Triethylamine → 1-Cyclopropyl-6,8-difluoro-7-(1,5-dioxa-8-azaspiro[5.4]dec-8-yl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 846693Notes

Reaction equation

HRID 846693 reaction equation
[O:1]1[C:6]2([CH2:10][CH2:9][NH:8][CH2:7]2)[O:5][CH2:4][CH2:3][CH2:2]1.C([O:13][C:14]([C:16]1[C:25](=[O:26])[C:24]2[C:19](=[C:20]([F:29])[C:21](F)=[C:22]([F:27])[CH:23]=2)[N:18]([CH:30]2[CH2:32][CH2:31]2)[CH:17]=1)=[O:15])C.C(N(CC)CC)C>N1C=CC=CC=1>[CH:30]1([N:18]2[C:19]3[C:24](=[CH:23][C:22]([F:27])=[C:21]([N:8]4[CH2:9][CH2:10][C:6]5([O:5][CH2:4][CH2:3][CH2:2][O:1]5)[CH2:7]4)[C:20]=3[F:29])[C:25](=[O:26])[C:16]([C:14]([OH:15])=[O:13])=[CH:17]2)[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 198833386,10-Dioxa-2-azaspiro[4.5]decane

Product 1

HCID 198833161-Cyclopropyl-6,8-difluoro-7-(1,5-dioxa-8-azaspiro[5.4]dec-8-yl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 0.276 g (1.8 mmol) sample of 1,5-dioxa-8-azaspiro[5.4]decane, from Step 2 Example 14, 0.400 g (1.29 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester (preparation described by K. Grohe, et al., DE 3318145, November 1984) and 0.52 mL (3.7 mmol) of triethylamine and 12 mL of pyridine were heated at 65° C. for 48 hours in dry glassware and under dry nitrogen. The solvent was evaporated and the ester purified by chromatography on a silica gel column using as eluant 0.5% methanol in methylene chloride increasing to 2% methanol in methylene chloride. The solvent was removed to afford 0.218 g of the title compound, which was taken to the next step directly.

Workup

  1. customThe solvent was evaporated
  2. customthe ester purified by chromatography on a silica gel column
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-fb3230be422543d79ac3070afa9e9637
Source dataset
uspto-grants-1992_08
Patent number
US05137892

Reaction notes

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