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[ CAS No. 187669-60-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 187669-60-9
Chemical Structure| 187669-60-9
Chemical Structure| 187669-60-9
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Product Details of [ 187669-60-9 ]

CAS No. :187669-60-9 MDL No. :MFCD03648601
Formula : C11H16N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :KNQFDOLIXOOIGX-UHFFFAOYSA-N
M.W : 240.32 Pubchem ID :735904
Synonyms :

Calculated chemistry of [ 187669-60-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 70.89
TPSA : 57.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 0.42
Log Po/w (WLOGP) : 0.82
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 0.88
Consensus Log Po/w : 0.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.74
Solubility : 4.37 mg/ml ; 0.0182 mol/l
Class : Very soluble
Log S (Ali) : -1.2
Solubility : 15.1 mg/ml ; 0.063 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.21
Solubility : 0.147 mg/ml ; 0.000612 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 187669-60-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 187669-60-9 ]

* 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 [ 187669-60-9 ]

[ 187669-60-9 ] Synthesis Path-Downstream   1~19

YieldReaction ConditionsOperation in experiment
Synthesis of 1-(4-Methanesulfonyl-phenyl)-piperazine Piperazine (0.98 g, 11.5 mmol), Pd(II)acetate (0.017 g), sodium t-butoxide (0.37 g, 4.2 mmol) and BINAP (0.049 g) were stirred at room temperature in 10 mL dry toluene for 15 min. 1-Bromo-4-methanesulfonyl-benzene (0.9 g, 3.8 mmol) in 10 mL dry toluene was added into the reaction mixture. Then the reaction mixture was refluxed at 110 C. for 20 hrs. The reaction mixture was filtered through a celite bed and washed with toluene. The toluene was concentrated and the reaction mixture was taken in ethyl acetate and extracted with 1.5 (N) HCl solution three times. The combined aqueous layers were washed with diethyl ether. The aqueous layer was neutralized with 10% aqueous sodium hydroxide solution and then extracted with ethyl acetate three times. The combined ethyl acetate layers were washed with water and saturated brine solution, dried over anhydrous sodium sulfate, concentrated and chromatographed (9/1-CHCl3/MeOH) to afford the product.
  • 2
  • [ 3466-32-8 ]
  • [ 187669-60-9 ]
  • 3
  • [ 110-85-0 ]
  • [ 3466-32-8 ]
  • [ 187669-60-9 ]
YieldReaction ConditionsOperation in experiment
20% With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 15h;Inert atmosphere; Step 1: Synthesis of 1-(4-(methylsulfonyl)phenyl)piperazin [231] 1-Bromo-4-(methylsulfonyl)benzene (275 mg, 1.169 mmol), piperazine (302 mg, 3.507 mmol), Pd2(dba)3 (21 mg, 0.023 mmol), BINAP (44 mg, 0.070 mmol), and sodium-tert-butoxide (169 mg, 1.754 mmol) were suspended in toluene (5 ml), and then the resulting liquid was stirred at 100oC under nitrogen stream for 15 hours. Distilled water (15 ml) was added to the resulting reaction liquid, followed by extraction with MC (20 ml x 3). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (15% MeOH/MC), to obtain 56 mg of pale yellow solid (20%).
[0105] Piperazine (0.98g, 11.5MMOL), Pd (II) acetate (0.017g), sodium t-butoxide (0.37g, 4. [2MMOL)] and BINAP (0.049g) were stirred at room temperature in 10 mL dry toluene for 15 min. [1-BROMO-4-METHANESULFONYL-BENZENE] (0.9 g, 3.8mmol) in 10 mL dry toluene was added into the reaction mixture. Then the reaction mixture was refluxed at [110C] for 20 hrs. The reaction mixture was filtered through a celite bed and washed with toluene. The toluene was concentrated and the reaction mixture was taken in ethyl acetate and extracted with 1.5 (N) [HCL] solution three times. The combined aqueous layers were washed with diethyl ether. The aqueous layer was neutralized with 10% aqueous sodium hydroxide solution and then extracted with ethyl acetate three times. The combined ethyl acetate layers were washed with water and saturated brine solution, dried over anhydrous sodium sulfate, concentrated and chromatographed [(9/1-CHC13/MEOH)] to afford the product.
