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[ CAS No. 22952-32-5 ] {[proInfo.proName]}

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Chemical Structure| 22952-32-5
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Product Details of [ 22952-32-5 ]

CAS No. :22952-32-5 MDL No. :MFCD00052959
Formula : C7H6Cl2O3S Boiling Point : -
Linear Structure Formula :- InChI Key :FCJGLIMDVOTBLO-UHFFFAOYSA-N
M.W : 241.09 Pubchem ID :2734272
Synonyms :

Calculated chemistry of [ 22952-32-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.03
TPSA : 51.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 2.54
Log Po/w (WLOGP) : 3.36
Log Po/w (MLOGP) : 1.82
Log Po/w (SILICOS-IT) : 1.98
Consensus Log Po/w : 2.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.14
Solubility : 0.173 mg/ml ; 0.000717 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.128 mg/ml ; 0.000532 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.69
Solubility : 0.0493 mg/ml ; 0.000205 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 22952-32-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22952-32-5 ]

* 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 [ 22952-32-5 ]

[ 22952-32-5 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 623-12-1 ]
  • [ 22952-32-5 ]
YieldReaction ConditionsOperation in experiment
64% With chlorosulfonic acid; In dichloromethane; at 0 - 5℃; for 3h;Inert atmosphere; General procedure: A solution of the respective anisole (175 mmol) in CH2Cl2 (50 mL) was added dropwise to a 0 C chlorosulfonic acid (100 mL) so as to maintain the reaction temperature below 5 C. After the addition was complete, the reaction mixture was stirred for 3 h and poured over ice. The organic phase was separated, washes with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by short-path chromatography on silica gel using 10% ethyl acetate in hexanes as eluent to provide the analytically pure target compound.
With chlorosulfonic acid; at 15 - 50℃;Cooling with ice; Freshly distilled chlorosulfonic acid (13.2 g, 0.1 mol, 1.0 equiv) was cooled to 15 C in an ice-water bath and 4-chloroanisole (27 mL, 0.2 mol, 2.0 equiv) was carefully added, keeping the temperature of the mixture below 50 C. The reaction mixture was carefully poured into 250 mL ice water. The resultant white solid (5-chloro-2-methoxybenzene-1-sulfonyl chloride) was filtered and dried. (0051) 3,5-Bis(trifluoromethyl)aniline (2.3 g, 10 mmol, 1.0 equiv) and 4-dimethylaminopyridine (50 mg, 0.4 mmol, 0.04 equiv) were dissolved in anhydrous pyridine (20 mL, 0.5 M). 5-Chloro-2-methoxybenzene-1-sulfonyl chloride (2.41 g, 10 mmol, 1 equiv) was added. The resulting mixture was stirred at room temperature (10 h). Water (20 mL) was added to quench the reaction. The precipitate formed was filtered and washed with water, cold THF, and Et2O to afford a brown solid (N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-methoxybenzene-sulfonamide). 1H NMR (300 MHz, DMSO-d6): delta 3.79 (s, 3H), 7.23 (d, J = 9.0 Hz, 1H), 7.66-7.68 (m, 3H), 7.75 (s, 1H), 7.81 (d, J = 2.6 Hz, 1H), 11.12(s, 1H). (0052) Boron tribromide (5 mL, 1.7 mmol, 1.7 equiv) was added to a solution of N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-methoxybenzenesulfonamide (434 mg, 1 mmol, 1.0 equiv) in DCM (5 mL, 0.2 M) at -70 C and allowed to warm to room temperature (12 h). The mixture was added dropwise to 10 mL ice water, with stirring continued for an additional 0.5 h. The mixture was cooled to room temperature and concentrated sodium hydroxide was added dropwise until the pH reached 6-7, followed by extraction with DCM. The organic extracts were combined, dried (MgSO4), concentrated under vacuum, and purified by chromatography (1:2 EtOAc:Hex) (340 mg, 81%). Slightly yellow solid. Mp 135-138 C. 1H NMR (300 MHz, DMSO-d6): delta 6.95 (d, J = 8.8 Hz, 1H), 7.49 (dd, J1 = 8.8 Hz, J2 = 2.3 Hz, 1H), 7.68-7.71 (m, 4H), 11.27 (s, 2H). IR (neat): 3354, 3238, 1413, 1374, 1276, 1125, 966, 826 cm-1. HRMS (APCI), m/z calcd for C14H8ClF6NO3S-H: 417.9766, found 417.9753.
