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[ CAS No. 17147-85-2 ] {[proInfo.proName]}

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Chemical Structure| 17147-85-2
Chemical Structure| 17147-85-2
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Product Details of [ 17147-85-2 ]

CAS No. :17147-85-2 MDL No. :MFCD03422293
Formula : C7H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 155.15 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 17147-85-2 ]

* 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 [ 17147-85-2 ]

[ 17147-85-2 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 17147-85-2 ]
  • 3-ethyl-5-methyl-isoxazole-4-carboxylic acid diethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride Behandeln des Reaktionsprodukts mit Diaethylamin in Aether;
  • 2
  • [ 17448-81-6 ]
  • [ 17147-85-2 ]
  • [ 69083-54-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; ethanol; hydroxylamine Erwaermen des Reaktionsprodukts mit wss. NaOH;
  • 3
  • [ 53064-41-8 ]
  • [ 17147-85-2 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide In tetrahydrofuran; ethanol; water at 20℃; 16.A Example 16 [ 4-R2- 1-VIL-PHENOL] Step A 3-Ethyl-5-methyl-isoxazole-4-carboxylic acid To 3-ethyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester (2.82g, 15.4 [MMOL)] in THF [(25MOI)] and [ETOH] [(20MI)] was added [NAOH] as a 5N solution in water (25ml). The reaction was stirred at room temperature overnight, acidified to pH=3 [WITH 6N] HCI, diluted with water to a volume of [100MOL] and extracted with EtOAc (3x150ml). The organics were combined, washed with brine [(150MOI),] [DRIED (MGS04),] filtered and concentrated by vacuum to give [3-ETHYL-5-METHYL-ISOXAZOLE-4-CARBOXYLIC] acid as a white solid (2. [1G,] 13.5 mmol, 88%). 1H NMR 400 MHz (CDCI3) [No.H ] 2.90 (2H, q J 7.5 Hz), 2.69 (3H, s) and 1.30 (3H, t J 7.5 Hz).
With sodium hydroxide
With sodium hydroxide In tetrahydrofuran; ethanol; water 16.A 3-Ethyl-5-methyl-isoxazole-4-carboxylic acid Step A 3-Ethyl-5-methyl-isoxazole-4-carboxylic acid To 3-ethyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester (2.82 g, 15.4 mmol) in THF (25 ml) and EtOH (20 ml) was added NaOH as a 5N solution in water (25 ml). The reaction was stirred at room temperature overnight, acidified to pH=3 with 6N HCl, diluted with water to a volume of 100 ml and extracted with EtOAc (3*150 ml). The organics were combined, washed with brine (150 ml), dried (MgSO4), filtered and concentrated by vacuum to give 3-ethyl-5-methyl-isoxazole-4-carboxylic acid as a white solid (2.1 g, 13.5 mmol, 88%). 1H NMR 400 MHz (CDCl3) δH 2.90 (2H, q J 7.5 Hz), 2.69 (3H, s) and 1.30 (3H, t J 7.5 Hz).
