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[ CAS No. 77095-51-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 77095-51-3
Chemical Structure| 77095-51-3
Chemical Structure| 77095-51-3
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Product Details of [ 77095-51-3 ]

CAS No. :77095-51-3 MDL No. :MFCD01006751
Formula : C9H6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :RVDHGRQELZPGCO-UHFFFAOYSA-N
M.W : 162.14 Pubchem ID :17867234
Synonyms :

Calculated chemistry of [ 77095-51-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.17
TPSA : 50.44 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) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 2.13
Log Po/w (MLOGP) : 1.08
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 1.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.513 mg/ml ; 0.00316 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.478 mg/ml ; 0.00295 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.65
Solubility : 0.363 mg/ml ; 0.00224 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.07

Safety of [ 77095-51-3 ]

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

Application In Synthesis of [ 77095-51-3 ]

* 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.

  • Downstream synthetic route of [ 77095-51-3 ]

[ 77095-51-3 ] Synthesis Path-Downstream   1~60

  • 1
  • [ 588703-29-1 ]
  • [ 77095-51-3 ]
YieldReaction ConditionsOperation in experiment
100% With lithium hydroxide; water; In tetrahydrofuran; at 20℃; for 1h; A mixture of 20 mmol of compound 1.10 and 80 mmol of LiOH-H20 in 60 mL of THF and 15 mL of H20 was stirred at room temperature for 1 hour, followed by adding 80 mL of 1. ON aq. HC1. The organic solvent was removed and the residue was diluted with 50 mL of brine. The mixture was then extracted with EtOAc, and the extract was dried with anyhydrous Na2S04. The solvent was removed and the residue was dried in vacuo to give a quantitative yield of compound 1. 11. 1H NMR (400 MHz, CD30D) : No. 8.14 (s, 1H), 7.92 (m, X2H), 7.67 (d, J=8. 5 Hz, 1H), 6.92 (s, 1H) ppm; ESI-MS (mlz) : (M+H 163.1.
97% With water; lithium hydroxide; In methanol; [00132] The benzofuranyl carbonyl moiety was prepared by protecting the hydroxyl groupof compound 13 by reacting with tert-butyldimethylsilyl chloride (1.0 equivalents) andtriethylamine (TEA, 1.1 equivalents) in acetone, to give compound 14 in 79% yield. A solutionof compound 14 in methanol was then treated with sodium borohydride (1.0 equivalent) at roomtemperature overnight. The reaction was quenched with an addition of acetone, stirred at roomtemperature for a further 2.5 hours, aqueous HC1 (4N) was added with the temperature controlledto below 28 C, tetrahydrofuran (THF) was added, and the solution stirred overnight under argonand in the absence of light. The product, compound 15, was isolated quantitatively by extractioninto methylene chloride, concentrated at low heat, and used without further purification. Thetriflate ester, compound 16, was produced in 69% yield from compound 15 by reacting it with Nphenyl-bis(trifluoromethanesulfonimide) (1.0 equivalent) in methylene chloride for 72 hours.Compound 16 in a mixture of DMF, methanol, and triethylamine, was added to a preparedsolution of palladium acetate, 1,3-Bis(diphenylphosphino)propane (dppp), DMF and methanol inan autoclave. Carbon monoxide was charged into the autoclave to a pressure of 8 bar, and the reaction mixture was heated at 70 C for 6 hours. After workup, compound 17 was isolated in 91% yield. Lithium hydroxide (4 equivalents) in methanol and water was used to hydrolyze the ester and permit the isolation of compound 18? in 97% yield.
95% With hydrogenchloride; In dichloromethane; water; at 20℃; for 2h; Methyl 6-formate benzofuran 15.3 g (0.0869 mol)Dissolved in 100mL of dichloromethane, dissolved and added with concentrated hydrochloric acid (37%) 20ml,After stirring at room temperature for 2 h, the reaction was completely monitored by TLC, and washed twice with saturated brine.After 100 mL of each time, the dichloromethane layer was dried over anhydrous magnesium sulfate, filtered, and dichloromethane evaporated.Obtaining 13.37 g of benzofuran 6-formic acid,Yield 95%, HPLC purity 98%,
  • 2
  • [ 77095-51-3 ]
  • benzofuran-6-carboxylic chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride; N,N-dimethyl-formamide; In toluene;Inert atmosphere; Heating; Benzofuran-6-carboxylic acid (50.0 g, 0.308 moles), toluene and a catalytic amount of dimethyl formamide (DMF) are added, in sequence, to a reactor in N2 atmosphere. The suspension is heated under stirring to 55±5C. SOCl2 (0.370 moles) dissolved in toluene is added slowly, maintaining the temperature at 55±5C until conversion is complete. The solution is then concentrated under vacuum until an almost solid yellow residue is obtained. Residue = 55.6 g, molar yield = quantitative. ?HNMR (300MHz, CDC13): d 8.32 (s,lH), 8.01 (dd,l H,J;=8.3 l Hz J2=l .34Hz), 7.87 (d, 1 H, =2.08 Hz), 7.69 (d, 1 H, J=8.31 Hz), 6.88 (br d, 1 H).
With oxalyl dichloride; In N,N-dimethyl-formamide; for 5.5h; [00142] The benzofuran carboxylic acid 18? was treated with oxalyl chloride (1.2 equivalents) and a catalytic amount of DMF, stirring for 5.5 hours until a clear solution was obtained. The solvent was removed under reduced pressure and the acid chloride of compound 18? was stored under argon until use, on the next day. The acid chloride, in methylene chloridewas added slowly to a methylene chloride solution of the compound of Formula 12 and diisopropylethylamine (DIPEA) which was cooled to 0-5 C. The reaction was not permitted to rise above 5C, and after completion of addition, was stirred at 5C for a further 0.5 hour. Upon aqueous workup and extraction with methylene chloride, the product, compound 19, was isolated in quantitative yield.
