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Chemical Structure| 7356-11-8
Chemical Structure| 7356-11-8
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Product Details of [ 7356-11-8 ]

CAS No. :7356-11-8 MDL No. :MFCD00130054
Formula : C9H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :YFPBHPCMYFCRKS-UHFFFAOYSA-N
M.W : 195.17 Pubchem ID :81816
Synonyms :

Calculated chemistry of [ 7356-11-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.51
TPSA : 72.12 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 2.27
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.16
Log Po/w (SILICOS-IT) : 0.03
Consensus Log Po/w : 1.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.491 mg/ml ; 0.00252 mol/l
Class : Soluble
Log S (Ali) : -3.42
Solubility : 0.074 mg/ml ; 0.000379 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.25
Solubility : 1.11 mg/ml ; 0.00568 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.98

Safety of [ 7356-11-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7356-11-8 ]

* 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 [ 7356-11-8 ]
  • Downstream synthetic route of [ 7356-11-8 ]

[ 7356-11-8 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 7356-11-8 ]
  • [ 1670-82-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439
[2] Patent: US2012/277224, 2012, A1,
  • 2
  • [ 7356-11-8 ]
  • [ 18595-18-1 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 1921 - 1930
[2] European Journal of Medicinal Chemistry, 1983, vol. 18, # 4, p. 307 - 314
[3] Patent: EP2551262, 2013, A1, . Location in patent: Paragraph 0150
[4] Patent: EP2554165, 2013, A1, . Location in patent: Paragraph 0123
[5] Patent: US2680730, 1950, ,
  • 3
  • [ 67-56-1 ]
  • [ 96-98-0 ]
  • [ 7356-11-8 ]
YieldReaction ConditionsOperation in experiment
99% for 3 h; Example 97 PREPARATION OF 1-CYCLOHEXVI-2-(2-PHENYL-QUINOLIN-7-VI)-1 H-BENZOIMIDAZOLE-S- CARBOXYLIC ACID (COMPOUND 405) Step 1: 4-methyl-3-nitro-benzoic acid methyl ester (Compound 405a); [0483] 4-Methyl-3-nitro benzoic acid (12.5 g, 69MMOL) was dissolved in anhydrous methanol (500 mL) in a IL flask. HCL gas was then bubbled through the solution until saturation (3 h). The HCl source was then removed, and the reaction was stirred at room temperature overnight. The reaction was then concentrated to dryness and dried over phosphorus pentoxide overnight to yield 13.34g (99percent) of product which was 99percent pure by QC HPLC. [0484] H -NMR (CDCl3) : ZU (ppm) 8.59 (d, 1H, AR-H2), 8.13 (dd, 1H, Ar- H6), 7.43 (d, 1H, Ar-H5), 3.96 (s, 3H, OCH3), 2.67 (s, 3H, CH3)
94% at 0 - 20℃; for 13 h; Example 18; Ethyl 2-Methyl-4-r2- (4-trifluoromethylphenyl)-2H-indazol-6- ylmethylsulfanyllphenoxyacetic Acid; Step A; 4-Bromomethyl-3-nitro-benzoic acid methyl ester; Add acetyl chloride (30.0 mL) dropwise to a solution of commercially available 4- methyl-3-nitro-benzoic acid (18.12 g, 100.0 mmol) in methanol (200 mL) at 0 °C under nitrogen, stir for Ih, warm to room temperature and stir for 12 h. Remove the solvent under reduced pressure, dilute with ethyl acetate (600 mL), wash with saturated aqueous NaHC03 solution (3 x 150 mL) and brine (150 mL) and dry over MgS04 and remove the solvents under reduced pressure to provide methyl 4-methyl-3-nitrobenzoate (XCH-E- 138) as off white solid (18.42 g, 94percent). Dilute some of the ester (11.71 g, 60.0 mmol) with carbon tetrachloride (400 mL), treated with benzoyl peroxide (0.872 g, 3.60 mmol) and N-bromosuccinimide (10.68 g, 60.0 mmol) and heat at reflux under nitrogen for 12 h. Treat the mixture with silica gel (40 g), remove the solvents under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (1: 9), to provide methyl 4-bromomethyl-3-nitrobenzoate as a viscous yellow oil (11.16 g, 68percent) : lH NMR (CDC13) 8 3.98 (s, 3H), 4.85 (s, 2H), 7.68 (d, 1H), 8.25 (dd, 1H), 8.66 (d, 1H).
69% for 3 h; Reflux Step 1.
Methyl 4-methyl-3-nitrobenzoate
A solution of 4-methyl-3-nitrobenzoic acid (20.6 g, 113.81 mmol, 1.00 equiv) in methanol (200 mL) was placed into a 500-mL round-bottom flask.
Then 2 mL of concentrated hydrochloric acid was added.
The resulting solution was heated to reflux for 3 h.
The resulting mixture was concentrated in vacuo, and diluted with 200 mL of ethyl acetate.
The pH value of the solution was adjusted to pH 8 with sat. NaHCO3.
The resulting mixture was concentrated under vacuum.
This resulted in 15.3 g (69percent) of methyl 4-methyl-3-nitrobenzoate as a brown yellow solid.
26.9 g for 16 h; Reflux To a solution of 4-Methyl-3-nitrobenzoic acid (25.4 g) in methanol (300 mL) was slowly added concentrated sulfuric acid (2 mL), and then the reaction mixture was heated at reflux for 16 hours. The reaction mixture was concentrated under reduced pressure, and then the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give the titled compound (26.9 g) as a pale yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 8.62 (1H, s), 8.15 (1H, dd, J = 7.8, 1.2 Hz), 7.45 (1H, d, J = 7.8 Hz), 3.96 (3H, s), 2.67 (3H, s).

