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[ CAS No. 20880-92-6 ] {[proInfo.proName]}

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Chemical Structure| 20880-92-6
Chemical Structure| 20880-92-6
Structure of 20880-92-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 20880-92-6 ]

CAS No. :20880-92-6 MDL No. :MFCD00022183
Formula : C12H20O6 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 260.28 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 20880-92-6 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.16
TPSA : 66.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.49
Log Po/w (XLOGP3) : -0.26
Log Po/w (WLOGP) : 0.38
Log Po/w (MLOGP) : -0.06
Log Po/w (SILICOS-IT) : 0.91
Consensus Log Po/w : 0.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.22
Solubility : 15.5 mg/ml ; 0.0597 mol/l
Class : Very soluble
Log S (Ali) : -0.68
Solubility : 55.0 mg/ml ; 0.211 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.17
Solubility : 17.6 mg/ml ; 0.0675 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.45

Safety of [ 20880-92-6 ]

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

Application In Synthesis of [ 20880-92-6 ]

* 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.

  • Upstream synthesis route of [ 20880-92-6 ]

[ 20880-92-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 20880-92-6 ]
  • [ 97240-79-4 ]
YieldReaction ConditionsOperation in experiment
76% With 4-methyl-morpholine; sulphamoyl chloride In di-isopropyl ether; N,N-dimethyl-formamide at 5℃; for 1 h; Crude product recrystalization EXAMPLE 3The procedure of example 1 was followed with 100 ml dimethylformamide instead of dimethyl acetamide.Water content (by Karl Fisher) = 0.13percent; Chemical assay (by HPLC) = 99.0percent; Yield = 76percent (by theory)
75% With sulphamoyl chloride; triethylamine In di-isopropyl ether; N,N-dimethyl acetamide at 5℃; for 1 h; Crude product recrystalization EXAMPLE 2The procedure of example 1 was followed with 26 gm of triethylamine instead of N- methylmorpholine .Water content (by Karl Fisher) = 0.17percent; Chemical assay (by HPLC) = 99.1percent; Yield = 75percent (by theory)
72% With 4-methyl-morpholine; sulphamoyl chloride In di-isopropyl ether; N,N-dimethyl acetamide at 5 - 10℃; for 1 h; Crude product recrystalization EXAMPLE 1Topiramate crude2,3:4,5-bis-O-(l-methylethylidene)-?-D-fructopyranose (50 gm) (III) and N- methylmorpholine (26 gm) were suspended in 100 ml dimethyl acetamide. The mass was cooled to 50C followed by addition of 29.8 gm of sulfamoyl chloride (V). The reaction mass was stirred at that temperature for 1 hr and extracted with 250 ml ethyl acetate followed by further extraction with 2 x 100 ml ethyl acetate. The organic layer was washed with 400 ml water and 200 ml 20percent sodium chloride solution and concentrated in vacuum to a mass. This was then crystallized with a mixture of 75 ml ethyl acetate and 150 ml cyclohexane. The crystalline product was filtered and dried at 550C under vacuum to get 50 gm of Topiramate crude.Topiramate pure50 gm of the above crude was dissolved in 2200 ml diisopropyl ether at reflux temperature till a clear solution was obtained. Activated carbon (2.5 gm) was added and the contents were refluxed for another 30 min followed by filtration under hot conditions. The filtrate was concentrated till a residual volume of 250 ml was achieved. The crystallized product was cooled to 100C and filtered. The product was dried at 500C under vacuum to get 45 gm of Topiramate pure.Water content (by Karl Fisher) = 0.15percent; Chemical assay (by HPLC) = 99.2percent; Yield = 77percent (by theory)EXAMPLE 4The procedure of example 1 was followed with the change that the reaction temperature was maintained at 100C instead of 5C.Water content (by Karl Fisher) = 0.17percent; Chemical assay (by HPLC) = 99.3percent; Yield = 72percent (by theory)
Reference: [1] Patent: WO2007/99388, 2007, A1, . Location in patent: Page/Page column 6
[2] Patent: WO2007/99388, 2007, A1, . Location in patent: Page/Page column 5-6
[3] Patent: WO2007/99388, 2007, A1, . Location in patent: Page/Page column 5; 6
[4] Journal of Medicinal Chemistry, 1987, vol. 30, # 5, p. 880 - 887
[5] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 6; 13; 46
[6] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[7] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 32-33
[8] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 32-33
[9] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[10] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[11] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 31; 33
[12] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 31; 33-34
[13] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 31; 33-34
[14] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22; 31; 33-34
[15] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[16] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[17] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 32-33
[18] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 28; 32-33
[19] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 19; 21; 22-23; 28; 32-33
[20] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 32-33
[21] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22; 28; 32-33
[22] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 16-18; 22
[23] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22
[24] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 29; 32; 34
[25] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 29; 32; 34
[26] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32-33
[27] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 16-25; 29; 32; 34-38; 39-41
[28] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32-33
[29] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32; 34
[30] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27-28; 32-34
[31] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32; 34
[32] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22; 29; 32; 34
[33] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 29; 32; 34
[34] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32; 34
[35] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 29; 32; 34
[36] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 29; 32; 34
[37] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 16-18; 22; 29; 32; 34
[38] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 41-42
[39] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22; 27; 32-33; 39-41
[40] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[41] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[42] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[43] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 25-26
[44] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 30; 32; 34
[45] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 30; 32; 34
[46] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 30; 32; 34
[47] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[48] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22
[49] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 30; 33-34
[50] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[51] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[52] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 37-38
[53] Journal of Sulfur Chemistry, 2015, vol. 36, # 5, p. 463 - 470
[54] Patent: CN103910770, 2017, B,
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