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[ CAS No. 4093-29-2 ] {[proInfo.proName]}

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Chemical Structure| 4093-29-2
Chemical Structure| 4093-29-2
Structure of 4093-29-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4093-29-2 ]

CAS No. :4093-29-2 MDL No. :MFCD00065258
Formula : C11H13NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :OERVVBDWGVOBIS-UHFFFAOYSA-N
M.W : 223.23 Pubchem ID :77720
Synonyms :
Chemical Name :Methyl 4-acetamido-2-methoxybenzoate

Calculated chemistry of [ 4093-29-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 58.53
TPSA : 64.63 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) : -6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 1.22
Log Po/w (WLOGP) : 1.25
Log Po/w (MLOGP) : 1.14
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.94
Solubility : 2.56 mg/ml ; 0.0115 mol/l
Class : Very soluble
Log S (Ali) : -2.17
Solubility : 1.49 mg/ml ; 0.00669 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.225 mg/ml ; 0.00101 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 4093-29-2 ]

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 [ 4093-29-2 ]

* 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 [ 4093-29-2 ]
  • Downstream synthetic route of [ 4093-29-2 ]

[ 4093-29-2 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 4093-29-2 ]
  • [ 7206-70-4 ]
Reference: [1] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493
  • 2
  • [ 4093-29-2 ]
  • [ 364-62-5 ]
Reference: [1] Archiv der Pharmazie, 1980, vol. 313, # 4, p. 297 - 300
  • 3
  • [ 27492-84-8 ]
  • [ 108-24-7 ]
  • [ 4093-29-2 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: at 60 - 65℃; for 2 h;
Stage #2: With sodium hydrogencarbonate In water
To a solution of methyl 4-amino-2^methoxybenzoate (501 mg, 2.77 mmol) in ethanol (8 ml) was added acetic anhydride (0.42 ml, 4.44 mmol, 1.6 eq) and the clear solution heated at 60-65 °C for 2 h. After cooling to room temperature the solvent was removed by rotary evaporator and the residue treated with water (10 ml) and saturated sodium bicarbonate solution (10 ml) before extracting with ethyl acetate (20 ml, 2 x 10 ml). The combined ethyl acetate extract was washed with water, then brine, dried (MgSC>4) and evaporated to give methyl 4-acetamido-2-methoxybenzoate (545 mg, 88percent) as a white solid. 'H nmr1 (400 MHz, c1/4-dmso) δ 2.07, s, 3H, 4-AcNH; 3.74, s, 3H, 2-OMe or COOMe; 3.77, s, 3H, COOMe or 2-OMe; 7.19, br d (J = 8.8 Hz), IH, H5; 10.22, s, IH, NH.Ref. 17: J. Med. Chem. 2007, 50(15), 3561-3572.
84.1% at 50℃; for 2 h; [0542] To a solution of 269-2 (14.4 g, 8 mmol) in EtOH (120 mL) was added acetic anhydride (9.0 g, 88 mmol). The mixture was allowed to stir at 50 °C for 2 h. The mixture was cooled to r.t., and neutralized with aqueous NaHC03 solution. The mixture was extracted with EA (3 x 60 mL). The organic phase was dried over anhydrous sodium sulfate, and concentrated at low pressure. The residue was purified by flash column chromatography on silica gel (PE:EA 1 : 1 ) to give 269-3 (15.0 g. 84.1 percent). +ESI-MS:m/z 223.9 [M+H]+.
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3561 - 3572
[2] Patent: WO2011/123890, 2011, A1, . Location in patent: Page/Page column 118-119
[3] Patent: WO2015/26792, 2015, A1, . Location in patent: Paragraph 0542
[4] Archiv der Pharmazie, 1980, vol. 313, # 4, p. 297 - 300
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 7, p. 2311 - 2315
  • 4
  • [ 4093-28-1 ]
  • [ 74-88-4 ]
  • [ 4093-29-2 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4 h; General procedure: 2-hydroxy-4-acetyl-aminobenzoic acid methyl ester (10g, 47.8mmol) dissolved in DMF (50 ml) in, adding K2CO3(9.90g, 71 . 7mmol), benzyl chloride (9.03g, 71 . 7mmol), heating 60 °C reaction 4h. the response finishes, cooling, filtering, distilling solvent filtrate under reduced pressure, the residue with petroleum ether/ethyl acetate to obtain white solid is recrystallized (12.86g, 90percent).Iodomethane as starting material, to give the desired product according to the method of Example 58, a white solid (92percent).
Reference: [1] Tetrahedron, 1986, vol. 42, # 12, p. 3259 - 3268
[2] Patent: CN102952062, 2016, B, . Location in patent: Paragraph 0393; 0394; 0395; 0465; 0466; 0467
  • 5
  • [ 27492-84-8 ]
  • [ 75-36-5 ]
  • [ 4093-29-2 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With triethylamine In dichloromethane at 0℃; for 0.25 h;
