Dimethylformamide → HCID 23284755, compound

HRID 369288Notes

Reaction equation

[CH3:1]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].CI.[C:14]([O:18][C:19]([NH:21][C:22]1[C:23]([F:48])=[CH:24][C:25]([F:47])=[C:26]([N:28]2[C:37]3[C:32](=[CH:33][C:34]([F:40])=[C:35]([F:39])[C:36]=3[CH3:38])[C:31](=[O:41])[C:30]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:29]2)[CH:27]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>O.C(OCC)(=O)C>[C:14]([O:18][C:19]([N:21]([C:22]1[C:23]([F:48])=[CH:24][C:25]([F:47])=[C:26]([N:28]2[C:37]3[C:32](=[CH:33][C:34]([F:40])=[C:35]([F:39])[C:36]=3[CH3:38])[C:31](=[O:41])[C:30]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:29]2)[CH:27]=1)[CH3:1])=[O:20])([CH3:15])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

N,N-Dimethylformamide (4 ml), potassium carbonate (0.6 g) and methyl iodide (0.6 g) were added to ethyl 1-(5-tert-butoxycarbonylamino-2,4-difluorophenyl)-6,7-difluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (1.0 g), and the mixture was stirred overnight at 60° C. Ethyl acetate and water were added to the reaction mixture to collect an organic layer. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off. Ethanol was added to the residue, and solids deposited were collected to obtain the title compound (410 mg) as a colorless powder.

Workup

customto collect an organic layer
dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off
additionEthanol was added to the residue, and solids
customdeposited were collected

Sources & evidence

ORD record: ord-cd3cc7c0fc1b495e8039b246f18c623d
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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