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Chemical Structure| 16401-14-2 Chemical Structure| 16401-14-2

Structure of 16401-14-2

Chemical Structure| 16401-14-2

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Product Details of [ 16401-14-2 ]

CAS No. :16401-14-2
Formula : C4H3NO2
M.W : 97.07
SMILES Code : O=CC1=CC=NO1
MDL No. :MFCD07778412
InChI Key :GSIPOZWLYGLXDM-UHFFFAOYSA-N
Pubchem ID :21817604

Safety of [ 16401-14-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 16401-14-2 ]

* 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 [ 16401-14-2 ]

[ 16401-14-2 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 98019-60-4 ]
  • [ 16401-14-2 ]
YieldReaction ConditionsOperation in experiment
45% With Dess-Martin periodane; In dichloromethane; at 20℃; for 1.5h; Step 2Isoxazole-5-carbaldehydeIn a round-bottomed flask, isoxazol-5-yl-methanol (511 mg, 5.16 mmol) was dissolved in dichloromethane (30 ml). Dess-Martin periodinane (2.3 g, 5.41 mmol) was added and the reaction mixture was stirred at room temperature for 1.5 h. The reaction was quenched with 50 ml of a 1 :1 solution of 10%> aqueous Na2S203 and saturated aqueous NaHCC>3 and then extracted with dichloromethane (2x). The organic layers were washed with saturated aqueous NaHCC>3, water and brine. The aqueous layers were back extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was chromato graphed over silica gel with EtOAc/hexanes (gradient 0-40% EtOAc) to afford 226 mg (45%) of isoxazole-5-carbaldehyde as a colorless oil. 1H NMR (CDC13, 300 MHz): ? (ppm)10.05 (s, 1H), 8.44 (d, J=1.9 Hz, 1H), 7.02 (d, J=1.9 Hz, 1H).
  • 2
  • [ 16401-14-2 ]
  • [ 64-17-5 ]
  • [ 16352-98-0 ]
  • 3
  • [ 16401-14-2 ]
  • [ 109-92-2 ]
  • [ 16361-29-8 ]
  • 4
  • [ 16401-14-2 ]
  • (2-(4-Methoxy-benzyloxycarbonyl)-7-{2-[(Z)-methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl)-triphenyl-phosphonium; iodide [ No CAS ]
  • 3-((Z)-2-Isoxazol-5-yl-vinyl)-7-{2-[(Z)-methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester [ No CAS ]
  • 5
  • [ 16401-14-2 ]
  • [7-{2-[(Z)-Cyclopentyloxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-2-(4-methoxy-benzyloxycarbonyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-triphenyl-phosphonium; iodide [ No CAS ]
  • 7-{2-[(Z)-Cyclopentyloxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-((Z)-2-isoxazol-5-yl-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester [ No CAS ]
  • 6
  • [ 16401-14-2 ]
  • (2-(4-Methoxy-benzyloxycarbonyl)-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl)-triphenyl-phosphonium; iodide [ No CAS ]
  • 3-((Z)-2-Isoxazol-5-yl-vinyl)-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
By reacting any of the following aldehydes: ... 3-furaldehyde, isoxazolyl-3-carboxaldehyde and isoxazole-5-carboxaldehyde
  • 9
  • [ 16401-14-2 ]
  • [ 134482-51-2 ]
  • [ 220779-47-5 ]
  • 10
  • [ 16401-14-2 ]
  • [ 300767-72-0 ]
  • (6R,7R)-7-{2-[5-Chloro-2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-3-((Z)-2-isoxazol-5-yl-vinyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester [ No CAS ]
  • 11
  • [ 15055-81-9 ]
  • [ 16401-14-2 ]
YieldReaction ConditionsOperation in experiment