With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 0℃; for 0.166667h; To a solution of the compound benzofurancarboxylic acid (9) in THF was added dropwise oxalyl chloride (1.2 equivalents) and a small amount of DMF in 10 minutes. The reaction solution was stirred at 0 C until a clear solution was obtained. TLC and LCMS show that the starting material (9) is consumed and the solvent is removed under reduced pressure. The resulting acid chloride compound was dissolved in methylene chloride under argon and allowed to cool to 0-5 C. To a solution of the intermediate (8) and diisopropylethylamine (DIPEA) in dichloromethane was slowly added under cooling with ice. After completion of the addition, the mixture was stirred at 5 C for 0.5 hour. LCMS and TLC show that the intermediate reaction is complete. The reaction was quenched by addition of water, extracted with dichloromethane, and the combined organic phases were washed with water. Dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude product. The crude product was purified by silica gel column chromatography (eluent MeOH: DCM = 1: 10) to give the product compound (10) in a yield of 70-90%.
With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 20 - 30℃; for 2h;Inert atmosphere; Benzofuran carboxylic acid (II) (1.0 g, 6.17 mmol, 1.0 equiv), DMF (0.01 eq) and THF (10 mL, 10 vol) is charged to a two-neck round bottom flask under nitrogen atmosphere. Oxalyl chloride (1.1 mL, 13.34 mmol, 2.0 equiv) is slowly added while keeping the temperature between 20 to 30 C. The resulting solution was stirred at 20-30 C. for over 2 hr. When the reaction was complete as determined by TLC analysis, the solvent was removed under reduced pressure and the acid chloride of compound of Formula II (Formula IIb) was stored under nitrogen.
With thionyl chloride; In N,N-dimethyl-formamide; acetonitrile; at 0 - 30℃; for 3.5h; Benzofuran-6-carboxylic acid (compound of formula VII, 10 gm), acetonitrile (240 mL) and N,N-Dimethylformamide (1 mL) were charged into a 1000 mL RBF and the mixture was cooled to 0 C. Thionyl chloride (17.61 gm) was added slowly over a period of 30 minutes. The resulted mixture was stirred for 3 hours at 30 C. The reaction mixture was concentrated completely under vacuum and the resulted crude was dissolved in acetonitrile (15 mL). Compound of formula V-A (HCI salt, 17.43 gm) and N,N- Dimethylacetamide (50 mL) were charged into another RBF and stirred for 10 minutes. To the clear solution Hunig's base (DIPEA, 31 .9 gm) was added. The reaction mixture was cooled to 0 C and above acid chloride solution was added slowly over a period of 30 minutes and the reaction mixture was stirred for 30 minutes at 15 C. Water (100 mL) and aqueous hydrochloric acid were added and stirred for 10 minutes. Isopropyl alcohol (25 mL) was added and stirred for 2 hours. The precipitation was filtered and the solid was washed with water (50 mL). The wet solid and MTBE (80 mL) were charged into 500 mL RBF and stirred for 30 minutes. The precipitation was filtered and the solid was washed with MTBE (50 ml_). The wet solid and isopropyl alcohol (75 ml_) were charged into 500 ml_ RBF and stirred for 30 minutes. The precipitation was filtered and the solid was washed with isopropyl alcohol (30 ml_). The wet compound was dried under vacuum at 50 C for 3 hours to yield 19 gm of compound of formula VIII. Purity: 93.3 by HPLC. Example-5: Purification of compound of formula VIIIEthylacetate (80 ml_) and compound of formula VIII (18 gm) were charged into a 500 ml_ RBF and stirred for 10 minutes. 5% Sodium bicarbonate solution was charged into the mass and stirred for 10 minutes at 28 C. Layers were separated and the aqueous layer was washed with ethylacetate. The aqueous layer was treated with charcoal and filtered through a hyflow bed. The aqueous layer was charged into another 1000 ml_ RBF and aqueous hydrochloric acid was added slowly by stirring the aqueous layer. The resulted mixture was stirred for 1 hour at 28 C. The precipitation was filtered and washed with water. The wet compound was slurried in isopropyl alcohol and the suspension was filtered and washed with isopropyl alcohol. The wet compound was dried under vacuum at 60C. Dry weight: 17 g. Purity: 98.015% by HPLC.
