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Chemical Structure| 383-31-3 Chemical Structure| 383-31-3

Structure of 383-31-3

Chemical Structure| 383-31-3

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Product Details of [ 383-31-3 ]

CAS No. :383-31-3
Formula : C8H10FNO2S
M.W : 203.23
SMILES Code : O=S(C1=CC=C(F)C=C1)(N(C)C)=O
MDL No. :MFCD01211990
InChI Key :WURMPFYVFDHATI-UHFFFAOYSA-N
Pubchem ID :799301

Safety of [ 383-31-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 383-31-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 47.2
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

45.76 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.45
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.58
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.4
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.66
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.62

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.22
Solubility 1.22 mg/ml ; 0.00598 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.02
Solubility 1.96 mg/ml ; 0.00962 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.72
Solubility 0.389 mg/ml ; 0.00191 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.51 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.97

Application In Synthesis of [ 383-31-3 ]

* 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 [ 383-31-3 ]

[ 383-31-3 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 613-91-2 ]
  • [ 383-31-3 ]
  • [ 16237-45-9 ]
  • 2
  • [ 2475-92-5 ]
  • [ 383-31-3 ]
  • [ 16267-42-8 ]
  • 4
  • [ 349-88-2 ]
  • [ 124-40-3 ]
  • [ 383-31-3 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In tetrahydrofuran; water; at 20℃; for 0.333333h; (1) 4-Fluoro-1-(N,N-dimethylaminosulfonyl)benzene To a solution of 4-fluorobenzenesulfonyl chloride (1.95 g, 10.0 mmol) in THF (40 mL) were added triethylamine (2.09 mL, 15.0 mmol) and 50% aqueous dimethylamine solution (1.26 mL, 14.0 mmol) at room temperature, and the solution was stirred at the same temperature for 20 minutes. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 4-fluoro-1-(N,N-dimethylaminosulfonyl)benzene (2.03 g, 10.0 mmol).yield: quantitative
100% In methanol; dichloromethane; at 20℃; for 0.0833333h; [00728] A mixture of 4-fluorobenzene-1 -sulfonyl chloride (2.0 g, 10.3 mmol), HNMe2 (2.0M in MeOH; 1 1 .0 mL, 22.0 mmol) and DCM (1 1 .0 mL) was stirred at rt for 5 min. DCM (30 mL) was added. The organic phase was washed with 1 M HCI (30 mL) and brine (30 mL), dried over MgSCv and filtered. The solvent was removed under reduced pressure to afford 4-fluoro-/V,/V- dimethylbenzenesulfonamide as a white solid (2.12 g, quant.). A mixture of 4-fluoro-/V,/V- dimethylbenzenesulfonamide (1 .50 g, 7.39 mmol), NaSMe (2.08 g, 29.7 mmol) and DMF (9.0 mL) was stirred at 170 C in a sealed tube for 16 h. After cooling to rt, 1 M NaOH (40 mL) was added. The aqueous phase was washed with Et20 (2 chi 40 mL), acidified to pH <2 with 2 M HCI and then extracted with Et20 (3 chi 40 mL). The combined organic phase was dried over MgSCv and filtered. The solvent was removed under reduced pressure to afford 4-mercapto-/V,/V- dimethylbenzenesulfonamide as an orange oil (503 mg, 31 %). H NMR (500 MHz, CDCI3) delta 7.67 - 7.58 (m, 2H), 7.43 - 7.35 (m, 2H), 3.67 (s, 1 H), 2.71 (s, 6H).
86% In tetrahydrofuran; at 0℃; for 0.5h; A cooled (0 0C) solution of 4-fluorobenzenesulfonyl chloride (2.00 g; 10.3 mmol) in THF (40 ml) is treated with a 2 M solution of dimethylamine in THF (1 1.3 ml; 22.6 mmol) and stirred at 0 0C for 30 minutes. The solvents were removed under reduced pressure, the residue taken up in EtOAc, the organic phase was washed with a saturated solution of NH4CI twice and with water. The organic phase was dried on MgSO4, filtered and the solvent removed under reduced pressure to afford the title compound (1.80 g, 86%).
In tetrahydrofuran; water; at 0 - 20℃; for 24h; (1) A solution of 50 g of 4-fluorobenzenesulfonyl chloride in 250 ml of THF was cooled to 0C, and then, 100 ml of an aqueous 50% dimethylamine solution was added dropwise thereto, and the mixture was stirred at room temperature for 1 day. To the reaction mixture were added water and ethyl acetate, the mixture was stirred and then the liquids were separated. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and dried, the solvent was evaporated, and diisopropyl ether and hexane were added to the residue. Then, the precipitates were collected by filtration and washed with hexane to obtain 49.9 g of 4-fluoro-N,N-dimethyl-benzenesulfonamide

