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[ CAS No. 28721-07-5 ] {[proInfo.proName]}

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Chemical Structure| 28721-07-5
Chemical Structure| 28721-07-5
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Product Details of [ 28721-07-5 ]

CAS No. :28721-07-5 MDL No. :MFCD00865307
Formula : C15H12N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CTRLABGOLIVAIY-UHFFFAOYSA-N
M.W : 252.27 Pubchem ID :34312
Synonyms :
GP 47680

Calculated chemistry of [ 28721-07-5 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 75.36
TPSA : 63.4 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 1.71
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 2.14
Log Po/w (SILICOS-IT) : 1.73
Consensus Log Po/w : 1.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.88
Solubility : 0.33 mg/ml ; 0.00131 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.556 mg/ml ; 0.0022 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.29
Solubility : 0.0131 mg/ml ; 0.0000519 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.67

Safety of [ 28721-07-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 28721-07-5 ]

* 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 [ 28721-07-5 ]
  • Downstream synthetic route of [ 28721-07-5 ]

[ 28721-07-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 28721-07-5 ]
  • [ 29331-92-8 ]
YieldReaction ConditionsOperation in experiment
97.3% With sodium tetrahydroborate In methanol; water at 20 - 45℃; for 1.5 h; At room temperature,The (100.0g, 0.4mol) oxcarbazepine,400 mL methanol and 200 mL water were added to a 1 L round bottom flask,Sodium borohydride (15.0 g, 0.4 mol) was added portionwise,After stirring at room temperature for 30min, the reaction was continued at 45 ° C for 1h.The reaction is completed,The reaction mixture was concentrated under reduced pressure to 200-300 mL,filter,Washed 3 times,Got pale yellow solid powder 99.0g,For compound 1,Yield 97.3percent.
94% With sodium tetrahydroborate In ethanol; water at 45 - 50℃; Sodium borohydride (6.0 g, 0.162 mol) was portion-wise added to the suspension of Azepine amide (45.0 g, 0.178 mol) in Ab. Ethanol (185 ml) and DM water (103 ml) at an ambient temperature. Reaction mixture was allowed to stir for 2-3 hr at 45-50° C. Progress of reaction was monitored by TLC (Solvent system: 10percent Methanol in DCM). After completion of reaction, acetone was slowly added to reaction mixture at 10-15° C. Reaction mixture was further stirred for 30 min. at an ambient temperature. Organic solvents from reaction mixture were distilled off under reduced pressure at 45-50° C. Residue thus obtained was stirred in DM water (100 ml) for 1-2 hr at 0-5° C. Suspension was filtered and washed with ice-cold water (2*25 ml). Air dry the product for 12-15 hr at 50-60° C. to get pure desired compound (42.8 g, 94percent) with 99percent purity by HPLC.
93.8% With sodium tetrahydroborate; water In methanol at 25 - 65℃; for 2.75 h; Sodium borohydride (15.6 g, 0.412 mol) was added to a stirred suspension of oxcarbazepine (200 g, 0.793 mol) in a mixture of methanol (400 mL) and water (220 mL) at 25°C to 30°C in three portions at 15 minutes intervals. The reaction mixture was stirred at 60°C to 65°C for 2 hours and cooled to 25°C to 30°C and pH was adjusted to 6.8 to 7.2 using diluted hydrochloric acid (31 mL concentrated hydrochloric acid in 100 mL deionised water). Deionised water (700 mL) was added to the reaction mixture with stirring and was cooled to 0°C to 5°C for 3 hours. The crystalline product was filtered, washed with deionised water (100 mL) and dried at 40°C to 45°C to constant weight to give the titled compound. Yield: 189.1 g (93.8percent) Purity: 99.93percent
93.8% With sodium tetrahydroborate; water In methanol at 25 - 65℃; for 2.25 h; Sodium borohydride (15.6 g, 0.412 mol) was added to a stirred suspension of oxcarbazepine (200 g, 0.793 mol) in a mixture of methanol (400 mL) and water (220 mL) at 25° C. to 30° C. in three portions at 15 minutes intervals. The reaction mixture was stirred at 60° C. to 65° C. for 2 hours and cooled to 25° C. to 30° C. and pH was adjusted to 6.8 to 7.2 using diluted hydrochloric acid (31 mL concentrated hydrochloric acid in 100 mL deionised water). Deionised water (700 mL) was added to the reaction mixture with stirring and was cooled to 0° C. to 5° C. for 3 hours. The crystalline product was filtered, washed with deionised water (100 mL) and dried at 40° C. to 45° C. to constant weight to give the titled compound. Yield: 189.1 g (93.8percent) Purity: 99.93percent
2.42 kg With sodium tetrahydroborate In ethanol at 20℃; for 4.5 h; Large scale To a 200 L autoclave, oxcarbazepine (2.52 kg, 10 mol)And ethanol (25 L),Stir at room temperature to completely dissolve.Sodium borohydride (0.378 kg, 10 mol) was aliquoted into 5 batches,Each batch of 30 minutes,Add to the above solution with stirring.After the addition is complete, stirring is continued for 2 hours at room temperature.After the reaction was complete, add water (50L)After stirring and adjusting the pH of the reaction solution to 7 with concentrated hydrochloric acid,The precipitated solid was filtered and collected.The filtrate was then concentrated to 50 L and filtered once and the solid was collected.Two batches of solids were combined and dried,2.42 kg of licacizidine (rac) solid was obtained.

Reference: [1] Patent: CN106588773, 2017, A, . Location in patent: Paragraph 0093; 0094; 0095; 0096
[2] Patent: US2016/122332, 2016, A1, . Location in patent: Paragraph 0137-0138
[3] Patent: WO2013/8194, 2013, A2, . Location in patent: Page/Page column 12; 13
[4] Patent: US2015/65704, 2015, A1, . Location in patent: Paragraph 0072
[5] Journal of Medicinal Chemistry, 1999, vol. 42, # 14, p. 2582 - 2587
[6] RSC Advances, 2016, vol. 6, # 101, p. 98730 - 98736
[7] Patent: WO2010/113179, 2010, A2, . Location in patent: Page/Page column 13
[8] Patent: WO2011/91131, 2011, A2, . Location in patent: Page/Page column 39
[9] Patent: WO2011/138795, 2011, A2, . Location in patent: Page/Page column 22
[10] Patent: WO2012/121701, 2012, A1, . Location in patent: Page/Page column 13
[11] Patent: CN106938986, 2017, A, . Location in patent: Paragraph 0028; 0029; 0034; 0035; 0036
  • 2
  • [ 3564-73-6 ]
  • [ 28721-07-5 ]
  • [ 29331-92-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 578 - 586
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