1,1'-Carbonyldiimidazole → HCID 66636954, compound

HRID 469231Notes

Reaction equation

[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:26])[C:13]([C:23](O)=[O:24])=[CH:14][N:15]3[CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C=O)C>[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:26])[C:13]([CH2:23][OH:24])=[CH:14][N:15]3[CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 90 ml DMF solution of 15.0 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was added 9.9 g of 1,1′-carbonyldiimidazole, followed by stirring at 80° C. for 24 hours. After cooling, the reaction mixture was poured into ice water, and the solid precipitated was collected by filtration. Next, 1.9 g of sodium borohydride was added at 0° C. to a mixed solution of 200 ml THF and 100 ml water of the resulting solid, followed by stirring at the same temperature for 2 hours. Water was added, the solvent was evaporated under a reduced pressure, and the insoluble materials were collected by filtration to obtain 13.8 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-(hydroxymethyl)quinolin-4(1H)-one.

Workup

temperatureAfter cooling
customthe solid precipitated
filtrationwas collected by filtration
additionNext, 1.9 g of sodium borohydride was added at 0° C. to a mixed solution of 200 ml THF and 100 ml water of the resulting solid
stirringby stirring at the same temperature for 2 hours
additionWater was added
customthe solvent was evaporated under a reduced pressure
filtrationthe insoluble materials were collected by filtration

Sources & evidence

ORD record: ord-def8f8e3581843e68bc2727c7c803359
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629126B2

Reaction notes

Loading…