8.4 Hz, 1H), 7.67 (d, J=7.7 Hz, 2H), 7.49 (br. s., 1H), 7.33 (t, J=7.5 Hz, 2H), 7.25 (t, J=7.2 Hz, 1H), 7.04 (d, J=8.8 Hz, 1H), 5.80 (d, J=11.0 Hz, 1H), 3.98 (br. s., 3H), 3.90 (d, J=8.4 Hz, 1H), 3.74 (d, J=8.4 Hz, 1H), 3.47 (d, J=9.2 Hz, 4H), 3.26 (t, J= 1.6 Hz, 2H), 2.85 (s, 7H), 2.28 (s, 3H), 1.71 (d, J=12.8 Hz, 1H), 1.57 (d, J=12.8 Hz, 1H), 1.34 (d, J=8.8 Hz, 1H), 0.99 (d, J=l 1.0 Hz, 1H). LC/MS (M+H) = 629.2; HPLC conditions: Rt = 3.39 min. : Column: Phenomenex LUNA C 18 2 x 50 mm (4 min grad) eluting with 10-90% aqueous MeOH containing 0.1 %TFA, 0.8 mL/min, monitoring at 254 nm); Temperature: 40°C
  • 66
  • [ 98961-97-8 ]
  • [ 191530-31-1 ]
  • C27H31N5O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% In N,N-dimethyl-formamide at 20℃; for 12h; General synthetic procedure for target compounds 12a-p. General procedure: To a solution of 7-bromomethyl-camptothecin (0.1 mmol) in dry DMF (10mL), sulfonylpiperazines (0.15 mmol) dissolved in DMF (3mL) was added and stirred at room temperature. After the reaction was completed, the mixture was evaporated to dryness and and the residue was purified by chromatography on silica gel usingCHCl3/MeOHas eluant to give target compounds 12a-p.
  • 67
  • [ 98961-97-8 ]
  • (3R,4S)-4-(4-bromophenyl)-1-(2-fluoro-6-methylbenzyl)-N,N-dimethylpyrrolidin-3-amine [ No CAS ]
  • C26H38FN5O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In 1,4-dioxane at 100℃; for 8h; Inert atmosphere; Sealed tube;
  • 68
  • [ 98961-97-8 ]
  • 4-(4-cyano-4-methylpiperidin-1-yl)-6-fluoroquinoline-3-carboxylic acid [ No CAS ]
  • 4-(4-(4-cyano-4-methylpiperidin-1-yl)-6-fluoroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;
  • 69
  • [ 98961-97-8 ]
  • 4-(4-cyano-4-phenylpiperidin-1-yl)-6-fluoroquinoline-3-carboxylic acid [ No CAS ]
  • 4-(4-(4-cyano-4-phenylpiperidin-1-yl)-6-fluoroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;
  • 70
  • [ 98961-97-8 ]
  • 4-(4-(1-cyanocyclopropyl)phenyl)-6-fluoroquinoline-3-carboxylic acid [ No CAS ]
  • 4-(4-(4-(1-cyanocyclopropyl)phenyl)-6-fluoroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
39.6% With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1.5h;
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