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[ CAS No. 57805-85-3 ] {[proInfo.proName]}

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Chemical Structure| 57805-85-3
Chemical Structure| 57805-85-3
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Product Details of [ 57805-85-3 ]

CAS No. :57805-85-3 MDL No. :MFCD00466275
Formula : C10H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OBUMBRZSVRGWFY-UHFFFAOYSA-N
M.W : 191.18 Pubchem ID :674268
Synonyms :

Calculated chemistry of [ 57805-85-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.9
TPSA : 65.46 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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.95
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 0.8
Log Po/w (SILICOS-IT) : 1.5
Consensus Log Po/w : 1.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.259 mg/ml ; 0.00135 mol/l
Class : Soluble
Log S (Ali) : -3.4
Solubility : 0.0769 mg/ml ; 0.000402 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.188 mg/ml ; 0.000984 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.52

Safety of [ 57805-85-3 ]

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 [ 57805-85-3 ]

* 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 [ 57805-85-3 ]
  • Downstream synthetic route of [ 57805-85-3 ]

[ 57805-85-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 57805-85-3 ]
  • [ 57-13-6 ]
  • [ 62208-68-8 ]
YieldReaction ConditionsOperation in experiment
72% at 200℃; for 2 h; In a 2000 mL round bottom flask, a mixture of 3-aminobenzofuran-2-carboxylic acid methyl ester (65.0 g, 340.0 mmol) and urea (91.9 g, 1.5 mol) was stirred at 200° C. for 2 hours. The reaction mixture at high temperature was cooled to room temperature and poured into a sodium hydroxide solution. After removing impurities by filtration, the reactant was acidified (HCl, 2N), and the resulting precipitate was dried to obtain Intermediate I1 (49.4 g, Yield 72percent).
72% at 200℃; for 2 h; A mixture of methyl 3-aminobenzofuran-2-carboxylate (65.0 g, 340.0 mmol) and urea (91.9 g, 1.5 mol) was stirred in a 2000 mL round flask at 200 ° C for 2 hours. The reaction mixture was cooled to room temperature, poured into sodium hydroxide solution, the impurities were removed by filtration, the reaction product was acidified (HCl, 2N) and the resulting precipitate was dried to obtain Compound B1 (49.4 g, yield 72percent of (49.4 g, yield 72percent).
70% at 200℃; for 2 h; A mixture of methyl 3-aminobenzofuran-2-carboxylate (48 g, 0.25 mol) and urea (75 g, 1.24 mol) was stirred in a 2000 mL round flask at 200 & lt; 0 & gt; C for 2 hours. The reaction mixture was cooled to room temperature, poured into sodium hydroxide solution, the impurities were removed by filtration, the reaction product was acidified (HCl, 2N) and the resulting precipitate was dried to obtain Compound F1 (35 g, yield 70percent).
70% at 200℃; for 2 h; To a 2000 mL round flask was added methyl 3-aminobenzofuran-2-carboxylate (48 g, 0.25 mol)And urea (75 g, 1.24 mol) was stirred at 200° C for 2 hours.The reaction mixture was cooled to room temperature, poured into sodium hydroxide solution, the impurities were removed by filtration, the reaction product was acidified (HCl, 2N) and the resulting precipitate was dried to obtain Compound F1 (35 g, yield 70percent).

