Preparation method for enrofloxacin-d5
A technology of deuterated enrofloxacin and -d5, which is applied in the fields of organic chemistry methods, chemical instruments and methods, isotope introduction of heterocyclic compounds, etc., and can solve the problems such as the inability to obtain isotopic abundances.
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example 1
[0052] Example 1: 4-Ethyl-1-Boc-piperazine- d 5 preparation of
[0053] 1-Boc-piperazine (2.42 g, 13 mmol) was mixed with CD 3 cd 2 I (1.47 g, 9 mmol) dissolved in CH 2 Cl 2 (20 mL), add K to the above mixture 2 CO 3 (1.8 g, 13 mmol), stirred at room temperature for 18 h, then added CD 3 cd 2 I (1.47 g, 9 mmol), continue stirring at room temperature for 18 h, after the reaction is complete, add H 2 O (10 mL), split CH 2 Cl 2 layer, water soluble with CH 2 Cl 2 Extract (2 × 10 mL), combine CH 2 Cl 2 layer, washed with saturated NaCl, anhydrous MgSO 4 Drying and concentration under reduced pressure gave 2.72 g yellow oil crude product 4-ethyl-1-Boc-piperazine- d 5 , the yield was 98%, and could be directly used in the next step without purification. ESI-MS(m / z): 220.1 (M+H) +1 , 1 HNMR (400 MHz, CDCl 3 ): δ = 3.43-3.45 (4H, m), 2.38-2.44(4H, m), 1.46 (9H, s).
example 2
[0054] Example 2: 1-Ethyl-piperazine- d 5 preparation of
[0055] 4-Ethyl-1-Boc-piperazine- d 5 (1.50 g, 7 mmol) dissolved in CH 2 Cl 2 (15 mL), to which was added CF 3 COOH (0.62 mL, 8.4 mmol), stirred at room temperature for 10 min, concentrated under reduced pressure to remove CH2 Cl 2 , to which CH 3 OH (10mL), concentrated under reduced pressure again to remove CH 3 OH, 0.79 g yellow oil crude product 1-ethyl-piperazine- d 5 , the yield was 95%, and could be directly used in the next step without further purification. ESI-MS (m / z): 120.1 (M+H) +1 , 1 HNMR (400 MHz, CDCl 3 ): δ =5.1 (1H, br s), 3.51-3.75 (8H, m).
example 3
[0056] Example 3: Ethyl 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-ethyl-1-piperazinyl)-3-quinolinecarboxylate- d 5 Preparation (coupling method)
[0057] 1-Ethyl-piperazine- d 5 (0.79 g, 6.7 mmol), ethyl 1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.6 g, 5 mmol), Cs 2 CO 3 (3.3 g, 10 mmol), Pd(dba) 3 (0.1 g, 0.1 mmol) and BINAP (0.1 g, 0.15 mmol) were dissolved in DMF (20 mL), N 2 protection, stirred at 115°C for 2 h, after the reaction was completed, concentrated under reduced pressure to remove most of the solvent, and added CH 2 Cl 2 (20 mL), filtered through a sand core, and the filtrate was concentrated under reduced pressure to obtain a brownish-red oily crude product, which was subjected to silica gel column chromatography (CH 3 OH) to obtain 1.8 g of light yellow solid 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-ethyl-1-piperazinyl)-3-quinolinecarboxylic acid ethyl ester- d 5 , the yield is 93%. ESI-MS (m / z): 393.1 (M+H)...
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