With chlorosulfonic acid; In chloroform; at 0 - 20℃; for 2h; General procedure: The solution of 1-halo-4-alkoxybenzene 9 (8.5 g) in chloroform(50 mL) was introduced in a 250 mL three-necked flask, equippedwith a magnetic stirrer, a thermometer, a calcium chloride guardand a dropping reagent. The solution was cooled to 0 C and addeddropwise to chlorosulfonic acid (15 mL). After completion, thereaction mixture was heated to room temperature, left for 2 h,and then poured over crushed ice. The resulting mixture wasextracted with chloroform. The organic extracts were dried oversodium sulfate and concentrated under reduced pressure untilcrystallization. The resulting sulfonyl chlorides (7-8 g) (10a-c)were dissolved in 60 mL dioxane and added dropwise to a 30%m/v solution of ammonia (100 mL). The reaction mixture was concentratedunder reduced pressure, leading to a solid which wascollected by filtration, washed with cold water, and dried.
With chlorosulfonic acid; 5-Chloro-N-(2-chloro-4-(trifluoromethyl)phenyl)-2-hydroxybenzenesulfonamide (4) p-Chloroanisole was chlorosulfonylated using the method of Guo (Guo, et al. Tetrahedron 1997, 53, 4145) to produce 5-chloro-2-methoxybenzenesulfonyl chloride which was used without purification. To an ice-cold solution of 5-chloro-2-methoxybenzenesulfonyl chloride (0.398 g, 1.8 mmol), CH2Cl2 (5 mL) and pyridine (0.28 g, 3.6 mmol) was added 2-chloro-4-(trifluoromethyl)aniline (0.347 g, 0.18 mmol) over 1 min. After the reaction was complete by HPLC/MS, water was added and the reaction mixture was extracted with CH2Cl2. The CH2Cl2 layer was washed three times with dilute acid, one time with brine, dried over Na2SO4, and filtered through glass wool. The filtrate containing 5-chloro-N-(2-chloro-4-(trifluoromethyl)phenyl)-2-methoxybenzenesulfonamide was concentrated and used directly without further purification. To a dry round-bottom flask containing 5-chloro-N-(2-chloro-4-(trifluoromethyl)phenyl)-2-methoxybenzenesulfonamide in dry DMF (5 mL) was added a solution of freshly prepared 1M sodium benzenethiolate in DMF (3.6 mL). The resultant dark colored mixture was heated in an oil bath at 135-145 C. for 3.5 h, cooled to rt, poured into water (100 mL), and the aqueous mixture extracted 2 times with EtOAc. The EtOAc layers were combined, washed 5 times with water, 1 time with brine, dried with Na2SO4, decanted, and concentrated onto 5 mL of silica gel. The solids were eluted on a column of 100 mL of silica gel with a gradient of 10-30% EtOAc/Hexane. The material with rf=0.25 (25% EtOAc/Hexane) was combined and concentrated to give 0.22 g of the title compound as a light tan solid. 1H NMR (300 MHz, DMSO-d6) delta 11.3 (br s, 1H), 9.9 (br s, 1H), 7.83 (s, 1H), 7.66-7.47 (m, 4H), 6.98 (d, J=8.8, 1H). m/z (ESI-)=384, 386 (M-1). FTIR (thin film) 3339 br, 1615 w, 1323 st, m/z (ESI-)=384, 386 (M-1).

  • 2
  • [ 46170-99-4 ]
  • [ 22952-32-5 ]
  • 4
  • [ 22952-32-5 ]
  • [ 108-88-3 ]
  • 4-chloro-1-methoxy-2-(toluene-4-sulfonyl)-benzene [ No CAS ]
  • 5
  • [ 22952-32-5 ]
  • [ 6325-22-0 ]
  • [ 81514-22-9 ]
  • 6
  • [ 22952-32-5 ]
  • [ 22952-33-6 ]
YieldReaction ConditionsOperation in experiment
97% With hydrazine hydrate; In tetrahydrofuran; at 0 - 20℃; General procedure: To solution of 1 mmol of arylsulfonyl chloride 4i-w in 10 ml of THF, 1.1 mmol of hydrazine-hydrate in 10 ml THF were added drop wise at 0-5 8C with stirring. After stirring 1-2 h at rt 20 ml of water were added, the precipitate was filtered, dried and crystallized from benzene or hexane. HPLC analysis revealed single peaks for all tested compounds. Yield 97%, m.p. 110-112 C. 1H NMR (DMSO-d6): delta 3.95 (s, 3H, CH3O), 7.19 (d, 1H, JHH = 8.8 Hz, HAr), 7.52 (dd, 1H, JHH = 8.8, 2.8 Hz, HAr), 7.72 (d, 1H, JHH = 2.8 Hz, HAr), 7.95 (s, 1H, NH). EI-MS (m/z): 237 [M+1]+. Anal. calcd. for C7H9ClN2O3S: C, 35.52; H, 3.83; Cl, 14.98; N, 11.84; O, 20.28; S, 13.55; found: C, 35.68; H, 3.72; N, 11.88.
