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[ CAS No. 34084-89-4 ] {[proInfo.proName]}

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Chemical Structure| 34084-89-4
Chemical Structure| 34084-89-4
Structure of 34084-89-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 34084-89-4 ]

CAS No. :34084-89-4 MDL No. :MFCD13180959
Formula : C10H7NO4S Boiling Point : -
Linear Structure Formula :- InChI Key :RJUVQMBNXODKGH-UHFFFAOYSA-N
M.W : 237.23 Pubchem ID :57722418
Synonyms :

Calculated chemistry of [ 34084-89-4 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.93
TPSA : 100.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 2.6
Log Po/w (MLOGP) : 1.17
Log Po/w (SILICOS-IT) : 1.3
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.39
Solubility : 0.0958 mg/ml ; 0.000404 mol/l
Class : Soluble
Log S (Ali) : -4.73
Solubility : 0.00441 mg/ml ; 0.0000186 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.81
Solubility : 0.371 mg/ml ; 0.00156 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.49

Safety of [ 34084-89-4 ]

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 [ 34084-89-4 ]

* 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 [ 34084-89-4 ]
  • Downstream synthetic route of [ 34084-89-4 ]

[ 34084-89-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 58755-57-0 ]
  • [ 2365-48-2 ]
  • [ 34084-89-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 17, p. 4016 - 4026
[2] Patent: US2003/225053, 2003, A1, . Location in patent: Page 24
  • 2
  • [ 34084-89-4 ]
  • [ 616238-78-9 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With hydrogenchloride; acetic acid; tin(ll) chloride In water at 20℃; for 12 h;
Stage #2: With sodium hydrogencarbonate In water at 0℃;
To a mixture of 7-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (100 mg) in acetic acid (4 mL) was added a solution of SnC2.2H2O (10 eq) in 1.5 mL of concentrated HCl.
The reaction was stirred at room temperature 12 h.
The excess acid was partially removed in vacuo, and the reaction mixture was then poured into a flask (250 mL) and was neutralized with saturated NaHCO3 solution at 0° C.
The pH was brought up to pH 9 by adding solid NaHCO3.
The resulting aqueous mixture was diluted with EtOAc, and the Tin-by product was removed by filtering through a pad of diatomaceous earth.
The pad was rinsed with EtOAc and the combined filtrates were partitioned in a separatory funnel.
The aqueous layer was extracted with EtOAc two times times.
The combined organics were dried over MgSO4, filtered and concentrated to give the desired 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (100percent).
To a mixture of 7-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (100 mg) in acetic acid (4 mL) was added a solution of SnCl2.2H2O (10 eq) in 1.5 mL of concentrated HCl. The reaction was stirred at room temperature 12 h. The excess acid was partially removed in vacuo, and the reaction mixture was then poured into a flask (250 mL) and was neutralized with saturated NaHCO3 solution at 0° C. The pH was brought up to pH 9 by adding solid NaHCO3. The resulting aqueous mixture was diluted with EtOAc, and the Tin-by product was removed by filtering through a pad of diatomaceous earth. The pad was rinsed with EtOAc and the combined filtrates were partitioned in a separatory funnel. The aqueous layer was extracted with EtOAc two times times. The combined organics were dried over MgSO4, filtered and concentrated to give the desired 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (100percent).
100% With hydrogen In ethyl acetate at 20℃; for 12 h; 7-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (1 g, 4.22 mmol) was suspended in EtOAc (40 mL) and a suspension of 10percent Pd/C (400 mg) in 20 mL EtOAc was added.
Hydrogen gas was introduced into the flask from an H2-filled balloon attached to a needle inserted through a septum.
The black suspension was stirred 12 h at room temperature.
After stirring 12 h, the black suspension was filtered through diatomaceous earth and the filter cake was washed several times with EtOAc.
The combined filtrates were dried (MgSO4), filtered and the solvent was removed to afford 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester as a yellow solid (860 mg, 100percent).
Reference: [1] Patent: US2003/225053, 2003, A1, . Location in patent: Page 27, 35, 36
[2] Patent: US2003/225053, 2003, A1, . Location in patent: Page 28
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 17, p. 4016 - 4026
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