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[ CAS No. 728865-23-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 728865-23-4
Chemical Structure| 728865-23-4
Structure of 728865-23-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 728865-23-4 ]

CAS No. :728865-23-4 MDL No. :MFCD22665727
Formula : C24H27N3O5 Boiling Point : -
Linear Structure Formula :- InChI Key :FQYBTYFKOHPWQT-VGSWGCGISA-N
M.W : 437.49 Pubchem ID :11546620
Synonyms :

Calculated chemistry of [ 728865-23-4 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.33
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 4.0
Molar Refractivity : 121.15
TPSA : 111.13 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) : -8.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.57
Log Po/w (XLOGP3) : 1.32
Log Po/w (WLOGP) : 0.45
Log Po/w (MLOGP) : 1.03
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 1.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.13
Solubility : 0.322 mg/ml ; 0.000735 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.243 mg/ml ; 0.000556 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.81
Solubility : 0.00676 mg/ml ; 0.0000155 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.01

Safety of [ 728865-23-4 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:1325
Hazard Statements:H315-H319-H228 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 728865-23-4 ]

* 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 [ 728865-23-4 ]
  • Downstream synthetic route of [ 728865-23-4 ]

[ 728865-23-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 728878-12-4 ]
  • [ 728865-23-4 ]
YieldReaction ConditionsOperation in experiment
81% With hydroxylamine hydrochloride; sodium methylate In tetrahydrofuran; methanol at 0 - 20℃; for 5 h; Inert atmosphere Sodium methoxide (25 wtpercent in MeOH, 1.860 g, 8.60 mmol) was added to a stirred solution of hydroxylaminehydrochloride (400 mg, 5.76 mmol) in anhydrous MeOH (5 mL) at 0 °C under N2 atmosphere. After stirring 20 min, asolution of methyl ester 4 (829 mg, 1.90 mmol) in 1:1 MeOH/THF (6 mL) was added and the reaction mixture stirred at0 °C for 1 h and at room temperature for 4 h. The reaction was quenched with 1.0 M HCl (6 mL), concentrated by rotaryevaporation to remove organic solvents, and diluted with DMSO (4 mL). Analytical RP-HPLC (C18 column, CH3CNgradient 5-35percent, 0.1percent TFA, UV analysis 300 nm, 16 min) indicated a purity of 85percent for the crude product mixture.Purification by preparative RP-HPLC and lyophilization of the collected fractions gave 701 mg (81percent) of 5 as a fluffywhite solid. LRMS (ES+) m/z 438.1 (C24H27N3O5 + H requires 438.20); RP-HPLC (300 nm,16 min run) 8.7 min.
81%
Stage #1: With hydroxylamine hydrochloride; sodium methylate In methanol at 0℃; for 0.333333 h;
Stage #2: at 0 - 20℃; for 5 h;
Preparation of (2S,3R)-N-(2-Hydroxy-1-hydroxycarbamoyl-propyl)-4-(4-morpholin-4-ylmethyl-phenylethynyl)-benzamide (5). Sodium methoxide (25 wt percent in MeOH, 1.860 g, 8.60 mmol) was added to a stirred solution of hydroxylamine hydrochloride (400 mg, 5.76 mmol) in anhydrous MeOH (5 mL) at 0° C. under N2 atmosphere. After stirring 20 min, a solution of methyl ester (4) (829 mg, 1.90 mmol) in 1 : 1 MeOH/THF (6 mL) was added and the reaction mixture stirred at 0° C. for 1 h and at room temperature for 4 h. The reaction was quenched with 1.0 M HCl (6 mL), concentrated by rotary evaporation to remove organic solvents, and diluted with DMSO (4 mL). Analytical RP-HPLC (C18 column, CH3CN gradient 5-35percent, 0.1percent TFA, UV analysis 300 ran, 16 min) indicated a purity of 85percent for the crude product mixture. Purification by preparative RP-HPLC and lyophilization of the collected fractions gave 701 mg (8 lpercent) of(5) as a fluffy white solid. LRMS (ES+) m/z 438.1 (C24H27N3O5+H requires 438.20); RP-HPLC (300 ran, 16 min run) 8.7 min.
Reference: [1] Patent: EP2295402, 2015, B1, . Location in patent: Paragraph 0221; 0222
[2] Patent: WO2008/154642, 2008, A2, . Location in patent: Page/Page column 93
  • 2
  • [ 110-91-8 ]
  • [ 728878-12-4 ]
  • [ 728865-23-4 ]
YieldReaction ConditionsOperation in experiment
4.5 g With potassium cyanide; hydroxylamine In tetrahydrofuran; methanol; water at 20℃; for 18 h; To a solution of compound 6 (7.8 g, 17.9 mmol) in methanol/THF (1:1) was added aqueous 50percent hydroxylamine (15 mL) followed by catalytic amount of KCN (10 mg) and the resulting solution was stirred at room temperature for 18 h. The reaction mass was acidified to pH ~6 with aqueous 10percent citric acid solution (20 mL) and diluted with water (100 mL). The solution was extracted with 10percent methanol in chloroform (150 mL x 2).The combined organic layer was washed with brine solution (100 mL), dried over anhydrous MgSO4 and evaporated under reduced pressure to get crude compound. The crude product was purified by column chromatography (silica gel, 100-200 mesh) using 1.5percent methanol in chloroform as mobile phase to yield pure product (4.5 g, 57percent). LC-MS 438.6 m/z (M+l). MW = 437.2 amu 'H NMR (400 MHz, DMSO-d6) 10.69(1H, NH, 1H), 8.87(s, OH, 1H), 8.14-8.17(d, NH, 1H), 7.94-7.96(d, 2H), 7.64-7.67(d, 2H), 7.54-7.56(d, 2H), 7.38-7.40(d, 2H), 4.90-4.91(s, NH, 1H), 4.26-4.28(dd, 1H), 4.01-5.05(dd, 1H), 3.57-3.59(br s, 4H), 3.50(s, 2H), 2.36-2.49(s, 4H), 1.09-1.10(s, 3H) ppm
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2362 - 2367
  • 3
  • [ 110-91-8 ]
  • [ 728865-23-4 ]
Reference: [1] Patent: WO2018/115432, 2018, A2, . Location in patent: Page/Page column 157; 158
  • 4
  • [ 728878-24-8 ]
  • [ 728865-23-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2362 - 2367
[2] Patent: EP2295402, 2015, B1,
[3] Patent: WO2008/154642, 2008, A2,
  • 5
  • [ 15164-44-0 ]
  • [ 728865-23-4 ]
Reference: [1] Patent: EP2295402, 2015, B1,
[2] Patent: WO2008/154642, 2008, A2,
  • 6
  • [ 728878-11-3 ]
  • [ 728865-23-4 ]
Reference: [1] Patent: EP2295402, 2015, B1,
[2] Patent: WO2008/154642, 2008, A2,
  • 7
  • [ 619-44-3 ]
  • [ 728865-23-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2362 - 2367
  • 8
  • [ 75867-41-3 ]
  • [ 728865-23-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2362 - 2367
  • 9
  • [ 144693-65-2 ]
  • [ 728865-23-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2362 - 2367
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