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Product Details of [ 2327-45-9 ]

CAS No. :2327-45-9 MDL No. :MFCD00662902
Formula : C9H9NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :UAPJKEJWOPOJJY-UHFFFAOYSA-N
M.W : 211.17 Pubchem ID :12719167
Synonyms :

Calculated chemistry of [ 2327-45-9 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.04
TPSA : 81.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.98
Log Po/w (WLOGP) : 1.39
Log Po/w (MLOGP) : 0.61
Log Po/w (SILICOS-IT) : -0.41
Consensus Log Po/w : 1.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.787 mg/ml ; 0.00373 mol/l
Class : Soluble
Log S (Ali) : -3.31
Solubility : 0.102 mg/ml ; 0.000485 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.99
Solubility : 2.17 mg/ml ; 0.0103 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 2327-45-9 ]

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 [ 2327-45-9 ]

* 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 [ 2327-45-9 ]
  • Downstream synthetic route of [ 2327-45-9 ]

[ 2327-45-9 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 2327-45-9 ]
  • [ 55414-72-7 ]
Reference: [1] Patent: WO2005/121152, 2005, A1,
  • 2
  • [ 67-56-1 ]
  • [ 1882-69-5 ]
  • [ 2327-45-9 ]
YieldReaction ConditionsOperation in experiment
87% at 85℃; for 96 h; Inert atmosphere; Sealed tube A pressure flask was charged with 2-nitro-4-methoxybenzoic acid (3.98 g, 0.020 mol) and methanol(10 mL). Concentrated H2SO4 (150 μl) was added dropwise. The flask was sealed and stirred at85 °C for 4 days. The mixture was cooled and concentrated to approximately half of its originalvolume. Ethyl acetate (25 mL) was added, and the mixture was washed with water (25 mL),saturated aqueous NaHCO3 solution (2 × 25 mL), brine (2 × 25 mL) and water (2 × 25 mL). Theorganic layer was dried over MgSO4, filtered, and concentrated in vacuo to give the title compoundas a yellow oil (3.57 g, 87percent); 1H NMR (300 MHz, CDCl3) δ 8.04 (d, J = 8.8 Hz, 1H, H6), 7.04 (d,J = 2.3 Hz, 1H, H3), 7.00 (dd, J = 8.8, 2.8 Hz, 1H, H4), 3.93 (s, 3H, OMe), 3.91 (s, 3H, OMe);13C {1H} NMR (75 MHz, CDCl3) δ 166.7, 163.5, 140.2, 131.4, 126.8, 115.9, 114.2, 56.4, 53.5; datain accordance with literature values.5
77% With hydrogenchloride In water at 0 - 20℃; for 22 h; Heating / reflux Fuming hydrochloric acid was passed through an ice-cooled solution of 5-methoxy-2-nitrobenzoic acid (10g, 50.7mmol) in methanol (70mL) until saturated. The reaction mixture was warmed to room temperature for 18 hours and was then heated under reflux for 4 hours. The solvent was then evaporated under reduced pressure and the residue was partitioned between ethyl acetate and sodium hydrogen carbonate solution. The organic layer was separated and washed with sodium hydrogen carbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a brown oil in 77percent yield, 8.23g. 1H NMR(CDCI3, 400MHz) No.: 3.90-3.95 (m, 6.98-7.05 (m, 8.00-8.05(m, 1 H). MS APCI+ m/z 212 [MH]+
Reference: [1] Synlett, 2016, vol. 27, # 8, p. 1237 - 1240
[2] Patent: WO2005/121152, 2005, A1, . Location in patent: Page/Page column 30
  • 3
  • [ 1882-69-5 ]
  • [ 74-88-4 ]
