Home Cart 0 Sign in  
X

[ CAS No. 13452-14-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 13452-14-7
Chemical Structure| 13452-14-7
Chemical Structure| 13452-14-7
Structure of 13452-14-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 13452-14-7 ]

Related Doc. of [ 13452-14-7 ]

Alternatived Products of [ 13452-14-7 ]

Product Details of [ 13452-14-7 ]

CAS No. :13452-14-7 MDL No. :MFCD07787266
Formula : C9H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :GFYDDTFAVDJJAI-UHFFFAOYSA-N
M.W : 177.16 Pubchem ID :18475689
Synonyms :

Calculated chemistry of [ 13452-14-7 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.93
TPSA : 63.33 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) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : 1.69
Log Po/w (WLOGP) : 1.83
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 1.69
Consensus Log Po/w : 1.54

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.45
Solubility : 0.629 mg/ml ; 0.00355 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.411 mg/ml ; 0.00232 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.67
Solubility : 0.376 mg/ml ; 0.00212 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.17

Safety of [ 13452-14-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13452-14-7 ]

* 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 [ 13452-14-7 ]
  • Downstream synthetic route of [ 13452-14-7 ]

[ 13452-14-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 13452-14-7 ]
  • [ 5676-60-8 ]
Reference: [1] Patent: EP2589592, 2018, B1,
  • 2
  • [ 136663-23-5 ]
  • [ 13452-14-7 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With sodium hydroxide In ethanol; water at 20℃; for 2 h;
Stage #2: With hydrogenchloride In ethanol; water
Preparation Example K-2.
2-Methyl-benzoxazole-6-carboxylic acid
To a solution of 2-methyl-benzoxazole-6-carboxylic acid methyl ester (301 mg, 1.57mmol) in ethanol (10mL) was added an aqueous solution of 2N sodium hydroxide (10mL), and the mixture was stirred for 2 hours at room temperature. 2N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, and the solution was extracted with ethyl acetate.
The organic layer was washed with brine, dried over anhydrous sodium sulfate, then, evaporated in vacuo, and the title compound (270mg, 1.52mmol, 97percent) was obtained.
This was used in the next reaction without purification.
1H-NMR Spectrum (DMSO-d6) δ (ppm): 2.64 (3H, s), 7.73 (1H, d, J=8.0Hz), 7.93(1 H, dd, J=1.2, 8.0Hz), 8.15 (1 H, d, J= 1.2Hz).
97%
Stage #1: at 20℃; for 2 h;
Stage #2: With hydrogenchloride In water
To a solution of 2-methyl-benzoxazole-6-carboxylic acid methyl ester (301 mg, 1.57mmol) in ethanol (10mL) was added an aqueous solution of 2N sodium hydroxide (10mL), and the mixture was stirred for 2 hours at room temperature. 2N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, and the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, then, evaporated in vacuo, and the title compound (270mg, 1.52mmol, 97percent) was obtained. This was used in the next reaction without purification. 1H-NMR Spectrum (DMSO-d6) δ(ppm) : 2.64 (3H, s), 7.73 (1 H, d, J=8.0Hz), 7.93(1 H, dd, J=1.2, 8.0Hz), 8.15 (1 H, d, J= 1.2Hz).
90% With lithium hydroxide monohydrate; water In tetrahydrofuran for 2 h; To methyl 2-methyl-1,3-benzoxazole-6-carboxylate (8) (12.2 g, 0.064 mol) in THF (300 mL)/H2O (100 mL) was added lithium hydroxide monohydrate (5.4 g, 0.128 mol), and the mixture was vigorously stirred. After 2 h the THF was removed under vacuum. The remaining aqueous phase was acidified with HOAc and exhaustively extracted with CH2Cl2. The pooled organic extract was dried (Na2SO4) and concentrated to give a beige solid (10.2 g, 90percent yield): mp 245–246 °C (lit.40 245–246 °C); TLC (SiO2, ethyl acetate/methanol (90:10), UV) single spot Rf 0.38. 1H NMR (300 MHz, DMSO); δ 2.66 (s, 3H, NCH3), 7.75 (d, J = 8.3 Hz, 1H, H-5), 7.96 (dd, J = 8.3, 1.4 Hz, 1H, H-4), 8.16 (d, J = 0.7 Hz, 1H, H-7), 13.12 (bs, 1H, OH).
65%
Stage #1: With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 25℃; for 2 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; methanol
To a solution of methyl 2-methylbenzo[d]oxazole-6-carboxylate (2.0 g, 10 mmol) in tetrahydrofuran/methanol/water (1: 1 : 1, 15 mL) was added lithium hydroxide hydrate (0.88 g, 21 mmol). The resulting mixture was stirred at 25 °C for 2 hours. On completion, the mixture was acidified with hydrochloric acid, resulting in formation of a solid. The solid was collected by filtration, washed with water and dried in vacuo to give compound B-130 (1.2 g, 65percent yield) as a white solid.

