Water → Ethyl 5-benzylamino-6,7-difluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylate

HRID 561180Notes

Reaction equation

F[C:2]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:20]([O-:22])=[O:21])=[CH:6][N:7]2[CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:32](N(CC)CC)[CH3:33].O>C1(C)C=CC=CC=1>[CH2:24]([NH:31][C:2]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:20]([O:22][CH2:32][CH3:33])=[O:21])=[CH:6][N:7]2[CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 5,6,7-trifluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylate (95.0 mg, 0.267 mmol), benzylamine (0.032 mL, 0.292 mmol) and triethylamine (0.11 mL, 0.789 mmol) in toluene (2 mL) was heated at 100° C. for 2 h. The reaction mixture was poured into water and the whole mixture was extracted with CHCl3 two times. The combined extracts was dried over anhydrous Na2SO4, filtered, and then concentrated in vacuo. Flash chromatography of the residue (hexane: EtOAc=1:1) gave ethyl 5-benzylamino-6,7-difluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylate (117 mg, 99%) as a pale yellow powder.

Workup

extractionthe whole mixture was extracted with CHCl3 two times
dry with materialThe combined extracts was dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ca4ccb23c48845ccb9a4e2bd59afee7d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063221B2

Reaction notes

Loading…