Dimethylformamide → HCID 86744884, compound

HRID 1494724Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][NH:22]1.CN(C=O)C>C(Cl)(Cl)Cl>[CH:21]1([C:5]2[N:4]([CH:1]3[CH2:3][CH2:2]3)[C:13]3[C:8]([C:7](=[O:17])[C:6]=2[C:18]([OH:20])=[O:19])=[CH:9][C:10]([F:16])=[CH:11][C:12]=3[F:14])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][NH:22]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 136 mg of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 180 mg of isoindoline, and 1.5 ml of anhydrous DMF was heated at 120° C. for 1.5 hours while stirring. The resulting reaction mixture was evaporated under reduced pressure to dryness. The residue thus obtained was dissolved into 20 ml of chloroform. The solution was washed with 5% acetic acid and brine in this order, dried over anhydrous sodium sulfate, and condensed. The residue was crystallized by the addition of hot ethanol. After cooling the mixture, the crystals were collected by filtration and recrystallized from a mixed solvent of chloroform, methanol, and ethanol to obtain 123 mg of the target compound.

Workup

customThe resulting reaction mixture
customwas evaporated under reduced pressure to dryness
customThe residue thus obtained
washThe solution was washed with 5% acetic acid and brine in this order
dry with materialdried over anhydrous sodium sulfate, and condensed
customThe residue was crystallized by the addition of hot ethanol
temperatureAfter cooling the mixture
filtrationthe crystals were collected by filtration
customrecrystallized from a mixed solvent of chloroform, methanol, and ethanol

Sources & evidence

ORD record: ord-1126452c97f2422baeec4790a5149559
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05026856

Reaction notes

Loading…