  • 5
  • [ 383-31-3 ]
  • [ 811-93-8 ]
  • 1-[4-(N,N-dimethylaminosulfonyl)anilino]-2-methyl-2-propylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% 2) To <strong>[383-31-3]4-fluoro-1-(N,N-dimethylaminosulfonyl)benzene</strong> (2.03 g, 10.0 mmol) were added diisopropylethylamine (2.26 mL, 13.0 mmol) and 1,2-diamino-2-methylpropane (3.14 mL, 30.0 mmol), and the mixture was heated with stirring at 170 DEG C for 10 hours. To the mixture was added a 2 mol/L aqueous sodium hydroxide solution, and the aqueous layer was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography. (Chromatorex (registered trademark) NH, Fuji Silysia, hexane/chloroform = 1/1) to obtain the title compound (956 mg, 3.52 mmol).yield: 35%<1>H NMR (CDCl3) delta (ppm) : 7.55 (2H, d, J = 9.2 Hz), 6.64 (2H, d, J = 9.2 Hz), 4.83 (1H, t, J = 5.7 Hz), 3.00 (2H, d, J = 5.7 Hz), 2.66 (6H, s), 1.21 (6H, s).APCIMS (m/z): 272 (M + H)<+>
  • 6
  • aqueous dimethylamine [ No CAS ]
  • [ 349-88-2 ]
  • [ 383-31-3 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; ethyl acetate; 4-Fluoro-N,N-dimethylbenzenesulfonamide A solution of 38.9 g (0.20 mole) of 4-fluorobenzenesulfonylchloride in 20 ml of methylene chloride was added slowly to 300 ml of a 40% aqueous dimethylamine solution during 0.5 hour period. The reaction was exothermic. After the reaction mixture was cooled a yellow solid was precipitated. The solid was collected, dissolved in 300 ml of ethyl acetate, and dried over magnesium sulfate. The solution was concentrated to 100 ml and a light yellow crystal formed. The crystal was collected and air-dried to afford 39 g of the product, mp 40-43 C.
  • 7
  • 6-methyl-5-(1-piperazinyl)-2,4-pyrimidinediamine triacetate [ No CAS ]
  • [ 383-31-3 ]
  • 4-[4-(2,4-diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; potassium carbonate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dimethyl sulfoxide; N,N-dimethyl-formamide; EXAMPLE 24 4-[4-(2,4 -Diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]-N,N-dimethylbenzenesulfonamide A mixture of 10.4 g (0.05 mole) of 6-methyl-5-(1-piperazinyl)-2,4-pyrimidinediamine triacetate, 10.1 g (0.05 mole) of <strong>[383-31-3]4-fluoro-N,N-dimethylbenzenesulfonamide</strong>, 6.4 g (0.055 mole) of anhydrous potassium fluoride, and 27.6 g (0.2 mole) of powdered potassium carbonate in 100 ml of dimethylsulfoxide was heated at 120 C. for four hours. The reaction mixture was cooled and poured into 300 ml of ice water. The solid was collected and washed with ml of water. Recystallization from N,N-dimethylformamide gave 6.5 g of the product as an off-white solid, mp 301-304 C.
  • 8
  • [ 383-31-3 ]
  • [ 122536-76-9 ]
  • [ 870859-17-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 24h; (2) In 600 ml of DMSO were suspended 25 g of (S)-(-)-3-(tert-butoxycarbonylamino)pyrrolidine, 47.9 g of 4-fluoro-N,N-dimethyl-benzenesulfonamide and 139 g of potassium carbonate, and the mixture was stirred at 130C for 1 day. To the reaction mixture were added water and ethyl acetate, the resulting mixture was stirred and the liquids were separated. The organic layer was washed with water, and then dried, and the solvent was evaporated. The residue was dissolved in chloroform, NH silica gel was added thereto and the mixture was allowed to stand for a while, and silica gel was filtered off. The silica gel was further washed with ethyl acetate. The filtrate and the washed solution were combined, and the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=80:20? 67:33) to obtain 8.39 g of tert-butyl [(S)-1-(4-dimethylsulfamoylphenyl)-pyrrolidin-3-yl]carbamate. MS·APCI (m/z): 370 [M+H] +
  • 9
  • [ 349-88-2 ]
  • [ 506-59-2 ]