  • [ 2327-45-9 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In N,N-dimethyl-formamide at 20℃; 5-Methoxy-2-nitro-benzoic acid (3.2 g) was dissolved in N,N-dimethylformamide (60 ml). Potassium carbonate (5.61 g) and methyl iodide (5.05 ml) were added to the solution, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-hexane system to give methyl 5-methoxy-2-nitro-benzoate (3.38 g, yield 99percent). Methyl 5-methoxy-2-nitro-benzoate (3.38 g) was dissolved in N,N-dimethylformamide (34 ml). Triethylamine(7 ml) and 20percent palladium hydroxide (340 mg) were added to the solution, and the mixture was stirred under a hydrogen gas atmosphere at room temperature overnight. The reaction mixture was filtered and was washed with chloroform. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine, was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-hexane system to give methyl 2-amino-5-methoxy-benzoate (2.87 g, yield 99percent).
Reference: [1] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 49
  • 4
  • [ 59216-77-2 ]
  • [ 74-88-4 ]
  • [ 2327-45-9 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; Methyl 5-hydroxy-2-nitrobenzoate (26.45 g, 0.134 mol) was dissolved in DMF in a 1000 ml one-Methyl iodide (20.95 g, 0.148 mol) andK2CO3 (37.08 g, 0.268 mol),Reaction at room temperature 3h.The reaction was completed, the reaction solutionPour into the water that is solid precipitation, suction filtration,The filter cake was collected to obtain 28.05 g of methyl 2-nitro-5- (methoxy) benzoate in a yield of 99percent.
Reference: [1] Patent: CN106478548, 2017, A, . Location in patent: Paragraph 0087; 0088; 0119-0120; 0135-0136
  • 5
  • [ 1882-69-5 ]
  • [ 2327-45-9 ]
YieldReaction ConditionsOperation in experiment
83% With thionyl chloride In methanol for 20 h; Reflux 5-methoxy-2-nitrobenzoic acid (2 g, 10.14 mmol) was dissolved in MeOH (50.7mL). 50C12 (2.96 mL, 40.6 mmol) was added and the reaction mixture was heated to reflux for 20 hours. The reaction mixture was concentrated in vacuo. The cmde material was dissolved in EtOAc and washed with 1 N NaOH, then water, then brine, dried (Na2504), filtered, and concentrated in vacuo to give Intermediate 159A (1.7786 g, 8.42 mmol, 83percent) as a brown oil: ‘H NMR (400MHz, CHLOROFORM-d) 8.04 (d, J=9.0 Hz,1H), 7.07-6.99 (m, 2H), 3.94 (s, 3H), 3.92 (s, 3H); LC-MS: Method H, The compound did not ionize.
Reference: [1] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 563
[2] Journal of the Chemical Society, 1958, p. 2702,2703
  • 6
  • [ 74-88-4 ]
  • [ 2327-45-9 ]
Reference: [1] Patent: WO2003/97641, 2003, A2, . Location in patent: Page/Page column 63-64
  • 7
  • [ 1882-69-5 ]
  • [ 18107-18-1 ]
  • [ 2327-45-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2587 - 2602
[2] Patent: WO2006/52555, 2006, A2, . Location in patent: Page/Page column 35; 82-83
  • 8
  • [ 75-91-2 ]
  • [ 1882-69-5 ]
  • [ 2327-45-9 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 19, p. 9898 - 9905
  • 9
  • [ 50424-28-7 ]
  • [ 2516-95-2 ]
  • [ 6705-03-9 ]
  • [ 2327-45-9 ]
Reference: [1] Patent: US5457105, 1995, A,
  • 10
  • [ 2516-95-2 ]
  • [ 2327-45-9 ]
Reference: [1] Patent: CN106478548, 2017, A,
  • 11
  • [ 610-37-7 ]
  • [ 2327-45-9 ]
Reference: [1] Patent: CN106478548, 2017, A,
  • 12
  • [ 186581-53-3 ]
  • [ 1882-69-5 ]
  • [ 2327-45-9 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1097 - 1101[2] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 6, p. 1268 - 1274
  • 13
  • [ 74-88-4 ]
  • [ 2327-45-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2, 2002, # 8, p. 1449 - 1454
[2] Journal of the Chemical Society, Perkin Transactions 2, 2002, # 8, p. 1449 - 1454
  • 14
  • [ 2327-45-9 ]
