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[ CAS No. 934240-31-0 ] {[proInfo.proName]}

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Chemical Structure| 934240-31-0
Chemical Structure| 934240-31-0
Structure of 934240-31-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 934240-31-0 ]

CAS No. :934240-31-0 MDL No. :MFCD28900694
Formula : C18H20ClFN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HEPUBAGOKRIZEO-PPPUBMIESA-N
M.W : 350.82 Pubchem ID :16046067
Synonyms :
GSK-1014802 hydrochloride;Vixotrigine hydrochloride;Vixotrigine;GSK1014802A;CNV1014802;BIIB074;Raxatrigine (hydrochloride);CNV1014802 hydrochloride;Raxatrigine hydrochloride

Calculated chemistry of [ 934240-31-0 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.28
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 96.05
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.16
Log Po/w (WLOGP) : 3.05
Log Po/w (MLOGP) : 2.49
Log Po/w (SILICOS-IT) : 3.07
Consensus Log Po/w : 2.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.05
Solubility : 0.0316 mg/ml ; 0.00009 mol/l
Class : Moderately soluble
Log S (Ali) : -4.18
Solubility : 0.0231 mg/ml ; 0.0000658 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.61
Solubility : 0.000861 mg/ml ; 0.00000245 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.0

Safety of [ 934240-31-0 ]

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 [ 934240-31-0 ]

* 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 [ 934240-31-0 ]
  • Downstream synthetic route of [ 934240-31-0 ]