  • [ 383-31-3 ]
YieldReaction ConditionsOperation in experiment
50% With dmap; In tetrahydrofuran; at 20℃; Preparation of 4-fluoro-N,N-dimethyl-benzenesulfonamide A solution of 4-fluorobenzenesulfonyl chloride (1.95 g, 10 mmol) and dimethylamine hydrochloric acid salt (978 mg, 12 mmol) in tetrahydrofuran (10 mL) was added to a solution of 4-dimethylaminopyridine (3.05 g, 25 mmol) in tetrahydrofuran (10 mL) dropwise at room temperature. The resulting mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was purified by flash column (elution with 20% ethyl acetate in petroleum ether) to afford 4-fluoro-N,N-dimethyl-benzenesulfonamide (1.02 g, 50%) as a white solid. The following sulfonamides were prepared in an analogous manner as described for 4-fluoro-N,N-dimethyl-benzenesulfonamide by the reaction of 4-fluorobenzenesulfonyl chloride with commercially available amines.
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h; Dimethylamine hydrochloride (1.27g) was added to a solution OF 4-FLUORO- benzenesulphonyl chloride (3. 0G) and N, N-diisopropylethylamine (5. 37ML) in dichloromethane (30ML), the mixture was stirred at RT for lh, diluted with water, extracted with dichloromethane, dried and evaporated under reduced, yield 3.0g
  • 10
  • [ 383-31-3 ]
  • [ 1240287-91-5 ]
YieldReaction ConditionsOperation in experiment
82% A solution of 4-fluoro-Lambda/,Lambda/-dimethylbenzenesulfonamide (1.80 g; 8.86 mmol) in cone, sulfuric acid (7 ml; 130 mmol) was treated with Lambda/-bromosuccinimide (1 730 mg; 9.74 mmol) and stirred at RT for 3 h. The reaction mixture was carefully poured on crushed ice, extracted with AcOEt and the organic phase was washed with a 0.1 N solution of NaOH in water twice, then with brine twice. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give the title compound as a white solid (2.04 g, 82%).1H NMR (300MHz, DMSO-d6) delta [ppm] 8.04 (1 H, dd, J= 6.5 Hz, J= 2.2 Hz), 7.83 (1 H, ddd, J= 8.7 Hz, J= 4.6 Hz, J= 2.3 Hz), 7.66 (1 H, t, J= 8.7 Hz), 2.65 (6H, s).
  • 11
  • [ 1245215-57-9 ]
  • [ 383-31-3 ]
  • [ 1245216-78-7 ]
YieldReaction ConditionsOperation in experiment
53% With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; Preparation of ethyl 4-{4-f(dimethylamino)sulfonyllphenoxy}-2-methyl-2H- indazole-6-carboxylate (l-1f-35):(l-1f-35)The title compound was prepared by heating a mixture of ethyl 4- hydroxy-2-methyl-2H-indazole-6-carboxylate (l-1e-3, 70mg, 0.32 mmol), 4- fluoro-N,N-dimethylbenzenesulfonamide (71.1 mg, 0.35 mmol), and cesium carbonate (114 mg, 0.35 mmol) in N,N-dimethylformamide (0.795 ml_) at 1000C overnight. The reaction mixture was then cooled, concentrated, dissolved in water, and extracted three times with dichloromethane. The combined organic layers were concentrated and the crude product was purified by flash chromatography eluting with a 20-65% gradient of ethyl acetate in heptane to afford ethyl 4-{4-[(dimethylamino)sulfonyl]phenoxy}-2- methyl-2H-indazole-6-carboxylate (l-1f-35, 68 mg, 53%).1H NMR (400 MHz, CHLOROFORM-d) ppm 1.39 (t, J=7.13 Hz, 3H), 2.72 (s, 6 H), 4.22 (s, 3 H), 4.39 (q, 2 H), 7.13 (d, J=8.99 Hz, 2 H), 7.31 (d, J=1.17 Hz, 1 H), 7.69 - 7.78 (m, 3 H), 8.35 (s, 1 H). MS (M+1 ) 403.8.
  • 12
  • [ 383-31-3 ]
  • [ 1240286-13-8 ]
  • 13
  • [ 383-31-3 ]
  • C10H10Cl3NO5S [ No CAS ]
  • 16
  • [ 371-42-6 ]
  • [ 68-12-2 ]
  • [ 383-31-3 ]
  • 17
  • [ 383-31-3 ]
  • [ 73183-34-3 ]
  • C20H32B2FNO6S [ No CAS ]
  • 18
  • [ 383-31-3 ]
  • N-((5-((4-(N,N-dimethylsulfamoyl)phenyl)thio)thiophen-2-yl)methyl)-2,2,2-trifluoroacetamide [ No CAS ]
  • 19
  • [ 383-31-3 ]
  • 4-((5-cyanothiophen-2-yl)thio)-N,N-dimethylbenzenesulfonamide [ No CAS ]
  • 20
  • [ 383-31-3 ]
