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[ CAS No. 18595-16-9 ] {[proInfo.proName]}

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Chemical Structure| 18595-16-9
Chemical Structure| 18595-16-9
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Product Details of [ 18595-16-9 ]

CAS No. :18595-16-9 MDL No. :MFCD00661547
Formula : C9H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MDHYFUPTSWXVIA-UHFFFAOYSA-N
M.W : 165.19 Pubchem ID :1201104
Synonyms :

Calculated chemistry of [ 18595-16-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.09
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) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 2.24
Log Po/w (WLOGP) : 1.37
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 1.44
Consensus Log Po/w : 1.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.507 mg/ml ; 0.00307 mol/l
Class : Soluble
Log S (Ali) : -2.97
Solubility : 0.175 mg/ml ; 0.00106 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.531 mg/ml ; 0.00321 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.31

Safety of [ 18595-16-9 ]

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 [ 18595-16-9 ]

* 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 [ 18595-16-9 ]
  • Downstream synthetic route of [ 18595-16-9 ]

[ 18595-16-9 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 20587-30-8 ]
  • [ 18595-16-9 ]
YieldReaction ConditionsOperation in experiment
60% With ammonium chloride; zinc In methanol; water at 0 - 20℃; for 12 h; A solution of methyl 5-methyl-2-nitrobenzoate (8 g, 41.025 mmol) in methanol (80 mL) and water (10 mL) was cooled to 0°C. Zinc powder (13.33 g, 205.128 mmol) was then added, followed by NH4C1 (17.6 g, 328.2 mmol). The mixture was stirred for 12 h at rt. Progress of the reaction was followed by TLC (20percent ethyl acetate/hexane). After completion of the reaction, the mixture was filtered and the filtrate was evaporated to provide crude residue. The crude reside was basified with saturated NaHC03 solution and extracted with DCM (2 x 20 mL). The combined organic layers were dried over Na2S04, filtered and evaporated to give methyl 2-amino-5-methylbenzoate (Yield: 4 g, 60percent).1H NMR (400 MHz, CDC13): δ 7.65 (s, 1H), 7.25 (s, 1H), 7.10-7.07 (q, 1H, J=8 Hz), 6.58 (d, 1H), 3.86 (s, 3H), 2.22 (s, 3H).
Reference: [1] Patent: WO2015/38417, 2015, A1, . Location in patent: Paragraph 151; 152
[2] Journal of the Chemical Society, 1930, p. 1513,1516
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4416 - 4420
[4] Patent: EP1475368, 2004, A1, . Location in patent: Page 57
  • 2
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YieldReaction ConditionsOperation in experiment
64% at 0℃; for 18.5 h; Heating / reflux EXAMPLE 18; 5-Bromomethyl-2-propionylamino-benzoic acid methyl ester; 2-Amino-5-methyl-benzoic acid (23,58 g, 156 mmol) was dissolved in methanol. The solution was brought to 0°C on an ice-bath and thionyl chloride (46.3 mL, 636 mmol) was added dropwise during 30 minutes. After the addition the reaction mixture was refluxed for 18 hours and was then allowed to reach room temperature. The solvent was evaporated and the remain- der was divided between CH2Cl2 (500 mL) and aqueous saturated NaHC03 (500 mL). The organic layer was washed with an additional 500 mL of aqueous saturated NaHCO3, dried over MgS04 and evaporated to dryness (16.59 g, 64percent). 2-Amino-5-methyl-benzoic acid methyl ester (8.00 g, 48.4 mmol) was dissolved in CHC13 (275 mL) and propionyl chloride (12.6 mL, 145 mmol) was added dropwise during 10 min- utes after which the reaction mixture was left with stirring at room temperature for 72 hours. Aqueous saturated NaHCO3 (400 mL) was carefully added under vigorous stirring and when no more gas evolved the organic layer was separated, dried over MgSO4, filtered and evapo- rated to dryness (10.06 g, 94percent). The radical bromination was performed as described by Patil et al. 1989: 5-Methyl-2- propionylamino-benzoic acid methyl ester (8.85 g, 40 mmol) and 1, 3-dibromo-5, 5-dimethyl hydantoin (DDH) (5,72 g, 20 mmol) in a mixture of CHC13 (500 mL) and CCI4 (500 mL) was heated to reflux. Every 60 minutes 50 mg of dibenzoyl peroxide was added for six hours and then the reaction mixture was left at reflux over night. It was then allowed to reach room tem- perature and the solvents were removed by evaporation. Chromatography using silica gel 60 and heptane/ethyl acetate (18: 2-> 17: 3-> 16: 4) as eluent afforded the pure title compound (6.40 g, 53percent). 1H NMR (CDC13) 8 1.26 (t, 3H), 2.48 (q, 2H), 3.95 (s, 3H), 4.47 (s, 2H), 7.55 (dd, 1H), 8.04 (d, 1H), 8.72 (d, 1H), 11.06 (bs, 1H).
