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[ CAS No. 41019-56-1 ] {[proInfo.proName]}

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Chemical Structure| 41019-56-1
Chemical Structure| 41019-56-1
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Product Details of [ 41019-56-1 ]

CAS No. :41019-56-1 MDL No. :MFCD15144218
Formula : C10H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :QUPMFELCGIVSMG-UHFFFAOYSA-N
M.W :176.17 Pubchem ID :22326486
Synonyms :

Calculated chemistry of [ 41019-56-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.49
TPSA : 39.44 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) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 2.18
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 1.38
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 2.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.69
Solubility : 0.363 mg/ml ; 0.00206 mol/l
Class : Soluble
Log S (Ali) : -2.64
Solubility : 0.402 mg/ml ; 0.00228 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.36
Solubility : 0.0769 mg/ml ; 0.000437 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.33

Safety of [ 41019-56-1 ]

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 [ 41019-56-1 ]

* 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 [ 41019-56-1 ]
  • Downstream synthetic route of [ 41019-56-1 ]

[ 41019-56-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 67-56-1 ]
  • [ 177734-79-1 ]
  • [ 201230-82-2 ]
  • [ 41019-56-1 ]
YieldReaction ConditionsOperation in experiment
81% With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In dimethyl sulfoxide at 80℃; for 18 h; A mixture of 130 (3.88 g, 14.6 mmol), DPPP (0.180 g, 0.44 mmol), triethylamine (4.07 mL, 29.2 mmol) and Pd(OAc)2 (0.098 g, 0.44 mmol) in DMSO (50 mL) and MeOH (50 mL) in a Berghof pressure reactor was evacuated then purged three times with carbon monoxide. The mixture was heated to 80 °C for 18 h under 60 psi of carbon monoxide pressure, cooled and partitioned between EtOAc and water. Column chromatography with 3 : 1 hexanes:DCM eluted traces of impurities while elution with DCM gave 131 (2.08 g, 81percent). 1H NMR (CDC13) δ 7.99 (dd, J = 7.7, 0.9 Hz, 1H), 7.74 (d, J = 2.2 Hz, 1H), 7.70 (dt, J = 8.2, 0.9 Hz, 1H), 7.33-7.39 (m, 2H), 3.99 (s, 3H).
81% With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In dimethyl sulfoxide at 80℃; for 18 h; A mixture of the above sulfonate (3.88 g, 14.6 mmol), DPPP(0.180 g, 0.44 mmol), triethylamine (4.07 mL, 29.2 mmol) and Pd(OAc)2 (0.098 g, 0.44 mmol) in DMSO (50 mL) and MeOH (50 mL)in a Berghof pressure reactor was evacuated then purged threetimes with carbon monoxide. The mixture was heated to 80 Cfor 18 h under 60 psi of carbon monoxide pressure, cooled and partitioned between EtOAc and water. Column chromatographywith 3:1 hexanes:DCM eluted traces of impurities while elutionwith DCM gave methyl benzofuran-4-carboxylate (2.08 g, 81percent).1H NMR (CDCl3) d 7.99 (dd, J = 7.7, 0.9 Hz, 1H), 7.74 (d, J = 2.2 Hz,1H), 7.70 (dt, J = 8.2, 0.9 Hz, 1H), 7.33–7.39 (m, 2H), 3.99 (s, 3H).
Reference: [1] Patent: WO2017/155909, 2017, A1, . Location in patent: Paragraph 0189
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
  • 2
  • [ 1151739-02-4 ]
  • [ 41019-56-1 ]
YieldReaction ConditionsOperation in experiment
