Dimethylformamide → HCID 23284708, compound

HRID 369207Notes

Reaction equation

[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([NH:16][C:17]1[C:18]([F:43])=[CH:19][C:20]([F:42])=[C:21]([N:23]2[C:32]3[C:27](=[CH:28][C:29]([F:35])=[C:30](F)[C:31]=3[Cl:33])[C:26](=[O:36])[C:25]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:24]2)[CH:22]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10].CN1CCCC1.CN(C)C=O>C(OCC)(=O)C>[CH2:1]([NH:8][C:30]1[C:31]([Cl:33])=[C:32]2[C:27]([C:26](=[O:36])[C:25]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:24][N:23]2[C:21]2[CH:22]=[C:17]([NH:16][C:14]([O:13][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:15])[C:18]([F:43])=[CH:19][C:20]=2[F:42])=[CH:28][C:29]=1[F:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Benzylamine (750 mg) and ethyl 1-(5-tert-butoxycarbonylamino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (4,200 mg) were added to a solution of N-methylpyrrolidine (800 mg) and N,N-dimethylformamide (20 ml), and the mixture was stirred overnight at 80° C. After the reaction mixture was cooled to room temperature, ethyl acetate (100 ml) was added to the reaction mixture, and the resultant mixture was washed 3 times with water (100 ml). After an organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel (eluent; chloroform) to obtain the title compound (3,200 mg) as an amorphous substance.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
washthe resultant mixture was washed 3 times with water (100 ml)
dry with materialAfter an organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-5d97a7666e804425ac1cd6150087aff1
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

Loading…