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[ CAS No. 7659-07-6 ] {[proInfo.proName]}

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Product Details of [ 7659-07-6 ]

CAS No. :7659-07-6 MDL No. :MFCD02073839
Formula : C8H6FN3O Boiling Point : -
Linear Structure Formula :- InChI Key :OPZGULFMUGGIAS-UHFFFAOYSA-N
M.W : 179.15 Pubchem ID :853522
Synonyms :

Calculated chemistry of [ 7659-07-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.1
TPSA : 64.94 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) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.17
Log Po/w (WLOGP) : 1.89
Log Po/w (MLOGP) : 1.6
Log Po/w (SILICOS-IT) : 1.61
Consensus Log Po/w : 1.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.25
Solubility : 1.01 mg/ml ; 0.00565 mol/l
Class : Soluble
Log S (Ali) : -2.13
Solubility : 1.33 mg/ml ; 0.00743 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.3
Solubility : 0.0894 mg/ml ; 0.000499 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.29

Safety of [ 7659-07-6 ]

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

Application In Synthesis of [ 7659-07-6 ]

* 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.

  • Downstream synthetic route of [ 7659-07-6 ]

[ 7659-07-6 ] Synthesis Path-Downstream   1~92

  • 1
  • [ 831-38-9 ]
  • [ 7659-07-6 ]
  • 2
  • [ 120445-38-7 ]
  • [ 7659-07-6 ]
YieldReaction ConditionsOperation in experiment
81% General procedure: 5.1.3.1. 5-(5,6,7,8-Tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-amine (4A). To a vial was added 3A (0.18 g, 0.81 mmol, 1.0 eq.),sodium acetate (0.13 g, 1.62 mmol, 2.0 eq.) and acetic acid (0.5 mL).To a second vial was added the bromine (0.14 g, 0.89 mmol, 1.1 eq.)in acetic acid (0.5 mL). The bromine solutionwas then added to thefirst vial while stirring in a dropwise manner at room temperature.The reaction was then heated to 60 C and stirred for 1 h. The reactionwas then cooled to room temperature and poured onto icewater. A yellow precipitate formed and was filtered by vacuumfiltration then rinsed with DCM to provide 4A (0.16 g, 0.77 mmol,95%) as a pale yellow solid.
  • 8
  • [ 106-51-4 ]
  • [ 7659-07-6 ]
  • [ 80691-91-4 ]
  • 9
  • [ 6761-07-5 ]
  • [ 7659-07-6 ]
  • [ 135790-29-3 ]
  • 16
  • [ 108-24-7 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)acetamide [ No CAS ]
  • 17
  • [ 199339-19-0 ]
  • [ 3805-23-0 ]
  • [ 7659-07-6 ]
  • 18
  • [ 199339-13-4 ]
  • [ 4695-17-4 ]
  • [ 7659-07-6 ]
  • 19
  • [ 563-76-8 ]
  • [ 7659-07-6 ]
  • 2-Bromo-N-[5-(4-fluoro-phenyl)-[1,3,4]oxadiazol-2-yl]-propionamide [ No CAS ]
  • 20
  • [ 2912-62-1 ]
  • [ 7659-07-6 ]
  • 2-Chloro-N-[5-(4-fluoro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-phenyl-acetamide [ No CAS ]
  • 21
  • [ 622-59-3 ]
  • [ 7659-07-6 ]
  • 1-[5-(4-fluoro-phenyl)-[1,3,4]oxadiazol-2-yl]-3-<i>p</i>-tolyl-thiourea [ No CAS ]
  • 22
  • [ 2131-55-7 ]
  • [ 7659-07-6 ]
  • 1-(4-chloro-phenyl)-3-[5-(4-fluoro-phenyl)-[1,3,4]oxadiazol-2-yl]-thiourea [ No CAS ]
  • 23
  • [ 333-20-0 ]
  • [ 7659-07-6 ]
  • [5-(4-fluoro-phenyl)-[1,3,4]oxadiazol-2-yl]-thiourea [ No CAS ]
  • 24
  • [ 7659-07-6 ]
  • 2-(4-fluoro-phenyl)-1-oxa-3,3a,4,6-tetraaza-pentalene-5-thione [ No CAS ]
  • 25
  • [ 7659-07-6 ]
  • (4-chloro-phenyl)-[2-(4-fluoro-phenyl)-[1,2,4]thiadiazolo[3,2-<i>b</i>][1,3,4]oxadiazol-6-ylidene]-amine [ No CAS ]
  • 26
  • [ 7659-07-6 ]
  • [2-(4-fluoro-phenyl)-[1,2,4]thiadiazolo[3,2-<i>b</i>][1,3,4]oxadiazol-6-ylidene]-<i>p</i>-tolyl-amine [ No CAS ]
  • 27
  • [ 7659-07-6 ]
  • [ 199339-13-4 ]
  • 29
  • [ 403-43-0 ]
  • [ 7659-07-6 ]
  • 31
  • [ 3862-85-9 ]
  • [ 7659-07-6 ]
YieldReaction ConditionsOperation in experiment
76% General procedure: To a stirred solution containing the semicarbazone 1 (1 mmol) in acetic acid (8 mL) at 0 C was added NBS (0.178 g, 1 mmol). The temperature was allowed to warming to room temperature. After 30 min, sodium acetate (0.287 g, 3.5 mmol) was added and the reaction was stirred for additional 1 h at 25 C. Subsequently, the reaction mixture was poured into water and the product was extracted by simple filtration. Compounds 2e and 2m were extracted from water with chloroform (3 x 15 mL). When necessary the product was purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (7:3, 1:1, 3:7, v/v) and, finally, ethyl acetate:methanol (8:2, v/v).
