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Chemical Structure| 7143-01-3 Chemical Structure| 7143-01-3

Structure of Methanesulfonic anhydride
CAS No.: 7143-01-3

Chemical Structure| 7143-01-3

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Product Details of [ 7143-01-3 ]

CAS No. :7143-01-3
Formula : C2H6O5S2
M.W : 174.20
SMILES Code : CS(=O)(OS(C)(=O)=O)=O
MDL No. :MFCD00007556
InChI Key :IZDROVVXIHRYMH-UHFFFAOYSA-N
Pubchem ID :81560

Safety of [ 7143-01-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 7143-01-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 2
Num. H-bond acceptors 5.0
Num. H-bond donors 0.0
Molar Refractivity 30.74
TPSA ?

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

94.27 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.51
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

-0.78
Log Po/w (WLOGP)?

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

1.08
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.

-1.31
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

-0.77
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.25

Water Solubility

Log S (ESOL):?

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

-0.3
Solubility 88.0 mg/ml ; 0.505 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.72
Solubility 33.1 mg/ml ; 0.19 mol/l
Class?

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

Very 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

-0.24
Solubility 99.8 mg/ml ; 0.573 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

No
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

No
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.

-7.92 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

2.0
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)

3.09

Application In Synthesis of [ 7143-01-3 ]

* 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 [ 7143-01-3 ]

