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Chemical Structure| 349-88-2 Chemical Structure| 349-88-2

Structure of 349-88-2

Chemical Structure| 349-88-2

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Product Details of [ 349-88-2 ]

CAS No. :349-88-2
Formula : C6H4ClFO2S
M.W : 194.61
SMILES Code : O=S(C1=CC=C(F)C=C1)(Cl)=O
MDL No. :MFCD00007438
InChI Key :BFXHJFKKRGVUMU-UHFFFAOYSA-N
Pubchem ID :9588

Safety of [ 349-88-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 349-88-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 39.48
TPSA ?

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

42.52 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.66
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

2.04
Log Po/w (WLOGP)?

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

3.25
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.

1.95
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

1.77
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.13

Water Solubility

Log S (ESOL):?

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

-2.67
Solubility 0.417 mg/ml ; 0.00214 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.

-2.56
Solubility 0.535 mg/ml ; 0.00275 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

-3.22
Solubility 0.117 mg/ml ; 0.000601 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.

-6.04 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

1.0
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)

1.77

Application In Synthesis of [ 349-88-2 ]

* 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 [ 349-88-2 ]

[ 349-88-2 ] Synthesis Path-Downstream   1~23

  • 1
  • [ 349-88-2 ]
  • [ 117810-52-3 ]
  • Unifiram [ No CAS ]
  • 2
  • [ 2480-23-1 ]
  • [ 349-88-2 ]
  • (S)-2-[(4-Fluoro-benzenesulfonyl)-methyl-amino]-3-methyl-butyric acid [ No CAS ]
  • 3
  • [ 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