With thionyl chloride; In dichloromethane; l-<strong>[77095-51-3]benzofuran-6-carboxylic acid</strong> (5.0 g) was charged in dichloromethane and added thionyl chloride (4.5 g) followed by stirring to get clear solution. The solvent was removed under reduced pressure, MDC (20 ml) was charged to the residue. The acid chloride, in methylene chloride was added slowly to a solution of (S)-2-(5,7-dichloro-l,2,3,4- tetrahydroisoquinoline-6-carboxamido)-3-(3-(methyl sulfonyl)phenyl)propanoic acid (13.8 g) and diisopropylethyl amine (10 ml) below 5C. Reaction mass was stirred at 0-5C till, completion of reaction. Reaction mass was then quenched with water 25ml. Layers were separated and organic layer washed with sodium bicarbonate solution. Organic layer concentrated to get crude Lifitegrast. Crude lifitegrast was recrystaliized in acetone. (13 g, yield-72.8%)
With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 15 - 40℃; for 2h; Benzofuran-6-carboxylic acid (VI) (50 gms , 0.3086 moles) was suspended in 250 ml MDC and cooled to l5-20C. 5 ml DMF was added at l5-20C followed by thionyl Chloride ( 34 ml , 0.4629 moles). The temperature was raised to 35-40C and the reaction mixture was further stirred for 2 hours. The solvent was removed under vacuum at 45C. The residue was stirred in 250 ml MDC and the solution was cooled to 5-l0C. The solution of 5,7-dichloro-l,2,3,4-tetrahydroisoquinoline- 6-carboxylic acid HC1 (V) ( 74.12 gms , 0.2623 moles) and tri ethyl amine ( 215 ml , 1.5432 moles) in 500 ml MDC , was cooled to 5-l0C. To this solution was added benzofuran-6-carboxylic chloride (VII) maintaining temperature at 5-l0C. The temperature was raised to 25-30C and the reaction mixture was further stirred for 2 hours. The reaction mixture was quenched in 500 ml of water. The organic layer was separated, washed with water and stirred with 2.5 gms of charcoal for 30 minutes. The reaction mixture was filtered over hyflo and the clear filtrate evaporated under vacuum at 40-45C. The residue was stirred in 250 ml ethyl acetate and stirred for an hour at 25-30C. The solid was isolated by filtration and dried to yield titled compound. Yield: 95-98%

  • 4
  • [ 77095-51-3 ]
  • [ 6530-09-2 ]
  • N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In DMF (N,N-dimethyl-formamide); at 0℃; for 18h; 1-Benzofuran-6-carboxylic acid (162 mg, 1.0 mmol) is combined with (R)-3-aminoquinuclidine dihydrochloride (219 mg, 1.1 mmol), DIEA (522 muL, 3.0 mmol) and DMF (5 mL), cooled to 0 C., treated with HATU (380 mg, 1.0 mmol) and stirred for 18 h as the cooling bath expired. The mixture is concentrated under high vacuum and partitioned between a 1:1 solution of saturated NaCl/conc. NH4OH (10 mL) and CHCl3 (3×10 mL). The organics are dried (Na2SO4) and concentrated to an oil (530 mg). The crude material is chromatographed over 11 g slurry-packed silica gel, eluting with 2% conc. NH4OH/10% MeOH/CHCl3. The appropriate fractions are combined and concentrated to a dark yellow solid (274 mg). The solid is placed under high vacuum, dissolved in MeOH (5 mL), treated with 3N HCl MeOH (1 mL), stirred for 16 h, then concentrated to dryness. The residue is dissolved in MeOH (1 mL) and IPA (10 mL) and treated with Et2O (20 mL) until turbid. The mixture is stirred for 16 h, filtered under nitrogen and dried in a vacuum oven at 50 C. to afford 206 mg (67%) of Example 5 as an off-white solid. HRMS (FAB) calcd for C16H18N2O2+H: 271.1446, found 271.1447 (M+H)+. EXAMPLE 6
  • 5
  • [ 478169-68-5 ]
  • [ 77095-51-3 ]
  • 6
  • [ 157942-12-6 ]
  • [ 77095-51-3 ]
  • 7
  • [ 77095-51-3 ]
  • 6-(4,4-dimethyl-2-oxazolin-2-yl)benzo<b>furan [ No CAS ]
  • 8
  • [ 77095-51-3 ]
  • benzofuran-6-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide [ No CAS ]
  • 9
  • [ 103204-81-5 ]
  • [ 77095-51-3 ]
  • 10
  • [ 79250-46-7 ]
  • [ 77095-51-3 ]
  • 11
  • [ 79950-41-7 ]
  • [ 77095-51-3 ]
  • 12
  • 4-Allyl-3-hydroxy-benzoyl chloride [ No CAS ]
  • [ 77095-51-3 ]
  • 13
  • [ 166599-86-6 ]
  • [ 77095-51-3 ]
  • 14
  • [ 24589-98-8 ]
  • [ 77095-51-3 ]
  • 15
  • [ 77095-51-3 ]
  • N-(2S,3R)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride [ No CAS ]
  • [ 588705-51-5 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 72h; 1-Benzofuran-6-carboxylic acid (0.16 g, 1.0 mmol), HATU (0.46 g, 1.2 mmol) and 2S-methyl-2.2.2-Amine (0.213 g, 1.0 mmol) are dissolved in 12 mL CH3CN. DIEA (1.4 mL, 8.0 mmol) is added dropwise. After 3 days, the solvent is removed in vacuo. The residue is taken up in CHCl3, 1N NaOH is added and the mixture is extracted with CHCl3. The combined organic layers are dried (MgSO4), filtered and concentrated. The residue is purified by chromatography (Biotage 40S, 90:9:1 CHCl3/MeOH/NH4OH). The hydrochloride salt is prepared and recrystallized from MeOH/EtOAc to provide 203 mg (63%) of the product. HRMS (FAB) calculated for C17H20N2O2+H=285.1603, found 285.1617.
  • 16
  • [ 77095-51-3 ]
  • [ 851784-90-2 ]
  • [ 851784-92-4 ]
YieldReaction ConditionsOperation in experiment
92% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;dmap; In DMF (N,N-dimethyl-formamide); at 20℃; for 15h; e) Example 3.5 (10 mmol) was mixed with EDC (2.11 g, 11 mmol), ) N, N-dimethylaminopyridine ("DMAP", 0.1 g), triethylamine (2.02 g) and Example 1.11 (1.62g, 10 mmol) in anhydrous DMF (50 mL). After 15 hours at room temperature, the reaction mixture was diluted with ethyl acetate (200 mL), washed with water (30 mL, 3 times), dried with anhydrous magnesium sulfate and filtered. The residue after concentration of the filtrate was purified by column eluting with 10-30% ethyl acetate in hexane to give the title compound (3.7 g, 92%) : ESI-MS (m/z) : (M+1) 213.1.
