Potassium Carbonate → HCID 22129988, compound

HRID 1857646Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:21]([CH2:28][CH2:29][CH:30]3[CH2:34][CH2:33][CH2:32][N:31]3[CH3:35])C(=O)C(F)(F)F)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:36]([O-:38])=[O:37].C(=O)([O-])[O-].[K+].[K+]>CO.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:21][CH2:28][CH2:29][CH:30]3[CH2:34][CH2:33][CH2:32][N:31]3[CH3:35])=[C:7]([C:13]3[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:36]([O-:38])=[O:37]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-[7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yl]-2,2,2-trifluoro-N-[2-(1-methylpyrrolidin-2-yl)-ethyl]acetamide (50 mg in a mixture of 1.0 mL methanol and 0.10 mL water) was added 25 mg potassium carbonate and the mixture heated to 60° C. After 4 hours, the mixture was cooled to room temperature and the solvent removed in vacuo. The residue was dissolved in ethyl acetate and washed sequentially with water and brine then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (chloroform:methanol:ammonium hydroxide, 90:10:1) gave the title compound (31 mg). MASS: 455 (M+H)

Workup

temperaturethe mixture was cooled to room temperature
customthe solvent removed in vacuo
dissolutionThe residue was dissolved in ethyl acetate
washwashed sequentially with water and brine
dry with materialthen dried over sodium sulfate
customPurification of the
concentrationconcentrate by flash chromatography on silica gel (chloroform:methanol:ammonium hydroxide, 90:10:1)

Sources & evidence

ORD record: ord-6415ec06f9b846d1b40688f4d8fd2495
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147088

Reaction notes

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