With tetra-(n-butyl)ammonium iodide; at 120 - 140℃; for 5h; Production Example 366 1-(4-Methylsulfonylphenyl)piperazine A mixture of 3.0 g 1-bromo-4-methylsulfonyl benzene, 3.3 g piperazine and 470 mg tetrabutyl ammonium iodide was stirred at 120C to 140C for 5 hours.. water was added to the mixture, then insolubles were filtered off, the filtrate was extracted with dichloromethane.. The organic layer was washed with brine and dried over anhydrous magnesium sulfate.. The solvent was evaporated, and the residue was purified by NH silica gel column chromatography, to give 2.8 g of the title compound as a white solid.1H-NMR (CDCl3) delta: 3.00(s, 3H), 3.02(m, 4H), 3.31(m, 4H), 6.92(d, J=8.6Hz, 2H), 7.98(d, J=8.6Hz, 2H),
  • 4
  • [ 187669-60-9 ]
  • [ 137076-22-3 ]
  • 4-[4-(4-methanesulfonylphenyl)piperazin-1-ylmethyl]piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃; for 17h; Example 1; 4-[4-(4-Mcthancsulfonylphcnyl)pipcrazin-l -ylmcthyljpipcridinc-l -carboxylic acid tert-butyl ester; EPO <DP n="23"/>To a solution of l-(4-methanesulfonylphenyl)piperazine (0.41 mmol) and 4- formylpiperidine-1-carboxylic acid tert-mty ester (1.2 mmol) in DCM (3 mL) was added sodium triacetoxyborohydride (0.53 mmol). The resulting suspension was stirred at rt for 17 h. Polymer-supported isocyante scavenger resin (MP-NCO) (0.29 g, 1.44 mmol/g) was added and shaking continued until LCMS showed complete consumption of starting amine. The mixture was diluted with further DCM, shaken with water, and the organic layer separated using a hydrophobic frit. The crude mixture was purified via ion-exchange using an SCX column, to afford the title compound. deltaH (400 MHz, CHCl3) 1.14 (2H, m), 1.50 (9H, s), 1.70 (IH, m), 1.79 (2H, m), 2.26 (2H, d), 2.58 (4H, t), 2.74 (2H, m), 3.04 (3H, s), 3.38 (4H, t), 4.14 (2H, m), 6.96 (2H, d), 7.80 (2H, d).
  • 5
  • [ 187669-60-9 ]
  • [ 301221-79-4 ]
  • [ 918884-07-8 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate; In acetonitrile; for 4h;Heating / reflux; Example 67; 4-{2-[4-(4-Methanesulfonylphenyl)piperazin-l-yl]acetyl}piperidine-l- carboxylic acid tert-butyl ester; To a solution of l-(4-methanesulfonylphenyl)piperazine (0.055g, 0.23mmol) in MeCN (2mL) was added 4-(2-bromoacetyl)piperidine-l-carboxylic acid tert-butyl ester (0.07g, 0.23mmol) and K2CO3 (0.035g, 0.25mmol). The mixture was heated at reflux for 4h then allowed to cool. EtOAc (2OmL) was added and the organic phase washed with water, brine, dried (MgSO4) and the solvent removed in vacuo. The crude mixture was purified by flash chromatography with EtOAc as eluent to afford the title compound (0.07g, 65percent): RT = 2.45 min; m/z (ES+) = 466.4 [M+ H]+
  • 6
  • [ 187669-60-9 ]
  • [ 157688-46-5 ]
  • 4-{2-[4-(4-methanesulfonylphenyl)piperazin-1-yl]-2-oxoethyl}piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 18h; Example 80; 4-{2-[4-(4-Mcthancsulfonylphcnyl)pipcrazin-l-yl]-2-oxocthyl}pipcridinc-l- carboxylic acid ferf-butyl ester; To a solution of l-(4-methanesulfonylphenyl)piperazine (0.22 g, 0.91 mmol), 4-carboxy methylpiperidine-1-carboxylic acid tert-butyl ester (0.20 g, 0.80 mmol), HOBT.H2O (0.14 g, 0.91 mmol) and DIPEA (0.47 mL, 2.72 mmol) in DMF (5mL) was added EDCI (0.19 g, 0.99 mmol) and the mixture was stirred for 18h. The solvent was removed under vacuum and the resulting residue was partitioned between EtOAc and saturated NaHCO3 solution. The aqueous phase was re-extracted with EtOAc, the organic extracts were combined, washed with brine, dried (MgSO4) and adsorbed onto SiO2. The adsorbed sample was purified by flash chromatography eluting with 50:50 EtOAc:hexane to afford the title compound: RT = 3.26 min; m/z (ES+) = 466.33 [M+H]+.
