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Chemical Structure| 32380-69-1 Chemical Structure| 32380-69-1

Structure of 32380-69-1

Chemical Structure| 32380-69-1

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Product Details of [ 32380-69-1 ]

CAS No. :32380-69-1
Formula : C10H9NO4
M.W : 207.18
SMILES Code : O=C1N(OCCO)C(C2=C1C=CC=C2)=O
MDL No. :MFCD11846413
InChI Key :DOSUQMBAMQLTFF-UHFFFAOYSA-N
Pubchem ID :10679822

Safety of [ 32380-69-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H302
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 32380-69-1 ]

* 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 [ 32380-69-1 ]

[ 32380-69-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 32380-69-1 ]
  • [ 3279-95-6 ]
YieldReaction ConditionsOperation in experiment
78% With hydrazine; In methanol; at 70℃; for 1.5h; 13b. 2-(Aminooxy)ethan-l-olH2N. / LambdaDHA solution of the product of Example 13a (15.57 g, 75.2 mmol) and hydrazine hydrate (5.4 mL, 0.11 mol) in methanol (150 mL) were heated to 70 C for 1.5 hours. After cooling to room temperature, CHCl3 (100 mL) was added to the reaction mixture. The resulting slurry was filtered and washed with CHCl3 (100 mL x 2). The filtrate was concentrated and the residue was distilled under vacuum (0.025 mmHg) at 75 to 80 C to give a colorless oil (4.54 g, 78% yield); 1H NMR (300 MHz, CDCl3) delta 3.78 (s, 4H); 13C NMR (75 MHz, CDCl3) delta 76.3, 60.7.
73% With methylhydrazine; In dichloromethane; at 20℃; 2 was obtained flask 5L in step 4 (2-hydroxy - ethoxy) - isoindole-1,3-dione (555 g, 2.679 mol) was added, dissolved under stirring in methylene chloride (2.0 L), while the reaction vessel was cooled in an ice bath, methyl hydrazine (142 mL, 2.68 mol) the inner temperature was added dropwise so as not to exceed 20 C. With the progress of the reaction, a white insoluble matter has emerged. After completion of the dropwise addition, the mixture was stirred under about 15 minutes the ice bath, the precipitated insoluble substance was filtered off through a glass filter, washed white insolubles on the filter with dichloromethane (2 x 400 mL), the filtrate and washings was combined evaporated under reduced pressure. The yellow oily residue (230g) was distilled under reduced pressure (51~54 C / 2 mmHg), the objective compound as unemployed transparent liquid 2-aminooxyethanol (162g, 73%).
28% With hydrazine hydrate; In methanol; at 70℃; for 1.5h; To a stirred solution of Compound 172 (29.0 g, 139.97 mmol) in MeOH (300 mL) was added hydrazine hydrate (9.63 mL, 195.96 mmol) at room temperature. The resultant solution was stirred at 70 C for 1.5 hours. The reaction mixture was cooled to room temperature and diluted with CHCI3(1 x 300 mL). The resultant slurry was filtered through Buchner funnel and washed with CHCI3(2 x 300 mL). The filtrate was concentrated, and the residue was distilled under vacuum (0.025 mmHg) at 75-80 C to give the desired alcohol, 2-(aminooxy)ethan-1-ol (Compound 173, 3.0 g,28 %), as a colorless oil.
With hydrazine hydrate; In methanol; for 2h;Reflux; Hydrazine monohydrate (3.96 mg, 0.124 mmol) was added to a solution of 2-(2- hydroxyethoxy)isoindoline-1 ,3-dione (produced with a similar procedure for intermediate B) (25.6 mg, 0.124 mmol) in 5 ml_ of MeOH. The solution was heated at reflux for 2 h and then cooled to rt. White precipitate was filtered off and 1 -(3-(quinolin-6-ylmethyl)- [1 ,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (41.2) (15 mg, 0.049 mmol) was added. The pH value of the solution was adjusted to 5-6 with 1 N HCI solution. The reaction solution was then stirred at rt for 2 h. Solvent was evaporated and the crude was purified by HPLC (acidic with 0.05% TFA) to give 8 mg (44.5%) of the title compound as a white TFA salt. 1H-NMR (400MHz, MeOH-Cf4) delta ppm 9.09 (s, 1 H), 8.93 (d, 1 H), 8.27 (s, 1 H), 8.16 (m, 3H), 7.98 (d, 1 H), 7.93 (m, 1 H), 4.92 (s, 2H), 4.38 (t, 2H), 3.86 (t, 2H), 2.34 (s, 3H). LC-MS (method B): [MH]+ =363.1 , tR = 2.31 min.

  • 2
  • [ 504435-90-9 ]
  • [ 32380-69-1 ]
  • [ 3279-95-6 ]
  • N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-[(2-hydroxyethoxy) iminomethyl]-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
The title compound N-[5(S)-3-[3-fluoro-4-[(1alpha,5alpha,6alpha)-6-[(2-hydroxyethoxy) iminomethyl]-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (149 mg) was prepared from N-[5(S)-3-[3-fluoro-4-[(1alpha,5alpha,6alpha)-6-formyl-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (150 mg) and crude <strong>[3279-95-6]O-(2-hydroxyethyl)hydroxylamine</strong> (prepared from N-(2-hydroxyethoxy)phthalimide (414 mg)) in the same manner as described for EXAMPLE 66. MS (EI+) m/z: 420 (M+).
 

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