A solution of <strong>[77095-51-3]benzofuran-6-carboxylic acid</strong> (7.75 g, 0.478 mmol) in tetrahydrofuran (67.5 ml) was added with triethylamine (23.03 g, 2.275 mmol) and 3- [bis(dimethylamino)methyliumyl] -377-benzotriazol- 1 -oxide hexafluoro phosphate (HBTU, 18.98 g, 0.50 mmol) for 30 minutes at 25-35C. Dichloro quinoline ester (13.5 g, 0.455 mmol) was added to the above reaction mixture at 25-35C and stirred at 25-35C for 3 hours. Water (162 ml) was added to the reaction mass at 25-35C and stirred the mass for 1 h at 25-35C. The product was filtered and washed with water. The filter cake was washed with methanol. The compound was dried in vacuum oven at 60-65 C.
  • 17
  • [ 478169-68-5 ]
  • [ 77095-51-3 ]
  • [ 501892-53-1 ]
YieldReaction ConditionsOperation in experiment
1.83 g (93%) With sodium hydroxide; copper(I) iodide; In methanol; ethanol; water; triethylamine; Methyl-3-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate (3.0 g, 12.1 mmol) is dissolved in 30 ml 1:1 EtOH/Et3N, is treated with cuprous iodide (114 mg, 0.6 mmol), and the reaction is warmed to 75° C. for 3 h. The mixture is treated with DARCO and 15 ml MeOH and is heated to reflux for 1 h. The reaction is filtered through a fine fritted glass funnel, the filtrate is treated with 3N NaOH (24.2 ml, 72.5 mmol), and the mixture is stirred overnight at RT. The mixture is concentrated to dryness, the residue is dissolved in 20 ml water, and the pH of the mixture is adjusted to 2 with 12N HCl. The resulting yellow precipitate is collected, washed with water, and is dried to give 1.83 g (93percent) of benzofuran-6-carboxylic acid as a tan solid. HRMS (FAB) calcd for C9H6O3+H: 163.0395, found 163.0389 (M+H)+.
  • 18
  • [ 110-52-1 ]
  • [ 109-72-8 ]
  • [ 77095-51-3 ]
  • 2-(4-bromobutyl)benzofuran-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N,N,N,N,N-hexamethylphosphoric triamide; diisopropylamine; In tetrahydrofuran; hexane; A. 2-(4-Bromobutyl)<strong>[77095-51-3]benzofuran-6-carboxylic acid</strong> n-Butyllithium solution (2.29 M in hexane, 44 ml., 0.1 mole) is added to a solution of diisopropylamine (10.1 g., 0.1 mole) in tetrahydrofuran (150 ml.) and hexamethylphosphoramide (15 ml.). The resulting solution is treated with <strong>[77095-51-3]benzofuran-6-carboxylic acid</strong> (8.1 g., 0.05 mole) and then with 1,4-dibromobutane (10.8 g., 0.05 mole) at 0 C. The mixture is stirred at 0 C. for 6 hours. It is then quenched with water, acidified with hydrochloric acid and extracted with ethyl acetate. Evaporation of the solvent gives 2-(4-bromobutyl)<strong>[77095-51-3]benzofuran-6-carboxylic acid</strong>.
  • 19
  • 3-amino-1, 1-dichloro-3-methyl-2-pentanone hydrochloride [ No CAS ]
  • [ 77095-51-3 ]
  • [ 202195-49-1 ]
  • 20
  • [ 478169-68-5 ]
  • [ 67-56-1 ]
  • [ 77095-51-3 ]
YieldReaction ConditionsOperation in experiment
93% Methyl 3-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate (3.0 g, 12.1 mmol) is dissolved in 1:1 EtOH/Et3N (30mL), is treated with CuI (114 mg, 0.6 mmol), and the reaction is warmed to 75° C. for 3 h. The mixture is treated with DARCO and MeOH (15 mL) and heated to reflux for 1 h. The reaction is filtered through a fine fritted-glass funnel, the filtrate is treated with 3N NaOH (24.2 ml, 72.5 mmol), and the mixture is stirred overnight at RT. The mixture is concentrated to dryness, the residue is dissolved in H2O (20 mL), and the pH of the mixture is adjusted to 2 with 12N HCl. The resulting yellow precipitate is collected, washed with water, and is dried to give 1.83 g (93percent) of benzofuran-6-carboxylic acid as a tan solid. HRMS (FAB) calcd for C9H6O3+H: 163.0395, found 163.0389 (M+H)+.