  • 4
  • [ 17147-85-2 ]
  • [ 93599-36-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / Ambient temperature 2: CHCl3 / 0 - 20 °C 3: thionyl chloride / CHCl3 / 0 - 20 °C
  • 5
  • [ 17147-85-2 ]
  • [ 99298-90-5 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride Ambient temperature;
YieldReaction ConditionsOperation in experiment
/BRN= 972152/*SnCl4, Hydroxylaminhydrochlorid / NaOH;
  • 7
  • [ 17147-85-2 ]
  • [ 93599-43-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / Ambient temperature 2: CHCl3 / 0 - 20 °C 3: thionyl chloride / CHCl3 / 0 - 20 °C 4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight
Multi-step reaction with 2 steps 2: 1) n-BuLi / 1) THF, -78 deg C, 2 h
  • 8
  • [ 17147-85-2 ]
  • [ 93599-47-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / Ambient temperature 2: CHCl3 / 0 - 20 °C 3: thionyl chloride / CHCl3 / 0 - 20 °C 4: 1.) n-BuLi, 2.) molybdenumoxodiperoxy pyridine HMPA complex / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight
  • 9
  • [ 17147-85-2 ]
  • [ 99298-80-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / Ambient temperature 2: CHCl3 / 0 - 20 °C 3: thionyl chloride / CHCl3 / 0 - 20 °C 4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, from -78 deg C to RT, overnight
  • 10
  • [ 17147-85-2 ]
  • [ 99298-91-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / Ambient temperature 2: CHCl3 / 0 - 20 °C
  • 11
  • N-(4-methoxyphenyl)benzene-1,2-diamine dihydrochloride [ No CAS ]
  • [ 17147-85-2 ]
  • [ 639523-21-0 ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine In dichloromethane; ethyl acetate 16.B 3-Ethyl-5-methyl-isoxazole4-carboxylic acid [2-(4-methoxy-phenylamino)-phenyl]-amide Step B 3-Ethyl-5-methyl-isoxazole4-carboxylic acid [2-(4-methoxy-phenylamino)-phenyl]-amide To N-(4-methoxy-phenyl)-benzene-1,2-diamine di-hydrochloride salt (0.292 g, 1.02 mmol) 3-ethyl-5-methyl-isoxazole-4-carboxylic acid (0.189 g, 0.122 mmol), Et3N (1.4 ml, 10.2 mmol) and DMAP (cat.) in CH2Cl2 4 ml) was added PPM as a 50% solution in EtOAc (0.36 ml, 0.597 mmol). The reaction was stirred at room temperature overnight, diluted with EtOAc (35 ml) and washed with sat. NaHCO3 (2*15m1) and brine (1*15 ml), dried (MgSO4), filtered and concentrated by vacuum to give 3-ethyl-5-methyl-isoxazole4-carboxylic acid [2-(4-methoxy-phenylamino)-phenyl]-amide. The material was used without purification in the next step. 1H NMR 400 MHz (CDCl3) δH 8.20 (1H, m), 8.07 (1H, s), 7.22-7.09 (3H, overlapping; m) 6.77 (2H, m), 6.74 (2H, m), 5.30 (1H, s), 3.71(3H, s), 2.68 (2H, m), 2.46 (3H, s) and 1.19 (3H, m).
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 20℃; 16.B STEP B 3-ETHYL-5-METHYL-ISOXAZOLE-4=CARBOXYLIC-ACID- [2- (4-METHOXY-PHENYLAMINO)-PHENYL]-] amide To [N- (4-METHOXY-PHENYL)-BENZENE-1,] 2-diamine di-hydrochloride salt (0.292g, 1.02 [MMOL)] [3-ETHYL-5-METHYL-ISOXAZOLE-4-CARBOXYLIC] acid (0.189g, 0.122 [MMOL),] Et3N (1. 4ml, 10.2 [MMOL)] and DMAP (cat. ) in [CH2CI2] 4m.) was added PPAA as a [50%] solution in EtOAc (0. 36ml, 0.597 [MMOL).] The reaction was stirred at room temperature overnight, diluted with EtOAc [(35MI)] and washed with sat. NaHCO3 [(2X15ML)] and brine (1x15ml), dried (MgSO4), filtered and concentrated by vacuum to give 3-ethyl-5-methyl-isoxazole-4-carboxylic acid [[2- (4-METHOXY-PHENYLAMINO)-] phenyl]-amide. The material was used without purification in the [NEXT STEP.'H] NMR 400 MHz [(CDCI3) No.H ] 8.20 (1H, m), 8.07 (1H, s), 7.22-7. 09 (3H, overlapping, m) 6.77 (2H, m), 6.74 (2H, m), 5.30 (1H, s), 3.71 (3H, s), 2.68 (2H, m), 2.46 (3H, s) and 1.19 (3H, [M).]