Reference: [1] Patent: EP1782811, 2007, A1, . Location in patent: Page/Page column 60
[2] Patent: EP1669348, 2006, A1, . Location in patent: Page/Page column 68
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6661 - 6664
[4] Patent: WO2016/100184, 2016, A1, . Location in patent: Paragraph 00323-00324
[5] Patent: US2007/160538, 2007, A1, . Location in patent: Page/Page column 19-20
[6] Patent: EP1229027, 2002, A1, . Location in patent: Page 15
[7] Patent: EP1229028, 2002, A1, . Location in patent: Page 15
[8] Patent: EP1229037, 2002, A1, . Location in patent: Page 15
[9] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 2980 - 2985
  • 3
  • [ 1445-45-0 ]
  • [ 2374-03-0 ]
  • [ 13452-14-7 ]
YieldReaction ConditionsOperation in experiment
100% at 100℃; for 0.0833333 h; Microwave irradiation A heterogeneous mixture of 4-amino-3-hydroxybenzoic acid (7b) (7.732 g, 0.050 mol) and 1,1,1-trimethoxyethane (16 mL) was heated to 100 °C using a microwave (55 W) and held for 5 min. The reaction was repeated two more times (7.732 g and 7.625 g), and the combined reaction mixtures were concentrated in vacuo giving the product as a tan solid in quantitative yield: mp 245–246 °C (lit.40 245–246 °C); TLC (SiO2, ethyl acetate/methanol (90:10), UV) single spot Rf 0.38; MS MH+ 178.4. 1H NMR (300 MHz, DMSO); δ 2.66 (s, 3H, NCH3), 7.75 (d, J = 8.3 Hz, 1H, H-5), 7.96 (dd, J = 8.3, 1.4 Hz, 1H, H-7), 8.16 (d, J = 0.7 Hz, 1H, H-7), 13.12 (bs, 1H, OH).
95% at 100℃; for 0.0833333 h; Microwave irradiation A solution of compound 4.1 (1.10 g) and 1,1,1-trimethoxyethane (5 mL) was heated at 100° C. for 5 minutes in a microwave. The reaction mixture was concentrated under reduced pressure to provide 1.26 g of compound 4.2 (95percent pure) as a brown powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.66 (s, 3H), 7.74 (d, J=8.4 Hz, 1H), 7.96 (dd, J=8.3, 1.4 Hz, 1H), 8.16 (d, J=1.4 Hz, 1H), 13.07 (s(br), 1H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6661 - 6664
[2] Patent: US2010/305073, 2010, A1, . Location in patent: Page/Page column 20
[3] Patent: US2003/73707, 2003, A1,
[4] Patent: EP1229027, 2002, A1, . Location in patent: Page 18
[5] Patent: EP1229028, 2002, A1, . Location in patent: Page 18
[6] Patent: EP1229037, 2002, A1, . Location in patent: Page 18
[7] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4998 - 5002
[8] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3242 - 3253
  • 4
  • [ 64-19-7 ]
  • [ 2374-03-0 ]
  • [ 13452-14-7 ]
YieldReaction ConditionsOperation in experiment
62% at 130℃; for 72 h; (Intermediate Example 70)
2-Methylbenzoxazole-6-carboxylic acid
4-Amino-3-hydroxybenzoic acid (4.9 g) was added to acetic acid (250 ml) and stirred for 3 days at 130°C.
The solution was concentrated under reduced pressure, and precipitates were collected by filtration.
The precipitates were dissolved in methanol and chloroform.
The solution was concentrated under reducedpressure, and precipitates were collected by filtration, washed with methanol and dried under reduced pressure to give the title compound (3.5 g, Y.: 62percent).
1H NMR; (DMSO-d6) δ (ppm): 2.6 (s, 3H), 7.7 (d, 1H), 7.9 (dd, 1H), 8.1 (d, 1H).
ESI/MS (m/z): 178 (M+H)+, 176 (M-H)-.
Reference: [1] Patent: EP1595866, 2005, A1, . Location in patent: Page/Page column 27
  • 5
  • [ 63435-16-5 ]
  • [ 13452-14-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 2980 - 2985
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6661 - 6664
  • 6
  • [ 713-52-0 ]
  • [ 13452-14-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 2980 - 2985
  • 7
  • [ 6427-66-3 ]
  • [ 64-19-7 ]
  • [ 13452-14-7 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1966, p. 1980 - 1983
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 13452-14-7 ]

Carboxylic Acids

Chemical Structure| 15112-41-1

[ 15112-41-1 ]

Benzo[d]oxazole-5-carboxylic acid

Similarity: 0.91

Chemical Structure| 90322-32-0

[ 90322-32-0 ]

2-Methylbenzo[d]oxazole-5-carboxylic acid

Similarity: 0.86

Chemical Structure| 208772-23-0

[ 208772-23-0 ]

Benzo[d]oxazole-4-carboxylic acid

Similarity: 0.84

Chemical Structure| 154235-77-5

[ 154235-77-5 ]

Benzo[d]oxazole-6-carboxylic acid

Similarity: 0.78

Chemical Structure| 18735-74-5

[ 18735-74-5 ]

5-Methyl-2-phenyloxazole-4-carboxylic acid

Similarity: 0.77

Related Parent Nucleus of
[ 13452-14-7 ]

Benzoxazoles

Chemical Structure| 864274-04-4

[ 864274-04-4 ]

2-Methylbenzo[d]oxazole-6-carbaldehyde

Similarity: 0.92

Chemical Structure| 15112-41-1

[ 15112-41-1 ]

Benzo[d]oxazole-5-carboxylic acid

Similarity: 0.91

Chemical Structure| 924869-17-0

[ 924869-17-0 ]

Methyl benzo[d]oxazole-5-carboxylate

Similarity: 0.88

Chemical Structure| 5676-58-4

[ 5676-58-4 ]

2,5-Dimethylbenzoxazole

Similarity: 0.87

Chemical Structure| 90322-32-0

[ 90322-32-0 ]

2-Methylbenzo[d]oxazole-5-carboxylic acid

Similarity: 0.86