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[ CAS No. 4743-17-3 ] {[proInfo.proName]}

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Chemical Structure| 4743-17-3
Chemical Structure| 4743-17-3
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Product Details of [ 4743-17-3 ]

CAS No. :4743-17-3 MDL No. :MFCD00006701
Formula : C8H4ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MYQFJMYJVJRSGP-UHFFFAOYSA-N
M.W : 197.58 Pubchem ID :78480
Synonyms :

Calculated chemistry of [ 4743-17-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.11
TPSA : 63.07 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) : -6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.19
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 1.13
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.67
Solubility : 0.419 mg/ml ; 0.00212 mol/l
Class : Soluble
Log S (Ali) : -2.59
Solubility : 0.51 mg/ml ; 0.00258 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0339 mg/ml ; 0.000171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.48

Safety of [ 4743-17-3 ]

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

Application In Synthesis of [ 4743-17-3 ]

* 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 [ 4743-17-3 ]
  • Downstream synthetic route of [ 4743-17-3 ]

[ 4743-17-3 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 32315-10-9 ]
  • [ 635-21-2 ]
  • [ 4743-17-3 ]
YieldReaction ConditionsOperation in experiment
97% at 80℃; Step 1
6-Chloro-1H-benzo[d]1,3-oxazine-2,4-dione
A 500 mL 3-necked round bottom flask was charged with 2-amino-5-chlorobenzoic acid (17 g, 0.1 mol) and 1,2-dichloroethane (200 mL).
To the above was added dropwise a solution of triphosgene (21 g, 0.21 mol) in 1,2-dichloroethane (100 mL) at 80° C.
The resulting mixture was heated at 80° C. for further 3 h then cooled in ice-water.
The precipitate was collected by filtration and dried to afford 19 g (97percent) of the product as white solid. 1H NMR (300 MHz, DMSO-d6) δ: 11.85 (br, 1H), 7.88 (d, J=2.4 Hz, 1H), 7.78 (dd, J=8.7, 2.4 Hz, 1H), 7.15 (d, J=8.7 Hz, 1H).
97% at 80℃; for 3 h; A 500 mL 3-necked round bottom flask was charged with 2-amino-5- chlorobenzoic acid (17 g, 0.1 mol) and 1 ,2-dichloroethane (200 mL). To the above was added dropwise a solution of triphosgene (21 g, 0.21 mol) in 1,2- dichloroethane (100 mL) at 80 °C. The resulting mixture was heated at 80 °C for further 3 h then cooled in ice- water. The precipitate was collected by filtration and dried to afford 19 g (97percent) of the product as white solid. *H NMR (300 MHz, DMSO-d6) δ: 11.85 (br, 1H), 7.88 (d, J = 2.4 Hz, 1H), 7.78 (dd, J = 8.7, 2.4 Hz, 1H), 7.15 (d, J = 8.7 Hz, 1H).
Reference: [1] Patent: US2010/120741, 2010, A1, . Location in patent: Page/Page column 78
[2] Patent: WO2011/112731, 2011, A2, . Location in patent: Page/Page column 174
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 16, p. 6434 - 6456
[4] Chemical Biology and Drug Design, 2010, vol. 75, # 5, p. 444 - 454
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2295 - 2299
[6] Tetrahedron Letters, 2014, vol. 55, # 26, p. 3607 - 3609
[7] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
[8] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2006 - 2017
[9] Chemical Biology and Drug Design, 2018, vol. 92, # 5, p. 1914 - 1919
  • 2
  • [ 2148-56-3 ]
  • [ 75-36-5 ]
  • [ 4743-17-3 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With chloroformic acid ethyl ester In 1,4-dioxane for 1 h; Heating / reflux
Stage #2: at 50℃; for 10 h;
