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[ CAS No. 153813-69-5 ] {[proInfo.proName]}

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Chemical Structure| 153813-69-5
Chemical Structure| 153813-69-5
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Product Details of [ 153813-69-5 ]

CAS No. :153813-69-5 MDL No. :MFCD04039968
Formula : C9H7NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :WGOOPYYIMZJWMA-UHFFFAOYSA-N
M.W : 209.16 Pubchem ID :3457222
Synonyms :

Calculated chemistry of [ 153813-69-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.93
TPSA : 89.19 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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.19
Log Po/w (MLOGP) : 0.26
Log Po/w (SILICOS-IT) : -0.25
Consensus Log Po/w : 0.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.09
Solubility : 1.68 mg/ml ; 0.00804 mol/l
Class : Soluble
Log S (Ali) : -2.95
Solubility : 0.235 mg/ml ; 0.00112 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.81
Solubility : 3.24 mg/ml ; 0.0155 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.02

Safety of [ 153813-69-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153813-69-5 ]

* 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 [ 153813-69-5 ]
  • Downstream synthetic route of [ 153813-69-5 ]

[ 153813-69-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 104447-80-5 ]
  • [ 153813-69-5 ]
YieldReaction ConditionsOperation in experiment
93% With sodium periodate In tetrahydrofuran; water for 2 h; To a solution of the enamine (5 g, 20.0 mmol) in THF (50 ml_, 10 vol) and water (50 ml_, 10 vol) was added sodium periodate (12.8g, 60.0 mmol) and the mixture allowed to stir for 2 h. The mixture was filtered and the resulting solids washed with EtOAc (500 ml_). The organic layer was isolated, washed with NaHCO3 (3 x 100 mL) and dried (MgSO4). Concentration under vacuum afforded 4-formyl-3-nitrobenzoic acid methyl ester (3.9g, 93percent). LCMS m/z 210 [M++H]+, 1H NMR (300 MHz, DMSO), δ:3.96 (3H, s, OMe), 8.01 (1H, d, ArH), 8.39 (1H1 d, ArH), 8.54 (1H, s, ArH), 10.31 (1H, s, CHO).
93% With sodium periodate In tetrahydrofuran; water for 2 h; To a solution of the enamine (5 g, 20.0 mmol) in THF (50 mL, 10 vol) and water (50 mL, 10 vol) was added sodium periodate (12.8g, 60.0 mmol) and the mixture allowed to stir for 2 h. The mixture was filtered and the resulting solids washed with EtOAc (500 mL). The organic layer was isolated, washed with NaHCO3 (3 x 100 mL) and dried (MgSO4). Concentration under vacuum afforded 4-formyl-3-nitrobenzoic acid methyl ester (3.9g, 93percent). LCMS m/z 210 [M++H]+, 1H NMR (300 MHz, DMSO), δ: 3.96 (3H, s, OMe), 8.01 (1 H1 d, ArH), 8.39 (1H, d, ArH), 8.54 (1H, S, ArH), 10.31 (1H, s, CHO).
83% With sodium periodate; water In tetrahydrofuran at 20 - 40℃; for 1 h; Step 3: 4-Formyl-3-nitro-benzoic acid methyl ester (Compound 405c); [0487] The product from the previous step (16. 1 Og, 64.3 mmol) and NAI04 (41 g, 191.7 mmol) was dissolved in 250 mL of 1: 1 THF/H20 at room temperature. The dark red solution was warmed to about 40 °C while heavy precipitation occurred and the solution color changed to light brown. After 1 h, the precipitate was removed by filtration and was washed with 400 mL ethyl acetate. The organic layer was washed three times with saturated NAHCO3, once with brine and dried with NA2S04. The solution was evaporated to dryness and the resulting oil was purified on a silicagel pad eluting with ethyl acetate-hexane gradient (30percent to 40percent ethyl acetate) to yield 11.07g (83percent) of the title intermediate as a yellow solid after evaporation. [0488] H -NMR (CDC13) : U (PPM) 10.45 (s, 1H, CHO), 8.75 (d, 1H, Ar- H2) 8.41 (dd, 1H, AR-H6), 8.01 (d, 1H, AR-H5), 4.02 (s, 3H, OCH3)
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 2, p. 219 - 222
[2] Patent: WO2006/117548, 2006, A1, . Location in patent: Page/Page column 49-50
[3] Patent: WO2006/117549, 2006, A1, . Location in patent: Page/Page column 42; 43
