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[ CAS No. 150058-27-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 150058-27-8
Chemical Structure| 150058-27-8
Chemical Structure| 150058-27-8
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Product Details of [ 150058-27-8 ]

CAS No. :150058-27-8 MDL No. :MFCD14636510
Formula : C11H12N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :MOPLKVMMSFGZIR-UHFFFAOYSA-N
M.W : 220.23 Pubchem ID :15654707
Synonyms :

Calculated chemistry of [ 150058-27-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.27
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 58.67
TPSA : 64.21 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : 2.01
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 1.34
Log Po/w (SILICOS-IT) : 2.19
Consensus Log Po/w : 1.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.62
Solubility : 0.524 mg/ml ; 0.00238 mol/l
Class : Soluble
Log S (Ali) : -2.99
Solubility : 0.228 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.53
Solubility : 0.0654 mg/ml ; 0.000297 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 150058-27-8 ]

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 [ 150058-27-8 ]

* 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 [ 150058-27-8 ]
  • Downstream synthetic route of [ 150058-27-8 ]

[ 150058-27-8 ] Synthesis Path-Upstream   1~9

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  • [ 139481-44-0 ]
Reference: [1] Patent: WO2006/15134, 2006, A1, . Location in patent: Page/Page column 16; 21-22
[2] Patent: CN107089972, 2017, A, . Location in patent: Paragraph 0032; 0035; 0037
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Reference: [1] Patent: CN107056757, 2017, A,
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Reference: [1] Patent: CN107056757, 2017, A,
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  • [ 78-09-1 ]
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YieldReaction ConditionsOperation in experiment
83.1% at 25 - 35℃; for 2 - 3 h; Methyl 2-amino-3-nitrobenzoate (150.0 grams, 0.765 moles) was placed inan autoclave vessel and 1000 mlof ethyl acetate and 75 grams of Raney nickelwere added to the vessel and stirred under a 2-3 kg/cm2 hydrogen pressure for12-15 hours. The catalyst was removed by filtration, and the ethyl acetate wasevaporated under reduced pressure. Acetic acid (170 ml) was added to theresidue, and 180 grams of tetraethylorthocarbonate was slowly added at 25-35°C.The reaction mass was stirred for 2-3 hours, and water (750 ml) was added afterthe reaction mass was cooled to 10°C. The solid was filtered, washed with 150 mlof water, and dried at 50-60°C to get 140 grams (83.1 percent) of methyl 2-ethoxybenzimidazole-7-carboxylate.; 150 grams of 2-Amino-3-nitro-benzoic acid methylester, Raney nickel (75grams), ethyl acetate (1 litre) were charged in an autoclave vessel. 3.0kg/cm2 ofdry hydrogen gas was passed into the reaction suspension for about 20-25 hoursunder agitation. Reaction mass was filtered on celite, followed by washing thecelite with 150 ml of ethyl acetate. Solvent was removed completely from thefiltrate at about 45-50°C by distillation. 171 ml of acetic acid was charged andtetraethylorthocarbonate (180 grams) was added over about 30-45 minutes.Reaction mass was maintained for about 1-3 hours and was cooled to about 0-5°C. 750 ml of water was added over about 15-30 minutes and the separatedsolid was filtered and washed with 150 ml water, followed by 150 ml of ethylacetate. Solid obtained was dried at about 55-65°C for about 10-12 hours to yield140 grams of 2-Ethoxy-3H-benzoimidazole-4-carboxylic acid methylestercompound of Formula (IV).
Reference: [1] Patent: WO2006/15134, 2006, A1, . Location in patent: Page/Page column 15; 16
[2] Patent: CN104876877, 2018, B, . Location in patent: Paragraph 0033; 0069-0072
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Reference: [1] Patent: CN104876877, 2018, B,
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Reference: [1] Patent: CN104876877, 2018, B,
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  • [ 603-11-2 ]
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Reference: [1] Patent: CN104876877, 2018, B,
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Reference: [1] Patent: CN104876877, 2018, B,
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Reference: [1] Patent: CN104876877, 2018, B,
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