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CAS No. : | 6826-24-0 | MDL No. : | MFCD00087876 |
Formula : | C9H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IUHYFLKPKSFRCT-UHFFFAOYSA-N |
M.W : | 160.17 | Pubchem ID : | 12707563 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | In ethanol;Inert atmosphere; Reflux; | Step 1: To a solution of 2-hydroxyacetophenone (1.0 g, 7.4 mmol) in ethanol (20 mL) was added cyanamide (400 mg, 9.4 mmol) and the reaction mixture was heated at reflux under nitrogen overnight. The reaction mixture was poured into aqueous 6N HCl (40 mL) and washed with ethyl acetate and ethyl acetate layer discarded. The aqueous layer was made alkaline with aqueous NaOH and extracted 3 times with ethyl acetate. The combined organic phase was dried over Na2SO4 and concentrated in vacuo to afford 5-phenyl-oxazol-2-ylamine (250 mg, 21%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
200 mg | In ethanol; at 20 - 80℃; for 6.0h;Inert atmosphere; | [000318] Synthesis of 5-phenyloxazol-2-amine (396): To a stirred solution of compound 394 (800 mg, crude) in EtOH (10 mL) under inert atmosphere was added urea 395 (482 mg, 8.04 mmol) at RT; heated at 80 C and stirred for 6 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo and the residue was diluted with water (60 mL). The pH was neutralized with 10% aqueous NaHCO3 solution (10 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through flash column chromatography using 2-3% MeOH/ CH2C12 to afford compound 396 (200 mg, 32%) as an off-white solid. TLC: 5% MeOH/ CH2C12 (Rj: 0.5); 1H NMR (400 MHz, DMSOd 6): oe 7.45 (d, J 7.2 Hz, 2H), 7.36 (t, J 7.8 Hz, 2H), 7.21-7.16 (m, 2H), 6.81 (s, 2H); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; at 0 - 20℃; for 16.0h;Inert atmosphere; | [000216] To a stirred solution of compound 35 (50 mg, 0.17 mmol) in CH2C12 (5 mL) under argon atmosphere were added ethyl 2-amino-2-(pyridin-2-yl) acetate hydrochloride 249 (26 mg, 0.17 mmol), propylphosphonic anhydride (50% solution in EtOAc, 0.22 mL, 0.34 mmol), NMM (0.037 mL, 0.34 mmol) at 0 C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo and diluted with water (20 mL) or the pH of the reaction mixture was adjusted to 8 and extracted with CH2C12 (2 x 30 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified either through silica gel column chromatography or triturated to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 5.0h;Reflux; | To a solution of 4-nitrophenyl 4-( l-(4-(trifluoromethoxy)phenyl)- ltf-l,2,4-triazol-3-yl)phenethylcarbamate (C33) (0.174 g, 0.340 mmol) in tetrahydrofuran (3.4 mL) was added <strong>[6826-24-0]5-phenyloxazol-2-amine</strong> (0.0570 g, 0.360 mmole) and diisopropylethylamine (0.120 mL, 0.689 mmol). The mixture was refluxed for 5 hours. After cooling, the solution was diluted with methanol (5 mL) and adsorbed onto Celite. Purification by flash column chromatography using 0-100% ethyl acetate/(l : l hexanes/dichloromethane) as eluent provided the title molecule as a white solid (0.0310 g, 18%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With [2-(di-tert-butylphosphino)-2?,4?,6?-triisopropyl-1,1?-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; In 1,4-dioxane; at 125℃; for 1.16667h;Microwave irradiation; Inert atmosphere; | [00292] l-[6-chloro-4-(difluoromethyl)-2-pyridyl]-4-(oxetan-3-yl)piperazine (50 mg, 0.16 mmol), <strong>[6826-24-0]5-phenyloxazol-2-amine</strong> (53 mg, 0.33 mmol) and sodium t-butoxide (32 mg, 0.33 mmol) were suspended in 1,4-dioxane (3 mL) and purged with N2 for several minutes before addition chloro(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-l, - biphenyl)[2-(2-aminoethyl)phenyl] palladium(II) (-BuXPhos Palladacycle) (10 mg, 0.014 mmol). The mixture was microwaved at 125C for 70 minutes. The reaction was quenched with methanol (2 mL), diluted with dichloromethane (15 mL), washed with water (5 mL), brine (5 mL), dried over sodium sulfate, filtered and concentrated. The crude material was subjected to flash chromatography purification (12g silica; 0% to 5% to 10% of ethanol in ethyl acetate) to provide N-[4-(difluoromethyl)-6-[4- (oxetan-3-yl)piperazin-l-yl]-2-pyridyl]-<strong>[6826-24-0]5-phenyloxazol-2-amine</strong> (50 mg, 68%). XH NMR (300 MHz, CDC13) delta 7.55 (dd, J = 14.0, 6.7 Hz, 4H), 7.42 (t, J = 7.6 Hz, 2H), 7.35 - 7.25 (m, 2H), 6.68 (d, J = 56.0 Hz, 1H), 6.44 (s, 1H), 4.83 - 4.60 (m, 4H), 3.79 - 3.49 (m, 5H), 2.57 - 2.35 (m, 4H) ppm. ESI-MS m/z calc. 427.18, found 428.03 (M+l)+; Retention time: 0.67 minutes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With [2-(di-tert-butylphosphino)-2?,4?,6?-triisopropyl-1,1?-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; In 1,4-dioxane; at 125℃; for 1.0h;Microwave irradiation; Inert atmosphere; | [00299] <strong>[6826-24-0]5-phenyloxazol-2-amine</strong> (63 mg, 0.39 mmol), l-(3-bromo-5-methyl- phenyl)-4-(3-methyloxetan-3-yl)piperazine (80 mg, 0.25mmol) and sodium t-butoxide (50 mg, 0.52 mmol) were suspended in 1,4-dioxane (4 mL) and purged with N2 for several minutes before addition of chloro(2-di-t-but lphosphino-2',4',6'-tri-i-propyl- l,r-biphenyl)[2-(2-aminoethyl)phenyl] palladium(II) (i-BuXPhos Palladacycle) (13 mg, 0.02 mmol). The mixture was microwaved at 125 C for 60 minutes. The reaction was quenched with methanol (2 mL) and diluted with dichloromethane. After filtration (Florisil/10 g), the excess solvent was evaporated under reduced pressure. The crude material was subjected to flash chromatography purification (12g silica; 0% to 5% of ethanol in ethyl acetate) to give N-[3-methyl-5-[4-(3- methyloxetan-3-yl)piperazin-l-yl]phenyl]-5-phenyl-oxazol-2-amine (75 mg, 72%). XH NMR (300 MHz, CDC13) delta 7.61 - 7.49 (m, 2H), 7.40 (t, J = 7.7 Hz, 2H), 7.26 (d, J = 7.4Hz, 1H), 7.17 (s, 1H), 7.03 (s, 1H), 6.93 (s, 1H), 6.79 (s, 1H), 6.47 (s, 1H), 4.71 (d, J = 5.5 Hz, 2H), 4.30 (d, J = 5.8 Hz, 2H), 3.49 - 3.18 (m, 4H), 2.74 - 2.45 (m, 4H), 2.35 (s, 3H) ppm. ESI-MS m/z calc. 404.22, found 405.28 (M+l)+; Retention time: 0.64 minutes. |
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