Triethyl phosphite → HCID 86633056, compound

HRID 1094185Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([NH:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH:7]=1.[CH2:30]([O:32][P:33]([O:37]CC)[O:34][CH2:35][CH3:36])[CH3:31]>>[CH:19]1([NH:18][C:11]2[CH:10]=[C:9]3[C:14]([C:15](=[O:16])[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][P:33](=[O:37])([O:34][CH2:35][CH3:36])[O:32][CH2:30][CH3:31])=[CH:7][N:8]3[CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:13][C:12]=2[F:17])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 66636851HCID 66636851, compound

Product 1

HCID 86633056HCID 86633056, compound

Conditions

Temperature: 160 °C

Procedure

To 557 mg of 3-(4-bromobutyl)-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one was added 5 ml of triethylphosphite, followed by stirring at 160° C. for 4 hours. The reaction mixture was concentrated under a reduced pressure, and the resulting residue was purified by a column chromatography to obtain 240 mg of diethyl {4-[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]butyl}phosphonate.

Workup

concentrationThe reaction mixture was concentrated under a reduced pressure
customthe resulting residue was purified by a column chromatography

Sources & evidence

ORD record: ord-2ed2cdd99e844f0883eca936c7eb7666
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133882B2

Reaction notes

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