73% With iodine; potassium carbonate; In 1,4-dioxane; at 100℃; General procedure: To a stirred solution of semicarbazide hydrochloride (orthiosemicarbazide) (1 mmol) and sodium acetate (1 mmol) inEtOH 96% (5 mL) was added a solution of the aldehyde (1mmol) in EtOH 96% (5 mL). After being stirred at 80 C (incase of semicarbazide hydrochloride) or 100 C (thiosemicarbazide)until condensation was completed (monitored byTLC, 0.5-1 h), the solvent was evaporated under reducedpressure. The resulting residue was redissolved in 1,4-dioxane (10 mL), followed by addition of potassium carbonate(3 mmol) and iodine (1.2 mmol) in sequence. Thereaction mixture was stirred at 100 C until the conversionwas complete (monitored by TLC, 3-4 h). After being cooledto room temperature, it was treated with 5% Na2S2O3 (20mL) and extracted with EtOAc (3x10 mL). The combinedorganic layer was washed with brine, then dried over anhydroussodium sulfate and concentrated. The given residuewas purified through silica gel column chromatography usinga mixture of ethyl acetate (EA) and petroleum ether (PE)as eluent to afford the corresponding oxadiazoles and thiadiazoles1-2 in 58-87% yield. All compounds have shown highpurity which was assessed by high resolution 1H-NMR (500MHz).
73% With iodine; potassium carbonate; In 1,4-dioxane; at 100℃; General procedure: To a stirred solution of semicarbazide hydrochloride (orthiosemicarbazide) (1 mmol) and sodium acetate (1 mmol) inEtOH 96% (5 mL) was added a solution of the aldehyde (1mmol) in EtOH 96% (5 mL). After being stirred at 80 C (incase of semicarbazide hydrochloride) or 100 C (thiosemicarbazide)until condensation was completed (monitored byTLC, 0.5-1 h), the solvent was evaporated under reducedpressure. The resulting residue was redissolved in 1,4-dioxane (10 mL), followed by addition of potassium carbonate(3 mmol) and iodine (1.2 mmol) in sequence. Thereaction mixture was stirred at 100 C until the conversionwas complete (monitored by TLC, 3-4 h). After being cooledto room temperature, it was treated with 5% Na2S2O3 (20mL) and extracted with EtOAc (3x10 mL). The combinedorganic layer was washed with brine, then dried over anhydroussodium sulfate and concentrated. The given residuewas purified through silica gel column chromatography usinga mixture of ethyl acetate (EA) and petroleum ether (PE)as eluent to afford the corresponding oxadiazoles and thiadiazoles1-2 in 58-87% yield. All compounds have shown highpurity which was assessed by high resolution 1H-NMR (500MHz).
With sodium hypoiodite; In water monomer; at 80 - 85℃; General procedure: To an aqueous solution of semicarbazidehydrochloride (1:1g) and sodium acetate (8:2g),substituted benzaldehydes (1a-j) (0.02 mol) in 15 mlof ethanol were added by stirring, stirring wascontinued for another 15-30 min then the mixture waskept aside undisturbed for 1 hr and the obtainedprecipitate was collected and purified byrecrystallization from ethanol.The prepared semicarbazones (3a-j) (0.005 mol)were heated with stirring at 80-85 0 with water andsodium hypoiodate (NaOI) solution for 4-5 hr, thereaction mixture was cooled and the precipitate wascollected and recrystallized from ethanol.

  • 33
  • [ 148550-51-0 ]
  • [ 7659-07-6 ]
  • [ 1338083-85-4 ]
YieldReaction ConditionsOperation in experiment
60% General procedure: 60percent Sodium hydride (w/w) in mineral oil (0.0015 mol) was added to a mixture of appropriate III (0.001 mol) in THF (15 ml) under the condition of inert atmosphere using N2 flow at 5°C. The reaction mixture was kept for 1 h at room temperature. A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.0015 mol) in THF (15 ml) was slowly added to reaction mixture. The resulting reaction mixture was stirred for 2-3 h at 5°C. The distilled water (20 ml) was added. The reaction mixture was extracted (10 ml x 3) with dichloromethane. The separated organic layer was dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure to obtain crude product, recrytallized by ethyl acetate.
  • 34
  • [ 7659-07-6 ]
  • [ 1338084-18-6 ]
  • 35
  • [ 7659-07-6 ]
  • [ 1338083-63-8 ]
  • 36
  • [ 7659-07-6 ]
  • [ 1338084-42-6 ]
  • 38
  • [ 1022-46-4 ]
  • [ 7659-07-6 ]
  • [ 1261138-34-4 ]
  • 39
  • [ 1441-85-6 ]
  • [ 7659-07-6 ]
  • [ 1370641-56-7 ]
  • 40
  • [ 7659-07-6 ]
  • [ 1421633-72-8 ]
  • 41
  • [ 917-61-3 ]
  • [ 7659-07-6 ]
  • [ 1421633-61-5 ]
YieldReaction ConditionsOperation in experiment
64% With acetic acid; In water;Heating; General procedure: The appropriate 2-amino-5-aryl-1,3,4-oxadiazole III (a-j) (0.01 mol) was dissolved in 10-30 ml of glacial acetic acid diluted to 50 ml with distilled water. In some cases mixture was warmed to dissolve III (a-j). To this equimolar (0.01 mol) quantity of sodium cyanate in 20-30 ml of warm water was added with stirring. The reaction mixture was allowed to stand several h followed by cooling on an ice bath. The precipitates obtained were collected by filtration, washed with cold water and recrystallized from 90% aqueous ethanol.
