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[ CAS No. 5202-89-1 ] {[proInfo.proName]}

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Chemical Structure| 5202-89-1
Chemical Structure| 5202-89-1
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Product Details of [ 5202-89-1 ]

CAS No. :5202-89-1 MDL No. :MFCD00007837
Formula : C8H8ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IGHVUURTQGBABT-UHFFFAOYSA-N
M.W : 185.61 Pubchem ID :78878
Synonyms :

Calculated chemistry of [ 5202-89-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.14
TPSA : 52.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 3.3
Log Po/w (WLOGP) : 1.72
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 1.61
Consensus Log Po/w : 2.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.31
Solubility : 0.0914 mg/ml ; 0.000492 mol/l
Class : Soluble
Log S (Ali) : -4.07
Solubility : 0.0156 mg/ml ; 0.0000843 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.344 mg/ml ; 0.00185 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 5202-89-1 ]

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 [ 5202-89-1 ]

* 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 [ 5202-89-1 ]
  • Downstream synthetic route of [ 5202-89-1 ]

[ 5202-89-1 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 5202-89-1 ]
  • [ 77287-34-4 ]
  • [ 16064-14-5 ]
YieldReaction ConditionsOperation in experiment
94.1% at 150℃; for 2 h; Examples 13 to 21:; The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the type of the anthranilic acid derivative was changed. The results are shown in Table 4.
Reference: [1] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 8
[2] Journal of the Chemical Society, 1947, p. 890,894
[3] Bioorganic Chemistry, 2018, vol. 80, p. 433 - 443
  • 2
  • [ 5202-89-1 ]
  • [ 7253-22-7 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 890,894
[2] Patent: WO2015/164374, 2015, A1,
[3] Bioorganic Chemistry, 2018, vol. 80, p. 433 - 443
  • 3
  • [ 5202-89-1 ]
  • [ 20028-68-6 ]
Reference: [1] Patent: WO2006/122631, 2006, A1,
  • 4
  • [ 5202-89-1 ]
  • [ 1640-60-4 ]
Reference: [1] Journal of the Chemical Society, 1948, p. 1759,1765
  • 5
  • [ 5202-89-1 ]
  • [ 635-21-2 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 7, p. 1861 - 1866
  • 6
  • [ 67-56-1 ]
  • [ 635-21-2 ]
  • [ 5202-89-1 ]
YieldReaction ConditionsOperation in experiment
100% at 0℃; for 12 h; Reflux Example 1006-Chloro-3 ,3 -dimethyl-2- (3 -morpholin-4-yl-phenyl)- 1 ,2,3 ,4-tetrahydro-quinoline-8- carboxylic acidTo a stirred solution of 2-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropwise at 0 °C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3 x 100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-amino-5-chloro- benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8C1N02 (M+H)+: 186.61, observed: 185.9.
100% at 0℃; for 12 h; Reflux To a stirred solution of 2-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropwise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3.x.100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-amino-5-chloro-benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8ClNO2 (M+H)+: 186.61, observed: 185.9.
Reference: [1] Patent: WO2011/128251, 2011, A1, . Location in patent: Page/Page column 187
[2] Patent: US2011/257151, 2011, A1, . Location in patent: Page/Page column 69
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 2801 - 2809
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 143, p. 910[5] Bulletin de la Societe Chimique de France, 1907, vol. <4> 1, p. 224
[6] Journal of Medicinal Chemistry, 1996, vol. 39, # 17, p. 3248 - 3255
[7] Scientia Pharmaceutica, 2003, vol. 71, # 4, p. 331 - 356
[8] Tetrahedron Letters, 2006, vol. 47, # 26, p. 4365 - 4368
[9] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 1, p. 64 - 69
[10] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 2, p. 415 - 420
[11] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8332 - 8338
[12] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 11175 - 11183
[13] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 1919 - 1925
  • 7
  • [ 635-21-2 ]
  • [ 5202-89-1 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In water; acetone (109-8)
5-Chloroanthranilic acid (15.0 g), (CH3)2SO4 (11.6 g) and K2CO3 (12.7 g) were refluxed in acetone (150 g) for 30 minutes.
The mixture was concentrated to about 90 g, and thereto was added water (90 g).
The mixture was extracted with toluene (75 g), and the organic layer was concentrated to give methyl 5-chloroanthranilate (15.6 g, 96percent).
1H NMR (CDCl3, 400 MHz) δ 7.83 (d, 1H, J=2.6 Hz), 7.21 (dd, 1H, J=8.5 and 2.6 Hz), 6.61 (d, 1H, J=8.5 Hz), 5.73 (brs, 2H), 3.88 (s, 3H).
96% With potassium carbonate In water; acetone (109-8)
5-Chloroanthranilic acid (15.0 g), (CH3)2SO4 (11.6 g) and K2CO3 (12.7 g) were refluxed in acetone (150 g) for 30 minutes.
The mixture was concentrated to about 90 g, and thereto was added water (90 g).
The mixture was extracted with toluene (75 g), and the organic layer was concentrated to give methyl 5-chloroanthranilate (15.6 g, 96 percent).
