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[ CAS No. 153597-59-2 ]

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Chemical Structure| 153597-59-2
Chemical Structure| 153597-59-2
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CAS No. :153597-59-2 MDL No. :MFCD09263988
Formula : C9H12N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :196.20 g/mol Pubchem ID :11845247
Synonyms :

Safety of [ 153597-59-2 ]

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
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Application In Synthesis of [ 153597-59-2 ]

  • Upstream synthesis route of [ 153597-59-2 ]
  • Downstream synthetic route of [ 153597-59-2 ]

[ 153597-59-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 85230-37-1 ]
  • [ 109-64-8 ]
  • [ 153597-59-2 ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate In acetonitrile for 16 h; Heating / reflux Step 1: Preparation of ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2- carboxylate :; To the stirred suspension of ethyl 5-hydroxy-1H-pyrazole-3-carboxylate (10.34 g, 0.66 mol) and 36.62 g of potassium carbonate in 500 mi of acetonitrile was added 14.7 g of 1,3-dibromopropane, and refluxed for 16 hours. The reaction mixture was allowed to cool to room temperature, then filtered, the solid was washed with acetonitrile. The filtrate was concentrated to an oil. The residue was dissolved in ethyl acetate and extracted with water. The organic phase was dried over MgS04 and evaporated to dryness. 8.80 g of the desired product was obtained (68percent), m. p. 44-46°C (M+H) + 197. 1.
68% With potassium carbonate In acetonitrile for 16 h; Heating / reflux To the stirred suspension of ethyl 5-hydroxy-1H-pyrazole-3-carboxylate (10.34 g, 0.66 mol) and 36.62 g of potassium carbonate in 500 ml of acetonitrile was added 14.7 g of 1,3-dibromopropane, and refluxed for 16 hours. The reaction mixture was allowed to cool to room temperature, then filtered, the solid was washed with acetonitrile. The filtrate was concentrated to an oil. The residue was dissolved in ethyl acetate and extracted with water. The organic phase was dried over MgSO4 and evaporated to dryness. 8.80 g of the desired product was obtained (68percent), m.p. 44-46° C. (M+H)+197.1.
61% With potassium carbonate In acetonitrile for 16 h; Reflux Potassium carbonate (48.3 g, 349 mmol) was added to a solution of C1 (13.65 g, 87.42 mmol) in acetonitrile (250 mL). The mixture was stirred at room temperature for 15 minutes, whereupon 1 ,3-dibromopropane (10 mL, 98 mmol) was added drop-wise, and the reaction mixture was heated at reflux for 16 hours. It was then allowed to cool to room temperature and filtered; t e filtered solids were washed with acetonitrile (2 x 100 mL). The filtrate was concentrated in vacuo, and the residue was purified via chromatography on silica gel (Gradient: 50percent to 95percent ethyl acetate in heptane) to afford the product as an orange oil. Yield: 10.48 g, 53.4 mmol, 61 percent. LCMS m/z 197.0 [M+H]+. 1H NMR (400 MHz, CDCI3) δ 6.03 (s, 1 H), 4.39 (q, J=7.1 Hz, 2H), 4.34-4.30 (m, 2H), 4.26 (t, J=6.2 Hz, 2H), 2.33-2.26 (m, 2H), 1.39 (t, J=7.1 Hz, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4623 - 4637
[2] Patent: WO2003/93279, 2003, A1, . Location in patent: Page/Page column 137
[3] Patent: US2006/276445, 2006, A1, . Location in patent: Page/Page column 42
[4] Patent: WO2017/145013, 2017, A1, . Location in patent: Page/Page column 54-55
[5] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 4, p. 1097 - 1100
[6] Patent: US2004/132708, 2004, A1,
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  • [ 40876-98-0 ]
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Reference: [1] Patent: WO2017/145013, 2017, A1,
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