Stage #2: at 20℃;
To a stirred solution of methyl 4-amino-2-methoxybenzoate (10 g, 55 mmol) in dichloromethane (100 mL) was added triethylamine (15.4 mL, 110 mmol) at 0 °C and the mixture was stirred for 15 mm. To this mixture, acetyl chloride (5.68 g, 71 mmol) was added drop wise and the mixture was stirred at room temperature overnight. The reaction was quenched by addition of water (75 mL). The organiclayer was separated, washed with brine solution (100 mL), dried over sodium sulfate and concentrated under reduced pressure to afford methyl 4-acetamido-2- methoxybenzoate (13.0 g, 58.2 mmol, quantitative yield) as a yellow solid: LCMS (ESI) m/e 224.2 [(M+H), calcd for C11H14N04, 224.1]; LC/MS retention time (method B): tR = 1.21 mm.
91%
Stage #1: With triethylamine In dichloromethane at 0℃; for 0.166667 h;
Stage #2: for 3 h;
To a solution of methyl 4-amino-2-methoxybenzoate (2.0 g, 0.0 11 mol) in DCM (50 mL) cooled to 0 °C was added triethylamine (3.0 mL, 0.022 mol) and the reaction mixture was stirred for 10 minutes. Acetyl chloride (1.3 g, 0.0 165 mol) was addeddropwise and the reaction was stirred for 3 h. Water (50 mL) was added and the aqueous layer was extracted with DCM (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and volatiles were evaporated to dryness under reduced pressure to give methyl 4-acetamido-2-methoxybenzoate (2.3 g, 0.01 mol, 91percent yield) as a light brown solid. ‘H NMR (400 MHz, DMSO-d6) ö 10.22 (s,1H), 7.66 (d, J= 8.8 Hz, 1H), 7.47 (d, J= 1.6 Hz, 1H), 7.20 (dd, J 8.4, 2.0 Hz, 1H),3.74-3.79 (m, 6H), 2.07 (s, 3H); LCMS (ESI) m/e 224.2 [(M+H), calcd for C11H14NO4, 224.08]; LC/MS retention time (method B): ti = 1.20 mm.
Reference: [1] Patent: WO2015/6100, 2015, A1, . Location in patent: Page/Page column 176
[2] Patent: WO2016/53794, 2016, A1, . Location in patent: Page/Page column 125; 126
  • 6
  • [ 50-86-2 ]
  • [ 584-08-7 ]
  • [ 77-78-1 ]
  • [ 4093-29-2 ]
Reference: [1] Patent: US4138492, 1979, A,
  • 7
  • [ 65-49-6 ]
  • [ 4093-29-2 ]
Reference: [1] Tetrahedron, 1986, vol. 42, # 12, p. 3259 - 3268
[2] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493
[3] Patent: WO2015/26792, 2015, A1,
  • 8
  • [ 4136-97-4 ]
  • [ 4093-29-2 ]
Reference: [1] Tetrahedron, 1986, vol. 42, # 12, p. 3259 - 3268
[2] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493
  • 9
  • [ 50-86-2 ]
  • [ 77-78-1 ]
  • [ 4093-29-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1990, vol. 25, # 6, p. 467 - 477
  • 10
  • [ 39106-79-1 ]
  • [ 4093-29-2 ]
Reference: [1] Patent: WO2015/6100, 2015, A1,
[2] Patent: WO2016/53794, 2016, A1,
  • 11
  • [ 4093-28-1 ]
  • [ 77-78-1 ]
  • [ 4093-29-2 ]
Reference: [1] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493
  • 12
  • [ 67-56-1 ]
  • [ 55304-05-7 ]
  • [ 4093-29-2 ]
Reference: [1] Asian Journal of Chemistry, 2011, vol. 23, # 3, p. 1314 - 1316
  • 13
  • [ 4093-29-2 ]
  • [ 4093-31-6 ]
YieldReaction ConditionsOperation in experiment
90.3% With N-chloro-succinimide In N,N-dimethyl-formamide at 40 - 65℃; for 9 h; The 136gN, N-dimethyl formamide stock solution to 1L in the reaction bottle, inputs 50g4-acetamido-2-methoxybenzoic acid methyl ester, the agitation dissolves clear, inputs 50gN-chloro succinimide, slow heating to 40 °C, thermal insulation reaction 5h, and then raising the temperature to 65 °C, thermal insulation reaction 4h; after the reaction, cooling to 0 °C thermal crystallization 8h, by the splash zone 4-acetamido-5-chloro-2-methoxybenzoic acid methyl ester crude wet product, N, reservations N-dimethyl formamide mother liquor; the 4-acetamido-5-chloro-2-methoxybenzoic acid methyl ester product added to the wet product 100g deionized water, the temperature is increased to 50 °C insulating 4h, cooling to 5 °C filtered, dried to obtain the kind of white 4-acetamido-5-chloro-2-methoxybenzoic acid methyl ester 52.1g, molar yield 90.3percent, HPLC purity ≥ 99.8percent.
Reference: [1] Patent: CN105523952, 2016, A, . Location in patent: Paragraph 0029
[2] Journal of the American Chemical Society, 2006, vol. 128, # 23, p. 7416 - 7417
[3] Archiv der Pharmazie, 1980, vol. 313, # 4, p. 297 - 300
[4] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493
  • 14
  • [ 4093-29-2 ]
  • [ 201214-53-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3561 - 3572
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