Reference: [1] Patent: CN107915722, 2018, A, . Location in patent: Paragraph 0160-0163
[2] Patent: KR2018/41607, 2018, A, . Location in patent: Paragraph 0163-0166
[3] Patent: KR2018/10165, 2018, A, . Location in patent: Paragraph 0251-0254
[4] Patent: KR2018/10166, 2018, A, . Location in patent: Paragraph 0235; 0236; 0237
  • 2
  • [ 57805-85-3 ]
  • [ 62208-68-8 ]
Reference: [1] Patent: KR2015/84657, 2015, A,
[2] Patent: KR2015/84662, 2015, A,
[3] Patent: JP2016/147851, 2016, A,
  • 3
  • [ 57805-85-3 ]
  • [ 39876-88-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5464 - 5474
  • 4
  • [ 34844-79-6 ]
  • [ 57805-85-3 ]
YieldReaction ConditionsOperation in experiment
65% With potassium <i>tert</i>-butylate In diethyl ether at 20℃; for 0.416667 h; Inert atmosphere Compound 2 (2.62 g, 13.9 mmol, 1.00 eq.) was dissolvedin dried diethyl ether and poured into a flask in which an argon atmosphere was maintained. Then,potassium t-butoxide (0.78 g, 6.9 mmol, 0.50 eq.) was carefully added and the mixture stirred atroom temperature. After 25 min, several drops of water were added and the solvent evaporated.The remainder was mixed with water (30 mL) and the mixture extracted three times with 30 mL ofdiethyl ether. After drying by sodium sulfate, filtration, and the evaporation of ether, light yellowcrystals were obtained with a yield of 65percent; mp 94 °C. 1H-NMR: δ = 7.55 (d, J = 7.9, 1H, H4), 7.48–7.41(m, 2H, H7 and H6), 7.19–7.30 (m, 1H, H5), 5.00 (bs, 2H, NH2), 3.96 (s, 3H, COOCH3). 13C-NMR: δ = 162.1 (COOCH3), 154.3 (C7a), 138.9 (C3), 129.1 (C4), 125.6 (C3a), 122.5 (C5), 121.8 (C2), 119.8(C6), 112.8 (C7), 51.7 (COOCH3). MS (EI, 70 eV) Found: 191 (calculated for C10H9NO3: 191.19);m/z (percent) = 191 (M+, 100), 159 (50), 133 (25), 103 (90), 83 (20), 77 (50), 51 (25).
56% With NaH In dimethyl sulfoxide Methyl 3-aminobenzo[b]furan-2-carboxylate.
A solution of methyl 2-(2-cyanophenoxy) ethanoate (3.82 g, 20 mmol) in DMSO (40 mL) is added dropwise to a suspension of NaH (0.84 g, 21 mmol) and DMSO (10 mL) stirred under N2 at 25° C.
After 10 min the mixture is poured onto ice water and extracted with ether.
The combined extracts are washed with water, saturated brine and dried (MgSO4).
After removal of the solvent under reduced pressure, methyl 3-aminobenzo[b]furan-2-carboxylate (2.15 g, 56percent) is obtained as a yellow solid. 1 H NMR (DMSO) δ7.95 (1H, d, J=7.7 Hz), 7.48 (2H, d, J =3.4 Hz), 7.29-7.22 (1H, m), 6.40 (2H, brs), 3.80 (3H, s).
Reference: [1] Molecules, 2016, vol. 21, # 2,
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5464 - 5474
[3] Patent: US5679683, 1997, A,
  • 5
  • [ 611-20-1 ]
  • [ 96-32-2 ]
  • [ 57805-85-3 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In acetone for 4 h; Heating / reflux Example 72: 3-Hvdroxy-lH-benzo[4,51furo[3,2-dlpyrimidine-2,4-dioneStep a.) 3-Amino-benzofuran-2-carboxylic acid methyl ester ort/zoe-Cyanophenol (5.0 g, 41.3 mmol) was placed in a round bottom flask followed by acetone (200 ml) and K2CO3 (6.8 g, 49 mmol). Next, methyl bromoacetate (3.91 ml, 41.3 mmol) was added dropwise at 2°C and the reaction was heated to reflux. After 4 hours, the reaction was filtered and the acetone was evaporated providing the title compound (7.32 g, 93 percent) as a white solid.
Reference: [1] Patent: WO2006/14647, 2006, A2, . Location in patent: Page/Page column 51
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 7, p. 3209 - 3222
[3] Patent: KR2015/84657, 2015, A, . Location in patent: Paragraph 1169
  • 6
  • [ 96-35-5 ]
  • [ 394-47-8 ]
  • [ 57805-85-3 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12 h; Heating / reflux Preparation Example 1: Preparation of 3-amino-benzofuran-2-carboxylic acid methyl ester0.22 g (1.18 mmol) of σ-fluorobenzonitrile was dissolved in 5 ml of N5N- dimethylformamide, 0.16 ml (2.18 mmol) of methyl glyconate and 0.62 g (4.54 mmol) of potassium carbonate were added thereto at room temperature, and the mixture was refluxed with heating for 12 hrs. After the reaction was completed, the reaction mixture was diluted with 10 ml of ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure. The residue was subjected to silica gel column chromatography <n="19"/>(hexane:ethyl acetate = 4:1) to obtain the title compound (0.10 g, 48percent yield).1H NMR (300MHz, DMSO-d6): δ 3.97(s, 3H), 4.98(s, 2H), 7.23-7.28(m, IH), 7.44-7.47(m, 2H), 7.56(d, IH)Mass(m/e, M+): 192
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 22, p. 6362 - 6365
[2] Patent: WO2009/48274, 2009, A2, . Location in patent: Page/Page column 16-17
  • 7
  • [ 611-20-1 ]
  • [ 57805-85-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5464 - 5474
[2] Molecules, 2016, vol. 21, # 2,
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