1H NMR (CDCl3, 400MHz) δ 7.83 (d, 1H, J=2.6Hz), 7.21 (dd, 1H, J=8.5 and 2.6Hz), 6.61 (d, 1H, J=8.5Hz), 5.73 (brs, 2H), 3.88 (s, 3H).
Reference: [1] Patent: US2003/181496, 2003, A1,
[2] Patent: EP1479384, 2004, A1,
  • 8
  • [ 51282-49-6 ]
  • [ 5202-89-1 ]
YieldReaction ConditionsOperation in experiment
345 g With hydrogenchloride; tin(IV) chloride In ethyl acetate at 20℃; for 16 h; Reference Example 2
Preparation of Methyl 2-amino-5-chlorobenzoate
A mixture of methyl 5-chloro-2-nitrobenzoate (534 gm) as obtained in reference example 1 and concentrated hydrochloric acid (2250 ml) was added to ethyl acetate (1120 ml).
To the reaction mixture was added a solution of tin chloride (1680 gm) in ethyl acetate (2250 ml).
The reaction mass was stirred for 16 hours at room temperature and then poured to the ice water.
The pH of the reaction mass was adjusted to 8.0 to 9.0 with aqueous sodium hydroxide solution (2650 ml).
The separated aqueous layer was extracted with ethyl acetate and then concentrated to obtain a residual solid of methyl 2-amino-5-chlorobenzoate (345 gm).
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
[2] Patent: WO2012/46244, 2012, A1, . Location in patent: Page/Page column 6
[3] Patent: US2013/190490, 2013, A1, . Location in patent: Paragraph 0048; 0049
  • 9
  • [ 67-56-1 ]
  • [ 20028-53-9 ]
  • [ 5202-89-1 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: for 0.25 h; Green chemistry
Stage #2: With tert.-butylhydroperoxide In decane for 48 h; Green chemistry
General procedure: B(C6F5)3 (1 mol percent) was added to a stirringsolution of aldehyde (1 mmol) in MeOH (6 mL). After 15 min., 5.5 M TBHP indecane (3 mmol) was added slowly and reaction mixture was refluxed untilthe complete conversion of starting material (monitored by TLC). Aftercompletion of reaction, the methanol was evaporated in vacuo. Later, thereaction mixture was diluted with water (20 mL) and extracted with ethylacetate (3 15 mL). The organic layer was washed with cold saturated sodiumbicarbonate solution (2 20 mL) followed by brine. The organic layer wasdried over MgSO4 and concentrated under reduced pressure and products werepurified over silica gel column chromatography in ethyl acetate/hexane. Allcompounds were characterized and confirmed by comparison of their spectraldata and physical properties with reported literature.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 7, p. 889 - 892
  • 10
  • [ 134-20-3 ]
  • [ 5202-89-1 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 7, p. 1861 - 1866
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1910, vol. 150, p. 1179[3] Bulletin de la Societe Chimique de France, 1911, vol. <4> 9, p. 606
[4] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 2, p. 415 - 420
[5] Patent: WO2006/122631, 2006, A1, . Location in patent: Page/Page column 57
  • 11
  • [ 2516-95-2 ]
  • [ 5202-89-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 2801 - 2809
[2] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
[3] Patent: WO2012/46244, 2012, A1,
[4] Patent: US2013/190490, 2013, A1,
  • 12
  • [ 67-56-1 ]
  • [ 344779-31-3 ]
  • [ 5202-89-1 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 16, p. 2926 - 2929
  • 13
  • [ 635-21-2 ]
  • [ 5202-89-1 ]
Reference: [1] Patent: US5599814, 1997, A,
  • 14
  • [ 186581-53-3 ]
  • [ 635-21-2 ]
  • [ 5202-89-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3386 - 3396
  • 15
  • [ 134-20-3 ]
  • [ 5202-89-1 ]
  • [ 52727-62-5 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1910, vol. 150, p. 1179[2] Bulletin de la Societe Chimique de France, 1911, vol. <4> 9, p. 606
  • 16
  • [ 96-32-2 ]
  • [ 154598-53-5 ]
  • [ 5202-89-1 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2486 - 2493
  • 17
  • [ 134-20-3 ]
  • [ 5202-89-1 ]
  • [ 77820-58-7 ]
Reference: [1] Synlett, 1999, # 12, p. 1984 - 1986
  • 18
  • [ 77-76-9 ]
  • [ 635-21-2 ]
  • [ 5202-89-1 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 45, p. 8029 - 8033
  • 19
  • [ 2719-08-6 ]
  • [ 5202-89-1 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 143, p. 910[2] Bulletin de la Societe Chimique de France, 1907, vol. <4> 1, p. 224
  • 20
  • [ 7647-01-0 ]
  • [ 7782-50-5 ]
  • [ 64-19-7 ]
  • [ 134-20-3 ]
  • [ 5202-89-1 ]
  • [ 52727-62-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1911, vol. <4> 9, p. 605[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1910, vol. 150, p. 1179
  • 21
  • [ 134-20-3 ]
  • [ 5202-89-1 ]
  • [ 77820-58-7 ]
Reference: [1] Synlett, 1999, # 12, p. 1984 - 1986
  • 22
  • [ 5202-89-1 ]
  • [ 150683-30-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
[2] Patent: CN105315169, 2016, A,
  • 23
  • [ 5202-89-1 ]
  • [ 160129-45-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
  • 24
  • [ 5202-89-1 ]
  • [ 137973-76-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
[2] Patent: CN105315169, 2016, A,
  • 25
  • [ 5202-89-1 ]
  • [ 289039-82-3 ]
Reference: [1] Chemistry Letters, 2017, vol. 46, # 6, p. 858 - 861
  • 26
  • [ 5202-89-1 ]
  • [ 289039-82-3 ]
Reference: [1] Patent: US2003/181496, 2003, A1,
[2] Patent: EP1479384, 2004, A1,
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