Sodium Methoxide → 5-[[2-[N-(6-Bromopyridin-2-yl)amino]thiazol-5-yl]thio]-2-methylbenzoic acid
Reaktionsgleichung
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[S:10][C:11](Br)=[CH:12][N:13]=2)[CH:5]=[CH:4][CH:3]=1.[C:15]([C:18]1[CH:19]=[C:20]([SH:25])[CH:21]=[CH:22][C:23]=1[CH3:24])([OH:17])=[O:16].C[O-].[Na+]>CO.C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[S:10][C:11]([S:25][C:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[C:18]([CH:19]=3)[C:15]([OH:17])=[O:16])=[CH:12][N:13]=2)[CH:5]=[CH:4][CH:3]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 54 °C
Versuchsvorschrift
A suspension of 2-[(6-bromo-2-pyridinyl)amino]-5-bromothiazole (100 mg, 0.3 mmol), 3-carboxy-4-methylthiophenol (170 mg, 0.98 mmol) and sodium methoxide (210 μL, 25% w/w solution in methanol, 0.9 mmol) in methanol (4.9 mL) and THF (2 mL) was heated to 54° C. for 5.5 h. Supplemental sodium methoxide solution (1.42 mL) was added in portions over a period of 5 h. The mixture was heated to 54° C. for 16 h and concentrated. The residue was diluted with 1 N aqueous HCl solution at 0° C. and stirred for several minutes. The precipitated solid was filtered, washed several times with water and ether, and dried in vacuo over P2O5. Trituration with ether afforded the titled compound (103 mg, 81%) as an off-white solid.
Aufarbeitung
- temperatureThe mixture was heated to 54° C. for 16 h
- concentrationconcentrated
- additionThe residue was diluted with 1 N aqueous HCl solution at 0° C.
- filtrationThe precipitated solid was filtered
- washwashed several times with water and ether
- dry with materialdried in vacuo over P2O5
Quellen und Nachweise
- ORD-Eintrag
- ord-ef954bfc615b4c038770449f1a96e266
- Quelldatensatz
- uspto-grants-2004_03
- Patentnummer
- US06706717B2
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