Potassium Carbonate → 4-(4,5-dichloro-2-(4-chloro-2-methoxyphenoxy)benzamido)benzoic Acid

HRID 515098

Reaktionsgleichung

[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)=[O:7])=[C:4](F)[CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([O:31][CH3:32])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CO.CN1CCCC1=O>[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)=[O:7])=[C:4]([O:30][C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][C:26]=2[O:31][CH3:32])[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of methyl 4-[(4,5-dichloro-2-fluoro-benzoyl)amino]benzoate (34.21 mg, 0.1 mmol), 4-chloro-2-methoxyphenol (12.16 μl, 0.1 mmol), potassium carbonate 13.82 mg, 0.1 mmol) and N-methylpyrrolidinone (1 mL) were heated at 80° C. for 2.5 hours. Methanol (100 μL) and sodium hydroxide (3M, 100 μL, 0.3 mmol) were added and the reaction was stirred at 50° C. for 2 hours. An additional 100 μL of MeOH and 100 μL of 3M NaOH were added and the reactions were heated for another hour. The reaction mixture was filtered and purified by reverse phase preparative chromatography utilizing a gradient of 10-99% acetonitrile in water containing HCl as a modifier to yield 4-(4,5-dichloro-2-(4-chloro-2-methoxyphenoxy)benzamido)benzoic acid (18) (11.78 mg, 25%). ESI-MS m/z calc. 464.99, found 466.3 (M+1)+; Retention time: 2.20 minutes (3 minutes run).

Aufarbeitung

temperaturethe reactions were heated for another hour
filtrationThe reaction mixture was filtered
custompurified by reverse phase preparative chromatography
additioncontaining HCl as a modifier

Quellen und Nachweise

ORD-Eintrag: ord-90107f4e243b4436b44164a7c88a4546
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09108903B2

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