  • [ 2475-80-1 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen; triethylamine In N,N-dimethyl-formamide at 20℃; 5-Methoxy-2-nitro-benzoic acid (3.2 g) was dissolved in N,N-dimethylformamide (60 ml). Potassium carbonate (5.61 g) and methyl iodide (5.05 ml) were added to the solution, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-hexane system to give methyl 5-methoxy-2-nitro-benzoate (3.38 g, yield 99percent). Methyl 5-methoxy-2-nitro-benzoate (3.38 g) was dissolved in N,N-dimethylformamide (34 ml). Triethylamine(7 ml) and 20percent palladium hydroxide (340 mg) were added to the solution, and the mixture was stirred under a hydrogen gas atmosphere at room temperature overnight. The reaction mixture was filtered and was washed with chloroform. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine, was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-hexane system to give methyl 2-amino-5-methoxy-benzoate (2.87 g, yield 99percent).
99% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3 h; Inert atmosphere A mixture of compound 21 (1.01 g, 4.77 mmol), Pd/C (10percent, 50.9 mg) and methanol (15 mL) wasstirred at room temperature under an atmosphere of hydrogen for 3 h. The mixture was filteredthrough Celite® and concentrated in vacuo to give the title compound as a yellow oil (0.860 g,99percent); 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J = 3.0 Hz, 1H, H3), 6.94 (dd, J = 8.9 Hz, 3.0 Hz,1H, H4), 6.63 (d, J = 8.9 Hz, 1H, H6), 5.13 (br s, 2H, NH2), 3.87 (s, 3H, OMe), 3.76 (s, 3H, OMe);13C {1H} NMR (75 MHz, CDCl3) δ 168.4, 150.7, 145.1, 123.4, 118.4, 113.2, 110.9, 56.0, 51.7;
94% With hydrogen In water; ethyl acetate at 20 - 25℃; for 3 h; To an ethyl acetate (14mL) solution of methyl 5-methoxy-2-nitrobenzoate (1.60g, 7.58 mmol), 10percent palladium-carbon (containing 50percent water) (320mg) was added and stirred under a hydrogen atmosphere of 0.25MPa at 20-25°C for 3 hours. After the reaction, palladium-carbon was filtered off and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate = 10/1 - 5/1) to give methyl 2-amino-5-methoxybenzoate (1.29g, 94percent) 1H-NMR (CDCl3) δ :3.76(3H,s), 3.88(3H,s), 5.37(2H,br), 6.63(1H,d,J=8.8Hz), 6.95(1H,dd,J=8.8, 3.1Hz), 7.35(1H,d,J=3.1Hz)
85.3% With iron; ammonium chloride In ethanol; water for 13 h; Reflux Methyl 2-nitro-5- (methyloxy) benzoate (27.21 g, 0.129 mol) was added to a 1000 ml single-Soluble ethanol solution (absolute ethanol: water = 1: 1),Reducing iron powder (14.40 g, 0.258 mol) andAmmonium chloride (20.68 g, 0.387 mol),Reflux 13h.The reaction was complete, suction filtration, the filtrate was extracted with ethyl acetate, combined ethyl acetate layer, with anhydrousDried over sodium sulfate,The solvent was distilled off under reduced pressure to give 19.92 g of methyl 2-amino-5- (methoxy) benzoate, yield 85.3percent.

Reference: [1] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 50
[2] Synlett, 2016, vol. 27, # 8, p. 1237 - 1240
[3] Patent: EP1844768, 2007, A1, . Location in patent: Page/Page column 25
[4] Patent: CN106478548, 2017, A, . Location in patent: Paragraph 0089; 0090; 0121; 0122; 0137; 0138
[5] Australian Journal of Chemistry, 1972, vol. 25, p. 2621 - 2629
[6] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1097 - 1101[7] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 6, p. 1268 - 1274
[8] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2587 - 2602
[9] Patent: WO2006/52555, 2006, A2, . Location in patent: Page/Page column 35; 82-83
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