  • 43
  • C16H13FN3O3Pol [ No CAS ]
  • [ 7659-07-6 ]
  • 44
  • C16H15FN3O3PolS [ No CAS ]
  • [ 942-70-1 ]
  • [ 7659-07-6 ]
  • 45
  • [ 2251-65-2 ]
  • [ 7659-07-6 ]
  • [ 865285-47-8 ]
YieldReaction ConditionsOperation in experiment
0.022 g With pyridine; at 20℃; for 18h; General procedure: To a vial was added the 4A (0.050 g, 0.23 mmol, 1.0 eq.)followed by pyridine (0.3 mL). To the vial containing the 3-trifluoromethylbenzoyl chloride (carried over from previousstep) was add pyridine (0.3 mL) to form a suspension. The acylchloride suspension was added to the first vial while stirring atroom temperature. The reaction stirred for 18 h thenwas pouredinto ice water and a precipitate formed. This precipitate wasfiltered by vacuum filtration and was further purified by normalphase flash chromatography (0-5% MeOH:DCM). All fractionscontaining the desired product were isolated and concentratedto produce 6 (0.14 g, 0.035 mmol, 15%).
  • 46
  • [ 456-22-4 ]
  • [ 51433-48-8 ]
  • [ 7659-07-6 ]
  • 47
  • [ 2491-38-5 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-6-(4-hydroxyphenyl)imidazo[2,1-b]-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.2% In ethanol; for 0.00694444h;Microwave irradiation; Green chemistry; 1) added to the drying in the crucible 0.01mol abromo-p-hydroxyacetophenone, 0.01mol 2-amino-5-(pfluorophenyl)-1,3,4-oxadiazole is dissolved in anhydrous ethanol, get mixed solution A1, to a crucible of the reaction liquid is placed in the microwave oven, power modulation high fire files 700W, opening microwave oven radiation 25 seconds after the closing, of the crucible is taken out of the glass rod for stirring cooling, every 5 to detect reaction TLC (developing agent to volume ratio is: dichloromethane: methanol =10:1 mixture); 2) if the crucible is ethanol volatilizes in adding ethanol, to TLC detection reaction is complete, add water to the reaction solution of 15 ml, then the saturated NaOH solution for pH value adjusted to 7-8, to get mixed solution B1; 3) the mixture solution B1off the solvent, the crude product obtained after water washing, filtering, drying and recrystallized with absolute ethanol, to obtain 2 - (4-fluoro phenyl) - 6 - (4-hydroxy-phenyl)-imidazo [2,1-b] - 1, 3, 4-oxadiazole, yield 44.2%,
  • 48
  • [ 99-73-0 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-6-(4-bromophenyl)imidazo[2,1-b]-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
48.5% In ethanol; for 0.00694444h;Microwave irradiation; Green chemistry; 1) added to the drying in the crucible 0.01mol a-bromo-p-bromoacetophenone, 0.01mol 2-amino-5-(pfluorophenyl)-1,3,4-oxadiazole is dissolved in anhydrous ethanol, get mixed solution A1, to a crucible of the reaction liquid is placed in the microwave oven, power modulation high fire files 700W, opening microwave oven radiation 25 seconds after the closing, of the crucible is taken out of the glass rod for stirring cooling, every 5 to detect reaction TLC (developing agent to volume ratio is: dichloromethane: methanol =10:1 mixture);2) if the crucible is ethanol volatilizes in adding ethanol, to TLC detection reaction is complete, add water to the reaction solution of 15 ml, then the saturated NaOH solution for pH value adjusted to 7-8, to get mixed solution B1;3) the mixture solution B1off the solvent in the, the cake is washed with water, drying to obtain the crude product, recrystallized with absolute ethanol to get the 2-(4-fluorophenyl)-6-(4-bromophenyl)imidazo[2,1-b]-1,3,4-oxadiazole, yield 48.5%,
  • 49
  • [ 2227-64-7 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-6-(3-nitrophenyl)imidazo[2,1-b]-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.4% In ethanol; for 0.00694444h;Microwave irradiation; Green chemistry; 1) added to the drying in the crucible between 0.01mol α-bromo-m-nitroacetophenone, 0.01mol 2-amino-5-(p-fluorophenyl)-1,3,4-oxadiazole is dissolved in anhydrous ethanol, get mixed solution A1, to a crucible of the reaction liquid is placed in the microwave oven, power modulation high fire files 700W, opening microwave oven radiation 25 seconds after the closing, of the crucible is taken out of the glass rod for stirring cooling, every 5 to detect reaction TLC (developing agent to volume ratio is: dichloromethane: methanol =10:1 mixture); 2) if the crucible is ethanol volatilizes in adding ethanol, to TLC detection reaction is complete, add water to the reaction solution of 15 ml, then the saturated NaOH solution for pH value adjusted to 7-8, to get mixed solution B1; 3) the mixture solution B1off the solvent in the, the cake is washed with water, drying to obtain the crude product, recrystallized with absolute ethanol to get the 2-(4-fluorophenyl)-6-(3-nitrophenyl)-imidazo[2,1-b]-1,3,4-oxadiazole, yield 47.4%,
  • 50
  • [ 70-11-1 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-6-phenylimidazo[2,1-b]-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
