1,1'-Carbonyldiimidazole → HCID 9978175, compound

HRID 1741583Notes

Reaction equation

[CH:1]1N=CN(C(N2C=NC=C2)=O)[CH:2]=1.[CH:13]1([N:16]2[C:25]3[C:20](=[CH:21][C:22]([F:35])=[C:23]([C:27]4[CH:32]=[C:31]([CH3:33])[N:30]=[C:29]([CH3:34])[CH:28]=4)[C:24]=3[F:26])[C:19](=[O:36])[C:18]([C:37]([OH:39])=[O:38])=[CH:17]2)[CH2:15][CH2:14]1>CN(C=O)C.C(O)C>[CH:13]1([N:16]2[C:25]3[C:20](=[CH:21][C:22]([F:35])=[C:23]([C:27]4[CH:32]=[C:31]([CH3:33])[N:30]=[C:29]([CH3:34])[CH:28]=4)[C:24]=3[F:26])[C:19](=[O:36])[C:18]([C:37]([O:39][CH2:1][CH3:2])=[O:38])=[CH:17]2)[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 25 °C

Procedure

1,1'-Carbonyldiimidiazole (CDI) (3.9 g, 0.024 mol) was added to a suspension of (6.0 g, 0.016 mol) 1-cyclopropyl-7-(2, 6-dimethyl-4-pyridinyl )-6, 8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, described in U.S. Pat. No. 5,075,319, and incorporated herein by reference, in DMF (40 mL) and the mixture was stirred at 100° C. for 2 hr under a N2 atmosphere. The resulting solution was cooled to 25° C., diluted with and 60 mL ethanol and heated at reflux 17 h. Removal of the solvents in vacuo gave a residue that was stirred in 20 mL ethanol; after cooling in ice a solid separated and was collected (5.5 g, 86%); a 4.5 g portion of this material was recrystallized from ethanol to give 4.25 of ethyl 1-cyclopropyl-7-(2,6-dimethyl-4-pyridinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, mp 193°-195° C.

Workup

temperatureheated
temperatureat reflux 17 h
customRemoval of the solvents in vacuo
customgave a residue that
temperatureafter cooling in ice a solid
customseparated
customwas collected (5.5 g, 86%)
customa 4.5 g portion of this material was recrystallized from ethanol

Sources & evidence

ORD record: ord-a47ab7099d8a4ddfbcce470afb4579e5
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334595

Reaction notes

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