  • [ 18325-52-5 ]
YieldReaction ConditionsOperation in experiment
31% With sodium thiomethoxide; In N,N-dimethyl-formamide; at 170℃; for 16h;Sealed tube; [00728] A mixture of 4-fluorobenzene-1 -sulfonyl chloride (2.0 g, 10.3 mmol), HNMe2 (2.0M in MeOH; 1 1 .0 mL, 22.0 mmol) and DCM (1 1 .0 mL) was stirred at rt for 5 min. DCM (30 mL) was added. The organic phase was washed with 1 M HCI (30 mL) and brine (30 mL), dried over MgSCv and filtered. The solvent was removed under reduced pressure to afford 4-fluoro-/V,/V- dimethylbenzenesulfonamide as a white solid (2.12 g, quant.). A mixture of 4-fluoro-/V,/V- dimethylbenzenesulfonamide (1 .50 g, 7.39 mmol), NaSMe (2.08 g, 29.7 mmol) and DMF (9.0 mL) was stirred at 170 C in a sealed tube for 16 h. After cooling to rt, 1 M NaOH (40 mL) was added. The aqueous phase was washed with Et20 (2 chi 40 mL), acidified to pH <2 with 2 M HCI and then extracted with Et20 (3 chi 40 mL). The combined organic phase was dried over MgSCv and filtered. The solvent was removed under reduced pressure to afford 4-mercapto-/V,/V- dimethylbenzenesulfonamide as an orange oil (503 mg, 31 %). H NMR (500 MHz, CDCI3) delta 7.67 - 7.58 (m, 2H), 7.43 - 7.35 (m, 2H), 3.67 (s, 1 H), 2.71 (s, 6H).
  • 21
  • [ 383-31-3 ]
  • C13H16N2O2S3 [ No CAS ]
  • 22
  • [ 383-31-3 ]
  • 4-((5-(aminomethyl)thiophen-2-yl)sulfonyl)-N,N-dimethylbenzenesulfonamide [ No CAS ]
  • 23
  • [ 824-80-6 ]
  • [ 68-12-2 ]
  • [ 383-31-3 ]
YieldReaction ConditionsOperation in experiment
42% General procedure: An oven-dried Schlenk tube equipped with a magnetic stir bar was charged with formamide 1 (2.0 mmol), KO-t-Bu (2.0 mmol) and CH3CN (2.0 mL). The mixture was stirred at 50 C for 30 min and then a CH3CN (2.0 mL) solution containing sodium sulfinates 2 (0.5 mmol) and NIS (1.0 mmol) was slowly added dropwise. The resulting solution stirred at 50 C for 12 h under air. The mixture was then cooled to room temperature, diluted with 30 mL of H2O, and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the products.
  • 24
  • [ 110-18-9 ]
  • [ 349-88-2 ]
  • [ 383-31-3 ]
  • 25
  • [ 87-52-5 ]
  • [ 349-88-2 ]
  • [ 383-31-3 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine; In acetonitrile; at 25℃; for 24h; (1) 1 mmol of latinosyl N, N-dimethylamino-3-methylindole shown in Formula 1, 1.5 mmol of 4-fluorobenzenesulfonyl chloride as shown in Formula 2g was added to a 50 mL flask, Add 10mL of CH3CN to completely dissolve, slowly add 1.5mmol of Et3N, The reaction was stirred at 25 C for 24h to obtain a reaction solution; the reaction formula is as follows: (2) The reaction solution was concentrated under reduced pressure, CH2Cl2 and water were added, and the organic phases were combined. It was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was concentrated and evaporated to dryness, and then separated by silica gel column chromatography to obtain N, N-dimethylsulfonamide derivatives as shown in Formula 3g.
82% With triethylamine; In acetonitrile; at 25℃; for 24h; General procedure: To a solution of gramine (1, 1.0mmol) and arylsulfonyl chloride (2, 1.5mmol) in dryCH3CN (10ml) at 25 C, a solution of Et3N (1.5mmol) in dry CH3CN (5ml) was addeddrop wise for 10min [20-24]. After reaction for 24 h, the reaction solution was concentratedunder reduced pressure to give crude product. The crude product was dissolvedin CH2Cl2 (15ml) and diluted with water (15ml) and extracted with CH2Cl2 (30ml 3). Subsequently, the combined organic phase was washed by saturated aq. brine(30ml), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gelcolumn chromatography to obtain the target compounds in 76%-98% yields. The datafor 3a-o are shown as follows.
 