39.4% In ethanol; for 0.00694444h;Microwave irradiation; Green chemistry; 1) added to the drying in the crucible 0.01mol a-bromoacetophenone, 0.01mol 2-amino-5-(p-fluorophenyl)-1,3,4-oxadiazole is dissolved in anhydrous ethanol, get mixed solution A1, to a crucible of the reaction liquid is placed in the microwave oven, power modulation high fire files 700W, opening microwave oven radiation 25 seconds after the closing, of the crucible is taken out of the glass rod for stirring cooling, every 5 to detect reaction TLC (developing agent to volume ratio is: dichloromethane: methanol =10:1 mixture); 2) if the crucible is ethanol volatilizes in adding ethanol, to TLC detection reaction is complete, add water to the reaction solution of 15 ml, then the saturated NaOH solution for pH value adjusted to 7-8, to get mixed solution B1; 3) the mixture solution B1off the solvent in the, the cake is washed with water, drying to obtain the crude product, recrystallized with absolute ethanol to get the 2-(4-fluorophenyl)-6-phenylimidazo[2,1-b]-1,3,4-oxadiazole, yield 39.4%,
  • 51
  • [ 619-41-0 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-6-(4-methylphenyl)imidazo[2,1-b]-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
45.3% In ethanol; for 0.00694444h;Microwave irradiation; Green chemistry; 1) added to the drying in the crucible 0.01mol a-bromo-p-methylacetophenone, 0.01mol 2-amino-5-(p-fluorophenyl)-1,3,4-oxadiazole is dissolved in anhydrous ethanol, get mixed solution A1, to a crucible of the reaction liquid is placed in the microwave oven, power modulation high fire files 700W, opening microwave oven radiation 25 seconds after the closing, of the crucible is taken out of the glass rod for stirring cooling, every 5 to detect reaction TLC (developing agent to volume ratio is: dichloromethane: methanol =10:1 mixture); 2) if the crucible is ethanol volatilizes in adding ethanol, to TLC detection reaction is complete, add water to the reaction solution of 15 ml, then the saturated NaOH solution for pH value adjusted to 7-8, to get mixed solution B1; 3) the mixture solution B1off the solvent in the, the cake is washed with water, drying to obtain the crude product, recrystallized to get DMF for 2-(4-fluorophenyl)-6-(4-methylphenyl)imidazo[2,1-b]-1,3,4-oxadiazole, yield 45.3%,
YieldReaction ConditionsOperation in experiment
With pyridine; manganese(IV) oxide; at 115℃;Green chemistry; General procedure: To a dry threeneckedflask Amol 2(2 ', 4'dimethylphenyl)amino methylene urea, Bmol CmL manganese dioxide andpyridine at 115 C under stirring, the reaction process using TLC monitoring Measuring the reaction until the starting materialurea aminals point disappears, to obtain a reaction mixture wherein, A: B: C = 1: 1.1: 10 When monitored by TLC developingsolvent used is a mixture of ethyl acetate and petroleum ether made, and ethyl acetate and Petroleum ether volume ratio of1: 4[2]2)The reaction mixture was cooled to room temperature, vacuum filtration, and the filtrate was concentrated to dryness togive, as a white solid Body, a white solid was washed with water, vacuum filtration to give the crude product, the crudeproduct was recrystallized from anhydrous methanol 2Amino5(2 ', 4'dimethylphenyl)1,3,4oxadiazolepure, yield of 93%.
  • 53
  • [ 50-00-0 ]
  • [ 1271-55-2 ]
  • [ 7659-07-6 ]
  • 1-(5’-p-fluorophenyl-1’,3’,4’-oxadiazol-2’-amino)ethylferrocenyl ketone [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.2% With benzothiazole ionic liquid; In ethanol;Reflux; Add a solution of 2-amino 5-p-fluorophenyl-1,3,4-oxadiazole (1mol) and 37% formaldehyde (5mol) to a dry three-necked flask, using absolute ethanol as a solvent, and stir well; Thiazole ionic liquid (1.2mol), then slowly add acetylferrocene (1mol) absolute ethanol solution, heating and refluxing until the end of the reaction (TLC monitoring), the solvent was distilled off under reduced pressure, and ethyl acetate was added to the residue Ester, suction filtration, the filter cake is benzothiazole ionic liquid, which can be recycled and reused; the filtrate is evaporated to dryness to obtain the crude product, and the crude product is recrystallized from absolute ethanol to obtain 1- (5'-p-fluorophenyl-1 ', 3 ', 4'-oxadiazole-2'-amino) -ethyl-ferrocenyl ketone, mp148.1-151 C, yield: 91.2%
90.9% With benzimidazole ionic liquid; In ethanol;Reflux; Add a solution of 2-amino 5-p-fluorophenyl-1,3,4-oxadiazole (1mol) and 37% formaldehyde (5mol) to a dry three-necked flask, using absolute ethanol as a solvent, and stir well; add benzo Imidazole ionic liquid (1.2 mol), then slowly add acetylferrocene (1 mol) absolute ethanol solution, heating and reflux until the end of the reaction (TLC monitoring), the solvent is distilled off under reduced pressure, and ethyl acetate is added to the residue Ester, suction filtration, the filter cake is the benzimidazole ionic liquid, which can be recycled and reused; the filtrate is evaporated to dryness to obtain the crude product, and the crude product is recrystallized from anhydrous ethanol to obtain 1- (5'-p-fluorophenyl-1 ', 3 ', 4'-oxadiazole-2'-amino) -ethyl-ferrocenyl ketone, mp148.1-151 C, yield: 91.6%.