Reference: [1] Patent: WO2005/12288, 2005, A1, . Location in patent: Page/Page column 181
[2] Patent: WO2005/66136, 2005, A1, . Location in patent: Page/Page column 93
[3] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 10, p. 1692 - 1695
[4] Patent: US2012/277224, 2012, A1, . Location in patent: Page/Page column 83
[5] Journal of the Chemical Society, 1911, vol. 99, p. 2131
[6] Justus Liebigs Annalen der Chemie, 1847, vol. 63, p. 297
[7] Patent: EP2551262, 2013, A1, . Location in patent: Paragraph 0150
[8] Patent: EP2554165, 2013, A1, . Location in patent: Paragraph 0123
[9] Patent: WO2013/131408, 2013, A1, . Location in patent: Page/Page column 73
[10] Patent: EP2669270, 2013, A1, . Location in patent: Paragraph 0523-0524
  • 4
  • [ 96-98-0 ]
  • [ 7356-11-8 ]
YieldReaction ConditionsOperation in experiment
97% With sulfuric acid; sodium carbonate In methanol; dichloromethane; water EXAMPLE 32
COMPOUND 32: [3-Amino-4-(3,3"-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2';6',2"]terpyridin-1'-ylmethyl)-phenyl]-methanol
To a solution of 4-methyl-3-nitrobenzoic acid (5.52 g, 30.5 mmol) in MeOH (100 mL) was added 98percent sulfuric acid (2 mL) and the resultant mixture was refluxed overnight, then cooled to room temperature.
The mixture was concentrated and the residue was dissolved in CH2Cl2 (50 mL) and water (20 mL).
Solid Na2CO3 was added until the aqueous phase was basic to litmus paper.
The phases were separated and the aqueous phase was extracted with CH2Cl2 (5*20 mL).
The combined organic extracts were dried (Na2SO4) and concentrated and provided 5.79 g (97percent) of 4-methyl-3-nitrobenzoic acid methyl ester as a white solid.
Reference: [1] Patent: US2005/154201, 2005, A1,
  • 5
  • [ 96-98-0 ]
  • [ 77-78-1 ]
  • [ 7356-11-8 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 1921 - 1930
  • 6
  • [ 99-75-2 ]
  • [ 7356-11-8 ]
  • [ 1571-08-0 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 24 - 32[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 1, p. 30 - 39
  • 7
  • [ 67-56-1 ]
  • [ 939-79-7 ]
  • [ 7356-11-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1928, vol. 467, p. 171
[2] Journal fuer Praktische Chemie (Leipzig), 1925, vol. <2> 109, p. 221[3] Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 248
[4] Chemische Berichte, 1911, vol. 44, p. 1122
  • 8
  • [ 99-75-2 ]
  • [ 7356-11-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 155
[2] Patent: US2680730, 1950, ,
  • 9
  • [ 159583-78-5 ]
  • [ 7356-11-8 ]
  • [ 882-33-7 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 88, # 1-4, p. 113 - 122
  • 10
  • [ 99-75-2 ]
  • [ 7697-37-2 ]
  • [ 7356-11-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 155
  • 11
  • [ 7647-01-0 ]
  • [ 67-56-1 ]
  • [ 939-79-7 ]
  • [ 7356-11-8 ]
Reference: [1] Chemische Berichte, 1911, vol. 44, p. 1122
  • 12
  • [ 7356-11-8 ]
  • [ 88089-94-5 ]
YieldReaction ConditionsOperation in experiment
79% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 100℃; for 15 h; Inert atmosphere methyl 4-(bromomethyl)-3-nitrobenzoate