[ 934240-31-0 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 934240-30-9 ]
  • [ 934240-31-0 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogenchloride In 1,4-dioxane; ethyl acetate at 20℃; for 0.583333 h; Cooling with ice A solution of (2S,5f?)-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxamide (which may be prepared as described herein for Description 6) (5.46 g, 17.37 mmol) in ethyl acetate (140 ml_) was stirred for 30 minutes and filtered. The filtrate was treated with 4M HCI in dioxan (6.51 ml_, 26.05 mmol) and the mixture was stirred at room temperature for 20 minutes and then cooled in an ice bath for 15 minutes. The resulting solid was collected by filtration and washed with cold ethyl acetate (2 x 20 ml) and then dried under vacuum at 35°C overnight, then at 50°C for 2 hours to give product as an off white solid (E1), (5.87 g, 96percent). LC-MS MH+ = 315 (C18H19FN2O2) NMR (d6-DMSO): 1.95-2.20 (2H, m), 2.30 (2H, m), 3.35 (1 H, s), 4.30 (1 H, m), 4.61 (1 H, m), 5.18 (2H, s), 7.10 (2H, d, J = 9 Hz), 7.18-7.30 (2H, m), 7.40 (1 H, m), 7.47 (2H, d, J = 9 Hz), 7.56 (1 H, ), 7.72 (1 H, s), 8.07 (1 H, s), 10.60 (1 H, br s).
93% With hydrogenchloride In 1,4-dioxane; methanol; ethyl acetate at 0℃; for 1.5 h; To a solution of E1 ( 72 mg, 0.23 mmol) in a mixture of ethyl acetate (1.0 ml) and methanol (1.0 ml) was added 4M HCI in 1 ,4-dioxane (57.5 uL, 0.23 mmol) at 0°C. The mixture was stirred for 1.5h and slowly allowed to warm to room temperature. After evaporating the solvent, the residue was triturated with diethyl ether to afford the title compound as a white solid (75 mg, 93percent yield).1H NMR (300 MHz, DMSO-d6) δ 10.89 (1 H, br. s), 8.12 (1 H, s), 8.1 1 (1 H, br. s), 7.73 (1 H, s), 7.60-7.39 (4H, m), 7.30-7.21 (2H, m), 7.13-7.06 (2H, m), 5.18 (2H, s), 4.66-4.56 (1 H, m), 4.36-4.28 (1 H, m), 2.42-1.94 (4H, m).
Reference: [1] Patent: WO2016/102967, 2016, A1, . Location in patent: Page/Page column 43
[2] Patent: WO2011/29762, 2011, A1, . Location in patent: Page/Page column 23-24
[3] Patent: WO2007/42239, 2007, A1, . Location in patent: Page/Page column 45
[4] Patent: WO2007/42239, 2007, A1, . Location in patent: Page/Page column 45-46
[5] Patent: WO2007/42239, 2007, A1, . Location in patent: Page/Page column 46
[6] Patent: WO2008/90114, 2008, A1, . Location in patent: Page/Page column 31
[7] Patent: WO2008/90114, 2008, A1, . Location in patent: Page/Page column 31-32
[8] Patent: WO2008/90114, 2008, A1, . Location in patent: Page/Page column 32
[9] Patent: WO2008/90114, 2008, A1, . Location in patent: Page/Page column 32-33
  • 2
  • [ 934240-45-6 ]
  • [ 934240-31-0 ]
YieldReaction ConditionsOperation in experiment
100% With acetyl chloride In methanol; ethyl acetate at 0℃; for 1.5 h; (5R)-5-(4-{r(2-fluorophenyl)methylloxy)phenyl)-L-prolinamide hydrochloride (E2):.HCIProcedure 1 : To a solution of 1 ,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-[(2- fluorophenyl)methyl]oxy}phenyl)-1-pyrrolidinecarboxylate (D10, 51mg, 0.123mmol) in a mixture of ethyl acetate (0.9ml) and methanol (1ml) was added acetylchloride (28 μl, 2.5eq) at 00C. The mixture was shaken for 1.5h and slowly allowed to warm to room temperature. After evaporating the solvent, the residue was triturated with EPO <DP n="46"/>diethyl ether to afford the title compound as a white solid (42mg, quant.); Chiral HPLC: Column: chiralcel OD 10 urn, 250 x 4.6 mm; Mobile phase: A: n-Hexane; B: Ethanol; Gradient: isocratic 30percent B; Flow rate: 0.8 ml/min; UV wavelength range: 200-400 nm; Analysis time: 22 min; ret. time: 12.0min. [α]D = -30.5°. MS: (ES/+) m/z: 315 [MH+], C18H19FN2O2 requires 314; 1H NMR (400 MHz, DMSO-d6) δ ppm 10.19 (br. s., 1 H), 8.13 (br. s., 1 H), 7.94 (s, 1 H), 7.60 - 7.77 (m, 1 H), 7.51 (dt, 1 H), 7.43 (d, 2H), 7.34 - 7.41 (m, 1 H), 7.23 (d, 1 H), 7.18 (dd, 1 H), 7.05 (d, 2H), 5.13 (s, 2H), 4.49 - 4.60 (m, 1H), 4.19 - 4.28 (m, 1 H), 2.17 - 2.38 (m, 2H), 2.05 - 2.16 (m, 1 H), 1.92 - 2.03 (m, 1 H).
100% With acetyl chloride In methanol; ethyl acetate at 0℃; for 1.5 h; To a solution of 1 ,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-[(2- fluorophenyl)methyl]oxy}phenyl)-1-pyrrolidinecarboxylate (51 mg, 0.123mmol) in a mixture of ethyl acetate (0.9ml) and methanol (1 ml) was added acetylchloride (28 μl, 2.5eq) at 00C. The mixture was shaken for 1.5h and slowly allowed to warm to room temperature. After evaporating the solvent, the residue was triturated with diethyl ether to afford the title compound as a white solid (42mg, quant.); Chiral HPLC: Column: chiralcel OD 10 urn, 250 x 4.6 mm; Mobile phase: A: n-Hexane; B: Ethanol; Gradient: isocratic 30percent B; Flow rate: 0.8 ml/min; UV wavelength range: 200-400 nm; Analysis time: 22 min; ret. time: 12.0min. [α]D = -30.5°. MS: (ES/+) m/z: 315 [MH+], C18H19FN2O2 requires 314; 1H NMR (400 MHz, DMSO-d6) δ ppm 10.19 (br. s., 1 H), 8.13 (br. s., 1 H), 7.94 (s, 1 H), 7.60 - 7.77 (m, 1 H), 7.51 (dt, 1 H), 7.43 (d, 2H), 7.34 - 7.41 (m, 1 H), 7.23 (d, 1 H), 7.18 (dd, 1 H), 7.05 (d, 2H), 5.13 (s, 2H), 4.49 - 4.60 (m, 1 H), 4.19 - 4.28 (m, 1 H), 2.17 - 2.38 (m, 2H), 2.05 - 2.16 (m, 1 H), 1.92 - 2.03 (m, 1 H).
Reference: [1] Patent: WO2007/42239, 2007, A1, . Location in patent: Page/Page column 44-45
[2] Patent: WO2008/90114, 2008, A1, . Location in patent: Page/Page column 31
  • 3
  • [ 446-48-0 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2011/29762, 2011, A1,
  • 4
  • [ 99-76-3 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2011/29762, 2011, A1,
  • 5
  • [ 1272317-41-5 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2011/29762, 2011, A1,
  • 6
  • [ 1272317-42-6 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2011/29762, 2011, A1,
  • 7
  • [ 128982-48-9 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2011/29762, 2011, A1,
  • 8
  • [ 405-24-3 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2011/29762, 2011, A1,
  • 9
  • [ 934240-38-7 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2016/102967, 2016, A1,
[2] Patent: WO2016/102967, 2016, A1,
[3] Patent: WO2016/102967, 2016, A1,
[4] Patent: WO2016/102967, 2016, A1,
  • 10
  • [ 6793-92-6 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2016/102967, 2016, A1,
[2] Patent: WO2016/102967, 2016, A1,
[3] Patent: WO2016/102967, 2016, A1,
[4] Patent: WO2016/102967, 2016, A1,
  • 11
  • [ 108963-96-8 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2016/102967, 2016, A1,
[2] Patent: WO2016/102967, 2016, A1,
[3] Patent: WO2016/102967, 2016, A1,
[4] Patent: WO2016/102967, 2016, A1,
  • 12
  • [ 934240-37-6 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2016/102967, 2016, A1,
[2] Patent: WO2016/102967, 2016, A1,
[3] Patent: WO2016/102967, 2016, A1,
[4] Patent: WO2016/102967, 2016, A1,
  • 13
  • [ 934584-88-0 ]
  • [ 934240-31-0 ]
Reference: [1] Patent: WO2016/102967, 2016, A1,
[2] Patent: WO2016/102967, 2016, A1,
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[ 934240-31-0 ]

Chemical Structure| 934240-30-9

A138601[ 934240-30-9 ]

(2S,5R)-5-(4-((2-Fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxamide

Reason: Free-salt