With pyridine; hydrazine hydrate; In ethanol; at 70℃; for 2h; General procedure: In a 50 mL round-bottomed flask, different substituted sulfonylchloride (1 mmol) were treated with hydrazine hydrate (5 mL) inethanol (10 mL) in the presence of few drops of pyridine at 70 C for 2 h.Reaction progress was checked by TLC periodically. The pure productswas obtained via collection of the precipitate by filtration, washing withhexane and water to remove impurities. Extra pure products were obtainedby crystallization from ethanol.
  • 7
  • [ 22952-32-5 ]
  • 5-Chlor-2-methoxy-benzolsulfonsaeureazid [ No CAS ]
  • 8
  • [ 22952-32-5 ]
  • (R,R)-1,2-diaminocyclohexane tartrate [ No CAS ]
  • C6H10(NHSO2C6H3(OCH3)Cl)2 [ No CAS ]
  • 9
  • [ 504-15-4 ]
  • [ 22952-32-5 ]
  • [ 197959-76-5 ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydrogencarbonate; In tetrahydrofuran; dibutyl ether; at 20 - 50℃; a) 3-(5-Chloro-2-methoxyphenylsulfonyloxy)-5-methylphenol Saturated aqueous NaHCO3 (70 mL) was added to a solution of <strong>[22952-32-5]5-chloro-2-methoxybenzenesulfonyl chloride</strong> (3.83 g, 15.9 mmol) and orcinol monohydrate (3.39 g, 23.9 mmol) in di-n-butyl ether (53 mL) and tetrahydrofuran (17 mL). The biphasic solution was mixed vigorously at 50C for 7 h and then at ambient temperature overnight. The reaction mixture was combined with that from a previous reaction (which used 4.53 g [18.8 mmol] of <strong>[22952-32-5]5-chloro-2-methoxybenzenesulfonyl chloride</strong>), the layers were separated, and the aqueous layer was extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were washed with brine (250 mL), dried over Na2SO4, filtered, and evaporated to give 18.25 g of a clear brown oil. The product was purified by flash column chromatography (1% to 4% ethyl acetete in dichloromethane) to give the title compound (9.86 g, 86%) as a pale yellow oil which crystallized upon standing. 1H-NMR (300 MHz, CDCl3) delta 7.81 (d, 1 H, J = 2.6 Hz), 7.55 (dd, 1 H, J = 2.6, 8.9 Hz), 7.02 (d, 1H, J = 8.9 Hz), 6.53 (m, 2 H), 6.41 (t, 1 H, J = 2.2 Hz), 3.99 (s, 3 H), 2.24 (s, 3 H). Mass spectrum (MALDI-TOF, alpha-cyano-4-hydroxycinnamic acid matrix) calcd. for C14H13ClO5S: 351.0 (M + Na). Found: 351.1.