Into a 1000-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, were placed methyl 4-methyl-3-nitrobenzoate (10 g, 51.24 mmol, 1.00 equiv), NBS (9.13 g, 51.29 mmol, 1.00 equiv), BPO (1.24 g, 5.12 mmol, 0.10 equiv) and tetrachloromethane (400 mL). The resulted solution was stirred for 15 h at 100° C. The crude product was purified by silica gel column chromatography eluted with ethyl acetate/ petroleum ether (0:1-1:9). This resulted in 11.1 g (79percent) of methyl 4-(bromomethyl)-3-nitrobenzoate as yellow oil. The crude product was used in the next step without further purification.
68% With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane for 12 h; Heating / reflux Example 18; Ethyl 2-Methyl-4-r2- (4-trifluoromethylphenyl)-2H-indazol-6- ylmethylsulfanyllphenoxyacetic Acid; Step A; 4-Bromomethyl-3-nitro-benzoic acid methyl ester; Add acetyl chloride (30.0 mL) dropwise to a solution of commercially available 4- methyl-3-nitro-benzoic acid (18.12 g, 100.0 mmol) in methanol (200 mL) at 0 °C under nitrogen, stir for Ih, warm to room temperature and stir for 12 h. Remove the solvent under reduced pressure, dilute with ethyl acetate (600 mL), wash with saturated aqueous NaHC03 solution (3 x 150 mL) and brine (150 mL) and dry over MgS04 and remove the solvents under reduced pressure to provide methyl 4-methyl-3-nitrobenzoate (XCH-E- 138) as off white solid (18.42 g, 94percent). Dilute some of the ester (11.71 g, 60.0 mmol) with carbon tetrachloride (400 mL), treated with benzoyl peroxide (0.872 g, 3.60 mmol) and N-bromosuccinimide (10.68 g, 60.0 mmol) and heat at reflux under nitrogen for 12 h. Treat the mixture with silica gel (40 g), remove the solvents under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (1: 9), to provide methyl 4-bromomethyl-3-nitrobenzoate as a viscous yellow oil (11.16 g, 68percent) : lH NMR (CDC13) 8 3.98 (s, 3H), 4.85 (s, 2H), 7.68 (d, 1H), 8.25 (dd, 1H), 8.66 (d, 1H).
Reference: [1] Patent: US2015/315198, 2015, A1, . Location in patent: Paragraph 1365; 1366
[2] Patent: WO2005/66136, 2005, A1, . Location in patent: Page/Page column 93
[3] Tetrahedron Letters, 2002, vol. 43, # 34, p. 5949 - 5952
[4] Patent: WO2013/131408, 2013, A1, . Location in patent: Page/Page column 73
[5] Patent: US6348474, 2002, B1, . Location in patent: Page column 87
  • 13
  • [ 7356-11-8 ]
  • [ 88089-94-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 1983, vol. 18, # 4, p. 307 - 314
  • 14
  • [ 7356-11-8 ]
  • [ 153813-69-5 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 2, p. 219 - 222
[2] Patent: WO2017/202703, 2017, A1,
[3] Patent: WO2017/216054, 2017, A1,
[4] Patent: WO2017/202704, 2017, A1,
[5] Patent: WO2006/117548, 2006, A1,
[6] Patent: WO2006/117549, 2006, A1,
  • 15
  • [ 7356-11-8 ]
  • [ 170487-40-8 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 1921 - 1930
  • 16
  • [ 7356-11-8 ]
  • [ 184150-96-7 ]
Reference: [1] Patent: EP2669270, 2013, A1,
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