2-Aminothiazole → 3-Hydroxy-5-[(propan-2-yl)oxy]-N-(1,3-thiazol-2-yl)benzamide

After adding 2.45 g (24.5 mmol) of 2-aminothiazole, 3.40 ml (24.5 mmol) of triethylamine and 4.14 g (24.5 mmol) of 2-chloro-1,3-dimethylimidazolinium chloride to a solution of 2.40 g (12.2 mmol) of the obtained carboxylic acid in chloroform (50 ml) while cooling on ice, the mixture was stirred at room temperature for 13 hours. Saturated aqueous ammonium chloride was added to the reaction mixture, extraction was performed with chloroform, and the organic layer was dried and then concentrated under reduced pressure. After adding 10 ml of 4N aqueous sodium hydroxide to a solution of the obtained residue in methanol (40 ml), the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and then saturated aqueous ammonium chloride was added, extraction was performed with chloroform, and the organic layer was dried and then concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (chloroform:methanol=100:1) to obtain 1.81 g of 5-hydroxy-3-isopropoxy-N-thiazol-2-yl-benzamide (yield: 53%) as a white solid.

1. temperaturewhile cooling on ice
2. customthe organic layer was dried
3. concentrationconcentrated under reduced pressure
4. additionAfter adding 10 ml of 4N aqueous sodium hydroxide to a solution of the obtained residue in methanol (40 ml)
5. stirringthe mixture was stirred at room temperature for 1 hour
6. concentrationThe reaction mixture was concentrated under reduced pressure
7. additionsaturated aqueous ammonium chloride was added
8. extractionextraction
9. customthe organic layer was dried
10. concentrationconcentrated under reduced pressure
11. customThe obtained residue was purified by silica gel chromatography (chloroform:methanol=100:1)

ORD record

ord-5f0298999e0e49d2aaf987a24cc71135

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07432287B2