Triethylamine → 1-(2,4-Difluorophenyl)-7-(1,5-dioxa-8-azaspiro[5.4]dec-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester

HRID 846692Notes

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.[CH2:11]([O:13][C:14]([C:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][C:21](F)=[C:22]([F:27])[CH:23]=2)[N:18]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[F:36])[CH:17]=1)=[O:15])[CH3:12].C(N(CC)CC)C>N1C=CC=CC=1>[CH2:11]([O:13][C:14]([C:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][C:21]([N:8]3[CH2:9][CH2:10][C:6]4([O:5][CH2:4][CH2:3][CH2:2][O:1]4)[CH2:7]3)=[C:22]([F:27])[CH:23]=2)[N:18]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[F:36])[CH:17]=1)=[O:15])[CH3:12]

Participants

Conditions

Temperature: 45 °C

Procedure

Into oven-dried glassware under a N2 atmosphere were placed 0.176 g (1.23 mmol) of 1,5-dioxa-8-azaspiro[5.4]decane, from Step 2, then 0.300 g (0.82 mmol) of 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester (preparation described by H. Narita, et al., Yakugaku Zasshi, 106(9), 795-801, 1986; CA106:196218) dissolved in 10 mL of pyridine, and 0.46 mL (3.28 mmol) of triethylamine. The solution was then heated at 45° C. for 24 hours. The solvent was removed by evaporation to afford the title product which was purified by column chromatography over silica gel (0.5% methanol/chloroform increasing to 2.0% methanol/chloroform). The ester was not further purified, but was taken directly to the next step.

Workup

customInto oven-dried glassware under a N2 atmosphere
customThe solvent was removed by evaporation

Sources & evidence

ORD record: ord-0d9f813a2809465bb74c5e1a051b87be
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05137892

Reaction notes

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