  • 11
  • [ 7647-01-0 ]
  • [ 22952-32-5 ]
  • tin [ No CAS ]
  • [ 768-13-8 ]
  • 12
  • [ 107-10-8 ]
  • [ 22952-32-5 ]
  • [ 13331-27-6 ]
  • [ 7693-46-1 ]
  • FMOC-L-p-bromophenylalanine [ No CAS ]
  • (S)-2-(5-Chloro-2-methoxy-benzenesulfonylamino)-3-[3'-(3-propyl-ureido)-biphenyl-4-yl]-propionic acid [ No CAS ]
  • 13
  • [ 22952-32-5 ]
  • [ 143322-01-4 ]
  • 5-chloro-2-methoxy-<i>N</i>-[3-(1-methyl-pyrrolidin-2-ylmethyl)-1<i>H</i>-indol-5-yl]-benzenesulfonamide [ No CAS ]
  • 14
  • [ 22952-32-5 ]
  • [ 840527-23-3 ]
  • 5-chloro-2-methoxy-<i>N</i>-[3-(1-methyl-pyrrolidin-2-ylmethyl)-1<i>H</i>-indol-5-yl]-benzenesulfonamide [ No CAS ]
  • 15
  • [ 22952-32-5 ]
  • [ 840527-70-0 ]
  • 2-[5-(5-chloro-2-methoxy-benzenesulfonylamino)-1<i>H</i>-indol-3-ylmethyl]-pyrrolidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 16
  • [ 22952-32-5 ]
  • [ 172842-90-9 ]
  • 2-[5-(5-chloro-2-methoxy-benzenesulfonylamino)-1<i>H</i>-indol-3-ylmethyl]-pyrrolidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 17
  • 5-<i>tert</i>-butyl-4-methyl-thiazol-2-ylamine; hydrochloride [ No CAS ]
  • [ 22952-32-5 ]
  • [ 612539-31-8 ]
  • 18
  • 4-chloro-5-isopropyl-thiazol-2-ylamine; hydrochloride [ No CAS ]
  • [ 22952-32-5 ]
  • [ 847652-84-0 ]
  • 20
  • [ 885679-18-5 ]
  • [ 22952-32-5 ]
  • [ 885679-19-6 ]
  • 21
  • [ 885679-25-4 ]
  • [ 22952-32-5 ]
  • 1-(5-chloro-2-methoxyphenylsulfonyl)-5-fluoro-N-(2-methoxybenzyl)-1,2,3,6-tetrahydropyridine-2-carboxamide [ No CAS ]
  • 22
  • [ 885679-26-5 ]
  • [ 22952-32-5 ]
  • 1-(5-chloro-2-methoxyphenylsulfonyl)-N-(4-chloro-3-trifluoromethylbenzyl)-5-fluoro-1,2,3,6-tetrahydropyridine-2-carboxamide [ No CAS ]
  • 23
  • [ 870249-31-3 ]
  • [ 22952-32-5 ]
  • C26H36ClN3O4S [ No CAS ]
  • C26H36ClN3O4S [ No CAS ]
  • 24
  • C18H30N4O [ No CAS ]
  • [ 22952-32-5 ]
  • C25H35ClN4O4S [ No CAS ]
  • 25
  • [ 910606-15-4 ]
  • [ 22952-32-5 ]
  • C26H35ClN4O4S [ No CAS ]
  • 26
  • [ 910605-32-2 ]
  • [ 22952-32-5 ]
  • 5-chloro-N-cis-{4-[4-(2-cyclopropoxy-phenyl)-piperidin-1-yl]-cyclohexyl}-2-methoxy-benzenesulfonamide [ No CAS ]
  • 5-chloro-N-trans-{4-[4-(2-cyclopropoxy-phenyl)-piperidin-1-yl]-cyclohexyl}-2-methoxy-benzenesulfonamide [ No CAS ]
  • 27
  • [ 946605-81-8 ]
  • [ 22952-32-5 ]
  • 5-chloro-2-methoxy-N-cis-(4-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperidin-1-yl}-cyclohexyl)-benzenesulfonamide [ No CAS ]
  • 5-chloro-2-methoxy-N-trans-(4-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperidin-1-yl}-cyclohexyl)-benzenesulfonamide [ No CAS ]
  • 28
  • [ 938447-07-5 ]
  • [ 22952-32-5 ]
  • [ 76-05-1 ]
  • NH2CNHC10H6CH2NSO2CH3C5H9NSO2C6H3ClOCH3*CF3CO2H [ No CAS ]
  • 31
  • [ 22952-32-5 ]
  • [ 913563-88-9 ]
  • 32
  • [ 22952-32-5 ]
  • 1-(5-chloro-2-methoxybenzenesulfonyl)-5-trifluoromethyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid 2-chlorobenzylamide [ No CAS ]
  • 33
  • [ 22952-32-5 ]
  • [ 913563-89-0 ]
  • 34
  • [ 22952-32-5 ]
  • 1-(5-chloro-2-methoxybenzenesulfonyl)-5-trifluoromethyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid 2-methoxybenzylamide [ No CAS ]
  • 35
  • [ 22952-32-5 ]
  • [ 913563-93-6 ]
  • 36
  • [ 22952-32-5 ]
  • 1-(5-chloro-2-methoxybenzenesulfonyl)-5-trifluoromethyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid 3,4-difluorobenzylamide [ No CAS ]
  • 37
  • [ 22952-32-5 ]
  • [ 913563-90-3 ]
  • 38
  • [ 22952-32-5 ]
  • [ 913563-92-5 ]
  • 39
  • [ 22952-32-5 ]
  • 1-(5-chloro-2-methoxybenzenesulfonyl)-5-trifluoromethyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid 4-chloro-3-trifluoromethylbenzylamide [ No CAS ]
  • 40
  • [ 22952-32-5 ]
  • [ 913563-91-4 ]
  • 41