63% With hydrogenchloride; In ethanol; water; at 80℃; for 12h; To a dry three-necked flask equipped with a reflux condenser were added 0.85 mol of 2-amino-5- (4-fluorophenyl) -1,3,4-oxadiazole,Mass percentage concentration of 37% formaldehyde solution,100mL of anhydrous ethanol as a solvent,During mixing,Add 0.5mL concentrated hydrochloric acid as a catalyst,Then, a solution of acetyl ferrocene in absolute ethanol at a concentration of 0.5 g / mL was added dropwise,80 heating reflux 12h,The complete reaction was monitored by TLC plate (the developing solvent used for TLC was a mixture of dichloromethane and methanol in a volume ratio of 10: 1). After the reaction,The reaction solution was cooled,The solvent was evaporated under reduced pressure absolute ethanol,After silica gel column chromatography,Obtained reddish brown oily3- (<strong>[7659-07-6]2-amino-5-p-fluorophenyl-1,3,4-oxadiazole</strong>) -ethyl ferrocenyl ketone 126 mg,Yield 63%.Which formaldehyde solution contains formaldehyde 10mol,Acetylferrocene in absolute ethanol solution containing acetyl ferrocene 1mol,Silica gel column chromatography specific steps: the volume ratio of 3: 1 mixture of petroleum ether and ethyl acetate as the first eluent,The unreacted acetyl ferrocene was washed away,The second eluent was a mixture of petroleum ether and ethyl acetate in a volume ratio of 2: 1,Collect the second band,The solvent was distilled off under reduced pressure,That is the purpose of the product.
45.5% To a dry three-necked flask equipped with a reflux condenser, 0.8 mmol of 2-amino-5- (4-fluorophenyl) -1,3,4-oxadiazole and 35 mmol formaldehyde in a concentration of 37% formaldehyde solution and adding 22 mL of anhydrous ethanol as a solutionAgent, 1.3mmol of bismuth nitrate pentahydrate was added as a catalyst during the stirring, and a constant pressure titration funnel was added dropwise with 1mmol of acetylFerrocene concentration of 0.45g / mL of acetyl ferrocene absolute ethanol solution, the reaction at room temperature for 6h, by TLC plate supervisorThe reaction progress (when the starting point of 2-amino-5- (4-fluorophenyl) -1,3,4-oxadiazole disappears indicates complete reaction, TLC plateThe developing solvent used was a mixed solution of dichloromethane and methanol in a volume ratio of 10: 1). After the reaction was completed, the resulting product was purified by rotary evaporationThe solvent ethanol was distilled off under reduced pressure and the residue was separated by column chromatography (a mixture of petroleum ether and ethyl acetate in a volume ratio of 3: 1The first eluent, washed away unreacted acetyl ferrocene to a volume ratio of 2: 1 mixture of petroleum ether and ethyl acetate wasThe second eluent, the second band was collected and the solvent was distilled off under reduced pressure)That is, the resulting waxy yellow3- (2-Amino-5-p-fluorophenyl-1,3,4-oxadiazole) -ethyl ferrocenyl ketone in 45.5% yield.

  • 54
  • 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid [ No CAS ]
  • [ 7659-07-6 ]
  • 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)-N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)benzamide [ No CAS ]
  • 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)-N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;Sealed tube; General procedure: A 20 mL screw caped vial, charged with the corresponding acid (0.5 mmol), amine (0.5 mmol), BOP reagent (1.4 mmol) and diisopropylethylamine (13 mmol) in anhydrous DMF solvent (1 mL) was stirred at room temperature for 16 h. After completion, the reaction mixture was concentrated under reduced pressure, followed by flash column chromatography (hexanes:ethylacetate 80:20 to 60:40) give the desired product.
  • 55
  • [ 586-75-4 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-(bromo)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.038 g With pyridine; at 20℃; for 18h; General procedure: To a vial was added the 4A (0.050 g, 0.23 mmol, 1.0 eq.)followed by pyridine (0.3 mL). To the vial containing the 3-trifluoromethylbenzoyl chloride (carried over from previousstep) was add pyridine (0.3 mL) to form a suspension. The acylchloride suspension was added to the first vial while stirring atroom temperature. The reaction stirred for 18 h thenwas pouredinto ice water and a precipitate formed. This precipitate wasfiltered by vacuum filtration and was further purified by normalphase flash chromatography (0-5% MeOH:DCM). All fractionscontaining the desired product were isolated and concentratedto produce 6 (0.14 g, 0.035 mmol, 15%).
  • 56
  • [ 1711-05-3 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-3-(methoxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.017 g With pyridine; at 20℃; for 18h; General procedure: To a vial was added the 4A (0.050 g, 0.23 mmol, 1.0 eq.)followed by pyridine (0.3 mL). To the vial containing the 3-trifluoromethylbenzoyl chloride (carried over from previousstep) was add pyridine (0.3 mL) to form a suspension. The acylchloride suspension was added to the first vial while stirring atroom temperature. The reaction stirred for 18 h thenwas pouredinto ice water and a precipitate formed. This precipitate wasfiltered by vacuum filtration and was further purified by normalphase flash chromatography (0-5% MeOH:DCM). All fractionscontaining the desired product were isolated and concentratedto produce 6 (0.14 g, 0.035 mmol, 15%).
