Ethyl ((5-chlorothiophen-2-yl)sulfonyl)carbamate → 5-chloro-N-({[7-(cyclohexylamino)-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinolin-3-yl]amino}carbonyl)thiophene-2-sulfonamide

HRID 469216Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11](=[O:15])OCC)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[NH2:16][C:17]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][C:22]([NH:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[C:23]([F:28])[CH:24]=2)[N:19]([CH:36]([CH3:38])[CH3:37])[CH:18]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([NH:16][C:17]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][C:22]([NH:29][CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[C:23]([F:28])[CH:24]=3)[N:19]([CH:36]([CH3:38])[CH3:37])[CH:18]=2)=[O:15])(=[O:8])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

287 mg of ethyl [(5-chloro-2-thienyl)sulfonyl]carbamate was dissolved in 5.0 ml of toluene, and 250 mg of 3-amino-7-(cyclohexylamino)-6-fluoro-1-isopropylquinolin-4(1H)-one was added, followed by overnight stirring at 110° C. The reaction mixture was cooled to room temperature and concentrated under a reduced pressure. Then, ethyl acetate was added and the insoluble materials were collected by filtration, thereby obtaining 280 mg of 5-chloro-N-({[7-(cyclohexylamino)-6-fluoro-1-isopropyl-4-oxo-1,4-dihydroquinolin-3-yl]amino}carbonyl)thiophene-2-sulfonamide.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under a reduced pressure
additionThen, ethyl acetate was added
filtrationthe insoluble materials were collected by filtration

Sources & evidence

ORD record: ord-0a8b436641284b6fac22c6372ae31dee
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629126B2

Reaction notes

Loading…