Dimethylformamide → Ammonia

HRID 2266585Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8](=[O:31])[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=1)=[C:10]([CH2:17][CH3:18])[NH:11]2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[C:45](OC(=O)C)([F:47])[F:46]>[Cl-].[NH4+]>[NH3:11].[CH3:1][O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:31][CH:45]([F:47])[F:46])=[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([CH2:29][CH3:30])(=[O:27])=[O:28])=[CH:24][CH:25]=1)[C:10]([CH2:17][CH3:18])=[N:11]2

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of [3-(4-ethanesulfonylbenzyl)-2-ethyl-8-fluoro-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester (1.9 g), N,N-dimethylformamide (30 mL), potassium carbonate (1.7 g) and acetic acid chlorodifluoromethyl ester (2.2 mL) was stirred at 70° C. for 3 days. The mixture was diluted with saturated aqueous ammonium chloride solution, extracted with ethyl acetate and the combined extracts washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by Isolute SCX2 column, eluting with methanol and then 2.0 M ammonia in methanol gave title compound, 0.090 g.

Workup

extractionextracted with ethyl acetate
washthe combined extracts washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure and purification of the residue by Isolute SCX2 column
washeluting with methanol

Sources & evidence

ORD record: ord-f04a1332b6634751a55cb51bb7915fbf
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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