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[ CAS No. 4093-31-6 ] {[proInfo.proName]}

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Chemical Structure| 4093-31-6
Chemical Structure| 4093-31-6
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Product Details of [ 4093-31-6 ]

CAS No. :4093-31-6 MDL No. :MFCD00048191
Formula : C11H12ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :OUEXNQRVYGYGIK-UHFFFAOYSA-N
M.W :257.67 Pubchem ID :77721
Synonyms :

Calculated chemistry of [ 4093-31-6 ]

Physicochemical Properties

Num. heavy atoms : 17
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 : 63.54
TPSA : 64.63 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) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.65
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 1.9
Log Po/w (MLOGP) : 1.69
Log Po/w (SILICOS-IT) : 2.03
Consensus Log Po/w : 1.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.35
Solubility : 1.16 mg/ml ; 0.00452 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.784 mg/ml ; 0.00304 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.61
Solubility : 0.0634 mg/ml ; 0.000246 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.03

Safety of [ 4093-31-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4093-31-6 ]

* 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 [ 4093-31-6 ]
  • Downstream synthetic route of [ 4093-31-6 ]

[ 4093-31-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 4093-31-6 ]
  • [ 7206-70-4 ]
YieldReaction ConditionsOperation in experiment
84% With hydrogenchloride In ethanol; water EXAMPLE 14
2-methoxy-4-amino-5-chloro benzoic acid
25.75 grs (0.1 mol) methyl 2-methoxy-4-acetamido-5-chlorobenzoate were introduced into a 500 ml flask, suspended in 100 ml ethanol.
40 grs NaOH, dissolved in 150 cc of water, were added and the mixture was heated under reflux for 2.5 hours.
The mixture was diluted with water and made acid with concentrated HCl.
The white solid which precipitated was collected and recrystallized from methanol. Weight: 17 grs m.p. = 213°-215° C. Yield = 84percent.
Reference: [1] Patent: US4138492, 1979, A,
[2] Patent: US2005/49416, 2005, A1, . Location in patent: Page/Page column 11
[3] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493
  • 2
  • [ 4093-31-6 ]
  • [ 100-36-7 ]
  • [ 364-62-5 ]
Reference: [1] Archiv der Pharmazie, 1980, vol. 313, # 4, p. 297 - 300
  • 3
  • [ 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
  • 4
  • [ 20896-27-9 ]
  • [ 108-24-7 ]
  • [ 4093-31-6 ]
YieldReaction ConditionsOperation in experiment
80% at 50℃; for 5 h; Step 2.
Methyl 4-acetamido-5-chloro-2-methoxybenzoate
A solution of methyl 4-amino-5-chloro-2-methoxybenzoate (28 g, 129.85 mmol) and acetic anhydride (16 g, 156.73 mmol) in AcOH (150 mL) was stirred for 5 hours at 50° C.
The reaction was concentrated in vacuo, diluted with water (150 mL), adjusted to pH 8 with aqueous sodium bicarbonate (3N), and extracted with ethyl acetate (2*200 mL).
The organic layers were combined and dried over anhydrous magnesium sulfate and concentrated in vacuo to afford methyl 4-acetamido-5-chloro-2-methoxybenzoate as a light yellow solid (27 g, 80percent).
LC/MS (ES, m/z): [M+H]+ 258.0
1H-NMR (300 MHz, CDCl3) δ 8.31 (s, 1H), 7.88 (s, 1H), 7.79 (s, 1H), 3.93 (s, 3H), 3.88 (d, J=8.4 Hz, 3H), 2.28 (s, 3H)
Reference: [1] Patent: US2012/277224, 2012, A1, . Location in patent: Page/Page column 59
  • 5
  • [ 538372-32-6 ]
  • [ 4093-31-6 ]
Reference: [1] Patent: US2005/26174, 2005, A1,
  • 6
  • [ 20896-27-9 ]
  • [ 4093-31-6 ]
Reference: [1] Patent: US4863921, 1989, A,
  • 7
  • [ 27492-84-8 ]
  • [ 4093-31-6 ]
Reference: [1] Archiv der Pharmazie, 1980, vol. 313, # 4, p. 297 - 300
  • 8
  • [ 4093-28-1 ]
  • [ 4093-31-6 ]
Reference: [1] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493
  • 9
  • [ 65-49-6 ]
  • [ 4093-31-6 ]
Reference: [1] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493
  • 10
  • [ 4136-97-4 ]
  • [ 4093-31-6 ]
Reference: [1] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493
  • 11
  • [ 7206-70-4 ]
  • [ 4093-31-6 ]
Reference: [1] Patent: US2012/277224, 2012, A1,
  • 12
  • [ 4093-31-6 ]
  • [ 24190-77-0 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With boron trichloride In dichloromethane at 0 - 15℃; for 4 h;
Stage #2: With water In dichloromethane
A stirred suspension of methyl 4-(acetylamino)-5-chloro-2- (methyloxy)benzoate (103g, 0.4mol) in dry DCM (460ml) was cooled to 00C under argon. A solution of BCI3 in DCM (1 M) (800ml) was then cannulated directly from the reagent bottle with argon pressure by T-piece bleed control so that the rate of addition was easily controlled. The apparatus was set to control the internal temperature at 00C during the addition. The addition was carried out over 55 minutes. The temperature range (internally) varied 0-->11°C. During the addition the apparatus was kept under argon only by the supply of BCI3 through argon pressure. The vessel was capped with a silica drying tube. The suspension was present throughout the addition - it did not dissolve at any stage. After the complete addition of the BCI3 solution the temperature was adjusted to 15°C and stirred for 1.5 hours under argon. After 1.5 hours under argon the mixture was poured into water (1 L), ice (35Og) with stirring and more DCM (0.8L) and water (0.8L) was added to this mixture. The whole mixture was transferred to a 5L separating funnel and vigorously shaken (solids virtually dissolved). Layers were separated and the aqueous layer extracted with DCM (2x 0.8L). The combined organic extracts were dried (MgSO4) and combined with the same extract obtained from repeating the above-mentioned reaction using the same reactant quantities. The combined extracts from the two experiments were concentrated in vacuo to a cream solid. This solid was stirred with Et2O (800ml) for 10 minutes. Then hexane (800ml) was added and the reaction continued to stir at room temperature for 0.5 hours. The solid was then filtered and washed with hexane (2 x 300ml) and dried at 45°C under vacuum for 16 hours (185g, 0.759mol, 95percentth) and identified as pure product. <n="25"/>LCMS RT 2.44 mins (MH+)HPLC -99percent (RT 11.9 min) at 254nm detection
Reference: [1] Patent: WO2007/96352, 2007, A1, . Location in patent: Page/Page column 12; 23-24
[2] Patent: WO2006/133802, 2006, A1, . Location in patent: Page/Page column 74-75
  • 13
  • [ 4093-31-6 ]
  • [ 538372-37-1 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5707 - 5716
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