  • 12
  • [ 17147-85-2 ]
  • [ 354795-54-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diphenylphosphoranyl azide; triethylamine / toluene / 4 h / 100 °C 2: dichloromethane; trifluoroacetic acid / 1 h / 20 °C
  • 13
  • [ 17147-85-2 ]
  • [ 75-65-0 ]
  • tert-butyl N-(3-ethyl-5-methyl-isoxazol-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.3% With diphenylphosphoranyl azide; triethylamine In toluene at 100℃; for 4h; a (a)tert-butyl N-(3-ethyl-5-methyl-isoxazol-4-yl)carbamate (a)tert-butyl N-(3-ethyl-5-methyl-isoxazol-4-yl)carbamateDiphenylphosphoryl azide (2.51 mL, 11.6 mmol) was added to a solution of 3-ethyl-5- methyl-isoxazole-4-carboxylic acid (1.5 g, 9.67 mmol), triethylamine (2.7 mL, 19.3 mmol), and tert-butylalcohol (0.92 mL, 9.67 mmol) in toluene (50 mL) and stirred for4 hat 100 °C. Thesolvent was removed by evaporation and the residue taken up in EtOAc (50 mL). The organic layer washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel in heptane/ethyl acetate = 10/0 to 7/3 v/v% as eluent. The fractions containing the title compound were pooled and evaporated to obtain the title compound. (1.67 g, 763%)
  • 14
  • [ 17147-85-2 ]
  • [ 1078691-95-8 ]
  • N-(3-ethyl-5-methyl-4-isoxazolyl)carboxamido-2-deoxyglucose [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 3-ethyl-5-methyl-isoxazole-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 1h; Stage #2: (+)-D-glucosamine hydrochloride In N,N-dimethyl-formamide at -5 - 20℃; for 24h; 2.3 4.2.3 Synthesis of N-(3-ethyl-5-methyl-4-isoxazole)-formylamino-2-deoxyglucose (A3) General procedure: A3 was prepared in a similar way to A1. A solution of 3-phenyl-5-methyl-4-isoxazole formic acid (0.2 g, 1 mmol) in DMF (5 mL) was stirred. EDCI (1-(3-dimethylamino propyl)-3-2 ethyl carbon imine hydrochloride) (0.22 g, 1.2 mmol) and HOBt (N-hydroxybenzotrizole) (0.16 g, 1.2 mmol) were added sequentially and activated for approximately 1 h. Glucosamine hydrochloride (0.43 g, 2 mmol) and triethylamine (0.4 g, 4 mmol) were then added, and the solution was stirred for an additional 24 h at room temperature. The reaction was monitored by TLC. The mixture was extracted with ethyl acetate (EA) after the end of the reaction. The organic layer was separated, washed with a saturated sodium chloride solution, dried over MgSO4, and concentrated in vacuo. The residue was washed with ethanol/dichloromethane (v/v = 2:5), and the title compound. 1H NMR (400 MHz, DMSO) δ 6.77 (s, 1H), 6.12 (s, 1H), 5.27 (d, 1H), 4.13 (m, 1H), 3.81 (m, 1H), 3.69 (s, 1H), 3.45 (d, J = 12.0 Hz, 2H), 3.22 (m, 1H), 3.07 (q, J = 7.8 Hz, 2H), 2.43 (s, 3H), 1.76 (s, 1H), 1.44 (s, 1H), 1.32 (t, 3H), 1.24 (s, 1H). 13C NMR (100 MHz, DMSO-d6) δ 169.67, 165.81, 165.46, 114.72, 93.90, 75.23, 71.19, 69.81, 61.95, 56.05, 20.54, 14.04, 11.54. HRMS (ESI) calcd for C13H20N2O7 [M+H]+: 317.1360, found 317.1365.
65% Stage #1: 3-ethyl-5-methyl-isoxazole-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at -5℃; for 1h; Stage #2: (+)-D-glucosamine hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; 1 Example 1 Synthesis of Derivatives of the InventionN- (3-ethyl-5-methyl-4-isoxazole) carboxamido-2-deoxy-glucose (a2)Synthesis: In a 25mL round bottom flask, take3-Ethyl-5-methyl-4-isoxazolecarboxylic acid (0.1 mmol, 0.2 g) was dissolved in 5 mL of DMF,EDCI is added with stirring under ice-cooling (-5 ° C)(1.2 mmol, 0.22 g) and HOBt (1 -hydroxybenzotriazole) (1.2 mmol, 0.16 g) were added to a solution of 1- (3-dimethylaminopropyl) -3- ethylcarbodiimideAnd activated at this condition for 1 h, then glucosamine hydrochloride (2 mmol, 0.43 g) andTriethylamine (4 mmol, 0.4 g) was stirred at room temperature for 24 h.TCL tracking reaction until the reaction is complete, washed with saturated salt water,Ethyl acetate, the organic layer was dried over anhydrous MgSO4, concentrated in vacuo,Silica gel as stationary phase column chromatography to obtain compound a2.