  • 57
  • [ 874-60-2 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-(methyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 58
  • [ 100-07-2 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-(methoxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 59
  • [ 100-07-2 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-3-(fluoro)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 60
  • [ 403-43-0 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-(fluoro)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 61
  • [ 122-01-0 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-(chloro)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 62
  • [ 16331-45-6 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-(ethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 63
  • [ 98-88-4 ]
  • [ 7659-07-6 ]
  • [ 126631-00-3 ]
YieldReaction ConditionsOperation in experiment
66% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 64
  • [ 21900-23-2 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-3,4-(dimethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.015 g With pyridine; at 20℃; for 18h; General procedure: To a vial was added the 4A (0.050 g, 0.23 mmol, 1.0 eq.)followed by pyridine (0.3 mL). To the vial containing the 3-trifluoromethylbenzoyl chloride (carried over from previousstep) was add pyridine (0.3 mL) to form a suspension. The acylchloride suspension was added to the first vial while stirring atroom temperature. The reaction stirred for 18 h thenwas pouredinto ice water and a precipitate formed. This precipitate wasfiltered by vacuum filtration and was further purified by normalphase flash chromatography (0-5% MeOH:DCM). All fractionscontaining the desired product were isolated and concentratedto produce 6 (0.14 g, 0.035 mmol, 15%).
  • 65
  • [ 854167-08-1 ]
  • [ 7659-07-6 ]
  • C20H19FN4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.006 g With pyridine; at 20℃; for 18h; General procedure: To a vial was added the 4A (0.050 g, 0.23 mmol, 1.0 eq.)followed by pyridine (0.3 mL). To the vial containing the 3-trifluoromethylbenzoyl chloride (carried over from previousstep) was add pyridine (0.3 mL) to form a suspension. The acylchloride suspension was added to the first vial while stirring atroom temperature. The reaction stirred for 18 h thenwas pouredinto ice water and a precipitate formed. This precipitate wasfiltered by vacuum filtration and was further purified by normalphase flash chromatography (0-5% MeOH:DCM). All fractionscontaining the desired product were isolated and concentratedto produce 6 (0.14 g, 0.035 mmol, 15%).
  • 66
  • [ 393-52-2 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-2-(fluoro)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.009 g With pyridine; at 20℃; for 18h; General procedure: To a vial was added the 4A (0.050 g, 0.23 mmol, 1.0 eq.)followed by pyridine (0.3 mL). To the vial containing the 3-trifluoromethylbenzoyl chloride (carried over from previousstep) was add pyridine (0.3 mL) to form a suspension. The acylchloride suspension was added to the first vial while stirring atroom temperature. The reaction stirred for 18 h thenwas pouredinto ice water and a precipitate formed. This precipitate wasfiltered by vacuum filtration and was further purified by normalphase flash chromatography (0-5% MeOH:DCM). All fractionscontaining the desired product were isolated and concentratedto produce 6 (0.14 g, 0.035 mmol, 15%).
  • 67
  • [ 14002-51-8 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-[1,1'-biphenyl]-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 68
  • [ 42498-44-2 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 69
  • 3-methyl-5-(trifluoromethyl)benzoyl chloride [ No CAS ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-3-(methyl)-5-(trifluoromethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 70
  • [ 261952-11-8 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-(methyl)-3-(trifluoromethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 71
  • [ 916420-92-3 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-3-(methoxy)-5-(trifluoromethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With pyridine; at 20℃; for 18h; General procedure: 5.1.4.1. N-(5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl)benzamide (1). To a vial was added the 4A (0.030 g, 0.14 mmol,1.0 eq.) followed by pyridine (0.6 mL) and 4-benzoyl chloride(0.020 g, 0.14 mmol, 1.0 eq.) at room temperature. The reactionstirred for 18 h then was poured into ice water and a precipitateformed. This precipitate was filtered by vacuum filtration and wasfurther purified by reverse-phase flash chromatography (5-100%MeCN:water). All fractions containing the desired product wereisolated and concentrated to produce 1 (0.028 g, 0.084 mmol, 40%)as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 12.21 (br s, 1H),8.26 (d, J 7.7 Hz, 2H), 7.84-7.74 (m, 2H), 7.62 (t, J 7.3 Hz, 1H),7.53 (t, J 7.5 Hz, 2H), 7.19 (d, J 7.8 Hz, 1H), 2.89-2.79 (m, 4H),1.89-1.79 (m, 4H). 13C NMR (200 MHz, DMSO-d6):δ 165.0, 161.5,157.7,141.1,137.9,132.9, 132.2,130.0,128.6, 128.3, 126.5, 123.1, 120.5,28.84, 28.58, 22.35, 22.30. ESI-MS: m/z 319.7 [M H]; HPLCretention time: 12.940 min. HPLC purity 96.5%.
  • 72
  • [ 696-59-3 ]
  • [ 7659-07-6 ]
  • C12H8FN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With acetic acid; at 150 - 160℃; General procedure: Compounds (5a-j) were synthesized by refluxinga mixture of 5-substituted-1,3,4-oxadiazol-2-amines(4a-j) (2g, 0.1 mol) in dried acetic acid (15 ml) and2,5-dimethoxytetrahydrofuran (1.9ml, 0.12 mol) for 45min to 1 hr at 150-160 0 , the reaction mixture was poured into ice cold water, the solid separated wasfiltered and recrystallized from aq. ethanol.5a: IR (KBr): cm -1 : 2921 (ArH), 1612 (C-O), 1584(C=N). 1 H NMR (400 MHz, CDCl3, δ ppm): 6.43 (dd,2H, C3 & C4-H of pyrrole), 7.43 (dd, 2H, C2 & C5-H ofpyrrole), 7.50-7.57 (t, 3H, C3, C4 & C5-H of phenyl),8.05 (d, 2H, C2 & C6-H of phenyl), 13 C NMR (100 MHz,CDCl3), 108.5 (C3, C4-pyrrole), 114.5 (C2, C5-pyrrole),118.1 (C1-phenyl), 121.7 (C2, C6-phenyl), 124.3 (C4-phenyl), 126.5 (C3, C5-phenyl), 152.2 (C5-oxadiazole),156.5 (C2-oxadiazole). Mass : m/z 212 (M + +1).