[ 7143-01-3 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 24316-19-6 ]
  • [ 7143-01-3 ]
  • [ 61568-61-4 ]
  • 2
  • [ 1585-90-6 ]
  • [ 7143-01-3 ]
  • [ 155863-36-8 ]
YieldReaction ConditionsOperation in experiment
43% at 105℃; for 3.5h;Inert atmosphere; To a flame dried round bottom flask 0.5 g (3.6 mmol) of l-(2-hydroxyethyl)-lW- pyrrole-2,5-dione and 0.7 g (4.0 mmol) of methanesulfonic anhydride was added. The flask was evacuated and refilled with nitrogen. The flask was heated to 105C and stirred for 3.5 hr. The reaction was cooled to room temperature and dissolved in ethyl acetate (5 mL). The solution was taken up into a separatory funnel and washed four times with a saturated solution of sodium carbonate (40 mL). The aqueous layers were collected and washed with ethyl acetate (50 mL). The organic layers were combined and dried with MgS04 and concentrated in vacuo. The product was recrystallized from t-butyl methyl ether to yield 43 % (0.347 g, 1.58 mmol) of 2-(2,5-dioxo-2,5-dihydro-lH-pyrrol- l-yl)ethyl methanesulfonate.XH NMR (400 MHz, CD3CI) 6.78 (s, 2H), 4.41 (t, J = 5.23, 2H), 3.90 (t, J = 5.23, 2H), 3.04 (s, 3H)
  • 3
  • [ 121282-70-0 ]
  • [ 7143-01-3 ]
  • [ 365996-28-7 ]
YieldReaction ConditionsOperation in experiment
95% With pyridine; In dichloromethane; at 0℃; for 1.5h; To a solution of the product from Part B (3.10 g, 14.4 mmol) in CH2C12 (50 mL) were added pyridine (1.34 mL, 16. 58 mmol) and methane sulfonic anhydride (2.81 g, 16.13 mmol) sequentially at 0C. The reaction mixture was stirred for 1.5 h at 0C, then quenched with H2O, and extracted with EtOAc (3 x 50 mL). The organic phase was washed with H20, brine, and dried (Na2S04). The solvent was evaporated to afford (1S, 2S)-METHANESULFONIC acid 2-TERT-BUTOXYCARBONYLAMINO- cyclohexyl ester (4.0 g, 95%) as a white solid. MS M/Z 294.2 ([M+H]+).
  • 4
  • [ 38222-83-2 ]
  • [ 204716-63-2 ]
  • [ 7143-01-3 ]
  • [ 204716-67-6 ]
YieldReaction ConditionsOperation in experiment
In methanol; dichloromethane; b 3-[1-(3-Methanesulfonyloxymethylbenzyl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-pyrrole-2,5-dione Methanesulfonic anhydride (0.35 g, 2.0 mmol) was added to a stirred solution of the product of step a) (0.234 g, 0.51 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.42 g, 2.0 mmol) in dry CH2 Cl2 (15 mL) at room temperature. The reaction mixture was stirred for 16 h, and thereafter quenched by adding methanol (1.5 mL). The solvent was evaporated and the crude product chromatographed (ethyl acetate/heptane: 2/1) to yield 0.285 g of the sub-title product. 1 H-NMR (CDCl3):delta7.76 (1H, s); 7.66 (1H, s); 7.58 (1H, s); 7.38-7.24 (3H, m); 7.22-7.00 (6H, m); 6.82 (1H, d, J=8.05 Hz); 6.77 (1H, t, J=8.30 Hz); 6.68 (1H, t, J=8.05 Hz); 5.34 (2H, s); 5.18 (2H, s); 3.86 (3H, s); 2.83 (3H, s).
  • 5
  • [ 10167-97-2 ]
  • [ 7143-01-3 ]
  • N-(5-methoxy-2-pyridinyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% In dichloromethane; at 0 - 20℃; for 6h; Preparation I; N-(5-methoxy-2-pyridinyl)methanesulfonamide; A solution of 10.7 g (86 mmol) of 5-methoxy-2-pyridinamine in 55 ml of dichioromethane is cooled to 0 C. and 72 ml (144 mmol) of a 2 M solution of methanesulfonic anhydride in dichloromethane are added gradually. The reaction mixture is stirred for 6 hours at room temperature and sodium bicarbonate solution is then added in a sufficient amount to bring the pH to about 9. The mixture obtained is concentrated under reduced pressure, the residue is taken up in 160 ml of ethanol at 50 C., the mixture obtained is dried and filtered and the filtrate is concentrated under reduced pressure. The residue is triturated in 50 ml of cold ethanol and the solid obtained is filtered off, rinsed with a little ethanol on the filter and then dried to give 8.7 g of the expected product in the form of a white powder (yield=50%).
  • 6
  • [ 52022-77-2 ]
  • [ 7143-01-3 ]
  • [ 206874-43-3 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In dichloromethane; at 20℃; for 16h; Procedure S: Intermediate 24 (1-24) - 3-Nitrophenethyl methanesulfonate.; [00134] To a solution of 1.6 g (10 mmol, 1.0 eq.) of 2-(3-nitrophenyl) (1-23) in 20 mL of methylene chloride was added 2.8 mL (20 mmol, 2.0 eq.) of triethylamine. A solution of 1.7 g (10 mmol, 1.0 eq.) of methanesulfonic anhydride in 10 mL of methylene chloride was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was washed with sat. brine and the organic layer was dried (Na2SC^). The solvent was removed in vacuo and the resulting residue was purified by flash chromatography to provide 2.2 g (9.0 mmol, 90%) of 3-nitrophenethyl methanesulfonate (1-24).
  • 7
  • [ 619-45-4 ]
  • [ 7143-01-3 ]
  • [ 7151-76-0 ]
  • 8
  • [ 1039948-89-4 ]
  • [ 7143-01-3 ]
  • [ 1202407-35-9 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; Intermediate 2 is obtained from 1 according to the procedure in Example 1. To a mixture of 2 and diisopropylethyiamine in CH2CI2 at 0 0C is added Ms2O. The reaction mixture is stirred until the reaction is complete, as determined by thin layer chromatography (TLC). The reaction mixture is diluted with ethyl acetate and washed with cold sat. NaHCOs and brine. The organic layer is dried over Na2SO4, filtered and concentrated to provide mesylate 8.
  • 9
  • [ 57053-02-8 ]
  • [ 7143-01-3 ]
  • [ 1418315-95-3 ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 80℃; A mixture of Example 59A (1.50 g, 7.17 mmol), pyridine (1.74 mL, 21.51 mmol) and methanesulfonic anhydride (2.50 g, 14.34 mmol) in 60 mL 1 ,2-dichloroethane was stirred overnight at 80 C. The reaction mixture was concentrated and the residue was purified by flash chromatography (0-7% methanol/CH2Cl2) to afford the title compound.
  • 10
  • [ 38361-37-4 ]
  • [ 7143-01-3 ]
  • 2-chloro-1,3-difluoro-4-(methylsulfonyl)benzene [ No CAS ]
  • 11
  • [ 90365-74-5 ]
  • [ 7143-01-3 ]
  • [ 104351-40-8 ]
YieldReaction ConditionsOperation in experiment
78% With triethylamine; In dichloromethane; at 0 - 20℃; for 6h; To a solution of (3S,4S)-1-benzylpyrrolidine-3,4-diol (3a) (6 g,31 mmol) and Et3N (12.8 mL, 93 mmol) in 200mL dry DCM wasadded dropwise a solution of methanesulfonic anhydride (12.9 g,74 mmol) in 100mL dry DCM at 0 C. The reaction was allowed towarm at R.T. for 6 h. The reaction mixture was washed with saturatedaqueous NaHCO3, 5% HCl and brine in sequence, dried overanhydrous Na2SO4, evaporated in vacuum, and purified by flashchromatography (petroleum ether:EtOAc 3:1) to afford 4a as lightyellow oil (8.5 g, 78%). 1H NMR (400 MHz, CDCl3) d 2.75 (dd,J 4.0 Hz, 11.2 Hz, 2H), 3.05 (s, 6H), 3.07-3.11 (m, 2H), 3.60-3.67(m, 2H), 5.12 (t, J 4.0 Hz, 2H), 7.26-7.34 (m, 5H); 13C NMR(100 MHz, CDCl3) d 38.3, 57.8, 59.1, 82.4, 127.5, 128.5, 128.7, 136.7;HRMS (ESI) m/z calcd for C13H19NO6S2 [MH] 350.0727, found350.0732. [a]D 20 24.6 (c 0.56, CHCl3).
 

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