  • 15
  • [ 17147-85-2 ]
  • N-((3S)-morpholin-3-ylmethyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide hydrochloride [ No CAS ]
  • N-(((3S)-4-((3-ethyl-5-methyl-1,2-oxazol-4-yl)carbonyl)morpholin-3-yl)methyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78 mg With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; 102 N-(((3S)-4-((3-ethyl-5-methyl-1,2-oxazol-4-yl)carbonyl)morpholin-3-yl)methyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide A mixture of N-((3S)-morpholin-3-ylmethyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide hydrochloride (100 mg), 3-ethyl-5-methyl-1,2-oxazole-4-carboxylic acid (59 mg), N-(3-(dimethylamino)propyl)-N'-ethylcarbodiimide hydrochloride (98 mg), 1H-benzotriazol-1-ol monohydrate (78 mg), DIEA (132 mg) and DMF (1.3 mL) was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (78 mg). 1H NMR (400 MHz, CDCl3) δ 1.09 (3H, brs), 2.22 (3H, brs), 2.52 (2H, brs), 3.21-3.55 (3H, m), 3.65-3.82 (2H, m), 3.90-4.06 (2H, m), 4.71 (1H, brs), 4.89 (1H, brs), 7.13 (1H, brs), 7.93 (2H, d, J = 8.1 Hz), 8.16 (2H, d, J = 8.6 Hz).
  • 16
  • [ 17147-85-2 ]
  • [ 93-05-0 ]
  • N-[4-(diethylamino)phenyl]-3-ethyl-5-methylisoxazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 96h; Inert atmosphere;
  • 17
  • [ 17147-85-2 ]
  • [ 4613-53-0 ]
  • 3-ethyl-5-methyl-N-(4-oxo-2-phenyl-4H-chromen-6-yl)isoxazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 96h; Inert atmosphere;
  • 18
  • [ 17147-85-2 ]
  • [ 91331-85-0 ]
  • 3-ethyl-N-(1-(2-methoxyphenyl)-3-methyl-1H-pyrazol-5-yl)-5-methylisoxazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: 2-(2-methoxyphenyl)-5-methyl-2H-pyrazol-3-ylamine With 1-methyl-1H-imidazole; methanesulfonyl chloride In dichloromethane at 0 - 20℃; for 0.333333h; Stage #2: 3-ethyl-5-methyl-isoxazole-4-carboxylic acid In dichloromethane at 0 - 45℃; for 3h; General procedure for the synthesis of final compounds 5a-j General procedure: To a solution of amino precursor 3 (1 mmol, 1 equiv.) in DCM (10 vol) taken in a round bottomed flask, NMI (2 mmol, 2 equiv.), and MsCl (1 mmol, 1 equiv.) was added at 0 . The reaction mixture was then warmed to room temperature, and stirred for 20 minutes. After 20 minutes, acids 4a-j (1.2 mmol, 1.2 equiv.) was added at 0 , and the reaction mixture was then brought to room temperature. After that, the reaction mixture was heated at 45 for about 3 hours.The completion of the reaction was monitored by TLC. After reaction completion, the reaction mixture was diluted with ice water, and the aqueous layer was extracted thrice with DCM. The combined organic layers were washed with brine, and dried over anhydrous sodium sulfate, and distilled under reduced pressure to getcrude residue. The crude mixture was purified by column chromatography using hexane, and ethyl acetate aseluent to obtain the titled pyrazole derivatives 5a-j in varying yields.
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