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[ CAS No. 198821-22-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 198821-22-6
Chemical Structure| 198821-22-6
Structure of 198821-22-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 198821-22-6 ]

CAS No. :198821-22-6 MDL No. :MFCD09837807
Formula : C23H24N4O6 Boiling Point : -
Linear Structure Formula :- InChI Key :JBPUGFODGPKTDW-SFHVURJKSA-N
M.W : 452.46 Pubchem ID :153241
Synonyms :
VX-497;MMPD;VI21497;MMP

Calculated chemistry of [ 198821-22-6 ]

Physicochemical Properties

Num. heavy atoms : 33
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.26
Num. rotatable bonds : 11
Num. H-bond acceptors : 7.0
Num. H-bond donors : 3.0
Molar Refractivity : 119.6
TPSA : 123.95 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.15
Log Po/w (XLOGP3) : 2.1
Log Po/w (WLOGP) : 3.48
Log Po/w (MLOGP) : 0.92
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 2.36

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.62
Solubility : 0.108 mg/ml ; 0.000238 mol/l
Class : Soluble
Log S (Ali) : -4.33
Solubility : 0.021 mg/ml ; 0.0000464 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.09
Solubility : 0.0000368 mg/ml ; 0.0000000813 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.14

Safety of [ 198821-22-6 ]

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 [ 198821-22-6 ]

* 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 [ 198821-22-6 ]
  • Downstream synthetic route of [ 198821-22-6 ]

[ 198821-22-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 138499-08-8 ]
  • [ 198821-22-6 ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine In DMF (N,N-dimethyl-formamide); dichloromethane at 0 - 20℃; A suspension of 168 (250 mg, 0.55 mmol) in 21 mL of CH2Cl2/DMF (20:1 by volume) was treated with triethyl amine (193 μL, 1.38 mmol) and stirred at ambient temperature until homogeneity was reached. The solution was cooled to 0 C., treated with (S) 3-tetrahydrofuranyl-N-oxysuccinimidyl carbonate (635 mg, 0.608 mmol) and allowed to stir overnight with warming to ambient temperature. The mixture was poured into ethyl acetate (500 mL), washed with NaHCO3(aq) (2.x.), water (2.x.), and brine(1.x.), dried over Na2SO4 and stripped in vacuo. Pure product 120 was isolated by tritration (30 mL CH2Cl2, 100 mL ether) in a yield of 212 mg (85percent). The 1H NMR was consistent with that of the desired product.
Reference: [1] Patent: US6344465, 2002, B1, . Location in patent: Page column 36
  • 2
  • [ 198821-79-3 ]
  • [ 198821-22-6 ]
YieldReaction ConditionsOperation in experiment
90.4% With N-ethyl-N,N-diisopropylamine In ethyl acetate at 20 - 85℃; for 25 h; Heating / reflux Added 15 g of {3- [ ( (S) -tetrahydro-furan-3- yloxycarbonylamino) -methyl] -phenyl} -carbamic acid phenyl ester 2e and 8.58 g of 3-methoxy-4- (oxazol-5-yl)benzenamine 2g into a 500 ml 3-necked flask and then purged the system with nitrogen before adding 225 ml of ethyl acetate. Next added 5.43 g of diisopropylethylamine over 1 minute, then heated at reflux for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature and stired for an additional 1 hour. Precipitated solid was filtered, washed with 45 ml of EtOAc 2 times, then dried at 58°C for 18 hours (until a LOD is achieved of less than 1percent) to give 17.46 g of crude (S) -tetrahydrofuran-3-yl 3- (3- (3-methoxy-4- (oxazol-5- yl) phenyl) ureido)benzylcarbamate 2h (90.4percent yield, 98.46percent a/a) as a white crystalline solid. (S) -tetrahydrofuran-3-yl 3- (3- (3-methoxy-4- (oxazol- 5-yl)phenyl)ureido)benzylcarbamate (2h)[0119] Added 2e (15 g, 1.0 eq) and 2g (8.58 g, 1.07 eq) into a jacketed reactor of suitable size before adding ethyl acetate (225 ml, 15 vol) and diisopropylethylamine (5.43 g, 1.0 eq) , then heated the mixture to reflux (75-85°C) for 24 hours. Once the reaction was complete, the mixture was cooled to room temperature and stired for an additional 1 hour. Precipitated solid was filtered, washed with EtOAc 2 times (45 ml, 3 vol each wash) , then dried at 580C for 18 hours (until a LOD is achieved of less than 1percent) to give 17.46 g of crude 2h(90.4percent yield, 98.46percent a/a) as a white crystalline solid.
Reference: [1] Patent: WO2006/122072, 2006, A2, . Location in patent: Page/Page column 53-54; 62-63
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