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Amines

Chemical Structure| 433-14-7

A696388 [433-14-7]

4-Fluoro-N-methylbenzenesulfonamide

Similarity: 0.94

Chemical Structure| 5183-78-8

A255148 [5183-78-8]

N-Methylbenzenesulfonamide

Similarity: 0.83

Chemical Structure| 402-46-0

A415842 [402-46-0]

4-Fluorobenzenesulfonamide

Similarity: 0.83

Chemical Structure| 1524-40-9

A755791 [1524-40-9]

3-Fluorobenzenesulfonamide

Similarity: 0.81

Chemical Structure| 640-61-9

A162891 [640-61-9]

N,4-Dimethylbenzenesulfonamide

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Sulfamides

Chemical Structure| 433-14-7

A696388 [433-14-7]

4-Fluoro-N-methylbenzenesulfonamide

Similarity: 0.94

Chemical Structure| 5183-78-8

A255148 [5183-78-8]

N-Methylbenzenesulfonamide

Similarity: 0.83

Chemical Structure| 402-46-0

A415842 [402-46-0]

4-Fluorobenzenesulfonamide

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Chemical Structure| 1524-40-9

A755791 [1524-40-9]

3-Fluorobenzenesulfonamide

Similarity: 0.81

Chemical Structure| 640-61-9

A162891 [640-61-9]

N,4-Dimethylbenzenesulfonamide

Similarity: 0.79