  • 21
  • [ 77095-51-3 ]
  • [ 198554-72-2 ]
  • [ 198554-13-1 ]
  • 22
  • [ 77095-51-3 ]
  • [ 851784-86-6 ]
  • C28H23Cl2N3O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
50 - 65% g) A mixture of 0.25 mmol of compound 1.11 and 0.26 mmol of HATU in 1 mmol of DIEA and 2 mL of DMF was stirred at room temperature for 30 min, followed by adding a solution of 0.22 mmol of compound 1.5 in 1 mL of DMF. The resulting mixture was stirred 45C for 12 hours. The solvent was removed, and the residue was purified to give compound 1. 6 in 50-65% yield. Subsequently, compound 1.6 was hydrolyzed with LiOH (1.0 M aqueous, 0.5 mL) in THF (3 mL) for 2 hours. The rexaction mixture was then acidified with HCl (aqueous), extracted with ethyl acetate (50 mL), dried over anhydrous magnesium sulfate and concentrated to give compound 1 in quantitative yield NMR (400 MHz, CD3OD) : 8 7.91 (s, 1H), 7.75 (d, J= 8.0 Hz, 1H), 7.67 (s, 3H), 7.36 (d, J= 8. 0 HZ, 1H), 7.13 (s, 1H), 6.96 (s, 1H), 5.01 (t, J= 6.8 Hz, 1H), 4.68 and 4.89 (m, 2H), 3.85 (d, J= 6. 8 Hz, 2H), 3.70 and 4.02 (m, 2H), 2.93 (m, 2H) ppm; ESI-MS (m/z) : (milz 586.10.
  • 23
  • [ 77095-51-3 ]
  • [ 852021-86-4 ]
  • [ 851784-92-4 ]
  • 28
  • [ 77095-51-3 ]
  • [ 1194550-67-8 ]
  • 30
  • (1-benzofuran-6-yloxy)(tert-butyl)dimethylsilane [ No CAS ]
  • [ 77095-51-3 ]
  • 31
  • [ 1289646-90-7 ]
  • [ 77095-51-3 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydroxide; In tetrahydrofuran; methanol; [00140] Compound 6? (875 mmol) was dissolved in methanol and tetrahydrofuran (THF). Sodium hydroxide (4 M, 3 equivalents) was added and the reaction was stirred overnight. Afterconcentration via rotary evaporation, the aqueous solution was extracted with methyl tert-butyl ether (MTBE), acidified to pH 2 with the addition of hydrochloric acid (HC1) and cooled resulting in fine crystals of benzofuran-6-carboxylic acid, i.e., compound 18?. Compound 18? was isolated, washed with water and dried to a final yield of 97% yield.
  • 32
  • [ 124-38-9 ]
  • [ 128851-73-0 ]
  • [ 77095-51-3 ]
YieldReaction ConditionsOperation in experiment
24% To a mixture of 6-bromobenzofuran ( 1.0 g, 5.1 mmol) in tetrahydrofuran (15 mL) was added magnesium (0.19 g, 7.6 mmol) and 1,2-dibromoethane (95 mg, 0.51 mmol). The mixture was stirred at 70 C for 2 hours, and then the reaction was stirred at -40 C under carbon dioxide gas overnight. On completion, the mixture was poured into water and washed with ethyl acetate. The aqueous phase was adjusted to pH=5.0 with hydrochloric acid, resulting in formation of a solid. The solid was collected by filtration and dried in vacuo to give compound B-128 (0.20 g, 24% yield) as a yellow solid.
  • 33
  • [ 77095-51-3 ]
  • benzyl N-[[2-(6-benzofurancarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl-1,1-D2]carbonyl]-3-(methylsulfonyl)-L-phenylalaninate [ No CAS ]
  • 34
  • [ 77095-51-3 ]
  • N-[[2-(6-benzofurancarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl-1,1-D2]carbonyl]-3-(methylsulfonyl)-L-phenylalanine [ No CAS ]
  • 35
  • [ 77095-51-3 ]
  • 20'-aminovinblastine [ No CAS ]
  • C55H63N5O10 [ No CAS ]
  • 36
  • [ 77095-51-3 ]
  • C10H9Cl2NO2*C2HF3O2 [ No CAS ]
  • 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3 ,4-tetrahydroisoquinoline-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% The compound of Formula II (200 mg, 1.23 mmol, 1.0 equiv), HATU (516 mg, 1.36 mmol, 1.1 equiv), DIPEA (967 muL, 5.55 mmol, 4.5 equiv) and THF (2 mL, 10 vol) is charged to a two-neck round bottom flask under nitrogen atmosphere. The reaction mixture was stirred at 20 to 30 C. for 2 hrs. The reaction mixture was slowly added III?a (606 mg, 1.68 mmol, 1.4 equiv) at 20 to 30 C. When the reaction was complete as determined by HPLC analysis, the solvent was evaporated and the mixture was purified by column chromatography, eluting with MeOH/EtOAc=10/90, to give the compound of Formula IV (471 mg, 98%) as white solid.
  • 38
  • [ 77095-51-3 ]
  • 3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylate [ No CAS ]
  • 40
  • [ 77095-51-3 ]
  • [ 851785-70-1 ]
  • [ 1025967-78-5 ]
YieldReaction ConditionsOperation in experiment
83.8% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -10 - 20℃; l-benzofuran-6-carboxylic acid (10 g), HOBt (12.5 g) and EDC.HC1 (17.75 g) was charged in THF (60 ml). To this solution was added di isopropyl ethyl amine (22.2 g). Reaction mass was cooled to 0~5C. Added (S)-2-(5,7-dichloro-l,2,3,4- tetrahydroisoquinoline-6-carboxamido)-3-(3-(methyl sulfonyl)phenyl)propanoic acid ( 28.5g) lot wise at -10C. Temperature of reaction mass was raised to room temperature. Stirred and monitored the reaction by TLC. After completion of reaction, Water (100 ml) and MDC (100 ml) were added. Stirred and separated the layers. Organic layer so obtained was washed with brine and 10% sodium carbonate solution. Organic layer was distilled to give crude lifitegrast which was then purified in acetone and methanol to give pure lifitegrast (3.1.2 g, 83.8%).