  • [ 22952-32-5 ]
  • N-(2-chlorobenzyl)-1-(5-chloro-2-methoxyphenylsulfonyl)-5-fluoro-1,2,3,6-tetrahydropyridine-2-carboxamide [ No CAS ]
  • 42
  • [ 22952-32-5 ]
  • 1-(5-chloro-2-methoxyphenylsulfonyl)-N-(3,4-difluorobenzyl)-5-fluoro-1,2,3,6-tetrahydropyridine-2-carboxamide [ No CAS ]
  • 43
  • [ 22952-32-5 ]
  • [ 885679-13-0 ]
  • 44
  • [ 22952-32-5 ]
  • [ 885679-12-9 ]
  • 45
  • [ 22952-32-5 ]
  • 5-chloro-N-(4-chloro-5-isopropyl-3-methyl-1,3-thiazol-2(3H)-ylidene)-2-hydroxybenzenesulfonamide [ No CAS ]
  • 46
  • [ 22952-32-5 ]
  • 5-chloro-N-(4-chloro-5-isopropyl-3-methyl-1,3-thiazol-2(3H)-ylidene)-2-methoxybenzenesulfonamide [ No CAS ]
  • 47
  • [ 22952-32-5 ]
  • N-(5-tert-butyl-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene)-5-chloro-2-methoxybenzenesulfonamide [ No CAS ]
  • 48
  • [ 22952-32-5 ]
  • 5-chloro-N-(4-chloro-5-isopropyl-3-methyl-1,3-thiazol-2(3H)-ylidene)-2-cyanobenzenesulfonamide [ No CAS ]
  • 49
  • [ 22952-32-5 ]
  • N-(5-tert-butyl-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene)-5-chloro-2-hydroxybenzenesulfonamide [ No CAS ]
  • 50
  • [ 22952-32-5 ]
  • N-(4-chloro-5-isopropyl-3-methyl-1,3-thiazol-2(3H)-ylidene)-2,5-dicyanobenzenesulfonamide [ No CAS ]
  • 51
  • [ 22952-32-5 ]
  • N-(5-tert-butyl-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene)-5-chloro-2-cyanobenzenesulfonamide [ No CAS ]
  • 52
  • [ 22952-32-5 ]
  • 2-[(5-tert-butyl-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene)amino]sulfonyl}-4-chlorobenzamide [ No CAS ]
  • 53
  • [ 22952-32-5 ]
  • 2-(5-<i>tert</i>-butyl-3,4-dimethyl-3<i>H</i>-thiazol-2-ylidenesulfamoyl)-4-chloro-benzoic acid [ No CAS ]
  • 54
  • [ 22952-32-5 ]
  • methyl 2-[(5-tert-butyl-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene)amino]sulfonyl}-4-chlorobenzoate [ No CAS ]
  • 55
  • [ 22952-32-5 ]
  • 4-chloro-2-[(4-chloro-5-isopropyl-3-methyl-1,3-thiazol-2(3H)-ylidene)amino]sulfonyl}phenyl trifluoromethanesulfonate [ No CAS ]
  • 56
  • [ 22952-32-5 ]
  • 2-[(5-tert-butyl-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene)amino]sulfonyl}-4-chlorophenyl trifluoromethanesulfonate [ No CAS ]
  • 57
  • [ 22952-32-5 ]
  • [ 197959-77-6 ]
  • 58
  • [ 22952-32-5 ]
  • [ 197960-30-8 ]
  • 59
  • [ 22952-32-5 ]
  • [ 197960-77-3 ]
  • 60
  • [ 22952-32-5 ]
  • [ 197959-79-8 ]
  • 61
  • [ 22952-32-5 ]
  • [ 197960-21-7 ]
  • 62
  • [ 22952-32-5 ]
  • [ 197959-78-7 ]
  • 63
  • [ 22952-32-5 ]
  • [ 197960-20-6 ]
  • 64
  • [ 22952-32-5 ]
  • C17H20N4O5S [ No CAS ]
  • 65
  • [ 22952-32-5 ]
  • C18H22N4O5S [ No CAS ]
  • 66
  • [ 22952-32-5 ]
  • C19H24N4O5S [ No CAS ]
  • 67
  • [ 106-48-9 ]
  • (+-)-2-ethoxy-1,1,1,2-tetrachloro-ethane [ No CAS ]
  • [ 22952-32-5 ]
  • 68
  • [ 22952-32-5 ]
  • [ 81514-26-3 ]
  • 69
  • [ 22952-32-5 ]
  • [ 81514-27-4 ]
  • 70
  • [ 22952-32-5 ]
  • [ 81533-88-2 ]
  • 71
  • [ 22952-32-5 ]
  • 4-chloro-2-[(4-methylphenyl)sulfonyl]phenol [ No CAS ]
  • 72
  • [ 6470-17-3 ]
  • [ 22952-32-5 ]
  • 74
  • [ 288321-54-0 ]
  • [ 22952-32-5 ]
  • C30H41ClN4O11S [ No CAS ]
  • 75
  • {2-[4-(1H-benzimidazol-2-yl)piperazin-1-yl]ethyl}methyl-amine hydrochloride salt [ No CAS ]
  • [ 22952-32-5 ]
  • [ 295790-36-2 ]
  • 76
  • [ 593270-47-4 ]
  • [ 22952-32-5 ]
  • 5-Chloro-2-methoxy-N-{2-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-ethyl}-benzenesulfonamide [ No CAS ]
  • 77
  • [ 593270-50-9 ]
  • [ 22952-32-5 ]
  • 5-chloro-2-methoxy-N-{4-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-butyl}-benzenesulfonamide [ No CAS ]
  • 78
  • [ 793665-17-5 ]
  • [ 22952-32-5 ]
  • 5-Chloro-2-methoxy-N-methyl-N-{3-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-propyl}-benzenesulfonamide [ No CAS ]