60% With diisobutylaluminium hydride; In dichloromethane; at -78℃; for 1h; Experiment 2If; Isoxazole-S-carboxylic acid, which was commercially available from TCI, was converted to the methyl ester, and then reduced by DIBAL-H to afford the isoxazole-5-carbaldehyde (1.05 g, yield 60 %).
  • 12
  • [ 329974-09-6 ]
  • [ 16401-14-2 ]
  • 7-bromo-2-isoxazol-5-yl[1,2,4]triazolo[1,5-a]pyridin-5-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; mesitylenesulfonylhydroxylamine; EXAMPLE 91 7-Bromo-2-isoxazol-5-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine The title compound, MS m/e (%): 280 (M+, 100), was prepared in accordance with the general method of example 63 from 4-bromo-pyridine-2,6-diamine, O-mesitylene-sulfonylhydroxylamine, and <strong>[16401-14-2]isoxazole-5-carbaldehyde</strong>. The purification was performed with reversed phase HPLC eluting with an acetonitrile/water gradient.
  • 13
  • [ 16401-14-2 ]
  • [ 1219004-56-4 ]
  • [ 1219004-75-7 ]
YieldReaction ConditionsOperation in experiment
General procedure: A solution of 19 (300 mg, 0.70 mmol) in tetrahydrofuran (3 mL) was slowly added to a solution of lithium diisopropylamide (LDA) in heptane/tetrahydrofuran/ethylbenzene (2 M, 0.38 mL, 0.76 mmol) at 78oC, and the resultant solution was stirred at -78oC for 30 minutes. Chlorotitanium triisopropoxide (1 M, 2.8 mL) was then added slowly, and the resulting mixture was stirred at 40oC for 1 hour. The reaction was cooled to -78oC, and propionaldehyde (49 mg, 0.84 mmol) was added slowly. This mixture was then warmed to 40oC, and stirred at 40oC for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (1 mL), diluted with 10 mL of tetrahydrofuran, and treated with Celite for 1 hour. The resultant slurry was filtered and concentrated. The resultant residue was purified by silica gel chromatography (gradient: 95:5 hexanes:ethyl acetate to 65:35 hexanes:ethyl acetate) to provide 20 as a white solid. Yield: 230 mg, 68%.
  • 14
  • [ 16401-14-2 ]
  • 5-((4-((1R,5S)-3,8-diazabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl)amino)-N,3-dimethylpicolinamide hydrochloride [ No CAS ]
  • N,3-dimethyl-5-({4-[(1R,5S)-8-(1,2-oxazol-5-ylmethyl)-3,8-diazabicyclo[3.2.1]oct-3-yl]pyrimidin-2-yl}amino)pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With N-(2,2,2-trifluoroethyl)-1H-imidazole-1-carboxamide; sodium tris(acetoxy)borohydride; In acetonitrile; at 20℃; for 1.5h; Example 53 N,3-dimethyl-5-({4-[(1R,5S)-8-(1,2-oxazol-5-ylmethyl)-3,8-diazabicyclo[3.2.1]oct-3-yl]pyrimidin-2-yl}amino)pyridine-2-carboxamide To a solution of N-(2,2,2-trifluoroethyl)-1H-imidazole-1-carboxamide (Preparation 82) and 5-((4-((1R,5S)-3,8-diazabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl)amino)-N,3-dimethylpicolinamide hydrochloride (Preparation 1, 50 mg, 0.12 mmol) and <strong>[16401-14-2]5-isoxazolecarboxaldehyde</strong> (32 mg, 0.33 mmol) in MeCN (1 mL) was added sodium triacetoxyborohydride (76 mg, 0.35 mmol) and the reaction was stirred at room temperature for 1.5 hours. The reaction was quenched by the addition of saturated aqueous NaHCO3 solution and extracted into EtOAc three times. The organic layer was collected, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-10% MeOH in DCM followed by trituration with diethylether to afford the title compound (30 mg, 59%). LCMS Rt=0.69 minutes; MS m/z 435 [M+H]+
 

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