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 10 - 20℃; for 1.5h; Benzofuran-6-carboxylic acid (compound of formula VI, 2.0 gm), N,N- Dimethylformamide (20 mL) and Triethylamine (3.74 gm) were charged into a 2000 mL RBF and the mixture was cooled to 10 C. HATU (5.63 gm) was charged into the mass and stirred for 30 minutes. Added above aqueous layer containing compound of formula II at 20 C and stirred for 1 hour. 1N aqueous hydrochloric acid (100 mL) was added and stirred for 10 minutes. Gummy solid was formed. The aqueous layer was decanted. Sodium carbonate solution (100 mL) and ethylacetate (60 mL) were added to the gummy mass and stirred for 30 minutes. Layers separated and the aqueous layer was washed with ethylacetate (60 mL). The aqueous layer was acidified with 1 N aqueous hydrochloric acid (100 mL) and stirred for 30 minutes. The precipitation was faltered and the wet solid was washed with water (20 mL). The solid was dried under vacuum at 50 C for 3 hours to yield 1 .5 gm of Lifitegrast. Purity: 94.85% by HPLC.
  • 41
  • [ 77095-51-3 ]
  • [ 530-62-1 ]
  • benzofuran-6-yl(1H-imidazol-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 60℃; for 1h; Benzofuran-6-carboxylic acid (compound II, 3.8 g, 23.6 mmol) was dissolved in DMSO (50 mL). CDI (4 g, 24.6 mmol) was added and the mixture heated at 60 C for 1 h. It was cooled down to room temperature. The obtained solution was used directly in the next step without further purification.
  • 42
  • [ 77095-51-3 ]
  • (S)-2-(5-(7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid) hydrochloride [ No CAS ]
  • [ 101-83-7 ]
  • lifitegrast dicyclohexylamine salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% 100 mL of DCM were added to the Compound lll-HCI solution in DMSO as obtained in step A-example 2) and the mixture was cooled to 0 - 5 C. Benzofuran-6-carboxylic acid solution obtained in section A was added dropwise maintaining the temperature below 5 C. The mixture was stirred at 0 - 5 C for 2 h. (0194) After reaction completion 850 mL of water and 850 mL of DCM were added maintaining the temperature below 10 C. After phase separation the aqueous phase was extracted with 400 mL of DCM. Organic phases were mixed and washed three times with 400 mL of water. The organic phase was distilled to almost dryness, 470 mL of acetone were added and then the remaining DCM was distilled. The solution was filtered through a 0,2 muetaeta filter. 240 mL of water were added and then dicyclohexylamine was added until pH = 8.3. The mixture was stirred at 20 - 25 C for 16 h and then cooled to 0 - 10 C and stirred for additional 25 h. The product was filtered, then washed twice with 200 mL of water and dryed in the oven at 50 C. Yield: 65% HPLC purity: 99% Chiral HPLC purity > 99.5%
  • 43
  • [ 77095-51-3 ]
  • [ 1289646-93-0 ]
  • 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3 ,4-tetrahydroisoquinoline-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
16 g Process-i: A mixture of compound of formula-2 (10 gm), HATU (35.17 gm), triethylamine (12.45 gm) and dimethylformamide (100 ml) was stirred for 5 hr at 25-30C under N2 atmosphere. Cooled the reaction mixture to 5-10C, water was added to it and stirred for 30 mm at same temperature. Filtered the solid, washed with water. The obtained compound was added to a mixture of dichloromethane (100 ml), Compound of formula-4a (i7.42 gm) and triethylamine (15.58 gm) at 25-30C under N2 atmosphere and stined the reaction mixture for 4 hr at same temperature. Filtered the reaction mixture and washed with dichloromethane. 50% Aqueous HC1 solution was added to the filtrate at 25-30C and stined the reaction mixture for 15 mm at the same temperature. Filtered the precipitated solid, washed with water and dried the material to get the title compound. Yield: 16.0 gm.
  • 44
  • [ 77095-51-3 ]
  • [ 771-61-9 ]
  • perfluorophenyl benzofuran-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Oxalyl chloride (29.35 gm) was slowly added to a pre-cooled mixture of compound of formula-2 (25 gm), dimethylformamide (5 ml) and tetrahydrofuran (325 ml) at 0-5C under nitrogen atmosphere. Raised the temperature of the reaction mixture to 25-30C and stirred for 5 hr at the same temperature. A solution of pentafluorophenol (31.21 gm) in tetrahydrofuran (25 ml) was added to the reaction mixture at 25-30C. Cooled the reaction mixture to 0-5C and Nu,Nu-diisopropylethyl amine (99.64 gm) was slowly added to it at the same temperature. Raised the temperature of the reaction mixture to 25-30C and stirred for 90 min at the same temperature. Methyl tert.butyl ether and water were added to the reaction mixture at 25-30C and stirred the reaction mixture for 10 min at the same temperature. Both the organic and aqueous layers were separated and washed the organic layer with 10% aqueous sodium bicarbonate solution followed by with water. Distilled off the solvent completely from the organic layer and co-distilled with acetonitrile. Compound of formula- 4a (47.92 gm), acetonitrile (250 ml) and N,N-diisopropylethylamine (59.78 gm) were added to the obtained compound at 25-30C and stirred the reaction mixture for 40 min at the same temperature. Heated the reaction mixture to 60-65 C and stirred for 3 hr at the same temperature. Cooled the reaction mixture to 5-10C, 50% aq.HCl solution was slowly added to it and stirred the reaction mixture for 2 hr at the same temperature. Filtered the solid and washed with water. Ethyl acetate (175 ml) and water (250 ml) were added to the obtained compound at 25-30C. Slowly basified the reaction mixture by using 10% aqueous potassium carbonate solution (25 gm of potassium carbonate in 250 ml of water) at 25-30C and stirred the reaction mixture for 10 min at the same temperature. Both the organic and aqueous layers were separated and washed the aqueous layer with ethyl acetate. Slowly acidified the aqueous layer by using 50% aqueous hydrochloric acid solution (25 ml of hydrochloric acid in 25 ml of water) at 25-30C and stirred the reaction mixture for 3 hr at the same temperature. Filtered the solid, washed with acetone and dried the material to get the title compound. The PXRD pattern of the obtained compound is illustrated in figure- 1.