  • 7
  • [ 187669-60-9 ]
  • [ 896103-70-1 ]
  • C24H39N3O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 81; 4-{2-[4-(4-Mcthancsulfonylphcnyl)pipcrazin-l-yl]-2-oxocthyl}pipcridinc-l- carboxylic acid tert-butyl ester; To a solution of 4-hydroxy-4-(3-hydroxypropyl)piperidine-l-carboxylic acid tert-butyl ester (1.00 g, 3.86 mmol) in DCM (60 mL) was added Dess-Martin periodinane (1.80 g, 4.24 mmol) and the mixture was stirred for Ih at rt, a further batch of Dess-Martin periodinane (0.20 g, 0.47 mmol). The reaction mixture was quenched with 2 M NaOH and extracted with Et2O, the aqueous phase was re-extracted with Et2O and the organic extracts were combined then washed with water, 2 M NaOH solution and brine, dried (MgSO4) and the solvent was removed under vacuum to give 2-hydroxy-l-oxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester. A solution of l-(4-methanesulfonylphenyl)piperazine (0.12 g, 0.50 mmol) and 2-hydroxy-l-oxa- 8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester (0.14 g, 0.56 mmol) in anhydrous MeOH (2 mL) was heated at 750C for Ih, then NaBH4 (25 mg, 0.65 mmol) was added and the reaction was stirred for 2h. The solvent was removed under vacuum and the resulting residue was partitioned between water and DCM. The aqueous phase was re-extracted with DCM, the EPO <DP n="52"/>organic extracts were combined and purified by flash chromatography eluting with 3:97 MeOH:DCM to afford the title compound: RT = 2.37 min; m/z (ES+) = 482.45 [M+H]+.
  • 8
  • [ 187669-60-9 ]
  • tert-butyl 4-vinyl-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
  • [ 918884-44-3 ]
  • 4-{2-[4-(4-methanesulfonylphenyl)piperazin-1-yl]ethylidene}piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 77; 4-{2-[4-(4-Methanesulfonylphenyl)piperazin-l-yl]ethylidene}piperidine-l- carboxylic acid tert-butyl ester; To a solution of 4-(2-hydroxyethylidene)piperidine-l-carboxylic acid tert-butyl ester (2.2g, 9.7mmol) in DCM (25mL) was added Et3N (2.02mL, 14.5mmol) and the reaction cooled to O0C. To this cooled mixture was added methanesulfonylchloride (0.98mL, 12.6mmol) dropwise. The reaction was stirred at O0C for 20 min then treated with saturated NaHCO3 solution. The two layers were separated and the organic layer washed with water, brine, dried (MgSO4) and the solvent removed in vacuo. The crude mixture was purified by flash chromatography with 10% EtOAc / Hexane as eluent to afford 4-(2-chloroethylidene) piperidine-1-carboxylic acid tert-butyl ester and 4-vinyl-3,6-dihydro-2H-pyridine-l-carboxylic acid tert-butyl ester in a 1:1 ratio (0.95Og). The mixture was dissolved in DMF (5mL) and treated with TBAI (0.068g, 0.18mmol). This suspension was thus added to a preformed mixture of l-(4-methanesulfonylphenyl)piperazine (0.487g, 2.03mmol) and sodium hydride (0.1 Ig of a 60% dispersion in mineral oil, 2.77mmol) in DMF (5mL) at rt. The mixture was allowed to stir for 2h then treated with water. The aqueous was extracted with EtOAc and the combined organic layers washed with water, brine, dried (MgSO4) and the solvent removed in vacuo. The crude mixture was purified by HPLC to afford the title compound (0.27g, 6%): RT = 2.41 min; m/z (ES+) = 450.2 [M+ H]+
  • 9
  • [ 110-85-0 ]
  • [ 455-15-2 ]
  • [ 187669-60-9 ]
  • 10
  • [ 187669-60-9 ]
  • [ 187219-34-7 ]
  • [ 946156-93-0 ]
  • 11
  • [ 187669-60-9 ]
  • [ 4036-83-3 ]
  • [4-(4-methanesulfonyl-phenyl)-piperazin-1-yl]-(2-morpholin-4-yl-5-nitro-phenyl)-methanone [ No CAS ]
  • 12
  • [ 187669-60-9 ]