  • 73
  • [ 530-62-1 ]
  • [ 7659-07-6 ]
  • C12H8FN5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one; at 65℃; for 18h; 1,1’-carbonyldiimidazole (0.543g, 3.3Smmol) was added to a suspension of <strong>[7659-07-6]5-(4-fluorophenyl)-1,3,4-oxadiazol-2-amine</strong> (0.500g, 2.79mmol) in NMP (7mL) and stirred at 65C for 18 hrs. To this was added a solution of tetrahydroisoquinoline (0.886mL, 6.98mmol) inNMP (3 mL) in a dropwise manner over -5 minutes. The reaction mixture was removed from heat and allowed to cool to room temperature over 2 hrs. The resultant heterogenous mixturewas diluted with water (- 100 mL), filtered and the collected precipitate washed sequentially with water (-25 mL) and methanol (-25 mL) and then dried in vacuo to provide a white powder (0.375g, 40%);
  • 74
  • [ 51362-38-0 ]
  • [ 7659-07-6 ]
  • C20H13FN4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1-methyl-pyrrolidin-2-one; at 65℃; for 18h; The reagents HATU (1 .06g, 2.79mmol), 5-(4-fluorophenyl)- 1,3 ,4-oxadiazol-2-amine (0.499g, 2.79mmol), and <strong>[51362-38-0]6-phenoxynicotinic acid</strong> (0.500g, 2.32mmol) were combined as solids and dissolved in NMP (5mL), to which diisopropylethylamine (0.53mL, 3.O2mmol) was added, and the resulting solution stirred at 65C for 18 hrs. At this point, the reaction mixture was diluted with water (-400 mL) and filtered to provide a brown solid that was dried under vacuum.This solid was triturated with MeOH (2 mL), filtered and dried under vacuum to provide an off- white solid (0.695 g, 80%); ?H NMR (DMSO): 12.33 (br, 1H), 8.79 (s, 1H), 8.42 (d, 1H), 8.05- 8.00 (m, 2H), 7.50-7.44 (m, 4H), 7.3 1-7.18 (m, 4H); LCMS: 377.2 (M+1).
  • 75
  • [ 506-68-3 ]
  • [ 456-06-4 ]
  • [ 7659-07-6 ]
YieldReaction ConditionsOperation in experiment
95% To a solution of sodium bicarbonate (5.45g, 64.9mmol) in 1:1 water:dioxane (100 mLtotal volume) was added 4-fluorobenzohydrazide (10.Og, 64.9mmol) and the resulting suspension stirred for 10 mm at 25 C. To this was added cyanogen bromide (6.87g, 64.9mmol) in threeportions over 15 mm. After stirring at 25 C for 18 hrs, the reaction was diluted with water (200mL), filtered, and the resultant solid rinsed with water. The solid was dried in vacuo (12 hrs) to provide a light brown powder (1 1.Og, 95%); ‘H NMR (DMSO): 7.87-7.82 (m, 2H), 7.4 1-7.35(m, 2H), 7.24 (br s, 2H); LCMS: 180.2 (M+1).
83% In ethanol; at 20℃;Inert atmosphere; General procedure: A mixture of corresponding hydrazine (1mmol), BrCN (1.2mmol), and EtOH (10 mL) was degassed with argon and stirred at room temperature overnight. The solvent was evaporated and the residue was purified by flash chromatography (DCM : MeOH = 20:1) to give the product.
  • 76
  • [ 1780-26-3 ]
  • [ 7659-07-6 ]
  • (6-chloro-2-methylpyrimidin-4-yl)-[5-(4-fluorophenyl)-[1,3,4]oxadiazol-2-yl]amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; In N,N-dimethyl-formamide; at 110℃; for 36h;Schlenk technique; Inert atmosphere; General procedure: A 10-ml Schlenk tube equipped with a stir-bar was charged with compound 1 (0.2 mmol), compound 2 (0.3 mmol), Pd(OAc)2 (0.02 mmol), Xantphos (0.04 mmol), NaOtBu (0.3 mmol), anhydrous DMF (2 mL).The reaction tube was purged with argon. The Schlenk tube was placed in an oil-bath at 110 oC for 36 hours and then cooled to room temperature. The reaction mixture was extracted with EtOAc (3 × 20 mL). The combined organic phase was dried over MgSO4 and concentrated under reduced pressure and the crude residue purified by flash chromatography on silica gel. The purified material was dried in vacuo to afford the corresponding products 3a-w.
  • 77
  • cis-4-((3,5-dimethylpiperidin-1-yl)sulfonyl)benzoic acid [ No CAS ]
  • [ 7659-07-6 ]
  • 4-((3,5-dimethylpiperidin-1-yl)sulfonyl)-N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)benzamide [ No CAS ]
  • 78
  • [ 70-11-1 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-5-phenyl-6-piperazin-1-ylmethylimidazo[2,1-b][1,3,4]oxadiazole [ No CAS ]
  • 79
  • [ 70-11-1 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-5-phenylimidazo[2,1-b][1,3,4]oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.1% In ethanol; for 0.266667h;Microwave irradiation; General procedure: The 2-Amino-5-aryl-1,3,4-oxadiazole (0.01 mol), α-bromoacetophenones derivatives (0.01 mol) and catalyst were treated by a microwave system for about the appropriate time. The microwave-accelerated reaction system was operated at 200 W. The progress of the reaction was monitored by TLC using dichloromethane/methanol (10:1) as eluent. After completion of the reaction, the solution pH was adjusted to 7-8. The crude product thus obtained was filtered, and recrystallized from N,N-Dimethylformamide to get the compounds (1a-1v).