  • 79
  • C17H25ClN3O3Pol [ No CAS ]
  • [ 22952-32-5 ]
  • C24H30Cl2N3O6PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 5h; [0161] 0.3 g of TentaGel HL12019 (bromoacetal linker, S=0.5 mmol/g, Rapp Polymere, Tubingen) was washed with DMSO. 20 equivalents of 2M isopropylamine solution (reagent 1) in DMSO were added, and the mixture was kept in a closed vessel at 60 C. for 15 hours. The polymer was washed 7 times with DMF. Fmoc-4-chlorophenylalanine (reagent 2) (3 equivalents) was coupled to the secondary amine on the polymer with HATU (3 equivalents) and DIEA (9 equivalents) in DMF. The final concentration was 0.2-0.3M. The reaction mixture was left at 55 C. for 4 hours. The polymer was washed 6 times with DMF. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). [0162] Fmoc-beta-alanine (3 equivalents) was then coupled on with HOBt (3 equivalents) and DIC (3 equivalents) in DMF (final concentration: about 0.2M) over a period of at least 4 hours. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). [0163] The polymer was washed 5 times with DMF and 4 times with DCM and mixed with a solution of 1.5 equivalents of 2-methoxy-4-chlorobenzenesulfonyl chloride (reagent 3) and 3 equivalents of DIEA in acetonitrile (final concentration: 0.1-0.15M) and reacted at room temperature for 5 hours. It was then washed 5 times with DMF and 5 times with THF and dried in vacuo. [0164] For the cyclative cleavage off, the dry polymer was mixed with 10 ml of formic acid and shaken at room temperature for 16 hours. The polymer was filtered off and washed with DCM. The combined filtrates were evaporated in vacuo. The crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and processes described under General processes were used in this case. MW=539.10 (calculated, monoisotopic); measured value (M+H)+: 540.3.
  • 80
  • C17H26N3O3Pol [ No CAS ]
  • [ 22952-32-5 ]
  • C24H31ClN3O6PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 5h; [0166] 0.3 g of TentaGel HL12019 (bromoacetal linker, S=0.5 mmol/g, Rapp Polymere, Tubingen) was washed with DMSO. 20 equivalents of 2M isopropylamine solution in DMSO were added, and the mixture was kept in a closed vessel at 60 C. for 15 hours. The polymer was washed 7 times with DMF. [0167] Fmoc-4-phenylalanine (3 equivalents) was coupled to the secondary amine on the polymer with HATU (3 equivalents) and DIEA (9 equivalents) in DMF. The final concentration was 0.2-0.3M. The reaction mixture was left at 55 C. for 4 hours. The polymer was washed 6 times with DMF. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). [0168] Fmoc-beta-alanine (3 equivalents) was then coupled on with HOBt (3 equivalents) and DIC (3 equivalents) in DMF (final concentration: about 0.2M) over a period of at least 4 hours. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). [0169] The polymer was washed 5 times with DMF and 4 times with DCM and mixed with a solution of 1.5 equivalents of 2-methoxy-4-chlorobenzenesulfonyl chloride and 3 equivalents of DIEA in acetonitrile (final concentration: 0.1-0.15M) and reacted at room temperature for 5 hours. It was then washed 5 times with DMF and 5 times with THF and dried in vacuo. [0170] For the cyclative cleavage off, the dry polymer was mixed with 10 ml of formic acid and shaken at room temperature for 16 hours. The polymer was filtered off and washed with DCM. The combined filtrates were evaporated in vacuo. The crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and processes described under General processes were used in this case. MW=505.14 (calculated, monoisotopic); measured value (M+H)+: 506.3.