  • 45
  • [ 77095-51-3 ]
  • benzyl (2S)-N-[(5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-yl)carbonyl]-3-(methylsulfonyl)-L-phenylalaninate [ No CAS ]
  • [ 1194550-67-8 ]
YieldReaction ConditionsOperation in experiment
80 g With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 12h; To a methylene dichloride solution of compound of formula IV (lOOgm) and 1- <strong>[77095-51-3]benzofuran-6-carboxylic acid</strong> (28.5gm), EDC.HC1 (48.10gm), HOBT (34.0gm) followed by TEA (50.8gm) was added and stirred at room temperature for 12 hours. After completion of reaction, water was added to reaction mass, stirred and the layers were separated. The organic layer was washed with water, separated and concentrated under vacuum to give foamy solid. The solid was stirred in 20% ethyl acetate in cyclohexane and then filtered. The obtained solid was washed with 20% ethyl acetate in cyclohexane and dried in vacuum oven at about 40-45C for 12 hours. (0330) Yield: 80 gm; HPLC purity: 98.5%
  • 46
  • [ 77095-51-3 ]
  • [ 1194550-65-6 ]
  • [ 1194550-67-8 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 12h; To a solution of benzyl-(2,S)-N-[(5,7-dichloro-l,2,3,4-tetrahydroisoquinolin-6- yl)carbonyl]-3-(methylsulfonyl)-L-phenylalaninate hydrochloride (100g) and 1- <strong>[77095-51-3]benzofuran-6-carboxylic acid</strong> (28.5g) in dichloromethane (2000mL) was added EDC.HC1 (48. lg), HOBT (34g) followed by triethylamine (50.8g) under stirring and the reaction mixture was stirred at about room temperature for about 12h. Water was added to the reaction mixture which was stirred for about 30min. The two layers were separated and the organic layer was concentrated under vacuum to give compound of formula IIIA as foamy solid. To the obtained solid, ethyl acetate (2000mL) and lithium iodide QOOg) was added. The reaction mixture was stirred for about 24h at about reflux temperature. Water was added to the reaction mixture and the two layers were separated. The organic layer was concentrated under vacuum to give a foamy solid which was dissolved in ethyl acetate and isopropanol. The reaction mixture was heated to about 70C to about 75C and benzyl amine (10.8g) was added to it. The reaction mixture was stirred at about the same temperature for about lh. The reaction mixture was cooled to about room temperature and was stirred for about 6h. The precipitated solid was filtered and dried to give crude benzyl amine salt of lifitegrast (62g). The crude benzyl amine salt of Lifitegrast was crystallized from 5% aqueous ethanol to give pure benzyl amine salt of lifitegrast (45g). HPLC purity: 99.88%; Compound of formula A: Not detected; Chiral purity: 100% (R- isomer not detected)
63.1 g 16.05 g (0.10 mol) of <strong>[77095-51-3]benzofuran-6-carboxylic acid</strong> (compound III) were added over a suspension of 16.05 g (0.10 mol) of 1 ,T-carbonyldiimidazole in 400 mL of ethyl acetate at 20-25 C, under nitrogen atmosphere. The mixture was stirred at 20-25 C for 1 hour, and the resulting solution was added over a mixture of 53.8 g (0.09 mol) of crude hydrochloride salt of benzyl (S)-2-(5,7-dichloro-1 ,2,3,4-tetrahydroisoquinoline-6- carboxamido)-3-[3-(methylsulfonyl)phenyl]propanoate (compound IV) as obtained in Example 1 and 37.6 ml. (0.22 mol) of /V,/V-diisopropylethylamine in a mixture of 200 ml. of ethyl acetate and 55 ml. of dimethylsulfoxide at 20-25 C. The resulting mixture was stirred at this temperature for 18 hours. 1.05 L of 0.5 M hydrochloric acid and 500 ml. of ethyl acetate were added. The organic phase was extracted, washed with 2 x 500 ml. of 4% (w/w) aqueous sodium bicarbonate and with 500 ml. of deionized water, in sequence. The organic layer was concentrated to dryness under reduced pressure, to give 63.1 g of benzyl (S)-2-[2-(benzofuran-6-carbonyl)-5,7-dichloro-1 ,2,3,4-tetrahydroisoquinoline-6- carboxamido]-3-[3-(methylsulfonyl)phenyl]propanoate (compound II) as a yellowish solid.
  • 47
  • [ 128851-73-0 ]
  • [ 77095-51-3 ]
  • 48
  • [ 123297-88-1 ]
  • [ 77095-51-3 ]
YieldReaction ConditionsOperation in experiment
70% With dihydrogen peroxide; sodium hydroxide; In water; at 75 - 90℃; 20 g of l-benzofuran-6-carbaldehyde was charged in solution of 16.5g of NaO in 200 ml of water. Temperature was raised to 75-90C and treated drop wise with aq. (30%, 18 g) within 2-3 hr. Reaction mass was stirred and monitored till completion of reaction. Reaction mass was acidified and filtered to get l-benzofuran-6-carboxylic acid in 70% yield.