98% With methanesulfonic acid In toluene at 20℃; for 2 h; Example 5Aromatization Unless mentioned otherwise, all the volumes are calculated from 2-methoxy-2,3-dihydrobenzofuran-4-carboxylic acid methyl ester (II).841 g of methane sulfonic acid (8.75 mol, 2 mol/mol) are added to the previous toluene solution while maintaining the temperature at 20° C.The reaction medium is stirred at 20° C. for 2 hours. The reaction medium is then cooled to 10° C., 3 water volumes are added while maintaining the temperature of the medium at 10° C.The phases are separated and the lower aqueous phase is then extracted with 2 volumes of toluene. The collected toluene phases are washed with 2.x.2 volumes of water and then with 2.x.2 volumes of 1N soda.The insolubles formed in the basic medium are left in the organic phase, the toluene phase is clarified and introduced as such to the following step. 747 g of 4-benzofuran-carboxylic acid methyl ester are obtained in solution in toluene with a 98percent yield.The reaction medium is extracted and then concentrated.A white solid is obtained corresponding to the compound of formula (I), 4-benzofuran-carboxylic acid methyl ester.1H NMR (200 MHz, CDCl3) δ (ppm): 3.97 (3H, s, CH3); 7.33-7.36 (1H, m, CH), 7.66-7.72 (1H, m, CH), 7.95-7.98 (1H, m, CH).13C NMR (50 MHz, CDCl3) δ (ppm): 51.9; 107.7; 115.8; 122.7; 123.5; 125.3; 127.8; 146.4; 155.1; 166.7.GPC/MS (EI): [M+H]+=177; ion fragments: 145; 133; 105; 91; 59. Mp (° C.): 40.1° C.
Reference: [1] Patent: US2009/131688, 2009, A1, . Location in patent: Page/Page column 11
  • 3
  • [ 166599-85-5 ]
  • [ 41019-56-1 ]
YieldReaction ConditionsOperation in experiment
53% at 20℃; for 0.5 h; The product from Step A (8.0 g, 41.0 mmol) was stirred in H3PO4 (85percent, 50 ml) at room temperature for 30 minutes.
The resulting cloudy mixture was diluted with water and extracted (4*) with diethyl ether.
The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and the solvent removed in vacuo.
The crude material was purified by flash chromatography on silica gel (20:1 hexanes/ethyl acetate) to afford benzofuran methyl ester 3.87 g (53percent) as a light yellow oil: 1H NMR (300 MHz, CDCl3) δ7.99 (d, 1H, J=7.1 Hz), 7.68-7.74 (m, 2H), 7.32-7.38 (m, 2H), 3.99 (m, 3H); CI MS m/z=177 [C10H8O3+H]+.
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
[2] Patent: US2006/111385, 2006, A1, . Location in patent: Page/Page column 9; 16
  • 4
  • [ 79250-46-7 ]
  • [ 41019-56-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
  • 5
  • [ 79950-39-3 ]
  • [ 41019-56-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
  • 6
  • [ 480-97-7 ]
  • [ 41019-56-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
  • 7
  • [ 41019-56-1 ]
  • [ 166599-84-4 ]
YieldReaction ConditionsOperation in experiment
99% With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 16 h; A solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) was added to a solution of 131 (2.02 g, 11.4 mmol) in THF (20mL) and MeOH (20 mL) and the solution was stirred at r.t. for 16 h and then evaporated. The residue was dissolved in water (50 mL) and acidified with cone. HC1 and the precipitate was filtered and dried to give 132 (1.83 g, 99percent). 1H NMR (DMSO-d6) δ 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H), 7.85-7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz, 1H). Found: [M-H] = 161.1.
99%
Stage #1: With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 16 h;
Stage #2: With hydrogenchloride In water
A solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) wasadded to a solution of the above ester (2.02 g, 11.4 mmol) in THF(20 mL) and MeOH (20 mL) and the solution was stirred at 20 Cfor 16 h and then evaporated. The residue was dissolved in water(50 mL) and acidified with conc. HCl and the precipitate was filteredand dried to give benzofuran-4-carboxylic acid (1.83 g,99percent). 1H NMR (DMSO d6) d 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H),7.85–7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz,1H). Found: [MH] = 161.1.
Reference: [1] Patent: WO2017/155909, 2017, A1, . Location in patent: Paragraph 0190
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
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