  • 4
  • 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.
  • 5
  • [ 349-88-2 ]
  • [ 192130-34-0 ]
  • [ 256943-83-6 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine; In tetrahydrofuran; water; 66-1) 1-[2-(4-Fluorobenzenesulfonylamino)ethyl]-4-(t-butoxycarbonyl)piperazine The 1-(2-aminoethyl)-4-(t-butoxycarbonyl)piperazine (2.01 g) obtained in Example 58 and 4-fluorobenzene sulfonylchloride (2.05 g) were dissolved in tetrahydrofuran (20 ml), and triethylamine (2.4 ml) was added thereto, and the mixture was stirred overnight at room temperature. Water (50 ml) was added to the reaction mixture which was then extracted with ethyl acetate, and the organic layer was washed with water, dried, and evaporated. The residue was purified by Cromatorex NH silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound (2.61g, 77percent) was obtained as a colorless oil.
  • 6
  • [ 349-88-2 ]
  • [ 67630-01-7 ]
  • N-t-butoxycarbonyl-DL-4-[(4-fluorophenyl)sulfonylamino]phenylalanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example II-14 N-t-butoxycarbonyl-DL-4-[(4-fluorophenyl)sulfonylamino]-phenylalanine In the same manner as in Example II-(11-2) and Example II-(11-3) except for using N-t-butoxycarbonyl-DL-4-aminophenylalanine ethyl ester in place of N-t-butoxycarbonyl-L-4-aminophenylalanine ethyl ester and using 4-fluorobenzenesulfonyl chloride in place of benzenesulfonyl chloride, the reactions were carried out to obtain the title compound (overall yeield-quantitative) as white solid. 1H-NMR (CDCl3) delta; 7.78-7.71 (m, 2H), 7.21 (s, 1H), 7.13-6.91 (m, 6H), 5.03-4.88 (m, 1H), 4.67-4.49 (m, 1H), 3.19-2.89 (m, 2H), 1.42 (s, 9H). CI-MS (m/z); 383
  • 7
  • [ 349-88-2 ]
  • [ 120-35-4 ]
  • 3-(4-Fluoro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 125 3-(4-Fluoro-benzenesulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using 4-fluorobenzenesulfonyl chloride (2.14 g 10 mmol) and 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10.0 mmol) to afford the product (3.522 g); m.p. 209-211 C. Calculated for C20H17FN2O4S: C, 59.99; H, 4.28; N, 7.00. Found: C, 59.96; H, 4.24; N, 6.87.
  • 8
  • [ 214147-48-5 ]
  • [ 349-88-2 ]
  • N-(1-acetylpiperidin-4-yl)-4-fluorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; EXAMPLE 8 To a suspension of <strong>[214147-48-5]1-acetyl-4-aminopiperidine hydrochloride</strong> (715 mg) in dichloromethane (7 ml) were added diisopropylethylamine (1.83 ml) and a solution of 4-fluorobenzenesulfonyl chloride (0.83 mg) in dichloromethane (2 ml) at ambient temperature. After stirring for 6.5 hours, the reaction mixture was diluted with dichloromethane and washed with water, saturated aqueous sodium hydrogen carbonate, and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. A residue was purified by column chromatography (silica gel 50 ml, dichloromethane:methanol=50:1 to 20:1). After rinse with diisopropyl ether, N-(1-acetylpiperidin-4-yl)-4-fluorobenzenesulfonamide (859 mg) was obtained. NMR (DMSO-d6, delta): 1.21 (2H, m), 1.54 (2H, m), 1.94 (3H, s), 2.66 (1H, br t, J=10.8 Hz), 3.02 (1H, dt, J=2.9, 12.0 Hz), 3.22 (1H, m), 3.64 (1H, br d, J=14.0 Hz), 4.05 (1H, br d, J=13.2 Hz), 7.44 (2H, t, J=8.9 Hz), 7.8-8.0 (3H, m)
  • 9
  • [ 349-88-2 ]
  • [ 162167-97-7 ]
  • [ 1016539-00-6 ]
  • 10
  • [ 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
  • 11
  • [ 349-88-2 ]
  • [ 24629-25-2 ]
  • [ 635288-63-0 ]
  • 12
  • [ 1185265-51-3 ]
  • [ 349-88-2 ]
  • [ 350800-81-6 ]
  • [ 1185265-18-2 ]
YieldReaction ConditionsOperation in experiment
In pyridine; N-{6-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-4-fluoro-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-4-fluoro-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 4-fluoro-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=295-297 C, (M+H)+=492.
  • 13
  • [ 349-88-2 ]
  • [ 350800-81-6 ]
  • [ 1185265-51-3 ]
YieldReaction ConditionsOperation in experiment
With pyridine; N-{6-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-4-fluoro-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-4-fluoro-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 4-fluoro-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=295-297 C, (M+H)+=492.
  • 14
  • [ 349-88-2 ]
  • [ 104-85-8 ]
  • [ 530-46-1 ]
  • 15
  • [ 349-88-2 ]
  • [ 114744-51-3 ]
  • [ 1332881-39-6 ]
YieldReaction ConditionsOperation in experiment
81% With pyridine; at 80℃; for 3.0h; 7-Bromo-1,2,3,4-tetrahydroquinoline (0.60 g, 2.8 mmol) was stirred with 4- fluorophenylsulphonyl chloride (1.65 g, 8.49 mmol) in pyridine (5 mL) at 80 C for 3 h. The mixture was cooled, concentrated, and the residue was chromatagraphed (EtOAc/Hexanes on Si02) to give 845 mg of a brown solid (81 %) of compound 43. C15H13BrFN02S 368.98, found 394.0 [M + Na]+ and 367.8 [M - H] 1H NMR (500 MHz, CDCW) delta 1.58 - 1.67 (m, 2 H) 2.41 (t, 7=6.71 Hz, 2 H) 3.72 - 3.82 (m, 2 H) 6.89 (d, 7=8.30 Hz, 1 H) 7.08 - 7.17 (m, 2 H) 7.18 - 7.24 (m, 1 H) 7.59 - 7.68 (m, 2 H) 7.92 - 8.01 (m, 1 H) ppm.
  • 16
  • [ 349-88-2 ]
  • [ 2133-34-8 ]
  • (2S)-1-[(4-fluorobenzene)sulfonyl]azetidine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 18h; 4-Fluorobenzene-1 -sulfonyl chloride (2.14 g, 11.00 mmol, 1.00 equiv) was added into a solution of <strong>[2133-34-8](2S)-azetidine-2-carboxylic acid</strong> (1 g, 9.89 mmol, 1.10 equiv) in saturated aqueous sodium hydroxide (6 mL)/tetrahydrofuran (6 mL) at 0C. The resulting mixture was stirred for 18 h at room temperature. The mixture was extracted with ether. The pH value of the aqueous solution was adjusted to 3 with 2 M hydrogen chloride. The resulting mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. This resulted in the title compound (1.7 g, 60%) as a white solid.
  • 17
  • [ 349-88-2 ]
  • [ 5930-94-9 ]
  • C10H7FN2O4S [ No CAS ]
  • 18
  • [ 349-88-2 ]
  • [ 32202-61-2 ]
  • N-(2,3-dihydro-1H-inden-4-yl)-4-fluorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With pyridine; at 0℃; for 2h;Inert atmosphere; General procedure: To an ice-cooled solution of the amine (20mmol) in pyridine (8mL) was slowly added the corresponding sulfonyl chloride (30mmol) in pyridine (6mL). The mixture was stirred at 0°C for 2h and allowed to reach room temperature. Water was added (100mL) and the solid was collected and recrystallized from MeOH:CH2Cl2.
  • 19
  • [ 349-88-2 ]
  • [ 105655-01-4 ]
  • 6-bromo-4-((4-fluorophenyl)sulfonyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With pyridine; In dichloromethane; at 20℃; for 4h; To a solution of <strong>[105655-01-4]6-bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine</strong> (350 mg, 1.6 mmol) in dichloromethane (5 mL) was added pyridine (0.53 mL, 6.5 mmol) followed by 4-fluorobenzenesulfonyl chloride (0.38 g, 2.0 mmol). The reaction mixture was stirred at ambient temperature for 4 hours. Then, the reaction mixture was concentrated in vacuo to provide a residue, which was redissolved in ethyl acetate, washed with 1M hydrogen chloride, brine, dried with sodium sulfate, filtered and concentrated in vacuo to provide the crude product. The crude product was purified by column chromatography (eluting with a gradient of 0-30% ethyl acetate in hexanes) to provide the title compound (0.49 g, 81% yield).
  • 20
  • [ 110-18-9 ]
  • [ 349-88-2 ]
  • [ 383-31-3 ]
  • 21
  • [ 349-88-2 ]
  • [ 114744-51-3 ]
  • [ 1332881-33-0 ]
  • 22
  • [ 349-88-2 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 4-fluorobenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.8% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 23
  • [ 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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