  • 49
  • [ 17450-68-9 ]
  • [ 77095-51-3 ]
YieldReaction ConditionsOperation in experiment
85.0% With water; sodium hydroxide; at 90℃; 10 g of l-benzofuran-6-carbonitrile was charged in solution of NaOH (14.0 g) in water (200 ml). Temperature was raised to 90C and stirred to complete conversion. Then pH of reaction mass was adjusted to acid pH and precipitated solid was filtered and dried to get l-benzofuran-6-carboxylic acid. (9.6 g, yield -85.0%)
  • 50
  • [ 77095-51-3 ]
  • (S)-2-(8-chloro-2,3-dihydro-1H-pyrrole[3,2,1-ij]isoquinazolin-7-carbonylamino)-3-(3-(methanesulfonyl)phenyl)propanoic acid benzyl ester trifluoroacetate salt [ No CAS ]
  • (S)-2-(8-chloro-2-(benzofuran-6-carbonyl)-2,3-dihydro-1H-pyrrole[3,2,1-ij]quinazolin-7-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Add HATU (418 mg, 1.1 mmol) and DIPEA (390 mg, 3 mmol) to a vigorously stirred solution of <strong>[77095-51-3]benzofuran-6-carboxylic acid</strong> (178 mg, 1.1 mmol) in DMF (5 mL). After the reaction mixture was reacted at room temperature for 1 hour, (S)-2-(8-chloro-2,3-dihydro-1H-pyrrole[3,2,1-ij]-quinazoline-7-carbonylamino)- 3-(3-(Methanesulfonyl)phenyl)propanoic acid benzyl ester trifluoroacetate (649 mg, 1 mmol), the mixture was stirred at room temperature for 2 hours. Ethyl acetate was added (100 mL), sequentially washed with water (20mL), saturated brine (20mL) was washed, and the organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated, the residue was purified by flash chromatography, Petroleum ether with 50% ethyl acetate in hexanes to afford the desired product as a white solid (661mg, 0.95mmol 95%).
  • 51
  • [ 77095-51-3 ]
  • methyl (2S,4aR,6aR/S,7R,10aR,10bR)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-2,4,4a,5,6,6a,7,10,10a,10b-decahydro-1H-benzo[f]isochromene-7-carboxylate [ No CAS ]
  • methyl (2S,4aR,6aR,7R,10aR,10bR)-9-((benzofuran-6-carbonyl)oxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-1,4,4a,5,6,6a,7,10,10a,10b-decahydro-2H-benzo[f]isochromene-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; An oven-dried flask was charged with 2 (40 mg, 0.103 mmol), EDC.HCl (29.5 mg, 0.154 mmol), DMAP (18.8 mg, 0.154 mmol), and the appropriate acid (0.154 mmol). To the flask was added CH2CI2 (8 mL). After stirring overnight at RT the reaction was quenched with HC1 (1 M, 8 mL) and the organic layer rinsed sequentially with saturated NaHCCh (8 mL) and brine (8 mL) then dried over NarSOu The solvent was removed in vacuo and the resulting residue purified by flash column chromatography (?FCC?) eluting with 30-35% EtOAc/Pent. Compounds <95% pure as indicated by HPLC were further purified by reverse phase semi -preparatory HPLC.
  • 52
  • [ 77095-51-3 ]
  • C30H26Cl2N2O7S [ No CAS ]
  • 53
  • [ 77095-51-3 ]
  • C29H23Cl2N2O7S(1-)*Na(1+) [ No CAS ]
  • 54
  • [ 77095-51-3 ]
  • C29H27Cl2N3O6S*(x)ClH [ No CAS ]
  • C38H31Cl2N3O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Benzofuran-6-carboxylic acid (4 g, 0.024 mmol) was added to triethyl amine (7.5 g, 0.72 mmol) and 3-[bis(dimethylamino) mcthylium-ylJ-3/7-bcnzotriazol- 1 -oxide hexaflorophosphate (HBTU, 11.2 g, 0.029 mmol), then stirred for 15 minutes at 25- 35C in dimethyl formamide (40 ml, 10 volumes) and then stage-IV (16.1 g, 0.024 mmol) was added to the reaction mass at 25-35C and stirred at 35-45C for 5 hours. After completion of the reaction, DMF was distilled under vacuum at below 60C. The residue was dissolved in ethyl acetate and washed with about 5% sodium bicarbonate solution (40 ml) and water (40 ml). The organic layer was distilled under vacuum at below 50C to get the product. The obtained crude was stirred in hexane (20 ml) for 30 min at 25-35C, filtered the product and washed with hexane (10 ml). The compound was dried in vacuum oven at 50-55C.
  • 55
  • [ 77095-51-3 ]
  • [ 67025-97-2 ]
  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(benzofuran-6-carboxamido)morphinan [ No CAS ]
  • 56
  • [ 77095-51-3 ]
  • [ 67025-97-2 ]
  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(benzofuran-6-carboxamido)morphinan hydrochloride [ No CAS ]
  • 57
  • [ 77095-51-3 ]
  • [ 67025-97-2 ]
  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(benzofuran-6-carboxamido)morphinan [ No CAS ]
  • 58
  • [ 77095-51-3 ]
  • [ 67025-97-2 ]
  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(benzofuran-6-carboxamido)morphinan hydrochloride [ No CAS ]
  • 59
  • [ 99-06-9 ]
  • [ 77095-51-3 ]
  • 60
  • [ 619-12-5 ]
  • [ 77095-51-3 ]
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