Diisopropylethylamine → Ofloxacin

HRID 1941532

Reaction equation

HRID 1941532 reaction equation
C(N1C2C(=CC(F)=C(F)C=2F)[C:6](=[O:16])C(C(O)=O)=C1)C.[C:20]([N:24]1[C:33]2[C:28](=[CH:29][C:30]([F:35])=[C:31](Cl)[N:32]=2)[C:27](=[O:36])[C:26]([C:37]([OH:39])=[O:38])=[CH:25]1)([CH3:23])([CH3:22])C.[CH:40]([N:43]([CH2:47]C)[CH:44](C)[CH3:45])(C)[CH3:41]>CO.C(Cl)Cl.CN(C=O)C>[F:35][C:30]1[C:31]([N:32]2[CH2:45][CH2:44][N:43]([CH3:47])[CH2:40][CH2:41]2)=[C:6]2[O:16][CH2:23][CH:20]([CH3:22])[N:24]3[CH:25]=[C:26]([C:37]([OH:39])=[O:38])[C:27](=[O:36])[C:28]([CH:29]=1)=[C:33]23

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 151890371-(Tert-butyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-napthyridine-3-carboxylic acid

Product 1

HCID 4583Ofloxacin

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Compound 4 (1.9 g), prepared in the same manner as Compound 5 in Example 11, in a 1:1 mixture of DMF and CH2Cl2 (60 mL) is slowly added a solution of Compound 3 (2.32 g) in a 1:1 mixture of DMF and CH2Cl2 (30 mL), under N2. N,N-Diisopropylethylamine (0.98 mL) is added dropwise and the reaction is allowed to stir at ambient temperature until complete. Upon completion, methanol (15 mL) is added and the mixture is stirred for 15 minutes. The volatiles are removed in vacuo until a small mount of DMF remains whereupon methanol (150 mL) is added. The mixture is stirred for 5 minutes and filtered to obtain Compound 5.

Workup

  1. stirringthe mixture is stirred for 15 minutes
  2. customThe volatiles are removed in vacuo until a small mount of DMF
  3. additionis added
  4. stirringThe mixture is stirred for 5 minutes
  5. filtrationfiltered

Sources & evidence

ORD record
ord-aa2162976f724c118f9bb8650ed5d929
Source dataset
uspto-grants-1997_12
Patent number
US05703231

Linked notes

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