  • rac-5-methanesulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)benzoic acid [ No CAS ]
  • [ 1229627-95-5 ]
  • 13
  • [ 187669-60-9 ]
  • 6-bromo-N-((E)-5-hydroxyadamantan-2-yl)picolinamide [ No CAS ]
  • N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% Step 2: Synthesis of N -(( E )-5-Hydroxyadamantan-2-yl)-6-(4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)picolinamide [233] 6-Bromo-N-((E)-5-hydroxyadamantan-2-yl)picolinamide(60 mg, 0.171 mmol), <strong>[187669-60-9]1-(4-(methylsulfonyl)phenyl)piperazin</strong>e (49 mg, 0.205 mmol), Pd2(dba)3 (3.1 mg, 0.003 mmol), xantphos (5.9 mg, 0.010 mmol), and sodium-tert-butoxide (25 mg, 0.257 mmol) were suspended in toluene (3 ml), and then the resulting liquid was stirred at 100oC under nitrogen stream for 4 hours. Distilled water (10 ml) was added to the resulting reaction liquid, followed by extraction with MC (15 ml x 2). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (4% MeOH/MC), to obtain 34 mg of pale yellow solid (39%). MS (ESI): 511[M+H]+
  • 14
  • [ 187669-60-9 ]
  • [ 1261236-56-9 ]
  • [ 76-05-1 ]
  • [ 1396675-72-1 ]
YieldReaction ConditionsOperation in experiment
Step 3: To a solution of 2-(6-bromopyridin-3-yl)-5-chloro-lH-berizimidazole (70mgs 0.227mmol) and l-[4-(meraylsulfonyl)phenyl]piperazine (54.5mgf 0.227mmol) in dry DMA (3mL) was added N,N-diisopropylethylamine (59mg, 0.454mmol). The mixture was heated to 110 C under argon for 16 hours. The mixture was filtered and was purified by reverse phase Prep HPLC using 30-60% C¾CN/H2O/0.1%TFA as gradient to give 5-cMoro-2-(6-{4-(4- (methylsulfonyl)phenyl]piperazin-l-yl}pyridin-3-yl)-lH-benzimidazole as the TFA salt. LC-MS (M+H)= 468
  • 15
  • [ 166438-71-7 ]
  • [ 187669-60-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium hydroxide, 20 wt% on carbon; In methanol; under 760.051 Torr; for 3h; Step 2: A solution of l-benzyl-4-[4-(methylsulfonyl)phenyl]piperazine (143mg, 0.433mol) in methanol (5mL) was treated with 20% Pd(OH)2 on carbon. The mixture was stirred under 1 atm of hydrogen for 3 hours and the catalyst was filtered. The solvent was evaporated to give l-[4- (methylsulfonyl)phenyl]piperazine as a yellow solid. LC-MS (M+H)= 241
  • 16
  • [ 187669-60-9 ]
  • [ 85-42-7 ]
  • [ 6011-14-9 ]
  • [ 1403499-38-6 ]
  • 17
  • [ 187669-60-9 ]
  • [ 85-42-7 ]
  • [ 127946-77-4 ]
  • [ 1095534-28-3 ]
  • 18
  • [ 187669-60-9 ]
  • [ 912332-40-2 ]
  • 5-chloro-3-[4-(4-methylsulfonylphenyl)piperazin-1-yl]thieno[3,2-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% at 80℃; General Procedure X, using 3-bromo-5-chlorothieno[3,2-B]pyridine (200 mg, 0.79 mmol) and 1-[4-(methylsulphonyl)phenyl]piperazine (208 mg, 0.87 mmol) at 80 C gave the title compound (20 mg, 6%). LCMS (Method 2, ES+) 1.36 min, 408 & 410 m/z (M+H)+.
  • 19
  • benzyl 4-(4-methanesulfonylphenyl)piperazine-1-carboxylate [ No CAS ]
  • [ 187669-60-9 ]
YieldReaction ConditionsOperation in experiment
81.6% With palladium 10% on activated carbon; hydrogen; In methanol; dichloromethane; at 50℃; for 5h; [00343] Step 2: 1-(4-methanesulfonylphenyl)piperazine. To a solution of benzyl 4-(4- methanesulfonylphenyl)piperazine-l-carboxylate (2.1 g, 5.61 mmol) in MeOH (20 mL) and DCM (4 mL) was added Pd/C (10%, 59.7 mg, 0.56 mmol). The mixture was stirred at 50 C for 5 h under hydrogen atmosphere (1 atm). The reaction mixture was cooled and filtered through a celite pad and concentrated to obtain l-(4-methanesulfonylphenyl)piperazine (1.1 g, 81.6%) as a light yellow solid. ES-MS (m/z): [M+l]+ = 241.2.
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