  • 81
  • C17H24Cl2N3O3Pol [ No CAS ]
  • [ 22952-32-5 ]
  • C24H29Cl3N3O6PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 5h; [0172] 0.3 g of TentaGel HL12019 (bromoacetal linker, S=0.5 mmol/g, Rapp Polymere, Tubingen) was washed with DMSO. 20 equivalents of 2M isopropylamine solution in DMSO were added, and the mixture was kept in a closed vessel at 60 C. for 15 hours. The polymer was washed 7 times with DMF. [0173] Fmoc-3,4-dichlorophenylalanine (3 equivalents) was coupled to the secondary amine on the polymer with HATU (3 equivalents) and DIEA (9 equivalents) in DMF. The final concentration was 0.2-0.3M. The reaction mixture was left at 55 C. for 4 hours. The polymer was washed 6 times with DMF. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). [0174] Fmoc-beta-alanine (3 equivalents) was then coupled on with HOBt (3 equivalents) and DIC (3 equivalents) in DMF (final concentration: about 0.2M) over a period of at least 4 hours. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). [0175] The polymer was washed 5 times with DMF and 4 times with DCM and mixed with a solution of 1.5 equivalents of 2-methoxy-4-chlorobenzenesulfonyl chloride and 3 equivalents of DIEA in acetonitrile (final concentration: 0. 1-0.15M) and reacted at room temperature for 5 hours. It was then washed 5 times with DMF and 5 times with THF and dried in vacuo. [0176] For the cyclative cleavage off, the dry polymer was mixed with 10 ml of formic acid and shaken at room temperature for 16 hours. The polymer was filtered off and washed with DCM. The combined filtrates were evaporated in vacuo. The crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and processes described under General processes were used in this case. MW=573.07 (calculated, monoisotopic); measured value (M+H)+: 574.3.
  • 82
  • C17H25ClN3O4Pol [ No CAS ]
  • [ 22952-32-5 ]
  • C24H30Cl2N3O7PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 5h; [0183] 0.5 g of TentaGel HL12019 (bromoacetal linker, S=0.5 mmol/g, Rapp Polymere, Tubingen) was washed with DMSO. 20 equivalents of 2M isopropylamine solution in DMSO were added, and the mixture was kept in a closed vessel at 60 C. for 15 hours. The polymer was washed 7 times with DMF. [0184] Fmoc-4-chlorophenylalanine (3 equivalents) was coupled to the secondary amine on the polymer with HOAt (3 equivalents) and DIC (3 equivalents) in DMF. The final concentration was 0.2-0.3M. The reaction mixture was left overnight at room temperature. [0185] The polymer was washed 6 times with DMF. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). [0186] Fmoc-isoserine (3 equivalents) was then coupled on with HOBt (3 equivalents) and DIC (3 equivalents) in DMF (final concentration: about 0.2M) over a period of at least 4 hours. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). The polymer was washed 5 times with DMF and 4 times with DCM and mixed with a solution of 1.5 equivalents of 2-methoxy-5-chlorobenzenesulfonyl chloride and 3 equivalents of DIEA in DCM (final concentration: 0.1-0.15M) and reacted at room temperature for 5 hours. It was then washed 5 times with DMF and 5 times with DCM and dried in vacuo. [0187] For the cyclative cleavage off, the dry polymer was mixed with 10 ml of formic acid and shaken at room temperature for 16 hours. The polymer was filtered off and washed with DCM. The combined filtrates were evaporated in vacuo. The crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and processes described under General processes were used in this case. MW=555.10 (calculated, monoisotopic); measured value (M+H)+: 556.3
  • 83
  • C16H23ClN3O3Pol [ No CAS ]
  • [ 22952-32-5 ]
  • C23H28Cl2N3O6PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 5h; [0189] 0.3 g of TentaGel HL12019 (bromoacetal linker, S=0.5 mmol/g, Rapp Polymere, Tuibingen) was washed with DMSO. 20 equivalents of 2M isopropylamine solution in DMSO were added, and the mixture was kept in a closed vessel at 60 C. for 15 hours. The polymer was washed 7 times with DMF. [0190] Fmoc-4-chlorophenylalanine (3 equivalents) was coupled to the secondary amine on the polymer with HOAt (3 equivalents) and DIC (3 equivalents) in DMF. The final concentration was 0.2-0.3M. The reaction mixture was left overnight at room temperature. The polymer was washed 6 times with DMF. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). [0191] Fmoc-glycine (3 equivalents) was then coupled on with HOBt (3 equivalents) and DIC (3 equivalents) in DMF (final concentration: about 0.2M) over a period of at least 4 hours. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). The polymer was washed 5 times with DMF and 4 times with acetonitrile and mixed with a solution of 1.5 equivalents of 2-methoxy-4-chlorobenzenesulfonyl chloride and 3 equivalents of DIEA in acetonitrile (final concentration: 0.1-0.15M) and reacted at room temperature for 5 hours. It was then washed 5 times with DMF and 5 times with DCM and dried in vacuo. [0192] For the cyclative cleavage off, the dry polymer was mixed with 10 ml of formic acid and shaken at room temperature for 24 hours. The polymer was filtered off and washed with DCM. The combined filtrates were evaporated in vacuo. The crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and processes described under [0193] ?General processes? were used in this case. MW=525.09 (calculated, monoisotopic); measured value (M+H)+: 526.3.
