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[ CAS No. 78515-16-9 ] {[proInfo.proName]}

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Chemical Structure| 78515-16-9
Chemical Structure| 78515-16-9
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Product Details of [ 78515-16-9 ]

CAS No. :78515-16-9 MDL No. :MFCD10565654
Formula : C10H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :CNRMXICSYWVJRD-UHFFFAOYSA-N
M.W : 194.18 Pubchem ID :10856352
Synonyms :

Calculated chemistry of [ 78515-16-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.6
TPSA : 52.6 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) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 1.5
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 1.0
Log Po/w (SILICOS-IT) : 1.9
Consensus Log Po/w : 1.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.04
Solubility : 1.76 mg/ml ; 0.00908 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.19 mg/ml ; 0.00613 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.55
Solubility : 0.542 mg/ml ; 0.00279 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 78515-16-9 ]

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

Application In Synthesis of [ 78515-16-9 ]

* 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 [ 78515-16-9 ]
  • Downstream synthetic route of [ 78515-16-9 ]

[ 78515-16-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 616-76-2 ]
  • [ 74-88-4 ]
  • [ 78515-16-9 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16 h; Methyl 5-formyl-2-methoxybenzoate. 5-Formyl salicylic acid (2.0 g, 12.0 mmol), methyl iodide (1.5 mL, 25 mmol) and potassium carbonate (3.06 g, 22.2 mmol) were combined in dimethylformamide (15 mL). After stirring at room temperature for 16 h, the solvent was removed in vacuo and the crude product dissolved in ethyl acetate, washed with water (2.x.), brine (2.x.), dried over sodium sulfate, concentrated, and purified by column chromatography to afford 1.85 g (79percent). 1H-NMR (CDCl3, 500 MHz) δ 9.91 (s, 1H), 8.31 (d, J=2.1 Hz, 1H), 8.02 (dd, J=8.5, 2.5 Hz, 1H), 7.11 (d, J=8.6 Hz, 1H), 3.99 (s, 3H), 3.91 (s, 3H). Mass spec.: 195.05 (MH)+.
72% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 46 h; To a solution of 5-formyl-2-hydroxybenzoic acid (500 mg, 3.01 mmol) inDMF (3.80 ml) were added K2CO3 (832 mg, 6.02 mmol) and MeI (750 L, 12.0 mmol). The reaction mixture was stirred for 46 h at rt,quenched with H2O, and diluted with EtOAc. After removal of theorganic layer, the aqueous layer was extracted with EtOAc. The organic layer was combined, dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (10:1 hexanes/EtOAc) afforded methyl 5-formyl-2-methoxybenzoate (417 mg, 72percent) as a white solid
6.24% With potassium carbonate In N,N-dimethyl-formamide at 60℃; Sealed tube A 100 mL sealed tube was charged with 5-formyl-2-hydroxybenzoic acid (2.2g, 13.2mmol) and DMF (20 mL). To the above stirred solution K2003 (5.4 g, 39.7 mmol) and0H31 (5.63 g, 39.7 mmol) was added and the mixture was heated at 60 00 over night.The reaction mixture was diluted with water and extracted with ethyl acetate, washed with water and dried. The product was obtained by concentrating under vacuo. The product was purified by combiflash to yield the title compound (0.160 g, 6.24percent) as a pale yellow solid. LOMS: (M+H) = 195.1; 1H NMR: (DMSO-d6, 300MHz) 6 9.92 (5, 1H), 8.20-8.21 (d, 1H), 8.08-8.11 (dd, 1H),7.37-7.39 (d, 1H), 3.94 (5, 3H), 3.83 (5,3H).
6.24% With potassium carbonate In N,N-dimethyl-formamide at 60℃; Sealed tube A 100 mL sealed tube was charged with 5-formyl-2-hydroxybenzoic acid (2.2g, 13.2 mmcl) and DMF (20 mL). To the above stirred solution K2003 (5.4 g, 39.7 mmol) and CH3I (5.63 g, 39.7 mmol) was added and heated at 60 00 over night. The reaction mixture was diluted with water and extracted with ethyl acetate, washed with waterand dried. The product was obtained by concentrating under vacuo. The product was purified by combiflash to yield the title compound (0.160 g, 6.24percent) as a pale yellow solid. LCMS: (M+H) = 195.1; 1H NMR: (DMSO-d6, 300MHz) 69.92 (5, 1H), 8.20-8.21 (d, 1 H), 8.08-8.1 1 (dd, 1 H),7.37-7.39 (d, 1 H), 3.94 (5, 3H), 3.83 (5, 3H).

Reference: [1] Patent: US2007/249607, 2007, A1, . Location in patent: Page/Page column 65; 67; 69
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 2, p. 313 - 316
[3] European Journal of Medicinal Chemistry, 2004, vol. 39, # 7, p. 573 - 578
[4] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 114
[5] Patent: WO2014/202528, 2014, A1, . Location in patent: Page/Page column 108; 109
[6] Angewandte Chemie - International Edition, 2006, vol. 45, # 5, p. 796 - 800
[7] Patent: US2003/216453, 2003, A1,
[8] Patent: US2001/34343, 2001, A1,
[9] Patent: US6194406, 2001, B1,
[10] Patent: US6423704, 2002, B1,
[11] Patent: US6211199, 2001, B1,
[12] Patent: WO2008/156820, 2008, A1, . Location in patent: Page/Page column 61
  • 2
  • [ 41489-76-3 ]
  • [ 74-88-4 ]
  • [ 78515-16-9 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate In acetonitrile at 20 - 100℃; for 2.5 h; Microwave irradiation Step 2:
Synthesis of methyl 5-formyl-2-methoxybenzoate (257)
A mixture of methyl 5-formyl-2-hydroxybenzoate (0.500 g, 2.78 mmol), potassium carbonate (0.767 g, 5.55 mmol) and iodomethane (0.208 ml, 3.33 mmol) in acetonitrile (20 ml) was stirred at RT for 1 hour.
Additional iodomethane (0.312 ml, 4.99 mmol) was added and the reaction was heated under microwave irradiation at 100° C. for 1 hour and then for further 30 minutes.
The mixture was portioned between EtOAc and 1N HCl and the organic phase was washed with 1N NaOH and brine.
The organic layer was dried over sodium sulfate and the solvent was removed yielding methyl 5-formyl-2-methoxybenzoate (0.352 g, 1.813 mmol, 65percent yield, MS/ESI+ 194.9 [MH]+) which was used without purification.
Reference: [1] Patent: US2014/155391, 2014, A1, . Location in patent: Paragraph 0632; 0634
[2] Journal of Fluorine Chemistry, 1995, vol. 74, p. 69 - 76
  • 3
  • [ 616-76-2 ]
  • [ 77-78-1 ]
  • [ 78515-16-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4986 - 4992
  • 4
  • [ 616-76-2 ]
  • [ 78515-16-9 ]
Reference: [1] Journal of Fluorine Chemistry, 1995, vol. 74, p. 69 - 76
[2] Patent: US2014/155391, 2014, A1,
  • 5
  • [ 69-72-7 ]
  • [ 78515-16-9 ]
Reference: [1] Patent: WO2014/202580, 2014, A1,
[2] Patent: WO2014/202528, 2014, A1,
  • 6
  • [ 41489-76-3 ]
  • [ 77-78-1 ]
  • [ 78515-16-9 ]
Reference: [1] Journal of the Chemical Society, 1922, vol. 121, p. 1027
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