61% at 0℃; for 16 h; Reflux Thionyl chloride (2.88 mL, 39.69 mmol) was added drop wise to a solution of 2-amino-5-methyl-benzoic acid (3.0 g, 19.84 mmol) in methanol (10 mL) at 0° C. and refluxed for 16 hr.
The reaction mixture was concentrated to dryness and the residue dissolved in chloroform (100 mL).
The organic layer was washed with sodium bicarbonate solution (5*30 mL), water (3*30 mL), brine (3*30 mL) and dried over anhydrous sodium sulphate.
The residue was concentrated under vacuum to yield the crude compound, which was purified by column chromatography over silica gel (100-200 mesh) using 2percent ethyl acetate in pet ether as eluent to afford 2-amino-5-methyl-benzoic acid methyl ester (2.0 g, 61percent) as a pale yellow semi solid.
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 9, p. 2104 - 2118
[2] Chemical Communications, 2011, vol. 47, # 3, p. 1057 - 1059
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8332 - 8338
[4] Patent: WO2005/75410, 2005, A1, . Location in patent: Page/Page column 31-32
[5] Journal of Chemical Research, Miniprint, 1986, # 7, p. 2001 - 2025
[6] Patent: US2011/160231, 2011, A1, . Location in patent: Page/Page column 10
[7] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 5, p. 1501 - 1507
[8] Scientia Pharmaceutica, 2003, vol. 71, # 4, p. 331 - 356
[9] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 2, p. 415 - 420
[10] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 11175 - 11183
[11] Organic and Biomolecular Chemistry, 2015, vol. 13, # 47, p. 11486 - 11491
[12] Patent: US2015/315198, 2015, A1, . Location in patent: Paragraph 1505; 1506
  • 3
  • [ 2941-78-8 ]
  • [ 18595-16-9 ]
YieldReaction ConditionsOperation in experiment
74% With sulfuric acid In methanol; water REFERENCE EXAMPLE 51
Methyl 2-amino-5-methylbenzoate
A mixture of 2-amino-5-methyl benzoic acid (10 g) in methanol (50 ml) containing conc. sulfuric acid (5.5 ml) was heated for 19 hours under reflux.
The solvent was distilled off, and the residue was dissolved in water.
The solution was neutralized with an aqueous sodium hydroxide, followed by extraction with ethyl acetate.
The organic layer was dried and concentrated to afford a pale brown oil (8.1 g, 74percent).
1 H-NMR(90MHz,CDCl3) δ: 2.24(3H,s), 3.89(3H,s), 5.55(2H,s), 6.59(1H,d), 7.10(1H,dd), 7.68(1H,d).
Reference: [1] Patent: US5128356, 1992, A,
  • 4
  • [ 2941-78-8 ]
  • [ 18107-18-1 ]
  • [ 18595-16-9 ]
Reference: [1] Patent: US2006/35908, 2006, A1, . Location in patent: Page/Page column 62
  • 5
  • [ 2941-78-8 ]
  • [ 80-11-5 ]
  • [ 18595-16-9 ]
Reference: [1] Heterocycles, 2006, vol. 67, # 1, p. 161 - 173
  • 6
  • [ 67-56-1 ]
  • [ 134-20-3 ]
  • [ 18595-16-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8211 - 8215[2] Angew. Chem., 2014, vol. 126, # 31, p. 8350 - 8354
  • 7
  • [ 3113-72-2 ]
  • [ 18595-16-9 ]
Reference: [1] Patent: WO2015/38417, 2015, A1,
[2] Patent: EP1475368, 2004, A1,
  • 8
  • [ 186581-53-3 ]
  • [ 2941-78-8 ]
  • [ 18595-16-9 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7033 - 7036
  • 9
  • [ 67-56-1 ]
  • [ 4692-99-3 ]
  • [ 18595-16-9 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1886, vol. <2>33, p. 58
  • 10
  • [ 18595-16-9 ]
  • [ 2967-93-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4416 - 4420
  • 11
  • [ 18595-16-9 ]
  • [ 90971-88-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4416 - 4420
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