[4] Patent: US6344/449, 2002, B1, . Location in patent: Example A4b)
[5] Patent: US6344449, 2002, B1, . Location in patent: Example A4b)
[6] Patent: WO2005/12288, 2005, A1, . Location in patent: Page/Page column 181-182
[7] Patent: US2001/36946, 2001, A1,
[8] Patent: US6087380, 2000, A,
  • 2
  • [ 88089-94-5 ]
  • [ 153813-69-5 ]
YieldReaction ConditionsOperation in experiment
66% With 4-methylmorpholine N-oxide In acetonitrile at 20℃; for 1.16667 h; Step B; Methyl 4-Formyl-3-nitrobenzoate; Add N-methylmorpholine oxide (NMO, 5.27 g, 45.0 mmol) to a mixture of methyl 4-bromomethyl-3-nitrobenzoate (8.22 g, 30.0 mmol) and 4 Å molecular sieves (20.05 g) in acetonitrile (150 mL) at room temperature under nitrogen and stir for 40 min. Add additional NMO (1.76 g, 15.02 mmol) and stir for an additional 30 min. Remove the solids by vacuum filtration and dilute the filtrate with ethyl acetate. (600 mL), wash with 1 N HC1 (100 mL) and brine (2 x 100 mL) and dry over MgS04. Remove the solvents under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (15: 85), to provide methyl 4-formyl-3- nitrobenzoate as a white solid (4.15 g, 66percent) : lH NMR (CDC13) 6 4.02 (s, 3H), 8.01 (d, 1H), 8.42 (dd, 1H), 8.75 (d, 1H), 10.47 (s, 1H).
Reference: [1] Patent: WO2005/66136, 2005, A1, . Location in patent: Page/Page column 93-94
  • 3
  • [ 133831-27-3 ]
  • [ 153813-69-5 ]
YieldReaction ConditionsOperation in experiment
84 g With sodium periodate In tetrahydrofuran; water at 10 - 25℃; for 18 h; To a solution of NaIO4 (327 g, 1.53 mol) in a mixed solvent of THF (1.3 L) and water (2.0 L) was added a THF (0.7 L) solution of methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate (compound A, 127 g, 0.51 mol) at 10 °C. After the reaction mixture was stirred at 25 °C for 18 hrs, the mixture was filtered and then extracted with EA. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (PE:EA = 20: 1-10: 1) to give methyl 4-formyl-3-nitrobenzoate (compound C, 84 g, 79percent) as a yellow solid. MS: calc'd 210 (M+H)+, measured 210 (M+H)+.
84 g With sodium periodate In tetrahydrofuran; water at 10 - 25℃; for 18 h; To a solution of NaTO4 (327 g, 1.53 mol) in a mixed solvent of THF (1.3 L) and water (2.0L) was added a THF (0.7 L) solution of methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate(compound A, 127 g, 0.51 mol) at 10 °C. After the reaction mixture was stuffed at 25 °C for 18 hrs, the mixture was filtered and then extracted with EA. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (PE:EA = 20:1-10:1) to givemethyl 4-formyl-3-nitrobenzoate (compound C, 84 g, 79percent) as a yellow solid. MS: calc’d 210 (M+H), measured 210 (M+H).
84 g With sodium periodate In tetrahydrofuran; water at 10 - 25℃; for 18 h; b) Preparation of Compound C (0255) To a solution of NaIO4 (327 g, 1.53 mol) in a mixed solvent of THF (1.3 L) and water (2.0 L) was added a THF (0.7 L) solution of methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate (compound A, 127 g, 0.51 mol) at 10° C. After the reaction mixture was stirred at 25° C. for 18 hrs, the mixture was filtered and then extracted with EA. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (PE:EA=20:1-10:1) to give methyl 4-formyl-3-nitrobenzoate (compound C, 84 g, 79percent) as a yellow solid. MS: calc'd 210 (M+H)+, measured 210 (M+H)+.
Reference: [1] Patent: WO2016/26937, 2016, A1, . Location in patent: Page/Page column 93
[2] Patent: WO2017/202703, 2017, A1, . Location in patent: Page/Page column 25
[3] Patent: WO2017/216054, 2017, A1, . Location in patent: Page/Page column 24
[4] Patent: WO2017/202704, 2017, A1, . Location in patent: Page/Page column 32
[5] Patent: US2016/257653, 2016, A1, . Location in patent: Paragraph 0253; 0255
  • 4
  • [ 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,
  • 5
  • [ 153813-69-5 ]
  • [ 953039-79-7 ]
Reference: [1] Patent: WO2007/117607, 2007, A2,
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