2-Amino-6-chlorobenzoic acid (30 g) was suspended in 1,4-dioxane (225 ml) and ethyl chloroformate (75 ml) was added. The mixture was heated at reflux for 1 hour, then cooled to 50° C. and acetyl chloride (75 ml) was added. The mixture was stirred for 10 hours, after which the precipitated product was filtered off and washed with toluene. Drying in vacuum yields 5-chloroisatoic anhydride (33 g, 97percent yield). 5-Chloroisatoic anhydride (30 gram) was dissolved in dimethylacetamide (300 ml), and cooled to 5° C. over a nitrogen atmosphere. Sodium hydride (5.8 g, 70percent) was added portionwise, followed by addition of methyl iodide (11.5 ml). The reaction mixture was stirred at room temperature for 18 hours and the evacuated (40 mbar) for 1 hour in order to remove excess methyl iodide. Sodium hydride (5.8 g, 70percent) was added followed by addition of dimethyl malonate (20 ml), and the mixture was heated to 85° C. After 3 hours at 85° C., the mixture was cooled and diluted with cold water (2.4 litre). The product was precipitated by addition of 5 M HCl (aq) until pH=1.5-2. Filtration of the precipitated product and recrystallisation from methanol gave the title compound (29 g, 70percent yield).
Reference: [1] Patent: US2004/34227, 2004, A1, . Location in patent: Page 3
  • 3
  • [ 635-21-2 ]
  • [ 503-38-8 ]
  • [ 4743-17-3 ]
YieldReaction ConditionsOperation in experiment
92% at 20℃; for 4 h; Heating / reflux Trichloromethyl CHLOROFORMATE (4.8 mL, 300 mmol) was added to a stirred solution of Compound 57 (6.84 g, 40 mmol) in dry dioxane at room temperature and the solution was refluxed for 4 h. The solution was cooled in an ice bath and the solids formed were filtered. The solids were washed by ether and dried under vacuum at room temperature to yield 7.3 g (92percent) of white SOLIDS. H NMR (DMSO-D6) : d 7.47 (d, J= 8.6 Hz, 1H), 7.70 (dd, J= 8.6, 1.8 Hz, 1H), 7.82 (d, J= 1.1, 1H), 11.63 (S, 1H).
Reference: [1] Patent: WO2004/74218, 2004, A2, . Location in patent: Page 116
  • 4
  • [ 124-38-9 ]
  • [ 201230-82-2 ]
  • [ 63069-48-7 ]
  • [ 4743-17-3 ]
Reference: [1] ACS Catalysis, 2017, vol. 7, # 12, p. 8072 - 8076
  • 5
  • [ 201230-82-2 ]
  • [ 635-21-2 ]
  • [ 4743-17-3 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 9, p. 4196 - 4200
  • 6
  • [ 17630-76-1 ]
  • [ 4743-17-3 ]
Reference: [1] Catalysis Science and Technology, 2015, vol. 5, # 10, p. 4830 - 4838
[2] Journal of Chemical Research, Miniprint, 1980, # 6, p. 2601 - 2609
[3] Journal fuer Praktische Chemie (Leipzig), 1886, vol. <2> 33, p. 36
  • 7
  • [ 201230-82-2 ]
  • [ 63069-48-7 ]
  • [ 4743-17-3 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 9, p. 4196 - 4200
  • 8
  • [ 17422-32-1 ]
  • [ 4743-17-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 43, p. 7455 - 7457
  • 9
  • [ 118-48-9 ]
  • [ 4743-17-3 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2689 - 2695
  • 10
  • [ 51108-30-6 ]
  • [ 117-21-5 ]
  • [ 126-71-6 ]
  • [ 5329-14-6 ]
  • [ 4743-17-3 ]
  • [ 63497-60-9 ]
Reference: [1] Patent: US4306074, 1981, A,
  • 11
  • [ 79-37-8 ]
  • [ 635-21-2 ]
  • [ 4743-17-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 1, p. 138 - 147
  • 12
  • [ 18928-48-8 ]
  • [ 100-58-3 ]
  • [ 4743-17-3 ]
  • [ 21259-25-6 ]
  • [ 7033-51-4 ]
  • [ 71526-50-6 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 10, p. 908 - 911
  • 13
  • [ 75-44-5 ]
  • [ 635-21-2 ]
  • [ 4743-17-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 1983, vol. 18, # 3, p. 241 - 247
  • 14
  • [ 91-56-5 ]
  • [ 4743-17-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1886, vol. <2> 33, p. 36
  • 15
  • [ 4743-17-3 ]
  • [ 16064-14-5 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 5, p. 616 - 620
  • 16
  • [ 4743-17-3 ]
  • [ 719-59-5 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 17, p. 4476 - 4479
[2] Organic Letters, 2018, vol. 20, # 15, p. 4516 - 4520
  • 17
  • [ 4743-17-3 ]
  • [ 71-43-2 ]
  • [ 719-59-5 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2689 - 2695
  • 18
  • [ 7647-01-0 ]
  • [ 4743-17-3 ]
  • [ 635-21-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1886, vol. <2> 33, p. 36
  • 19
  • [ 4743-17-3 ]
  • [ 784-38-3 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 15, p. 4516 - 4520
  • 20
  • [ 4743-17-3 ]
  • [ 2958-36-3 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 17, p. 4476 - 4479
[2] Organic Letters, 2018, vol. 20, # 15, p. 4516 - 4520
  • 21
  • [ 4743-17-3 ]
  • [ 63497-60-9 ]
  • [ 77820-58-7 ]
Reference: [1] Patent: US4306074, 1981, A,
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