  • 84
  • C17H25ClN3O3Pol [ No CAS ]
  • [ 22952-32-5 ]
  • C24H30Cl2N3O6PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 5h; [0195] 0.3 g of TentaGel HL12019 (bromoacetal linker, S=0.5 mmol/g, Rapp Polymere, Tuibingen) was washed with DMSO. 20 equivalents of 2M isopropylamine solution in DMSO were added, and the mixture was kept in a closed vessel at 60 C. for 15 hours. The polymer was washed 7 times with DMF. [0196] Fmoc-4-chlorophenylalanine (3 equivalents) was coupled to the secondary amine on the polymer with HOAt (3 equivalents) and DIC (3 equivalents) in DMF. The final concentration was 0.2-0.3M. The reaction mixture was left overnight at room temperature. The polymer was washed 6 times with DMF. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). [0197] Fmoc-(R)-alanine (3 equivalents) was then coupled on with HOBt (3 equivalents) and DIC (3 equivalents) in DMF (final concentration: about 0.2M) over a period of at least 4 hours. The Fmoc protective group was eliminated with 50% piperidine in DMF (5+15 minutes). The polymer was washed 5 times with DMF and 4 times with acetonitrile and mixed with a solution of 1.5 equivalents of 2-methoxy-4-chlorobenzenesulfonyl chloride and [0198] 3 equivalents of DIEA in acetonitrile (final concentration: 0.1-0.15M) and reacted at room temperature for 5 hours. It was then washed 5 times with DMF and 5 times with DCM and dried in vacuo. [0199] For the cyclative cleavage off, the dry polymer was mixed with 10 ml of formic acid and shaken at room temperature for 24 hours. The polymer was filtered off and washed with DCM. The combined filtrates were evaporated in vacuo. The crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and processes described under General processes were used in this case. MW=539.10 (calculated, monoisotopic); measured value (M+H)+: 540.3.
  • 85
  • [ 2963-77-1 ]
  • [ 22952-32-5 ]
  • N-[4-(1H-benzimidazol-2-yl)-phenyl]-5-chloro-2-methoxy-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
dmap; In pyridine; at 20℃; for 10h; EXAMPLE 10 : PREPARATION OF N- [4- (LH-BENZIMIDAZOL-2-L-PHENVL]-5-CHLORO-2-METHOXY- BENZENESULFONAMIDE (Compound 10) : 2- (4-AMINOPHENYL) benzimidazoles (0.4 mmol, 0.0836 g) and 4- dimethylaminopyridine (0.04 mmol, 0.005 g) were dissolved in anhydrous pyridine (2 ml). 5-CHLORO-2-METHOXYBENZENE-1-SULFONYL chloride (0.4 mmol, 0.0964 g) was added to the solution in 5 portions. The resulting mixture was stirred at room temperature for 10 h. Then, water (20 ml) was added to quench the reaction. The precipitate formed was filtered off and washed with water (3x5 ml), cold THF (2 ml) and ET2O (3 x 5 ml) to afford a brown solid. MS M/Z = 414 +H). IH NMR delta 3. 85 (s, 3H), 7.25-7. 10 (m, 5H), 7.64-7. 44 (m, 3H), 7.76 (s, 1H), 8.04-7. 95 (m, 2H), 10.51 (s, 1H), 12.75 (s, 1H).
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