  • 80
  • [ 619-41-0 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-6-piperazin-1-ylmethyl-5-p-tolylimidazo[2,1-b][1,3,4]oxadiazole [ No CAS ]
  • 81
  • [ 619-41-0 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-5-p-tolylimidazo[2,1-b][1,3,4]oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.1% In ethanol; for 0.35h;Microwave irradiation; General procedure: The 2-Amino-5-aryl-1,3,4-oxadiazole (0.01 mol), α-bromoacetophenones derivatives (0.01 mol) and catalyst were treated by a microwave system for about the appropriate time. The microwave-accelerated reaction system was operated at 200 W. The progress of the reaction was monitored by TLC using dichloromethane/methanol (10:1) as eluent. After completion of the reaction, the solution pH was adjusted to 7-8. The crude product thus obtained was filtered, and recrystallized from N,N-Dimethylformamide to get the compounds (1a-1v).
  • 82
  • [ 2491-38-5 ]
  • [ 7659-07-6 ]
  • 4-[2-(4-fluorophenyl)-6-piperazin-1-ylmethylimidazo[2,1-b][1,3,4]oxadiazol-5-yl]phenol [ No CAS ]
  • 83
  • [ 2491-38-5 ]
  • [ 7659-07-6 ]
  • 4-[2-(4-fluorophenyl)imidazo[2,1-b][1,3,4]oxadiazol-5-yl]phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.3% In ethanol; for 0.333333h;Microwave irradiation; General procedure: The 2-Amino-5-aryl-1,3,4-oxadiazole (0.01 mol), α-bromoacetophenones derivatives (0.01 mol) and catalyst were treated by a microwave system for about the appropriate time. The microwave-accelerated reaction system was operated at 200 W. The progress of the reaction was monitored by TLC using dichloromethane/methanol (10:1) as eluent. After completion of the reaction, the solution pH was adjusted to 7-8. The crude product thus obtained was filtered, and recrystallized from N,N-Dimethylformamide to get the compounds (1a-1v).
  • 84
  • [ 2227-64-7 ]
  • [ 7659-07-6 ]
  • 2-(4-fluorophenyl)-5-(3-nitrophenyl)imidazo[2,1-b][1,3,4]oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.6% In ethanol; for 0.4h;Microwave irradiation; General procedure: The 2-Amino-5-aryl-1,3,4-oxadiazole (0.01 mol), α-bromoacetophenones derivatives (0.01 mol) and catalyst were treated by a microwave system for about the appropriate time. The microwave-accelerated reaction system was operated at 200 W. The progress of the reaction was monitored by TLC using dichloromethane/methanol (10:1) as eluent. After completion of the reaction, the solution pH was adjusted to 7-8. The crude product thus obtained was filtered, and recrystallized from N,N-Dimethylformamide to get the compounds (1a-1v).
  • 85
  • [ 99-73-0 ]
  • [ 7659-07-6 ]
  • 5-(4-bromophenyl)-2-(4-fluorophenyl)imidazo[2,1-b][1,3,4]oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.8% In ethanol; for 0.416667h;Microwave irradiation; General procedure: The 2-Amino-5-aryl-1,3,4-oxadiazole (0.01 mol), α-bromoacetophenones derivatives (0.01 mol) and catalyst were treated by a microwave system for about the appropriate time. The microwave-accelerated reaction system was operated at 200 W. The progress of the reaction was monitored by TLC using dichloromethane/methanol (10:1) as eluent. After completion of the reaction, the solution pH was adjusted to 7-8. The crude product thus obtained was filtered, and recrystallized from N,N-Dimethylformamide to get the compounds (1a-1v).
  • 86
  • [ 99-73-0 ]
  • [ 7659-07-6 ]
  • 5-(4-bromophenyl)-2-(4-fluorophenyl)-6-piperazin-1-ylmethylimidazo[2,1-b][1,3,4]oxadiazole [ No CAS ]
  • 87
  • [ 330-17-6 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-4-((trifluoromethyl)thio)benzamide [ No CAS ]
  • 88
  • [ 7659-07-6 ]
  • 2-(5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yloxy)-N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)acetamide [ No CAS ]
  • 89
  • [ 7659-07-6 ]
  • 2-(2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yloxy)-N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)acetamide [ No CAS ]
  • 90
  • [ 563-41-7 ]
  • [ 459-57-4 ]
  • [ 7659-07-6 ]
  • 91
  • [ 91-21-4 ]
  • [ 530-62-1 ]
  • [ 7659-07-6 ]
  • MBX-4132 [ No CAS ]
  • 92
  • [ 645-12-5 ]
  • [ 7659-07-6 ]
  • N-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% General procedure: To a stirring solution of 4 (158.0mg, 1.0mmol) in DCM (5.0mL) were added HATU (456.0mg, 1.2mmol) and TEA (278.0µl, 2.0mmol). After stirring for 0.5h at room temperature, commercially available 7a-m (1.0mmol) was added and stirred for 1.5-2.5h. The reaction mixture was washed with brine and saturated NaHCO3 aq. The organic phase was concentrated and purified over silica gel column (DCM:MeOH=30:1) to yield 2a-m in a yield of 22-31%.
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